BEGIN IONS TITLE=GNPS2LIB00000000001 PEPMASS=343.2279 CHARGE=1 MSLEVEL=2 FRAGMENTATION_METHOD=N/A COLLISION_ENERGY=20 SOURCE_INSTRUMENT=ESI(-)-QTOF Agilent 6546 FILENAME=CEMBIO_standard_individual_20eV.mgf SEQ=*..* IONMODE=Negative ORGANISM=CEMBIO_OXYLIPINS NAME=10(11)-EpDPE PI=N/A DATACOLLECTOR=N/A SMILES=CC/C=C\C/C=C\C/C=C\CC1C(O1)C/C=C\C/C=C\CCC(=O)O INCHI=InChI=1S/C22H32O3/c1-2-3-4-5-6-7-8-11-14-17-20-21(25-20)18-15-12-9-10-13-16-19-22(23)24/h3-4,6-7,10-15,20-21H,2,5,8-9,16-19H2,1H3,(H,23,24)/b4-3-,7-6-,13-10-,14-11-,15-12- INCHIAUX=YYZNJWZRJUGQCW-UQZHZJRSSA-N PUBMED=N/A SUBMITUSER=N/A LIBRARYQUALITY=1 SPECTRUMID=GNPS2LIB00000000001 USI=mzspec:GNPS:CEMBIO_OXYLIPINS:accession:GNPS2LIB00000000001 SCANS=1 105.07069492649084 15.020489552052531 106.04228786160725 44.89034118441151 107.05023547943281 63.86932504143072 107.0869364158096 24.431124516392554 108.05814773775468 26.702765500862075 109.06603503162603 25.636343237704246 115.05472472017533 11.365590572436817 117.07091197012886 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TITLE=GNPS2LIB0000000000G PEPMASS=317.2122 CHARGE=1 MSLEVEL=2 FRAGMENTATION_METHOD=N/A COLLISION_ENERGY=20 SOURCE_INSTRUMENT=ESI(-)-QTOF Agilent 6546 FILENAME=CEMBIO_standard_individual_20eV.mgf SEQ=*..* IONMODE=Negative ORGANISM=CEMBIO_OXYLIPINS NAME=14(15)-EpETE PI=N/A DATACOLLECTOR=N/A SMILES=CC/C=C\CC1C(O1)C/C=C\C/C=C\C/C=C\CCCC(=O)O INCHI=InChI=1S/C20H30O3/c1-2-3-12-15-18-19(23-18)16-13-10-8-6-4-5-7-9-11-14-17-20(21)22/h3-4,6-7,9-10,12-13,18-19H,2,5,8,11,14-17H2,1H3,(H,21,22)/b6-4-,9-7-,12-3-,13-10- INCHIAUX=RGZIXZYRGZWDMI-QXBXTPPVSA-N PUBMED=N/A SUBMITUSER=N/A LIBRARYQUALITY=1 SPECTRUMID=GNPS2LIB0000000000G USI=mzspec:GNPS:CEMBIO_OXYLIPINS:accession:GNPS2LIB0000000000G SCANS=16 103.05520636052623 24.778580425293317 106.04249612754714 98.66158836067932 107.08679759293518 86.08311958051289 109.0659929831587 116.33087204925752 111.08146306820576 258.62579355840694 119.05041541142387 182.68663555456308 119.08615259271501 48.50608254716474 121.06583429304371 1000.0 121.10229243599969 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31.996213142847246 201.12797804913592 40.60100444679057 201.1644083686616 60.087881525157826 203.14311764737357 73.04086103555927 205.12375387008194 41.005327909069024 207.13925011831324 575.8833170483922 219.1388367169141 110.43376580764497 221.15545091071687 77.26221514887733 247.13394254879628 31.471747447557604 248.14140097342278 51.96528260135607 255.21198086290008 106.50604004748645 273.2218110654586 25.208085017691975 299.20174489614374 74.55353974783826 317.08010018772507 38.78830615975963 317.21169451180583 130.53788917057264 END IONS BEGIN IONS TITLE=GNPS2LIB0000000000H PEPMASS=319.2279 CHARGE=1 MSLEVEL=2 FRAGMENTATION_METHOD=N/A COLLISION_ENERGY=20 SOURCE_INSTRUMENT=ESI(-)-QTOF Agilent 6546 FILENAME=CEMBIO_standard_individual_20eV.mgf SEQ=*..* IONMODE=Negative ORGANISM=CEMBIO_OXYLIPINS NAME=14(15)-EpETrE PI=N/A DATACOLLECTOR=N/A SMILES=CCCCCC1C(O1)C/C=C\C/C=C\C/C=C\CCCC(=O)O 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229.19623674396527 75.73363377541688 257.2269349304136 295.7276576213897 275.23795890565225 69.90761289990564 283.2066747798132 29.441859508805692 301.2169200292773 318.86224409576624 319.22768661276746 255.27400548404415 END IONS BEGIN IONS TITLE=GNPS2LIB0000000000I PEPMASS=315.1966 CHARGE=1 MSLEVEL=2 FRAGMENTATION_METHOD=N/A COLLISION_ENERGY=20 SOURCE_INSTRUMENT=ESI(-)-QTOF Agilent 6546 FILENAME=CEMBIO_standard_individual_20eV.mgf SEQ=*..* IONMODE=Negative ORGANISM=CEMBIO_OXYLIPINS NAME=15-deoxy-PGJ2 PI=N/A DATACOLLECTOR=N/A SMILES=CCCCC/C=C/C=C/1\[C@H](C=CC1=O)C/C=C\CCCC(=O)O INCHI=InChI=1S/C20H28O3/c1-2-3-4-5-6-10-13-18-17(15-16-19(18)21)12-9-7-8-11-14-20(22)23/h6-7,9-10,13,15-17H,2-5,8,11-12,14H2,1H3,(H,22,23)/b9-7-,10-6+,18-13+/t17-/m0/s1 INCHIAUX=VHRUMKCAEVRUBK-GODQJPCRSA-N PUBMED=N/A SUBMITUSER=N/A LIBRARYQUALITY=1 SPECTRUMID=GNPS2LIB0000000000I USI=mzspec:GNPS:CEMBIO_OXYLIPINS:accession:GNPS2LIB0000000000I SCANS=18 106.04240285325804 50.0290412994241 107.05028203779949 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200.12130795926464 14.579412358826438 201.12781539827043 14.192713779042146 203.14415404349947 550.7388973831894 204.1474206629308 18.745858887325948 213.1285061372225 14.080146887580213 215.14448329613603 29.204539798999313 217.15987668136785 68.49621335148005 228.1511686475548 14.617924668198206 229.1595872854639 41.63232228948334 229.19599767542974 12.841543436002643 232.97499352784303 19.614270271964966 233.15417736249447 32.29286013505702 241.16001840659627 25.764990974168327 243.175555482936 82.27107781309707 253.19609763970885 12.922843136669144 255.17564096834013 16.09153924753877 255.23230585653184 19.173434449216074 269.19135217469676 24.39079370404893 271.20686326973015 1000.0 272.21029403052677 20.404257675159865 297.18628275093516 52.74137578349682 315.1966674478461 71.57888426590611 END IONS BEGIN IONS TITLE=GNPS2LIB0000000000J PEPMASS=317.2122 CHARGE=1 MSLEVEL=2 FRAGMENTATION_METHOD=N/A COLLISION_ENERGY=20 SOURCE_INSTRUMENT=ESI(-)-QTOF Agilent 6546 FILENAME=CEMBIO_standard_individual_20eV.mgf SEQ=*..* IONMODE=Negative ORGANISM=CEMBIO_OXYLIPINS NAME=15-HEPE PI=N/A DATACOLLECTOR=N/A SMILES=CC/C=C\CC(/C=C/C=C\C/C=C\C/C=C\CCCC(=O)O)O INCHI=InChI=1S/C20H30O3/c1-2-3-13-16-19(21)17-14-11-9-7-5-4-6-8-10-12-15-18-20(22)23/h3-5,8-11,13-14,17,19,21H,2,6-7,12,15-16,18H2,1H3,(H,22,23)/b5-4-,10-8-,11-9-,13-3-,17-14+ INCHIAUX=WLKCSMCLEKGITB-XWJJKCKWSA-N PUBMED=N/A SUBMITUSER=N/A LIBRARYQUALITY=1 SPECTRUMID=GNPS2LIB0000000000J USI=mzspec:GNPS:CEMBIO_OXYLIPINS:accession:GNPS2LIB0000000000J SCANS=19 105.07078024850101 41.17661574978849 106.04258549649757 88.1768808515771 107.08659473751878 227.29620047354513 109.06645351668857 43.78842555648979 109.10205120174848 41.9618937619741 111.08148537869393 354.6860633263878 115.05569207437286 32.77031341772307 117.07124074950407 33.00574625743793 119.0499983441495 173.90786584811596 119.08675688125045 109.00261201465561 121.06583875142593 1000.0 121.10229524657417 454.8635116367285 131.9730145837578 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221.15449047641508 188.09843191718468 227.18002723842562 67.74224037832916 229.12283007572498 43.62329003064321 247.13431441038279 97.60320779173105 248.14168436927062 136.90464354762022 255.2118090169997 595.1443927994575 273.2221847436172 88.83491014180133 281.18977085732746 29.461966141918445 299.20129189637305 260.21966575651845 317.08326551213275 43.522190270649645 317.21223647753015 243.8313168189796 END IONS BEGIN IONS TITLE=GNPS2LIB0000000000K PEPMASS=319.2279 CHARGE=1 MSLEVEL=2 FRAGMENTATION_METHOD=N/A COLLISION_ENERGY=20 SOURCE_INSTRUMENT=ESI(-)-QTOF Agilent 6546 FILENAME=CEMBIO_standard_individual_20eV.mgf SEQ=*..* IONMODE=Negative ORGANISM=CEMBIO_OXYLIPINS NAME=15-HETE PI=N/A DATACOLLECTOR=N/A SMILES=CCCCCC(/C=C/C=C\C/C=C\C/C=C\CCCC(=O)O)O INCHI=InChI=1S/C20H32O3/c1-2-3-13-16-19(21)17-14-11-9-7-5-4-6-8-10-12-15-18-20(22)23/h4-5,8-11,14,17,19,21H,2-3,6-7,12-13,15-16,18H2,1H3,(H,22,23)/b5-4-,10-8-,11-9-,17-14+ INCHIAUX=JSFATNQSLKRBCI-USWFWKISSA-N PUBMED=N/A SUBMITUSER=N/A 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IONS TITLE=GNPS2LIB0000000000L PEPMASS=321.2435 CHARGE=1 MSLEVEL=2 FRAGMENTATION_METHOD=N/A COLLISION_ENERGY=20 SOURCE_INSTRUMENT=ESI(-)-QTOF Agilent 6546 FILENAME=CEMBIO_standard_individual_20eV.mgf SEQ=*..* IONMODE=Negative ORGANISM=CEMBIO_OXYLIPINS NAME=15-HETrE PI=N/A DATACOLLECTOR=N/A SMILES=CCCCCC(/C=C/C=C\C/C=C\CCCCCCC(=O)O)O INCHI=InChI=1S/C20H34O3/c1-2-3-13-16-19(21)17-14-11-9-7-5-4-6-8-10-12-15-18-20(22)23/h4-5,9,11,14,17,19,21H,2-3,6-8,10,12-13,15-16,18H2,1H3,(H,22,23)/b5-4-,11-9-,17-14+ INCHIAUX=IUKXMNDGTWTNTP-RHDCIPCHSA-N PUBMED=N/A SUBMITUSER=N/A LIBRARYQUALITY=1 SPECTRUMID=GNPS2LIB0000000000L USI=mzspec:GNPS:CEMBIO_OXYLIPINS:accession:GNPS2LIB0000000000L SCANS=21 113.09711620688786 96.2594304141942 123.11744499574685 7.729649972209029 149.13373335521456 24.87738890236536 157.12304303366798 11.638863167518403 177.09218058410968 10.051379322294407 177.16475951109283 37.88259724631566 195.1390690593707 36.35445056434697 203.1442453655059 30.32882316109047 205.1960226560873 22.717810886858132 207.1390471266713 20.81214186849095 219.13873193183272 18.615071098001565 221.15472132111796 865.1496465654369 222.15841620530006 14.309936894450708 223.02833626952432 5.638085304861518 223.17044680482158 21.18142756239209 231.21160078374788 14.90520577889123 239.20071783068101 5.994523938626121 259.2427274007379 72.8486034187651 277.25317765731904 6.026647693723114 285.2224307456395 18.874596470342823 303.2328358546091 1000.0000000000001 304.2355358985437 25.995669721635036 321.24324722125886 312.92025350257967 END IONS BEGIN IONS TITLE=GNPS2LIB0000000000M PEPMASS=317.2122 CHARGE=1 MSLEVEL=2 FRAGMENTATION_METHOD=N/A COLLISION_ENERGY=20 SOURCE_INSTRUMENT=ESI(-)-QTOF Agilent 6546 FILENAME=CEMBIO_standard_individual_20eV.mgf SEQ=*..