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language=en_US getValue popupMenu = null getValue script = null Jmol applet jmolApplet0_object__1515030934759505__ ready call loadScript javascripts\jsmol\core\corescript.z.js call loadScript javascripts\jsmol\J\script\FileLoadThread.js starting QueueThread0_2 script 1 started starting HoverWatcher_3 starting HoverWatcher_4 The Resolver thinks Mol Marvin 02251316263D starting HoverWatcher_5 Time for openFile( Marvin 02251316263D 54 53 0 0 0 0 999 V2000 0.4680 -3.8991 -1.3360 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8667 -3.8991 -1.1791 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3204 3.3281 0.7314 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3459 2.8131 -0.2075 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1847 4.4223 1.2584 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6303 1.5368 0.3043 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6110 0.9559 -0.7052 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9110 -0.3295 -0.1982 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9257 -0.9212 -1.2342 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2107 -2.2093 -0.7568 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3228 -2.8467 -1.8562 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3177 2.6827 1.0327 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8175 -2.8467 -1.4816 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4101 -2.2422 -0.1875 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3536 -1.0599 -0.4864 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9543 -0.4455 0.7941 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8250 0.7777 0.4411 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5473 1.3549 1.6728 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4223 2.5695 1.2914 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1923 3.1133 2.5069 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9434 -4.7255 -1.0501 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2683 -4.7231 -0.7904 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8591 2.5978 -1.1487 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5896 3.5733 -0.4262 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1087 1.7693 1.2377 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3747 0.7653 0.5232 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8515 1.7128 -0.9219 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1309 0.7307 -1.6410 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3697 -0.1036 0.7251 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6694 -1.0817 0.0369 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1676 -0.1669 -1.4662 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4711 -1.1383 -2.1570 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6027 -1.9562 0.1177 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9570 -2.9434 -0.4383 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7680 -2.0566 -2.3609 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9621 -3.2818 -2.6288 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4609 1.8877 0.6811 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6214 -3.2703 -2.0894 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3979 -2.0365 -2.0778 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6023 -1.8843 0.4590 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9657 -3.0108 0.3591 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7986 -0.2853 -1.0251 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1672 -1.4019 -1.1343 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1543 -0.1336 1.4731 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5569 -1.1995 1.3097 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1901 1.5513 -0.0017 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5727 0.4874 -0.3035 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8047 1.6533 2.4191 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1741 0.5745 2.1144 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7898 3.3610 0.8789 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1396 2.2804 0.5173 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7960 3.9708 2.2089 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8520 2.3423 2.9100 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4946 3.4258 3.2861 H 0 0 0 0 0 0 0 0 0 0 0 0 11 1 1 0 0 0 0 1 2 2 0 0 0 0 13 2 1 0 0 0 0 3 4 1 0 0 0 0 3 5 2 0 0 0 0 3 12 1 0 0 0 0 4 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 14 13 1 0 0 0 0 15 14 1 0 0 0 0 16 15 1 0 0 0 0 17 16 1 0 0 0 0 18 17 1 0 0 0 0 19 18 1 0 0 0 0 20 19 1 0 0 0 0 1 21 1 0 0 0 0 2 22 1 0 0 0 0 4 23 1 0 0 0 0 4 24 1 0 0 0 0 6 25 1 0 0 0 0 6 26 1 0 0 0 0 7 27 1 0 0 0 0 7 28 1 0 0 0 0 8 29 1 0 0 0 0 8 30 1 0 0 0 0 9 31 1 0 0 0 0 9 32 1 0 0 0 0 10 33 1 0 0 0 0 10 34 1 0 0 0 0 11 35 1 0 0 0 0 11 36 1 0 0 0 0 12 37 1 0 0 0 0 13 38 1 0 0 0 0 13 39 1 0 0 0 0 14 40 1 0 0 0 0 14 41 1 0 0 0 0 15 42 1 0 0 0 0 15 43 1 0 0 0 0 16 44 1 0 0 0 0 16 45 1 0 0 0 0 17 46 1 0 0 0 0 17 47 1 0 0 0 0 18 48 1 0 0 0 0 18 49 1 0 0 0 0 19 50 1 0 0 0 0 19 51 1 0 0 0 0 20 52 1 0 0 0 0 20 53 1 0 0 0 0 20 54 1 0 0 0 0 M END): 20 ms reading 54 atoms ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false 1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them. Default Van der Waals type for model set to Babel 54 atoms created ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation Script completed Jmol script terminated
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| Oleic acid is a fatty acid that occurs naturally in various animal and vegetable fats and oils. It is an odorless, colorless oil, although commercial samples may be yellowish due to the presence of impurities. In chemical terms, oleic acid is classified as a monounsaturated omega-9 fatty acid, abbreviated with a lipid number of 18:1 cis-9, and a main product of Δ9-desaturase. It has the formula CH3−(CH2)7−CH=CH−(CH2)7−COOH. The name derives from the Latin word oleum, which means oil. It is the most common fatty acid in nature. The salts and esters of oleic acid are called oleates. It is a common component of oils, and thus occurs in many types of food, as well as in soap. |
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Read full article at Wikipedia
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InChI=1S/C18H34O2/c1- 2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H,19,20)/b10-9- |
| ZQPPMHVWECSIRJ-KTKRTIGZSA-N |
| CCCCCCCC\C=C/CCCCCCCC(O)=O |
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Neolitsea daibuensis
(IPNI:466954-1)
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Found in
root
(BTO:0001188).