* IONMODE=Negative ORGANISM=CEMBIO_OXYLIPINS NAME=15-oxo-ETE PI=N/A DATACOLLECTOR=N/A SMILES=CCCCCC(=O)/C=C/C=C\C/C=C\C/C=C\CCCC(=O)O INCHI=InChI=1S/C20H30O3/c1-2-3-13-16-19(21)17-14-11-9-7-5-4-6-8-10-12-15-18-20(22)23/h4-5,8-11,14,17H,2-3,6-7,12-13,15-16,18H2,1H3,(H,22,23)/b5-4-,10-8-,11-9-,17-14+ INCHIAUX=YGJTUEISKATQSM-USWFWKISSA-N PUBMED=N/A SUBMITUSER=N/A LIBRARYQUALITY=1 SPECTRUMID=GNPS2LIB0000000000M USI=mzspec:GNPS:CEMBIO_OXYLIPINS:accession:GNPS2LIB0000000000M SCANS=22 107.08654589473613 20.979344494640493 111.08153374733251 16.456343404053786 113.09719187810734 1000.0000000000001 114.1001882124216 12.671652214756891 117.07069121673554 8.548427885392343 119.0865247105704 11.070812919158113 121.10226794961582 54.677429666622615 133.10248406246845 18.742384395968863 137.09711252606522 6.801841944767445 139.11289919068952 513.5109530171321 140.115973820722 12.93666055541397 147.11781093456216 66.50723679298099 149.09733254605774 11.642303653640742 151.11277812014856 19.141296401204098 153.12860053328384 16.84820316331492 159.1181890838779 25.052735462962996 163.11249124979625 10.189617667592257 165.12840785232495 235.3327086969645 175.1493055647003 46.41104163825685 179.14424223509275 12.306440359700806 189.1281781526804 31.52763117626665 191.14409455972026 77.05242870258743 201.12896406421905 11.693125013803233 203.10767129632376 14.926381234546955 219.13919939973235 53.17093298973951 245.1906286594697 13.094137892699731 273.22237111394867 119.81595560600479 299.2018133542374 12.984276224736583 317.2123842460488 63.76890034785895 END IONS BEGIN IONS TITLE=GNPS2LIB0000000000N PEPMASS=343.2279 CHARGE=1 MSLEVEL=2 FRAGMENTATION_METHOD=N/A COLLISION_ENERGY=20 SOURCE_INSTRUMENT=ESI(-)-QTOF Agilent 6546 FILENAME=CEMBIO_standard_individual_20eV.mgf SEQ=*..* IONMODE=Negative ORGANISM=CEMBIO_OXYLIPINS NAME=16(17)-EpDPE PI=N/A DATACOLLECTOR=N/A SMILES=CC/C=C\CC1C(O1)C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O INCHI=InChI=1S/C22H32O3/c1-2-3-14-17-20-21(25-20)18-15-12-10-8-6-4-5-7-9-11-13-16-19-22(23)24/h3,5-8,11-15,20-21H,2,4,9-10,16-19H2,1H3,(H,23,24)/b7-5-,8-6-,13-11-,14-3-,15-12- INCHIAUX=BCTXZWCPBLWCRV-ZYADFMMDSA-N PUBMED=N/A SUBMITUSER=N/A LIBRARYQUALITY=1 SPECTRUMID=GNPS2LIB0000000000N USI=mzspec:GNPS:CEMBIO_OXYLIPINS:accession:GNPS2LIB0000000000N SCANS=23 105.07126423641922 47.989263380130666 106.04206902540001 102.47575427179233 107.08655242517267 118.55079236622255 109.06571809702804 117.79200181849443 111.0813143228794 291.09070466866507 117.07093933971557 46.131401596077296 119.05024646555611 183.8009463098231 119.08661225128084 108.27624310624068 121.06571415175038 1000.0 121.1023772008803 116.34225390438097 123.08165550424292 61.790668176409724 125.09697661723996 72.86319386357684 129.0714319858942 26.86840327820538 131.086213362695 31.76551856749595 133.10191131050982 87.39614510498757 135.08223035035036 43.56731252635293 135.11751649126708 98.42154533242382 137.09721877478918 81.46704155139477 145.06595767619604 31.0949027298364 147.08129389139512 499.97412669024266 147.11791014192178 164.0932488601744 149.09721908357707 28.8254725482628 151.1138658438474 25.287804599890784 153.09144033259813 30.88043684309533 159.11746648724917 74.05826596766904 161.0966155083188 31.669368630058546 161.13334462871174 76.25413350752275 163.0768899091424 46.5330601011579 173.0969360634147 69.19953449819572 173.1333723299108 160.32001032443577 175.14966840166258 37.92396256842428 179.1070228125607 27.28186583273377 187.14823437122203 36.05412660106011 189.1642681764662 118.78708723774886 199.14881770311956 28.623930353820363 201.0264674125528 42.05688353443308 201.16480541742945 165.39274750905878 215.14451637690732 25.075150233710133 217.1597457564306 30.656916594197202 227.1799862332852 45.02683746646062 229.15912252865192 53.35097536155747 233.1540357724663 228.04916696238632 245.15467056049584 46.37338379959561 247.17010022820725 38.08180466491108 273.1500656639713 27.389934862516803 274.1566691612366 46.88197386806085 281.2268894305397 99.54942590288519 299.2381755294673 36.76164042279996 325.2168226607069 44.19028440108006 343.22773056831625 97.9070086803658 END IONS BEGIN IONS TITLE=GNPS2LIB0000000000O PEPMASS=335.2228 CHARGE=1 MSLEVEL=2 FRAGMENTATION_METHOD=N/A COLLISION_ENERGY=20 SOURCE_INSTRUMENT=ESI(-)-QTOF Agilent 6546 FILENAME=CEMBIO_standard_individual_20eV.mgf SEQ=*..* IONMODE=Negative ORGANISM=CEMBIO_OXYLIPINS NAME=17,18-DiHETE PI=N/A DATACOLLECTOR=N/A SMILES=CCC(C(C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O)O)O INCHI=InChI=1S/C20H32O4/c1-2-18(21)19(22)16-14-12-10-8-6-4-3-5-7-9-11-13-15-17-20(23)24/h3,5-6,8-9,11-12,14,18-19,21-22H,2,4,7,10,13,15-17H2,1H3,(H,23,24)/b5-3-,8-6-,11-9-,14-12- INCHIAUX=XYDVGNAQQFWZEF-JPURVOHMSA-N PUBMED=N/A SUBMITUSER=N/A LIBRARYQUALITY=1 SPECTRUMID=GNPS2LIB0000000000O USI=mzspec:GNPS:CEMBIO_OXYLIPINS:accession:GNPS2LIB0000000000O SCANS=24 100.93355721635439 16.139849080334436 101.06071452709855 58.67300714667637 107.0860534021289 70.14860454160545 109.06642178355762 15.913315790735297 111.08267711551069 14.528451564867254 116.92881322002005 11.74599482331923 119.08675027590259 16.70800074064399 121.06563705053956 17.888191131155136 121.10251646256714 52.86485277377044 123.08164461927875 20.380000753363106 127.0765749136269 25.232799595140712 133.10240718648492 34.24741899756722 135.0821240097681 12.22655961450312 135.11766284926006 38.39812561791673 141.0918254913161 17.703713480845742 147.1174872426262 22.206013500853892 149.13345267858244 69.63319288492575 155.10827522854132 14.2297816176467 157.1237400357939 13.445007489603345 161.13558836982816 18.829355368225787 163.07609647700943 27.772581080704267 167.1076661664706 12.726021161676126 171.13849404262447 49.784713651086236 175.14931539279388 69.36233071955472 177.09216667056356 52.92406393411106 191.10721980963052 20.829748437872247 193.12305387174393 34.4999332246338 201.16416102146817 15.187670271068852 203.1802187321869 226.53953908853828 209.15486450073715 13.890309597992728 215.1804445004353 53.31968351900799 221.15391245562088 15.349968960461645 229.16009258603793 40.123810212179336 245.1547462983471 19.405655213101472 247.17019010708262 1000.0 248.174406781767 32.72580897255459 249.18541694919307 24.872637607397046 253.21703739430654 367.5243509948062 254.22163106782781 11.844687989043948 255.21127777315016 96.08493948879911 255.23183581040684 21.84568793792288 259.17012271815594 72.99615197779829 261.18419700170585 15.157187194099112 273.2218719485666 23.32858720691607 275.1644436606113 12.512544076633661 277.1810661872223 57.13112602835287 299.2016885110116 63.109435285864606 317.2119294258035 158.29608099533942 333.204070811666 14.258737483287813 335.2226993309319 429.7441451701353 END IONS BEGIN IONS TITLE=GNPS2LIB0000000000P PEPMASS=317.2122 CHARGE=1 MSLEVEL=2 FRAGMENTATION_METHOD=N/A COLLISION_ENERGY=20 SOURCE_INSTRUMENT=ESI(-)-QTOF Agilent 6546 FILENAME=CEMBIO_standard_individual_20eV.mgf SEQ=*..* IONMODE=Negative ORGANISM=CEMBIO_OXYLIPINS NAME=17(18)-EpETE PI=N/A DATACOLLECTOR=N/A SMILES=CCC1C(O1)C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O INCHI=InChI=1S/C20H30O3/c1-2-18-19(23-18)16-14-12-10-8-6-4-3-5-7-9-11-13-15-17-20(21)22/h3,5-6,8-9,11-12,14,18-19H,2,4,7,10,13,15-17H2,1H3,(H,21,22)/b5-3-,8-6-,11-9-,14-12- INCHIAUX=GPQVVJQEBXAKBJ-JPURVOHMSA-N PUBMED=N/A SUBMITUSER=N/A LIBRARYQUALITY=1 SPECTRUMID=GNPS2LIB0000000000P USI=mzspec:GNPS:CEMBIO_OXYLIPINS:accession:GNPS2LIB0000000000P SCANS=25 100.93326809138443 295.3618532463519 107.08662431465818 757.2932050532102 109.06504483581797 332.2969928521241 109.10244992797034 195.55994146223617 111.0815328297717 319.14724541110115 117.07250967962355 189.68057140313348 119.08689996555637 485.3098159181794 121.02945134103217 230.4837240493471 121.06605143339188 453.82077619419147 121.10163918669177 675.3656527601079 123.08125924295923 658.1657915679691 131.97199506100728 787.2891881640526 133.10221252272436 903.9032812231128 134.89560163942025 184.49561487430887 135.08269909069884 195.26609417535454 135.11752782613377 523.2695486219311 141.01733279019808 219.92334718548318 143.10843500449295 182.8760379675426 147.0817148147974 399.2383985967181 147.1171434956494 319.92328861127316 149.13443684926156 211.7664328644533 159.11705919265566 182.24553540863062 161.13314529762692 513.4361102455144 173.09699032969655 189.17610101942557 173.13333319943303 185.4166455148686 175.96137642657814 513.7250112657731 177.0926311303826 315.30243426606904 181.12215755115722 378.3063839901325 183.04356934775572 181.99747362923983 184.05236028344268 266.44549044967033 187.1483651621305 493.3622728980254 189.16508160741355 247.02469046133308 190.98671281335032 280.85448578221695 201.16559676882514 477.707404118574 207.1380314326173 191.48514518984683 211.04085932832115 234.1547162261756 212.04873231383783 306.04757891963646 215.1791220587041 849.8810683206983 217.12363564165025 354.5551601145556 221.15403321342768 218.3277043517514 229.16025131910027 218.20957969489868 234.9758527764749 257.1168804104673 255.2111865289779 1000.0 259.1719640947238 381.4822776568546 261.1852129247698 245.220230568917 272.9468657306633 197.37219497870632 273.22233340942233 353.9940842651189 299.2001172998301 713.3747830476344 317.08322105146357 831.5276856861032 317.21248340314935 699.2371164723435 END IONS BEGIN IONS TITLE=GNPS2LIB0000000000Q PEPMASS=343.2279 CHARGE=1 MSLEVEL=2 FRAGMENTATION_METHOD=N/A COLLISION_ENERGY=20 SOURCE_INSTRUMENT=ESI(-)-QTOF Agilent 6546 FILENAME=CEMBIO_standard_individual_20eV.mgf SEQ=*..* IONMODE=Negative ORGANISM=CEMBIO_OXYLIPINS NAME=17-HDoHE PI=N/A DATACOLLECTOR=N/A SMILES=CC/C=C\CC(/C=C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O)O INCHI=InChI=1S/C22H32O3/c1-2-3-15-18-21(23)19-16-13-11-9-7-5-4-6-8-10-12-14-17-20-22(24)25/h3,5-8,11-16,19,21,23H,2,4,9-10,17-18,20H2,1H3,(H,24,25)/b7-5-,8-6-,13-11-,14-12-,15-3-,19-16+ INCHIAUX=SWTYBBUBEPPYCX-VIIQGJSXSA-N PUBMED=N/A SUBMITUSER=N/A LIBRARYQUALITY=1 SPECTRUMID=GNPS2LIB0000000000Q USI=mzspec:GNPS:CEMBIO_OXYLIPINS:accession:GNPS2LIB0000000000Q SCANS=26 105.07052460536072 71.57928102335192 106.04243800616584 70.2043354902025 107.08631849888627 168.1313986786085 109.06628232344153 48.16311513662741 109.10261816663348 41.93518001435273 111.08179310714942 358.88244437103657 115.05546661593772 44.10231812756331 117.07061557237523 69.26788522398935 119.05024566515837 226.8436312661346 119.08642308505699 188.98089918967045 121.06592217345728 1000.0 121.10257660926557 274.4903412675993 122.02504419573786 32.683764817304656 123.08222242034697 28.07789673511749 131.08728998053874 29.62435429229733 133.10196272147712 245.30708847424143 134.0741309410664 40.61198008050345 135.08223948956237 33.41206419513826 135.11806820183457 113.89335279821798 137.09746573141786 66.47369082771127 143.08610305483757 38.722111592277365 145.06572032013665 30.602627132049395 145.10164516913093 61.484045280282714 147.08135195214004 127.87743697592518 147.1177020085172 505.39712220960126 149.13436403952934 49.32327264693795 159.11776102078696 81.33025887532573 161.1334713374057 114.93432943642483 163.07608237873347 50.49933418483839 163.1127635266232 34.17382633713661 167.10694179584468 43.28124786952951 173.13356439136524 555.1499813585139 175.1485783713238 105.40218096604305 187.1488866786543 63.827981075608314 189.16528285083083 69.29691190419288 193.12303489707898 27.506290194528113 199.1494372944228 98.03929585121743 201.0251653911293 93.96553303399325 201.16475102317148 501.754106543308 227.18064981858168 159.67965754205585 229.15953424006898 97.89436111984095 245.15459629544074 188.6182329878768 247.17069094903155 98.16150904942307 273.14982771794496 38.84894385964002 274.15698749628444 68.17900828966853 281.22758916863546 443.6887423074069 283.26439592567067 27.32564982330113 299.2391167751626 73.35076070396475 325.2171365607559 100.45604929817753 343.227761876533 166.40369428498127 END IONS BEGIN IONS TITLE=GNPS2LIB0000000000R PEPMASS=343.2279 CHARGE=1 MSLEVEL=2 FRAGMENTATION_METHOD=N/A COLLISION_ENERGY=20 SOURCE_INSTRUMENT=ESI(-)-QTOF Agilent 6546 FILENAME=CEMBIO_standard_individual_20eV.mgf SEQ=*..* IONMODE=Negative ORGANISM=CEMBIO_OXYLIPINS NAME=19(20)-EpDPE PI=N/A DATACOLLECTOR=N/A SMILES=CCC1C(O1)C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O INCHI=InChI=1S/C22H32O3/c1-2-20-21(25-20)18-16-14-12-10-8-6-4-3-5-7-9-11-13-15-17-19-22(23)24/h3-4,7-10,13-16,20-21H,2,5-6,11-12,17-19H2,1H3,(H,23,24)/b4-3-,9-7-,10-8-,15-13-,16-14- INCHIAUX=OSXOPUBJJDUAOJ-MBYQGORISA-N PUBMED=N/A SUBMITUSER=N/A LIBRARYQUALITY=1 SPECTRUMID=GNPS2LIB0000000000R USI=mzspec:GNPS:CEMBIO_OXYLIPINS:accession:GNPS2LIB0000000000R SCANS=27 105.07077010226672 204.4401180874849 107.0863629071537 788.6019787226929 109.06568925444569 187.86879312379878 111.0818155769592 123.05376194059738 113.06104289578684 58.299278054817755 115.05559098053942 87.1444002939224 117.07072299726845 182.21080403604302 119.08652990387385 478.3801928507539 121.06572522080933 173.62174411694673 121.10186139554467 480.9570285182504 123.0812341360362 484.13276177207644 131.08634294568517 77.05397719713473 133.1022364512395 1000.0 135.08151911517376 71.26636938976989 135.11783512590162 316.2669467617025 137.09645008522378 73.34345425679184 143.08633059999093 66.54686980834322 145.10217072638724 163.6898040722034 147.08146232833576 127.93293854852278 147.11778222112846 324.4694148092404 149.0967414477444 123.72448561874826 153.09220467730776 75.84605029839128 159.11771212652428 309.48107823398215 161.09650140966602 64.25868172939353 161.13329659847312 164.09311158612343 163.0756562251005 122.41209448363334 171.11780484395098 77.53745156727909 173.09727882319243 96.37574171398785 173.13313850159614 251.32937115753435 175.1492667907978 103.43536299893634 185.13326218576591 81.08303546513493 187.14908365596077 307.80306653576156 199.14919343645806 95.28396294449111 201.0242648529665 108.95992544141235 201.16353063327782 68.61539643704377 207.1383174714521 90.97328021625265 213.16463248082468 85.0743897255428 215.17925632397504 64.59558294267626 227.1798778551366 176.13772120082444 241.19609983311938 374.5995239112147 245.1905663094472 68.64712630816959 253.19633483672385 67.12404985218596 255.17492287113373 58.69222784034583 271.1725727851712 61.47779582763921 281.22693098179496 479.62202862400244 285.1857308101361 188.71786247188192 287.19848449781415 64.70211531337054 299.2376332869397 381.5970670529231 325.2156367783027 172.21916526857945 343.22723354545013 303.74744233615087 END IONS BEGIN IONS TITLE=GNPS2LIB0000000000S PEPMASS=365.197 CHARGE=1 MSLEVEL=2 FRAGMENTATION_METHOD=N/A COLLISION_ENERGY=20 SOURCE_INSTRUMENT=ESI(-)-QTOF Agilent 6546 FILENAME=CEMBIO_standard_individual_20eV.mgf SEQ=*..* IONMODE=Negative ORGANISM=CEMBIO_OXYLIPINS NAME=20-COOH-LTB4 PI=N/A DATACOLLECTOR=N/A SMILES=C(CCC(=O)O)C/C=C\C[C@H](/C=C/C=C/C=C\[C@H](CCCC(=O)O)O)O INCHI=InChI=1S/C20H30O6/c21-17(11-6-2-1-3-9-15-19(23)24)12-7-4-5-8-13-18(22)14-10-16-20(25)26/h2,4-8,12-13,17-18,21-22H,1,3,9-11,14-16H2,(H,23,24)(H,25,26)/b5-4+,6-2-,12-7+,13-8-/t17-,18-/m1/s1 INCHIAUX=SXWGPVJGNOLNHT-VFLUTPEKSA-N PUBMED=N/A SUBMITUSER=N/A LIBRARYQUALITY=1 SPECTRUMID=GNPS2LIB0000000000S USI=mzspec:GNPS:CEMBIO_OXYLIPINS:accession:GNPS2LIB0000000000S SCANS=28 107.05022028771486 43.97530299200813 107.08662240316995 30.580297598966148 108.05803387534387 106.9090014298006 109.06586069274375 203.5035999068967 111.04510853806501 166.8528755916561 113.02420535523034 62.085428577779915 115.04010811277595 231.13306280325352 121.06552752862623 34.732202634539306 123.0815327602508 314.01993370686733 125.09710648110268 59.354763249753326 129.05570942415545 512.0352914540366 133.0659246930556 24.236936572352878 133.10224592524048 46.78588848078362 134.073679909076 129.80206303003402 135.0815401161396 100.6547329500855 137.06058863834767 34.60716921990871 137.09702209994256 24.800109406645827 141.05583075208213 47.10766483523668 141.0922402024415 384.6641836630617 147.08138189848742 228.5184321733903 151.07638700306464 25.14017507585191 151.1127165185905 99.1085532300903 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365.19687487587765 1000.0 END IONS BEGIN IONS TITLE=GNPS2LIB0000000000T PEPMASS=319.2279 CHARGE=1 MSLEVEL=2 FRAGMENTATION_METHOD=N/A COLLISION_ENERGY=20 SOURCE_INSTRUMENT=ESI(-)-QTOF Agilent 6546 FILENAME=CEMBIO_standard_individual_20eV.mgf SEQ=*..* IONMODE=Negative ORGANISM=CEMBIO_OXYLIPINS NAME=20-HETE PI=N/A DATACOLLECTOR=N/A SMILES=C(CC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O)CCO INCHI=InChI=1S/C20H32O3/c21-19-17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-18-20(22)23/h1,3-4,6-7,9-10,12,21H,2,5,8,11,13-19H2,(H,22,23)/b3-1-,6-4-,9-7-,12-10- INCHIAUX=NNDIXBJHNLFJJP-DTLRTWKJSA-N PUBMED=N/A SUBMITUSER=N/A LIBRARYQUALITY=1 SPECTRUMID=GNPS2LIB0000000000T USI=mzspec:GNPS:CEMBIO_OXYLIPINS:accession:GNPS2LIB0000000000T SCANS=29 107.08656390283336 62.8065518957486 109.06590885216146 22.336015403172198 109.10189016624106 15.926032884744927 111.08212712854804 13.167594745224939 119.08573107135734 20.683671913894138 121.10259800532563 63.300567966194926 123.08139681704377 12.572406324258504 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SEQ=*..