Cold MeOH extract of dried roots
See:
PubMed
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Mus musculus
(NCBI:txid10090)
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Source: BioModels - MODEL1507180067
See:
PubMed
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Daphnia galeata
(NCBI:txid27404)
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See:
Is the fatty acid composition of Daphnia galeata determined by the fatty acid composition of the ingested diet?Weers P.M.M., Siewertsen K., and Gulati R.D.Freshwater Biology (1997), 38, 731-738
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Centella asiatica
(NCBI:txid48106)
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See:
MetaboLights Study
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Escherichia coli
(NCBI:txid562)
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See:
PubMed
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Escherichia coli
(NCBI:txid562)
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See:
PubMed
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solvent
A liquid that can dissolve other substances (solutes) without any change in their chemical composition.
antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
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Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
(via octadec-9-enoic acid )
EC 3.1.1.1 (carboxylesterase) inhibitor
Any EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that inhibits the action of carboxylesterase (EC 3.1.1.1 ).
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
Daphnia galeata metabolite
A Daphnia metabolite produced by the species Daphnia galeata.
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solvent
A liquid that can dissolve other substances (solutes) without any change in their chemical composition.
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View more via ChEBI Ontology
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Outgoing
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oleic acid
(CHEBI:16196)
has parent hydride
cis-octadec-9-ene
(CHEBI:37604)
oleic acid
(CHEBI:16196)
has role
Daphnia galeata metabolite
(CHEBI:83038)
oleic acid
(CHEBI:16196)
has role
Escherichia coli metabolite
(CHEBI:76971)
oleic acid
(CHEBI:16196)
has role
antioxidant
(CHEBI:22586)
oleic acid
(CHEBI:16196)
has role
EC 3.1.1.1 (carboxylesterase) inhibitor
(CHEBI:78444)
oleic acid
(CHEBI:16196)
has role
mouse metabolite
(CHEBI:75771)
oleic acid
(CHEBI:16196)
has role
plant metabolite
(CHEBI:76924)
oleic acid
(CHEBI:16196)
has role
solvent
(CHEBI:46787)
oleic acid
(CHEBI:16196)
is a
octadec-9-enoic acid
(CHEBI:36021)
oleic acid
(CHEBI:16196)
is conjugate acid of
oleate
(CHEBI:30823)
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Incoming
|
β-D-glucosyl-N-(oleoyl)sphingosine
(CHEBI:139140)
has functional parent
oleic acid
(CHEBI:16196)
(2S)-1-oleoyl-2-methylglycero-3-phosphothionate
(CHEBI:139223)
has functional parent
oleic acid
(CHEBI:16196)
(9Z)-12-(phosphonooxy)octadecenoic acid
(CHEBI:85140)
has functional parent
oleic acid
(CHEBI:16196)
(9Z)-12-hydroxyoctadec-9-enoic acid
(CHEBI:85639)
has functional parent
oleic acid
(CHEBI:16196)
(9Z)-17-hydroxyoctadec-9-enoic acid
(CHEBI:144923)
has functional parent
oleic acid
(CHEBI:16196)
(9Z,12R)-12,18-dihydroxyoctadecenoic acid
(CHEBI:129091)
has functional parent
oleic acid
(CHEBI:16196)