* IONMODE=Negative ORGANISM=CEMBIO_OXYLIPINS NAME=5(6)-EpETrE PI=N/A DATACOLLECTOR=N/A SMILES=CCCCC/C=C\C/C=C\C/C=C\CC1C(O1)CCCC(=O)O INCHI=InChI=1S/C20H32O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-15-18-19(23-18)16-14-17-20(21)22/h6-7,9-10,12-13,18-19H,2-5,8,11,14-17H2,1H3,(H,21,22)/b7-6-,10-9-,13-12- INCHIAUX=VBQNSZQZRAGRIX-QNEBEIHSSA-N PUBMED=N/A SUBMITUSER=N/A LIBRARYQUALITY=1 SPECTRUMID=GNPS2LIB0000000000W USI=mzspec:GNPS:CEMBIO_OXYLIPINS:accession:GNPS2LIB0000000000W SCANS=32 100.9338256840848 193.28838471609427 109.06569981724131 87.20867535185504 111.04419467159767 62.802926274473 112.98461729010813 61.41965895973146 114.97025519794917 68.32670195414126 115.03977224406819 1000.0 117.02145718770473 64.9361194756953 119.03704468027993 77.90264148210737 122.02460838492009 92.98669540853555 122.98345120907197 55.41069051855847 123.08218137359044 77.70686240507747 125.0609591016971 410.204875159604 125.09688019024878 79.89448476291876 127.04085449192682 54.91247499027929 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229.19613619895568 78.81007492440526 247.20566504286725 63.715192639244854 257.22642670240396 136.94339231867318 259.8399185477617 59.7708160240691 262.58840303249616 54.7724247341553 275.23654559224275 111.71600723485881 301.21683204669665 102.58421981322661 319.0882846154206 73.9265177910587 319.2279048134609 498.8555639581645 END IONS BEGIN IONS TITLE=GNPS2LIB0000000000X PEPMASS=317.2122 CHARGE=1 MSLEVEL=2 FRAGMENTATION_METHOD=N/A COLLISION_ENERGY=20 SOURCE_INSTRUMENT=ESI(-)-QTOF Agilent 6546 FILENAME=CEMBIO_standard_individual_20eV.mgf SEQ=*..* IONMODE=Negative ORGANISM=CEMBIO_OXYLIPINS NAME=5-HEPE PI=N/A DATACOLLECTOR=N/A SMILES=CC/C=C\C/C=C\C/C=C\C/C=C\C=C\C(CCCC(=O)O)O INCHI=InChI=1S/C20H30O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(21)17-15-18-20(22)23/h3-4,6-7,9-10,12-14,16,19,21H,2,5,8,11,15,17-18H2,1H3,(H,22,23)/b4-3-,7-6-,10-9-,13-12-,16-14+ INCHIAUX=FTAGQROYQYQRHF-FCWZHQICSA-N PUBMED=N/A SUBMITUSER=N/A LIBRARYQUALITY=1 SPECTRUMID=GNPS2LIB0000000000X 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163.1488615460227 158.85042011103508 167.07119978536664 22.71687415703585 171.13914814686842 51.75174637926992 175.14878540725428 79.88730182954107 177.09183443250694 128.48396208982697 177.1645135467905 19.254142629604043 179.07121106472405 75.29655741947064 181.08673272802122 268.6390633215525 187.14927355028337 33.59254157464197 195.1025894380188 1000.0 203.1800696848821 391.4923238862628 205.08652528917662 55.41498104741683 205.1611185940397 19.00336992115692 245.19102004999408 102.97977368159641 253.21736619636337 356.46884675225795 255.21128559094328 32.35431954603179 255.23190851951063 19.145177908954725 257.1902035881969 33.45282404754265 273.2224108652025 116.63954794915925 299.2018573285286 43.74785477879258 317.2116174536931 270.5717789857051 335.22277449682537 392.4842482120375 END IONS BEGIN IONS TITLE=GNPS2LIB00000000012 PEPMASS=343.2279 CHARGE=1 MSLEVEL=2 FRAGMENTATION_METHOD=N/A COLLISION_ENERGY=20 SOURCE_INSTRUMENT=ESI(-)-QTOF Agilent 6546 FILENAME=CEMBIO_standard_individual_20eV.mgf SEQ=*..* IONMODE=Negative ORGANISM=CEMBIO_OXYLIPINS NAME=7(8)-EpDPE PI=N/A DATACOLLECTOR=N/A SMILES=CC/C=C\C/C=C\C/C=C\C/C=C\CC1C(O1)C/C=C\CCC(=O)O INCHI=InChI=1S/C22H32O3/c1-2-3-4-5-6-7-8-9-10-11-12-14-17-20-21(25-20)18-15-13-16-19-22(23)24/h3-4,6-7,9-10,12-15,20-21H,2,5,8,11,16-19H2,1H3,(H,23,24)/b4-3-,7-6-,10-9-,14-12-,15-13- INCHIAUX=OHYKIJBTVXMLKX-MPQBXPHNSA-N PUBMED=N/A SUBMITUSER=N/A LIBRARYQUALITY=1 SPECTRUMID=GNPS2LIB00000000012 USI=mzspec:GNPS:CEMBIO_OXYLIPINS:accession:GNPS2LIB00000000012 SCANS=38 106.04214688418541 12.581355465125537 107.05010676381089 63.02929594109339 107.08637988410773 44.092643739468414 109.0658766048909 1000.0 109.08743075424493 6.495365116030164 110.06904823258839 14.228104380543073 111.08117010856536 11.609527824022269 113.06072746565023 255.70767227200892 119.05064279183229 14.996669823849453 119.08634765187871 19.586382106534742 121.06579249503497 117.32578401011344 121.10226088427046 75.30546648927903 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SMILES=CCCCC/C=C\C=C\C(CCCCCCCC(=O)O)O INCHI=InChI=1S/C18H32O3/c1-2-3-4-5-6-8-11-14-17(19)15-12-9-7-10-13-16-18(20)21/h6,8,11,14,17,19H,2-5,7,9-10,12-13,15-16H2,1H3,(H,20,21)/b8-6-,14-11+ INCHIAUX=NPDSHTNEKLQQIJ-ZJHFMPGASA-N PUBMED=N/A SUBMITUSER=N/A LIBRARYQUALITY=1 SPECTRUMID=GNPS2LIB0000000001D USI=mzspec:GNPS:CEMBIO_OXYLIPINS:accession:GNPS2LIB0000000001D SCANS=49 123.11781613675838 43.74781811312815 125.09715588920517 19.52032562121009 141.1284857651009 17.780006324483043 171.1027306318879 599.6942728159611 213.1859833751128 5.754305191575645 233.2274846895759 12.853266912313254 251.23801762162248 10.306264436319987 259.2067795448143 13.23929052212254 277.2176861780046 1000.0 277.2386203352561 52.63793709470704 277.2543017812428 42.76695834210073 278.22080961232035 16.34508991765021 295.22807780979736 426.6762629837213 295.26567103637166 17.28671756938998 END IONS BEGIN IONS TITLE=GNPS2LIB0000000001E PEPMASS=293.2122 CHARGE=1 MSLEVEL=2 FRAGMENTATION_METHOD=N/A COLLISION_ENERGY=20 SOURCE_INSTRUMENT=ESI(-)-QTOF Agilent 6546 FILENAME=CEMBIO_standard_individual_20eV.mgf SEQ=*..* IONMODE=Negative ORGANISM=CEMBIO_OXYLIPINS NAME=9-HOTrE PI=N/A DATACOLLECTOR=N/A SMILES=CC/C=C\C/C=C\C=C\C(CCCCCCCC(=O)O)O INCHI=InChI=1S/C18H30O3/c1-2-3-4-5-6-8-11-14-17(19)15-12-9-7-10-13-16-18(20)21/h3-4,6,8,11,14,17,19H,2,5,7,9-10,12-13,15-16H2,1H3,(H,20,21)/b4-3-,8-6-,14-11+ INCHIAUX=RIGGEAZDTKMXSI-CUHSZNQNSA-N PUBMED=N/A SUBMITUSER=N/A LIBRARYQUALITY=1 SPECTRUMID=GNPS2LIB0000000001E USI=mzspec:GNPS:CEMBIO_OXYLIPINS:accession:GNPS2LIB0000000001E SCANS=50 121.10224003553161 613.5993198471874 125.09718281142648 23.767184674543298 127.11299562484837 13.367371883386738 141.12799527297514 5.741398759222941 171.10266218817938 730.5918582210116 177.16463846356504 30.97398565039022 185.11812349854205 63.93302118450191 192.11567431633648 5.2802939839758265 193.15973820394703 9.145760872322164 197.11835772008885 15.64652722152176 203.18039305090764 16.59851479302367 220.14685874669243 57.18584591960586 221.15449888516264 110.26429513192006 231.21166109504733 99.09846979253685 236.10511185985948 71.70619050333363 257.191066998862 20.748099456712307 273.1860200523115 6.333305730761997 275.2017823614612 1000.0 275.2383563354452 41.36976288652578 293.1790450383792 9.106166693985145 293.2120741234548 166.048546343365 END IONS BEGIN IONS TITLE=GNPS2LIB0000000001F PEPMASS=293.2122 CHARGE=1 MSLEVEL=2 FRAGMENTATION_METHOD=N/A COLLISION_ENERGY=20 SOURCE_INSTRUMENT=ESI(-)-QTOF Agilent 6546 FILENAME=CEMBIO_standard_individual_20eV.mgf SEQ=*..* IONMODE=Negative ORGANISM=CEMBIO_OXYLIPINS NAME=9-oxo-ODE PI=N/A DATACOLLECTOR=N/A SMILES=CCCCC/C=C\C=C\C(=O)CCCCCCCC(=O)O INCHI=InChI=1S/C18H30O3/c1-2-3-4-5-6-8-11-14-17(19)15-12-9-7-10-13-16-18(20)21/h6,8,11,14H,2-5,7,9-10,12-13,15-16H2,1H3,(H,20,21)/b8-6-,14-11+ INCHIAUX=LUZSWWYKKLTDHU-ZJHFMPGASA-N PUBMED=N/A SUBMITUSER=N/A LIBRARYQUALITY=1 SPECTRUMID=GNPS2LIB0000000001F USI=mzspec:GNPS:CEMBIO_OXYLIPINS:accession:GNPS2LIB0000000001F SCANS=51 123.11789660002404 9.716724060793151 125.09728905874456 86.60217086444703 141.12844910450013 27.20379083006719 149.09712741283693 33.38512811083877 185.11835419915764 201.83202183304806 197.11828467571664 46.35770777408368 220.14693596098363 20.769386456440692 221.15456838370002 40.19475099475356 236.10534904373938 25.904382799618574 249.22212494254168 32.68962930582947 275.2017407741288 13.045040684430212 293.2126458635943 1000.0000000000001 293.2340547582611 46.94720862334645 293.25031769448964 41.893276527236715 END IONS BEGIN IONS TITLE=GNPS2LIB0000000001G PEPMASS=337.2385 CHARGE=1 MSLEVEL=2 FRAGMENTATION_METHOD=N/A COLLISION_ENERGY=20 SOURCE_INSTRUMENT=ESI(-)-QTOF Agilent 6546 FILENAME=CEMBIO_standard_individual_20eV.mgf SEQ=*..