(R)-oleoylcarnitine
(CHEBI:84651)
has functional parent
oleic acid
(CHEBI:16196)
(R,R)-2-oleoylglycero-1-phospho-1'-glycerol
(CHEBI:139585)
has functional parent
oleic acid
(CHEBI:16196)
(R,R)-bis(2-oleoylglycero)-3-phosphate
(CHEBI:139583)
has functional parent
oleic acid
(CHEBI:16196)
(S,S)-2-oleoylglycero-1-phospho-1'-glycerol
(CHEBI:139543)
has functional parent
oleic acid
(CHEBI:16196)
(S,S)-3-oleoylglycero-1-phospho-1'-glycerol
(CHEBI:139540)
has functional parent
oleic acid
(CHEBI:16196)
(S,S)-bis(2-oleoylglycero)-1-phosphate
(CHEBI:139541)
has functional parent
oleic acid
(CHEBI:16196)
(S,S)-bis-(3-oleoylglycero)-1-phosphate
(CHEBI:139539)
has functional parent
oleic acid
(CHEBI:16196)
1,1ʼ,2-trilinoleoyl-2ʼ-oleoyl cardiolipin
(CHEBI:84399)
has functional parent
oleic acid
(CHEBI:16196)
1,1'-dilinoleoyl-2-oleoyl monolysocardiolipin
(CHEBI:84583)
has functional parent
oleic acid
(CHEBI:16196)
1,1'-dioleyl 2,2'-dilysocardiolipin
(CHEBI:77560)
has functional parent
oleic acid
(CHEBI:16196)
1,2-di-[(9Z)-octadecenoyl]-sn-glycero-3-phosphoethanolamine
(CHEBI:84839)
has functional parent
oleic acid
(CHEBI:16196)
1,2-dioleoyl-3-lauroyl-sn-glycerol
(CHEBI:77685)
has functional parent
oleic acid
(CHEBI:16196)
1,2-dioleoyl-3-linoleoyl-sn-glycerol
(CHEBI:77683)
has functional parent
oleic acid
(CHEBI:16196)
1,2-dioleoyl-3-myristoyl-sn-glycerol
(CHEBI:77684)
has functional parent
oleic acid
(CHEBI:16196)
1,2-dioleoyl-3-palmitoylglycerol
(CHEBI:75848)
has functional parent
oleic acid
(CHEBI:16196)
1,2-dioleoyl-3-stearoyl-sn-glycerol
(CHEBI:77686)
has functional parent
oleic acid
(CHEBI:16196)
1,2-dioleoyl-sn-glycero-3-phospho-(1ʼ-sn-glycerol)
(CHEBI:75385)
has functional parent
oleic acid
(CHEBI:16196)
1,2-dioleoyl-sn-glycero-3-phospho-(1ʼ-sn-glycerol-3ʼ-phosphate)
(CHEBI:82848)
has functional parent
oleic acid
(CHEBI:16196)
1,2-dioleoyl-sn-glycero-3-phospho-1ʼ-(3ʼ-oleoyl)-sn-glycerol
(CHEBI:139551)
has functional parent
oleic acid
(CHEBI:16196)
1,2-dioleoyl-sn-glycero-3-phospho-N,N-dimethylethanolamine
(CHEBI:85963)
has functional parent
oleic acid
(CHEBI:16196)
1,2-dioleoyl-sn-glycero-3-phospho-N-methylethanolamine
(CHEBI:85962)
has functional parent
oleic acid
(CHEBI:16196)
1,2-dioleoyl-sn-glycero-3-phospho-L-serine
(CHEBI:60568)
has functional parent
oleic acid
(CHEBI:16196)
1,2-dioleoyl-sn-glycero-3-phosphocholine
(CHEBI:74669)
has functional parent
oleic acid
(CHEBI:16196)
1,3-dioleoyl-2-palmitoylglycerol
(CHEBI:75846)
has functional parent
oleic acid
(CHEBI:16196)
1,3-dioleoylglycerol
(CHEBI:75735)
has functional parent
oleic acid
(CHEBI:16196)
1,3-dipalmitoyl-2-oleoylglycerol
(CHEBI:75688)
has functional parent
oleic acid
(CHEBI:16196)
1-α-linolenoyl-2-oleoylglycerol
(CHEBI:75609)
has functional parent
oleic acid
(CHEBI:16196)
1-(1Z-hexadecenyl)-2-oleoyl-sn-glycero-3-phosphoethanolamine
(CHEBI:84533)
has functional parent
oleic acid
(CHEBI:16196)
1-(1Z-octadecenyl)-2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine
(CHEBI:79203)
has functional parent
oleic acid
(CHEBI:16196)
1-(1Z-octadecenyl)-2-oleoyl-sn-glycero-3-phosphoserine
(CHEBI:79206)
has functional parent
oleic acid
(CHEBI:16196)
1-(1Z-octadecenyl)-sn-glycero-3-phospho-(N-oleoyl)ethanolamine
(CHEBI:138095)
has functional parent
oleic acid
(CHEBI:16196)
1-(9Z)-octadecenoyl-2-(9Z)-hexadecenoyl-sn-glycero-3-phosphate
(CHEBI:75074)
has functional parent
oleic acid
(CHEBI:16196)