* IONMODE=Negative ORGANISM=CEMBIO_OXYLIPINS NAME=LTB3 PI=N/A DATACOLLECTOR=N/A SMILES=CCCCCCCC[C@@H](/C=C/C=C\C=C\[C@@H](CCCC(=O)O)O)O INCHI=InChI=1S/C20H34O4/c1-2-3-4-5-6-9-13-18(21)14-10-7-8-11-15-19(22)16-12-17-20(23)24/h7-8,10-11,14-15,18-19,21-22H,2-6,9,12-13,16-17H2,1H3,(H,23,24)/b8-7-,14-10+,15-11+/t18-,19-/m0/s1 INCHIAUX=NGTXCORNXNELNU-BOIFFFMUSA-N PUBMED=N/A SUBMITUSER=N/A LIBRARYQUALITY=1 SPECTRUMID=GNPS2LIB0000000001G USI=mzspec:GNPS:CEMBIO_OXYLIPINS:accession:GNPS2LIB0000000001G SCANS=52 105.07081437702475 16.371438852372847 107.05010927192076 10.695884737019265 109.06581939487741 53.051305014821445 111.04510486383705 31.965637351103023 113.02430376027665 44.09402972619395 115.04000570846262 22.098287780815223 123.08148157477405 461.62843861811353 129.0557642492809 89.3116151069045 133.10237531207582 41.2961365959936 135.08168812112424 122.48157937945825 141.0557845184594 19.33403801997911 141.12831675277616 45.0709256587118 151.11277146376548 334.1745987705058 153.05560447938717 13.103702780776084 155.07142605485416 10.497331476799195 155.14397743037998 76.58603178524064 157.12346495609964 10.355266007551384 159.08167502937093 20.019352547913233 177.09184391611012 86.99045214465667 177.1648401576686 20.4576540755179 181.08713913425893 30.43784785552694 195.10261023467498 1000.0 196.10640401895932 11.734614705986669 205.1961394083158 340.4699798705137 207.17504887296846 18.640743006987094 221.19135706675584 13.228769137339071 247.2067983596262 211.56291558923323 255.23315641427138 88.02544178032447 257.2275856887559 43.735504358682725 259.2061977938976 60.02444598491211 265.21712315668594 28.76907633403872 275.2379072866022 206.9070115149475 277.16552802449354 8.343156200570823 277.21697004374175 13.532562118585664 293.2485801604232 19.103541679169677 301.2174033797113 51.83378349007157 319.2278684308848 690.1419346708342 320.23061376413375 14.852473946139877 337.2052303683898 23.241790872912674 337.2384988464151 475.05548921107277 337.31006311638424 7.778513099822015 END IONS BEGIN IONS TITLE=GNPS2LIB0000000001H PEPMASS=335.2228 CHARGE=1 MSLEVEL=2 FRAGMENTATION_METHOD=N/A COLLISION_ENERGY=20 SOURCE_INSTRUMENT=ESI(-)-QTOF Agilent 6546 FILENAME=CEMBIO_standard_individual_20eV.mgf SEQ=*..* IONMODE=Negative ORGANISM=CEMBIO_OXYLIPINS NAME=LTB4 PI=N/A DATACOLLECTOR=N/A SMILES=CCCCC/C=C\C[C@H](/C=C/C=C/C=C\[C@H](CCCC(=O)O)O)O INCHI=InChI=1S/C20H32O4/c1-2-3-4-5-6-9-13-18(21)14-10-7-8-11-15-19(22)16-12-17-20(23)24/h6-11,14-15,18-19,21-22H,2-5,12-13,16-17H2,1H3,(H,23,24)/b8-7+,9-6-,14-10+,15-11-/t18-,19-/m1/s1 INCHIAUX=VNYSSYRCGWBHLG-AMOLWHMGSA-N PUBMED=N/A SUBMITUSER=N/A LIBRARYQUALITY=1 SPECTRUMID=GNPS2LIB0000000001H USI=mzspec:GNPS:CEMBIO_OXYLIPINS:accession:GNPS2LIB0000000001H SCANS=53 105.07073007055948 16.786164771389895 107.05024930016299 39.11501982393718 108.05830926701388 10.801540888769125 109.06580666700623 156.19752546895316 111.04515290879033 39.620499350565176 111.0809597079056 8.072007426990469 113.02425636530502 66.57910669259923 115.03993120279313 29.08790945642502 121.06552149084607 14.711208690275127 123.08152405825136 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254.0833026696469 215.42714924304042 272.0868862625591 531.876720908402 272.0929117528636 599.3806625374133 272.1005797662208 130.9775517972261 288.06521720234485 289.76986143764947 305.02372691696377 162.01851845299086 318.8655631567008 111.83418821651334 326.1903354513869 148.8460467192352 327.91304324331367 139.96743574980425 333.984223706962 142.08502191085725 339.8652692751297 131.55358062684917 339.901947788866 191.33713603434967 351.20108308446635 161.95539425641846 361.9439245670869 144.20259543443348 361.9660073019049 127.86834074479222 377.04695750728024 196.93273273303635 379.1619009987014 224.9969543680933 396.91078798504304 128.3913174468455 415.9577116568383 132.61707484874205 418.9339563666201 166.11519666694133 423.92865534876523 278.41834900970207 446.91053562837095 111.8083066640448 456.9642130503918 132.71450979480275 460.8826179783958 147.82064185239125 477.96170636032974 250.32028421179805 488.87118277825425 175.97977093815066 508.25455769678007 174.58332975271492 539.1139294691451 169.05830072443072 541.9440470804049 238.5502691024308 563.8645421049052 294.6355933017329 588.2715553992837 178.09959393259575 606.2840509851671 791.8831508565935 606.2927169371994 233.57807913385767 624.2833404900412 175.4298637730552 624.2952461052472 1000.0 624.3143707276572 215.1020627900617 END IONS BEGIN IONS TITLE=GNPS2LIB0000000001J PEPMASS=495.2535 CHARGE=1 MSLEVEL=2 FRAGMENTATION_METHOD=N/A COLLISION_ENERGY=20 SOURCE_INSTRUMENT=ESI(-)-QTOF Agilent 6546 FILENAME=CEMBIO_standard_individual_20eV.mgf SEQ=*..* IONMODE=Negative ORGANISM=CEMBIO_OXYLIPINS NAME=LTD4 PI=N/A DATACOLLECTOR=N/A SMILES=CCCCC/C=C\C/C=C\C=C\C=C\[C@H]([C@H](CCCC(=O)O)O)SC[C@@H](C(=O)NCC(=O)O)N INCHI=InChI=1S/C25H40N2O6S/c1-2-3-4-5-6-7-8-9-10-11-12-13-16-22(21(28)15-14-17-23(29)30)34-19-20(26)25(33)27-18-24(31)32/h6-7,9-13,16,20-22,28H,2-5,8,14-15,17-19,26H2,1H3,(H,27,33)(H,29,30)(H,31,32)/b7-6-,10-9-,12-11+,16-13+/t20-,21-,22+/m0/s1 INCHIAUX=YEESKJGWJFYOOK-IJHYULJSSA-N PUBMED=N/A SUBMITUSER=N/A LIBRARYQUALITY=1 SPECTRUMID=GNPS2LIB0000000001J USI=mzspec:GNPS:CEMBIO_OXYLIPINS:accession:GNPS2LIB0000000001J SCANS=55 115.00962030008219 11.866614531861858 115.03999416563792 42.468622756991024 143.04632226401347 657.8421929669008 160.01979856748432 33.49578311355982 177.03414555539416 1000.0 177.05089155892296 38.79921677921505 178.0370235773272 5.613882806960072 235.15232125709377 30.245341068171744 289.19956546327114 33.02736559828879 317.21203415973633 33.00331786964117 333.18928786107784 85.07607711916218 351.2000388718714 48.52620575013097 379.20598693662936 39.25934972839982 477.24280964992124 171.5892915653579 478.24607314015657 11.213343878681286 495.2535754901352 140.22009934675316 END IONS BEGIN IONS TITLE=GNPS2LIB0000000001K PEPMASS=438.232 CHARGE=1 MSLEVEL=2 FRAGMENTATION_METHOD=N/A COLLISION_ENERGY=20 SOURCE_INSTRUMENT=ESI(-)-QTOF Agilent 6546 FILENAME=CEMBIO_standard_individual_20eV.mgf SEQ=*..* IONMODE=Negative ORGANISM=CEMBIO_OXYLIPINS NAME=LTE4 PI=N/A DATACOLLECTOR=N/A SMILES=CCCCC/C=C\C/C=C\C=C\C=C\[C@H]([C@H](CCCC(=O)O)O)SC[C@@H](C(=O)O)N INCHI=InChI=1S/C23H37NO5S/c1-2-3-4-5-6-7-8-9-10-11-12-13-16-21(30-18-19(24)23(28)29)20(25)15-14-17-22(26)27/h6-7,9-13,16,19-21,25H,2-5,8,14-15,17-18,24H2,1H3,(H,26,27)(H,28,29)/b7-6-,10-9-,12-11+,16-13+/t19-,20-,21+/m0/s1 INCHIAUX=OTZRAYGBFWZKMX-FRFVZSDQSA-N PUBMED=N/A SUBMITUSER=N/A LIBRARYQUALITY=1 SPECTRUMID=GNPS2LIB0000000001K USI=mzspec:GNPS:CEMBIO_OXYLIPINS:accession:GNPS2LIB0000000001K SCANS=56 111.0272559586219 14.92019260953814 113.02423339645097 5.229780986471627 113.04296367715459 58.24754802552535 115.04004453435289 413.7606302546532 120.01240189405222 266.9166323222307 129.0378973348176 43.433090733695366 129.05551106661457 8.95317102055901 160.01985237895522 154.64866642343654 161.0278202512692 73.69655135787534 163.14914348847918 97.88614392070747 173.02763871525127 29.92773845799606 177.16481634655938 13.613595222237299 203.18045369000598 16.85089516210877 232.9758039052196 5.776129196856729 235.15252621867663 814.7212680753888 235.99858920280343 31.557704017771563 236.15580538076176 14.088094069319137 237.00157656587598 13.322553409083882 255.21162743406262 97.99214182330215 273.22232045830276 24.74979184179904 279.1785080383263 31.491691768720873 289.1995439790589 409.3369820280083 290.20318888233635 10.08471352193491 291.1781402011464 12.108776937344473 299.2014789505828 79.61990257941568 307.21034660230913 57.40638519143098 317.2121696642041 231.63389910411038 322.18436325232676 52.75738229558574 333.1893977221172 1000.0 333.2246563101113 38.953037909345966 334.1929348721395 25.827108290643775 351.2001021012505 552.8102357453009 352.2027582539588 13.137408329456322 420.2211874384477 71.78700223454055 438.23236152176827 27.504855205919295 END IONS BEGIN IONS TITLE=GNPS2LIB0000000001L PEPMASS=351.2177 CHARGE=1 MSLEVEL=2 FRAGMENTATION_METHOD=N/A COLLISION_ENERGY=20 SOURCE_INSTRUMENT=ESI(-)-QTOF Agilent 6546 FILENAME=CEMBIO_standard_individual_20eV.mgf SEQ=*..* IONMODE=Negative ORGANISM=CEMBIO_OXYLIPINS NAME=LXA4 PI=N/A DATACOLLECTOR=N/A SMILES=CCCCC[C@@H](/C=C/C=C\C=C\C=C\[C@H]([C@H](CCCC(=O)O)O)O)O INCHI=InChI=1S/C20H32O5/c1-2-3-8-12-17(21)13-9-6-4-5-7-10-14-18(22)19(23)15-11-16-20(24)25/h4-7,9-10,13-14,17-19,21-23H,2-3,8,11-12,15-16H2,1H3,(H,24,25)/b6-4-,7-5+,13-9+,14-10+/t17-,18+,19-/m0/s1 INCHIAUX=IXAQOQZEOGMIQS-SSQFXEBMSA-N PUBMED=N/A SUBMITUSER=N/A LIBRARYQUALITY=1 SPECTRUMID=GNPS2LIB0000000001L USI=mzspec:GNPS:CEMBIO_OXYLIPINS:accession:GNPS2LIB0000000001L SCANS=57 101.06064277965514 5.242802240474194 106.04233535498312 21.162307258635707 107.08650492208926 12.894325612145487 109.0656737277776 16.14814316829896 113.06082443093324 10.878459812645351 113.09720621181937 38.94212993115313 115.04013524128757 999.9999999999999 117.07108603207158 38.11638142165921 119.05018583787778 15.341747874485412 121.0658101530378 13.06480712125406 133.0659309087979 22.750038415979418 135.08166731140923 265.5047740970803 139.11290444795836 35.95422324755291 143.0717040507293 13.11810611256747 144.04298719326934 61.97586781103883 145.05048839446414 17.344265605198384 149.13354403536755 12.427816332269558 160.0891761587458 14.6515057961487 161.13358074544846 20.53612255392823 163.1493358230635 21.159835237002 165.12840977234046 21.840247531200898 169.08675922823863 12.987087905937328 173.13384891282024 5.245797393615722 175.11283265856454 5.17054118956225 175.1490487777181 15.890424312549015 179.1437668031434 11.01162354748588 189.12856789645627 33.24267840618292 189.16490428144243 36.69496474210242 191.14405362894027 14.699766400315875 199.14928587520498 49.19101289962794 208.92094062876356 5.3704495085129125 217.15998956766913 660.5492145161859 217.19227976936756 23.913472288934297 218.16314711200644 14.654072161661224 233.11790232630537 11.275139781586923 235.17039506379993 176.97698976116624 269.24861331369044 25.556527120833433 271.2068458910027 40.83817052420766 289.2174802982668 22.148308916713475 307.22877894251496 10.171406503138407 315.1968172599421 10.55080776168999 351.2177847703075 19.265049735548807 END IONS BEGIN IONS TITLE=GNPS2LIB0000000001M PEPMASS=333.2072 CHARGE=1 MSLEVEL=2 FRAGMENTATION_METHOD=N/A COLLISION_ENERGY=20 SOURCE_INSTRUMENT=ESI(-)-QTOF Agilent 6546 FILENAME=CEMBIO_standard_individual_20eV.mgf SEQ=*..* IONMODE=Negative ORGANISM=CEMBIO_OXYLIPINS NAME=PGB2 PI=N/A DATACOLLECTOR=N/A SMILES=CCCCC[C@@H](/C=C/C1=C(C(=O)CC1)C/C=C\CCCC(=O)O)O INCHI=InChI=1S/C20H30O4/c1-2-3-6-9-17(21)14-12-16-13-15-19(22)18(16)10-7-4-5-8-11-20(23)24/h4,7,12,14,17,21H,2-3,5-6,8-11,13,15H2,1H3,(H,23,24)/b7-4-,14-12+/t17-/m0/s1 INCHIAUX=PRFXRIUZNKLRHM-HKVRTXJWSA-N PUBMED=N/A SUBMITUSER=N/A LIBRARYQUALITY=1 SPECTRUMID=GNPS2LIB0000000001M USI=mzspec:GNPS:CEMBIO_OXYLIPINS:accession:GNPS2LIB0000000001M SCANS=58 106.04216537341881 11.898568253843314 107.05001167239082 37.61220903533006 109.0658526066103 419.25676324453656 111.08144837453149 59.1768449426007 113.09715280366353 969.9714953546887 121.06588666599639 103.78911238957502 123.08149336149845 29.315758857054526 125.06094528477455 22.380757858929623 125.09720856645603 16.899650395492174 127.07614375962339 12.982964055767917 135.0815604040157 44.149378874698336 137.09715242990438 121.5137124224349 157.1019546867821 14.932298948365172 158.93917515582302 14.417533367837 161.0970466518666 30.488222215083347 163.11289083297336 287.81710914104593 173.09726803390137 21.312624558163773 175.11289104938217 997.974470288477 176.11642153720769 13.70130540393356 177.1288667943834 16.50517731356935 183.1026222138188 52.899771397391454 185.1181056879245 39.49385080379875 187.11256335499928 20.070588071601353 189.09216258256347 19.520513600459374 189.12846616085102 99.43786719912639 191.14418438717107 261.1524454415683 195.10240271112895 26.672778280067206 197.11818664205117 16.133945901867488 204.11565898578365 218.80690764072907 206.1312237608792 286.56838613635335 207.10281605413874 293.44226013410906 207.13781561566717 26.051508134717935 209.11840407866777 65.24476197803224 217.12332226439878 129.0013902623314 217.159359851328 23.896584110159797 218.1313534924406 16.118965137702116 219.10259170219362 62.07866786007 221.11812821375972 65.31493893064075 233.11834632442066 12.582338821498993 235.13409416916915 953.643855284692 235.16918177131308 60.23388158682418 236.1373970356852 17.215324435638607 239.1648297535059 23.527651304829003 271.20667812815867 199.47158651360186 289.2171850788939 57.23540236406238 291.1965433258768 29.89829535499699 297.18594514678614 46.57315093805959 315.1967780280676 475.5656772111489 333.2073306619906 1000.0 333.2468940784888 40.81655892765823 END IONS BEGIN IONS TITLE=GNPS2LIB0000000001N PEPMASS=353.2334 CHARGE=1 MSLEVEL=2 FRAGMENTATION_METHOD=N/A COLLISION_ENERGY=20 SOURCE_INSTRUMENT=ESI(-)-QTOF Agilent 6546 FILENAME=CEMBIO_standard_individual_20eV.mgf SEQ=*..* IONMODE=Negative ORGANISM=CEMBIO_OXYLIPINS NAME=PGD1 PI=N/A DATACOLLECTOR=N/A SMILES=CCCCC[C@@H](/C=C/[C@@H]1[C@H]([C@H](CC1=O)O)CCCCCCC(=O)O)O INCHI=InChI=1S/C20H34O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h12-13,15-18,21-22H,2-11,14H2,1H3,(H,24,25)/b13-12+/t15-,16+,17+,18-/m0/s1 INCHIAUX=CIMMACURCPXICP-PNQRDDRVSA-N PUBMED=N/A SUBMITUSER=N/A LIBRARYQUALITY=1 SPECTRUMID=GNPS2LIB0000000001N USI=mzspec:GNPS:CEMBIO_OXYLIPINS:accession:GNPS2LIB0000000001N SCANS=59 101.0607313327645 11.477820548135982 123.08162941959725 155.40496199249822 191.14434963581016 160.56454900079402 193.12346608220864 15.560380382916525 205.15988609908155 135.36910453712986 217.12348165234286 60.07436182764135 219.17535528162264 25.202458334610004 235.1342266979291 722.8934021218337 235.16803603972983 26.4196997179244 236.13749605431522 11.2206659596485 245.11835890945815 14.65754583138587 245.19135519328427 11.808692184446414 255.23316070344524 8.442156451798619 273.2226302552422 554.331111194183 273.25890366757534 20.171225632838446 274.22641805755643 13.976262747733855 299.20197807179574 60.82396109120175 317.2126787881778 1000.0000000000001 317.2517560873525 43.16269225216914 318.2157007899843 24.905581498033982 335.2231835025406 25.819945860782322 353.2011084489768 16.133373372641476 353.3429813203309 12.385134753222992 END IONS BEGIN IONS TITLE=GNPS2LIB0000000001O PEPMASS=351.2177 CHARGE=1 MSLEVEL=2 FRAGMENTATION_METHOD=N/A COLLISION_ENERGY=20 SOURCE_INSTRUMENT=ESI(-)-QTOF Agilent 6546 FILENAME=CEMBIO_standard_individual_20eV.mgf SEQ=*..* IONMODE=Negative ORGANISM=CEMBIO_OXYLIPINS NAME=PGD2 PI=N/A DATACOLLECTOR=N/A SMILES=CCCCC[C@@H](/C=C/[C@@H]1[C@H]([C@H](CC1=O)O)C/C=C\CCCC(=O)O)O INCHI=InChI=1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,15-18,21-22H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,18-/m0/s1 INCHIAUX=BHMBVRSPMRCCGG-OUTUXVNYSA-N PUBMED=N/A SUBMITUSER=N/A LIBRARYQUALITY=1 SPECTRUMID=GNPS2LIB0000000001O USI=mzspec:GNPS:CEMBIO_OXYLIPINS:accession:GNPS2LIB0000000001O SCANS=60 107.05026674966062 14.960767117777825 109.06561404894073 14.412647540404514 121.06586303607318 50.64908946837284 135.08157336082454 25.912691746327646 158.0736987041038 36.208828279106065 160.08910313227184 28.16503621574016 161.0970888458908 25.028239606740897 173.0967967648489 11.285459823890827 187.1130443176003 21.02416518544209 189.12860441291045 933.7990560304305 189.15911749502948 32.214243579955216 190.13203015999926 16.059062274454455 203.14401598211916 78.00575690575799 208.9204838843038 5.003392026857131 215.10727938588153 19.844361281110732 217.15975906459778 32.99280973850967 231.1024381992146 21.98377115762718 233.11828749883503 192.18228535691088 243.17524799633884 17.171018115095563 269.2484083589279 34.38796322388328 271.20690673214204 1000.0 271.24311055574435 40.96401075874826 272.20969374716987 24.9911813950165 289.21687519620883 17.33662097951896 297.18584559021076 25.912634042795748 315.19655989333546 199.48773313230427 333.2066185712177 21.99210555471258 END IONS BEGIN IONS TITLE=GNPS2LIB0000000001P PEPMASS=353.2334 CHARGE=1 MSLEVEL=2 FRAGMENTATION_METHOD=N/A COLLISION_ENERGY=20 SOURCE_INSTRUMENT=ESI(-)-QTOF Agilent 6546 FILENAME=CEMBIO_standard_individual_20eV.mgf SEQ=*..* IONMODE=Negative ORGANISM=CEMBIO_OXYLIPINS NAME=PGE1 PI=N/A DATACOLLECTOR=N/A SMILES=CCCCC[C@@H](/C=C/[C@H]1[C@@H](CC(=O)[C@@H]1CCCCCCC(=O)O)O)O INCHI=InChI=1S/C20H34O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h12-13,15-17,19,21,23H,2-11,14H2,1H3,(H,24,25)/b13-12+/t15-,16+,17+,19+/m0/s1 INCHIAUX=GMVPRGQOIOIIMI-DWKJAMRDSA-N PUBMED=N/A SUBMITUSER=N/A LIBRARYQUALITY=1 SPECTRUMID=GNPS2LIB0000000001P USI=mzspec:GNPS:CEMBIO_OXYLIPINS:accession:GNPS2LIB0000000001P SCANS=61 109.06586148736935 30.49846578037786 113.09715571260922 93.51700450479832 123.08161878519898 17.31515750375357 125.06085511867109 6.438699324518895 137.09730186289713 49.3714111307663 163.11264237915995 14.869678278601542 177.1285609897112 22.989415868546207 185.11815239137846 17.659733656431662 191.14432316005923 108.20477928511885 209.11844562957967 73.1387931885377 217.12313803069674 19.123568787698417 219.1756409275297 60.253551059843424 221.1184095280808 101.81263769443318 223.13394515700452 75.20946386300504 235.13412067232701 483.6041046758657 235.16771098512186 18.27601160364062 255.2118549056004 12.770041021239505 255.23341254051155 5.76996313532742 273.22255172571874 414.271435561694 273.2564793996393 14.44920194265013 274.22628557755195 12.236870349158622 275.2018949088859 14.371173837664726 299.20211062943844 22.76097651226265 317.2126885619181 999.9999999999999 317.25163267295 45.28400762545319 318.2160651552827 28.278166412737324 335.2232586868957 93.41791096921925 353.1998142767375 12.106778761498969 353.342375716302 15.921829169140358 END IONS BEGIN IONS TITLE=GNPS2LIB0000000001Q PEPMASS=351.2177 CHARGE=1 MSLEVEL=2 FRAGMENTATION_METHOD=N/A COLLISION_ENERGY=20 SOURCE_INSTRUMENT=ESI(-)-QTOF Agilent 6546 FILENAME=CEMBIO_standard_individual_20eV.mgf SEQ=*..* IONMODE=Negative ORGANISM=CEMBIO_OXYLIPINS NAME=PGE2 PI=N/A DATACOLLECTOR=N/A SMILES=CCCCC[C@@H](/C=C/[C@H]1[C@@H](CC(=O)[C@@H]1C/C=C\CCCC(=O)O)O)O INCHI=InChI=1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,15-17,19,21,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,19+/m0/s1 INCHIAUX=XEYBRNLFEZDVAW-ARSRFYASSA-N PUBMED=N/A SUBMITUSER=N/A LIBRARYQUALITY=1 SPECTRUMID=GNPS2LIB0000000001Q USI=mzspec:GNPS:CEMBIO_OXYLIPINS:accession:GNPS2LIB0000000001Q SCANS=62 107.05009761737399 22.0316956728289 109.06581048887055 67.86681523626251 113.09709607357067 96.31078444856192 121.06583799274672 26.81256736247849 135.0815379278671 42.26040481459189 137.09710406778535 10.653800199258692 159.08131064504713 23.774064106750934 161.0970310645208 20.985629497738238 163.1126294320354 44.09063427989202 163.1491361847643 10.012079056426675 171.11759163393856 11.455309242063556 173.09681070440877 20.050840263871876 174.10478259817322 30.414377358371674 175.11274418045056 139.0234759093695 187.11256772973968 20.805042319526777 188.12057279974215 14.789788314010655 189.12844247753867 482.99373100871253 191.14388298149302 35.022063352099394 203.14387332746495 13.525545362105342 204.1154986588359 18.694851465563698 206.131017538145 36.28813206004665 207.1025752084258 35.40919854677867 209.1179627888756 9.016515476657856 217.12307097513536 12.554226024642544 217.15961622098314 64.44343062068822 221.1177676951826 15.68475337798686 229.15965855320152 10.03216772387288 231.1024949456889 10.160648081494696 233.11807980543628 27.14981211450649 235.1337683475057 112.0144952957908 243.17525811691323 17.870725950054094 253.19577747799715 14.463182390126216 269.19108913791456 10.712155899994219 269.24812543232576 14.170383988729952 271.20672028122146 1000.0 271.24303714815807 43.101476899224636 272.21018341331495 20.103800031451804 289.2169567084777 16.731225157731625 297.1859554779748 12.940470815437356 315.1963602152535 212.0375790164955 333.20685454092165 161.3608241194796 END IONS BEGIN IONS TITLE=GNPS2LIB0000000001R PEPMASS=349.2021 CHARGE=1 MSLEVEL=2 FRAGMENTATION_METHOD=N/A COLLISION_ENERGY=20 SOURCE_INSTRUMENT=ESI(-)-QTOF Agilent 6546 FILENAME=CEMBIO_standard_individual_20eV.mgf SEQ=*..* IONMODE=Negative ORGANISM=CEMBIO_OXYLIPINS NAME=PGE3 PI=N/A DATACOLLECTOR=N/A SMILES=CC/C=C\C[C@@H](/C=C/[C@H]1[C@@H](CC(=O)[C@@H]1C/C=C\CCCC(=O)O)O)O INCHI=InChI=1S/C20H30O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h3-4,6-7,12-13,15-17,19,21,23H,2,5,8-11,14H2,1H3,(H,24,25)/b6-3-,7-4-,13-12+/t15-,16+,17+,19+/m0/s1 INCHIAUX=CBOMORHDRONZRN-QLOYDKTKSA-N PUBMED=N/A SUBMITUSER=N/A LIBRARYQUALITY=1 SPECTRUMID=GNPS2LIB0000000001R USI=mzspec:GNPS:CEMBIO_OXYLIPINS:accession:GNPS2LIB0000000001R SCANS=63 107.05002714812655 22.61551235668167 109.06567621724854 90.38451682598404 111.0814093934472 48.40925244904119 121.06570668024527 35.83512523068624 123.08141600261926 21.053320863365254 135.0814039655466 71.44515867103941 137.097111356 15.853058768486193 159.08137643273366 31.061482488865416 161.0968870781539 62.9976995143721 161.1333835268495 21.721121589775976 163.11237943880977 31.377015449070004 171.11736196371547 20.360966916628918 172.08897121466163 12.487946466739377 173.0969527288395 35.640205098785906 174.10472810506008 29.856219574450897 175.11253245997705 120.7413604548398 185.09691115942027 21.98687278967508 186.10469439246197 43.06079828303779 187.11251518702562 60.71090479312516 189.12833875305202 786.7366806593883 189.15906422271465 27.770980092964134 191.14374328856704 24.777474424353098 199.11245576989393 14.586390661629633 200.12025836257533 17.522985888284328 201.1280310361249 27.756466255804646 202.09972204420987 62.13806556803254 204.1152767524061 32.194635656263685 207.10247415248836 22.279147814792545 209.11805398672794 48.52632999740677 214.13618234188746 14.340511572868039 215.14373848833597 71.71021609992759 217.12305967859697 26.506722655856986 219.1023277314589 16.324933764057867 221.11779958102463 34.1362460871315 223.13357660622594 78.87596283607448 227.1438996856242 14.158458494544066 228.15171912796768 12.634125494850624 233.11808078587796 61.74121747896722 235.13371492357751 76.88355582028414 241.15917083574652 19.330512155340465 251.18013985529728 15.27710889559685 262.1207520583121 145.84632800879336 267.1748587315376 15.78969865480458 269.1908760145154 1000.0 269.2271269554969 43.003145173975334 270.1940570562724 21.281313206967422 287.20116878385096 16.89391824980291 295.1699289326578 14.369847384843458 313.1802032015041 91.21468026544446 331.19105091577484 47.14710953740884 END IONS BEGIN IONS TITLE=GNPS2LIB0000000001S PEPMASS=353.2334 CHARGE=1 MSLEVEL=2 FRAGMENTATION_METHOD=N/A COLLISION_ENERGY=20 SOURCE_INSTRUMENT=ESI(-)-QTOF Agilent 6546 FILENAME=CEMBIO_standard_individual_20eV.mgf SEQ=*..* IONMODE=Negative ORGANISM=CEMBIO_OXYLIPINS NAME=PGF2a PI=N/A DATACOLLECTOR=N/A SMILES=CCCCC[C@@H](/C=C/[C@H]1[C@@H](C[C@@H]([C@@H]1C/C=C\CCCC(=O)O)O)O)O INCHI=InChI=1S/C20H34O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,18-,19+/m0/s1 INCHIAUX=PXGPLTODNUVGFL-YNNPMVKQSA-N PUBMED=N/A SUBMITUSER=N/A LIBRARYQUALITY=1 SPECTRUMID=GNPS2LIB0000000001S USI=mzspec:GNPS:CEMBIO_OXYLIPINS:accession:GNPS2LIB0000000001S SCANS=64 111.08141649046614 71.54132895374075 113.09710065396854 35.1662073222096 119.0865333740143 12.101071247094906 123.08157475761713 10.05526758636739 125.06054426505438 15.123499038180553 137.0971325337122 20.706644093449373 147.11782856203675 15.462243602704515 163.11239565663624 11.844970313245994 165.128358494546 140.76355576340526 167.1441570412883 10.190129547655895 171.1025842221308 152.98571324695564 173.13345836846457 52.01798907622803 181.1232325077813 72.8521209246363 183.13945321028794 10.359316938843477 185.1545582660863 12.782775356722944 191.1076721158189 36.57615718017895 191.14408503526482 57.471236093618806 193.12334314056181 250.7211287817674 193.1594257102409 108.84401427097566 201.16471082832078 13.059478247463273 207.13912666944873 10.596475916099367 209.11820989452923 193.82278170154152 211.1701776647585 37.557548284759605 217.1233154009649 62.008875714783535 217.1962782976935 12.210497287749762 219.13867821343771 18.690644070040555 219.17527684476528 39.472572325529704 221.11817699060018 41.579944714031704 229.19621401714863 31.926942494567093 235.13385408579654 98.43186001835663 235.20673750451607 10.485111868639319 237.185334022925 13.839894093963851 247.2066933237711 249.06512641790553 255.21167030236901 58.176528552926904 263.201397879356 78.36555132653397 265.2173347615278 37.339366098646984 273.18594769074247 37.98009941802078 273.2221747610045 108.69602638319532 281.211968474405 50.45596496977604 289.21690831860275 14.677794987117432 291.1964590207833 412.3166995247581 291.23257858164794 26.48851087935524 299.2014411180195 86.69189845683586 309.2070436807916 933.149304012117 309.24535226326594 39.16768962342844 310.2098932959149 21.73649273700699 317.211993634908 127.097875954188 335.22250503754185 146.36980684381226 353.23330559260273 1000.0 353.2739391072839 41.682310059309195 END IONS BEGIN IONS TITLE=GNPS2LIB0000000001T PEPMASS=333.2072 CHARGE=1 MSLEVEL=2 FRAGMENTATION_METHOD=N/A COLLISION_ENERGY=20 SOURCE_INSTRUMENT=ESI(-)-QTOF Agilent 6546 FILENAME=CEMBIO_standard_individual_20eV.mgf SEQ=*..* IONMODE=Negative ORGANISM=CEMBIO_OXYLIPINS NAME=PGJ2 PI=N/A DATACOLLECTOR=N/A SMILES=CCCCC[C@@H](/C=C/[C@@H]1[C@H](C=CC1=O)C/C=C\CCCC(=O)O)O INCHI=InChI=1S/C20H30O4/c1-2-3-6-10-17(21)13-14-18-16(12-15-19(18)22)9-7-4-5-8-11-20(23)24/h4,7,12-18,21H,2-3,5-6,8-11H2,1H3,(H,23,24)/b7-4-,14-13+/t16-,17-,18+/m0/s1 INCHIAUX=UQOQENZZLBSFKO-POPPZSFYSA-N PUBMED=N/A SUBMITUSER=N/A LIBRARYQUALITY=1 SPECTRUMID=GNPS2LIB0000000001T USI=mzspec:GNPS:CEMBIO_OXYLIPINS:accession:GNPS2LIB0000000001T SCANS=65 106.0422674669554 16.548008459494383 107.05015365534635 24.026452302284586 109.06572946500673 20.115266344315256 113.09722193082538 9.680723212542743 114.94918592729492 6.580380003926558 116.92827456132919 16.85624593833208 121.06585200304264 88.9773171782962 123.08118164000058 13.838579299740573 135.08150410068558 36.823686758966296 145.06611552234804 12.561418904985478 147.08123911676276 14.586146657080969 157.1233389692433 7.542598519467683 158.07339735833327 61.69761383189069 158.93923821856492 26.28223445965525 159.08170122163278 11.595769204636401 160.08892772452703 46.90395715547132 161.0969137765846 45.78384373876095 171.11765942985107 14.601395334859848 173.09696955199075 20.956050653041117 174.104806796366 15.42856525051394 175.1127927138132 12.57201329788776 187.11253094454247 36.86058186872927 189.1284126580418 1000.0 190.13198075770418 14.757376020537041 191.1440527148852 11.36372981469056 203.14395692570844 124.07675342510764 215.10775283234432 22.403316041958412 215.14405991457306 9.611083750942054 217.08663559906427 10.115135136923277 217.15955949073305 34.64725626758755 229.15940804374563 13.955444013991688 231.10223504103553 24.132558846701148 233.1182518032604 81.39311176803187 235.13377126562708 16.645940095759837 243.174769920073 23.326098001440084 271.2064642229633 867.9539957891719 271.24004952361264 31.051792742722153 272.2092600031487 17.527489760619734 289.08706602516867 13.658645366565205 297.1857480044176 25.733117121144787 315.19599130566377 87.37333468827576 333.20694408863574 9.596503538585306 END IONS BEGIN IONS TITLE=GNPS2LIB0000000001U PEPMASS=349.2021 CHARGE=1 MSLEVEL=2 FRAGMENTATION_METHOD=N/A COLLISION_ENERGY=20 SOURCE_INSTRUMENT=ESI(-)-QTOF Agilent 6546 FILENAME=CEMBIO_standard_individual_20eV.mgf SEQ=*..* IONMODE=Negative ORGANISM=CEMBIO_OXYLIPINS NAME=RvE1 PI=N/A DATACOLLECTOR=N/A SMILES=CC[C@H](/C=C/C=C\C[C@H](/C=C/C=C/C=C\[C@H](CCCC(=O)O)O)O)O INCHI=InChI=1S/C20H30O5/c1-2-17(21)11-8-5-9-14-18(22)12-6-3-4-7-13-19(23)15-10-16-20(24)25/h3-9,11-13,17-19,21-23H,2,10,14-16H2,1H3,(H,24,25)/b4-3+,9-5-,11-8+,12-6+,13-7-/t17-,18+,19-/m1/s1 INCHIAUX=AOPOCGPBAIARAV-OTBJXLELSA-N PUBMED=N/A SUBMITUSER=N/A LIBRARYQUALITY=1 SPECTRUMID=GNPS2LIB0000000001U USI=mzspec:GNPS:CEMBIO_OXYLIPINS:accession:GNPS2LIB0000000001U SCANS=66 105.07084387447637 11.463942927796086 107.05031851023365 14.371099940866001 107.08654714903979 1000.0 108.05789451565545 23.31432118566424 109.06585296117153 328.02091726651855 111.0448796766964 29.109449063214782 113.02433613005674 91.8108221608649 115.04011628161912 64.35619849227025 119.08665857147119 18.43717398922018 121.0657345466359 17.740934334824743 123.08150194494257 102.89832785085103 129.05575911591697 417.92952722245775 133.06577173815583 25.165404748475627 133.10205345016385 54.56810517789289 134.07368510186083 19.009994457426643 135.08146924386395 81.67356893773879 137.09726512346919 14.693859103349975 141.05565393893042 12.283110698436941 143.0864477757974 11.21378639122006 147.0809792854867 24.276944484607135 147.11795734946796 12.330525337263166 149.09724906511732 24.154087504661952 151.11288381453065 79.43351896939858 153.0557242534535 133.09478777076862 155.07121328156364 54.17068273151351 159.1178718714162 168.9251600594292 161.09719153305994 436.40557949447594 175.11276661476782 10.14825066567055 177.09195696979071 29.594786797807615 179.07134352428815 254.26197309296523 181.0868834747862 74.96095030166565 185.15499244232413 7.5860198041256925 187.0763826041886 14.645922415868796 195.1026637835929 402.73202311344147 199.1491470618312 83.5975626188527 201.12873028713693 14.14242656696105 205.08709751305048 202.849318152596 206.09451711332568 21.964312542833234 217.15948140301882 25.281102204010026 219.1385135000846 13.94810743663105 223.09753595058805 10.224893145016058 229.15986138860427 36.70747369168503 241.15941316786396 14.474981886403242 267.23298281458096 24.528367706271222 269.1909515675447 38.09117110947589 273.149208301765 27.5391427721517 291.1599072864498 31.30051365732519 313.18081608114267 32.20623480023789 331.19122366330095 66.51585985190579 349.2018590954291 100.40823608190291 END IONS BEGIN IONS TITLE=GNPS2LIB0000000001V PEPMASS=369.2283 CHARGE=1 MSLEVEL=2 FRAGMENTATION_METHOD=N/A COLLISION_ENERGY=20 SOURCE_INSTRUMENT=ESI(-)-QTOF Agilent 6546 FILENAME=CEMBIO_standard_individual_20eV.mgf SEQ=*..* IONMODE=Negative ORGANISM=CEMBIO_OXYLIPINS NAME=TXB2 PI=N/A DATACOLLECTOR=N/A SMILES=CCCCC[C@@H](/C=C/[C@@H]1[C@H]([C@H](CC(O1)O)O)C/C=C\CCCC(=O)O)O INCHI=InChI=1S/C20H34O6/c1-2-3-6-9-15(21)12-13-18-16(17(22)14-20(25)26-18)10-7-4-5-8-11-19(23)24/h4,7,12-13,15-18,20-22,25H,2-3,5-6,8-11,14H2,1H3,(H,23,24)/b7-4-,13-12+/t15-,16-,17-,18+,20?/m0/s1 INCHIAUX=XNRNNGPBEPRNAR-JQBLCGNGSA-N PUBMED=N/A SUBMITUSER=N/A LIBRARYQUALITY=1 SPECTRUMID=GNPS2LIB0000000001V USI=mzspec:GNPS:CEMBIO_OXYLIPINS:accession:GNPS2LIB0000000001V SCANS=67 125.09716370853998 49.962003054622535 141.09209889374762 10.634454899014488 151.07636018404074 10.18625826942417 151.1127824018962 36.14279994540216 163.1128397006867 10.73119222172809 167.10756291176529 16.066840514849172 169.0871488919796 1000.0 169.11625821857584 36.29884759231617 170.09053451023382 12.750817957888726 177.0921539456724 50.59744625174262 191.1077884338263 14.527191981984586 195.1027973459028 389.18749194465346 279.1964425195938 11.847806108437345 289.1809120485317 64.95119586704678 END IONS BEGIN IONS TITLE=GNPS2LIB0000000001W PEPMASS=335.222809 CHARGE=1 MSLEVEL=2 FRAGMENTATION_METHOD=N/A COLLISION_ENERGY=20 SOURCE_INSTRUMENT=ESI(-)-QTOF Agilent 6546 FILENAME=CEMBIO_standard_individual_20eV.mgf SEQ=*..* IONMODE=Negative ORGANISM=CEMBIO_OXYLIPINS NAME=11,12-DiHETE PI=N/A DATACOLLECTOR=N/A SMILES=CC/C=C\C/C=C\CC(C(C/C=C\C/C=C\CCCC(=O)O)O)O INCHI=InChI=1S/C20H32O4/c1-2-3-4-5-9-12-15-18(21)19(22)16-13-10-7-6-8-11-14-17-20(23)24/h3-4,6,8-10,12-13,18-19,21-22H,2,5,7,11,14-17H2,1H3,(H,23,24)/b4-3-,8-6-,12-9-,13-10- INCHIAUX=DNPZYIPMAWRQQE-BVILWSOJSA-N PUBMED=N/A SUBMITUSER=N/A LIBRARYQUALITY=1 SPECTRUMID=GNPS2LIB0000000001W USI=mzspec:GNPS:CEMBIO_OXYLIPINS:accession:GNPS2LIB0000000001W SCANS=68 109.10218454760805 13.199114481463656 125.06110139264077 10.355146060462472 135.11853024690973 10.917335040360756 141.01632773615654 12.77509467625283 149.0973076614166 75.12192360361837 151.11302703065704 11.664965137587776 163.1122665796264 48.59380861991441 167.10760923514601 1000.0 167.11564036202046 107.84394383845644 168.11149976285188 14.874688368971139 171.13858968459326 32.159874165298966 179.10716073460992 28.472943374850004 181.12257948734847 16.119226971188443 189.09197717429439 17.82632760869383 195.1012424130256 14.064636790428482 197.1177681492462 82.91612633554493 197.128175249974 10.36998649909187 207.1027510203756 38.79105779533731 225.11266950962724 45.672433547417725 253.1407952601431 11.046473402675698 255.21159084547628 12.634091235976603 299.20172045548634 15.046290531816155 317.2122285694446 36.61707063109124 335.2229626637134 82.73438423663664 335.2335965415159 17.064754553909143 END IONS BEGIN IONS TITLE=GNPS2LIB0000000001X PEPMASS=337.238495 CHARGE=1 MSLEVEL=2 FRAGMENTATION_METHOD=N/A COLLISION_ENERGY=20 SOURCE_INSTRUMENT=ESI(-)-QTOF Agilent 6546 FILENAME=CEMBIO_standard_individual_20eV.mgf SEQ=*..* IONMODE=Negative ORGANISM=CEMBIO_OXYLIPINS NAME=11,12-DiHETrE PI=N/A DATACOLLECTOR=N/A SMILES=CCCCC/C=C\CC(C(C/C=C\C/C=C\CCCC(=O)O)O)O INCHI=InChI=1S/C20H34O4/c1-2-3-4-5-9-12-15-18(21)19(22)16-13-10-7-6-8-11-14-17-20(23)24/h6,8-10,12-13,18-19,21-22H,2-5,7,11,14-17H2,1H3,(H,23,24)/b8-6-,12-9-,13-10- INCHIAUX=LRPPQRCHCPFBPE-KROJNAHFSA-N PUBMED=N/A SUBMITUSER=N/A LIBRARYQUALITY=1 SPECTRUMID=GNPS2LIB0000000001X USI=mzspec:GNPS:CEMBIO_OXYLIPINS:accession:GNPS2LIB0000000001X SCANS=69 125.06051986888797 14.506926562402628 149.09718082301052 50.279582030354085 151.112664897615 43.49719705543287 153.12877390987435 13.677083219566912 163.112740224387 46.48761529949486 167.1076671640318 999.9999999999999 167.1159938129058 90.25900472500433 169.12289496005118 187.94439458352218 179.1081828573994 42.47903252362846 181.12346726024373 25.687157593666512 197.11864354565384 85.61752405477198 197.12782127774616 10.154517045827392 207.10138546300428 15.295857014722008 207.1051512340574 11.071730131656391 208.11139735236713 18.190047509316148 225.11341971610383 29.9723877998466 255.2323715174328 40.623652298124526 257.2278004977766 13.049481199882926 275.2383283163766 14.117040912684015 301.21849899184156 21.71691075548582 319.22744007204267 43.738811120330716 319.2365501373407 13.267673244423134 337.20380414132535 21.186158854512026 337.2385760276722 191.83619278252672 337.2501443774129 24.413348442431772 END IONS BEGIN IONS TITLE=GNPS2LIB0000000001Y PEPMASS=361.238495 CHARGE=1 MSLEVEL=2 FRAGMENTATION_METHOD=N/A COLLISION_ENERGY=20 SOURCE_INSTRUMENT=ESI(-)-QTOF Agilent 6546 FILENAME=CEMBIO_standard_individual_20eV.mgf SEQ=*..* IONMODE=Negative ORGANISM=CEMBIO_OXYLIPINS NAME=16,17-DiHDPA PI=N/A DATACOLLECTOR=N/A SMILES=CC/C=C\CC(C(C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O)O)O INCHI=InChI=1S/C22H34O4/c1-2-3-14-17-20(23)21(24)18-15-12-10-8-6-4-5-7-9-11-13-16-19-22(25)26/h3,5-8,11-15,20-21,23-24H,2,4,9-10,16-19H2,1H3,(H,25,26)/b7-5-,8-6-,13-11-,14-3-,15-12- INCHIAUX=YXQCSWUATWXVGK-ZYADFMMDSA-N PUBMED=N/A SUBMITUSER=N/A LIBRARYQUALITY=1 SPECTRUMID=GNPS2LIB0000000001Y USI=mzspec:GNPS:CEMBIO_OXYLIPINS:accession:GNPS2LIB0000000001Y SCANS=70 107.08614399030918 61.82674659001637 109.06605141880803 69.07361693984505 110.0368076155002 22.27494345567246 111.0810356987355 21.03921747101732 121.06581190404698 30.02587765956623 121.1022989155769 51.34044084592235 125.0604255931253 31.220402719745753 125.09749539735355 18.20789439468369 127.0762599795621 266.9592189948045 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