1-(alk-1-enyl)-2-oleoyl-sn-glycero-3-phosphocholine
(CHEBI:75148)
has functional parent
oleic acid
(CHEBI:16196)
1-O-hexadecyl-2-oleoyl-sn-glycero-3-phosphocholine
(CHEBI:34112)
has functional parent
oleic acid
(CHEBI:16196)
1-O-oleoyl-N-acetylsphingosine
(CHEBI:76054)
has functional parent
oleic acid
(CHEBI:16196)
1-O-palmityl-3-oleoylglycerol
(CHEBI:76062)
has functional parent
oleic acid
(CHEBI:16196)
1-[(1Z)-octadecenyl]-2-[(9Z)-octadecenoyl]-sn-glycero-3-phosphocholine
(CHEBI:86241)
has functional parent
oleic acid
(CHEBI:16196)
1-[(1Z)-octadecenyl]-2-oleoyl-sn-glycero-3-phosphate
(CHEBI:140595)
has functional parent
oleic acid
(CHEBI:16196)
1-[(1Z,11Z)-octadecadienyl]-2-oleoyl-sn-glycero-3-phosphoethanolamine
(CHEBI:85020)
has functional parent
oleic acid
(CHEBI:16196)
1-[(2Z)-hexadecenoyl]-2-[(9Z)-octadecenoyl]-sn-glycero-3-phosphocholine
(CHEBI:84809)
has functional parent
oleic acid
(CHEBI:16196)
1-[(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl]-2-[(9Z)-octadecenoyl]-sn-glycero-3-phosphocholine
(CHEBI:86183)
has functional parent
oleic acid
(CHEBI:16196)
1-[(6Z,9Z,12Z)-octadecatrienoyl]-2-[(9Z)-octadecenoyl]-snglycero-3-phosphocholine
(CHEBI:86123)
has functional parent
oleic acid
(CHEBI:16196)
1-[(9Z)-hexadecenoyl]-2-[(9Z)-octadecenoyl]-sn-glycero-3-phosphocholine
(CHEBI:84811)
has functional parent
oleic acid
(CHEBI:16196)
1-[(9Z)-octadecenoyl]-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl]-sn-glycero-3-phosphocholine
(CHEBI:84814)
has functional parent
oleic acid
(CHEBI:16196)
1-[(9Z)-octadecenoyl]-2-[(5Z,8Z,11Z)-eicosatrienoyl]-sn-glycero-3-phosphocholine
(CHEBI:86178)
has functional parent
oleic acid
(CHEBI:16196)
1-[(9Z)-octadecenoyl]-2-[(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl]-sn-glycero-3-phosphocholine
(CHEBI:86187)
has functional parent
oleic acid
(CHEBI:16196)
1-[(9Z)-octadecenoyl]-2-[(6Z,9Z)-octadecadienoyl]-sn-glycero-3-phosphocholine
(CHEBI:84831)
has functional parent
oleic acid
(CHEBI:16196)
1-[(9Z)-octadecenoyl]-2-[(6Z,9Z,12Z)-octadecatrienoyl]-sn-glycero-3-phosphocholine
(CHEBI:86130)
has functional parent
oleic acid
(CHEBI:16196)
1-[(9Z)-octadecenoyl]-2-[(7Z,10Z,13Z,16Z)-docosatetraenoyl]-sn-glycero-3-phosphocholine
(CHEBI:86201)
has functional parent
oleic acid
(CHEBI:16196)
1-[(9Z)-octadecenoyl]-2-[(7Z,10Z,13Z,16Z,19Z)-docosapentaenoyl]-sn-glycero-3-phosphocholine
(CHEBI:86205)
has functional parent
oleic acid
(CHEBI:16196)
1-[(9Z)-octadecenoyl]-2-[(9Z)-hexadecenoyl]-sn-glycero-3-phosphocholine
(CHEBI:86100)
has functional parent
oleic acid
(CHEBI:16196)
1-[(9Z)-octadecenoyl]-2-[(9Z,12Z,15Z)-octadecatrienoyl]-sn-glycero-3-phosphocholine
(CHEBI:86133)
has functional parent
oleic acid
(CHEBI:16196)
1-[(9Z)-octadecenoyl]-2-docosanoyl-sn-glycero-3-phosphocholine
(CHEBI:86190)
has functional parent
oleic acid
(CHEBI:16196)
1-[(9Z)-octadecenoyl]-2-eicosanoyl-sn-glycero-3-phosphocholine
(CHEBI:86172)
has functional parent
oleic acid
(CHEBI:16196)
1-[(9Z)-octadecenoyl]-2-tetracosanoyl-sn-glycero-3-phosphocholine
(CHEBI:86217)
has functional parent
oleic acid
(CHEBI:16196)
1-[(9Z)-octadecenoyl]-2-tetradecanoyl-sn-glycero-3-phosphocholine
(CHEBI:86092)
has functional parent
oleic acid
(CHEBI:16196)
1-[(9Z,12Z,15Z)-octadecatrienoyl]-2-[(9Z)-octadecenoyl]-sn-glycero-3-phosphocholine
(CHEBI:86127)
has functional parent
oleic acid
(CHEBI:16196)
1-acyl-2-oleoyl-sn-glycero-3-phosphate
(CHEBI:75109)
has functional parent
oleic acid
(CHEBI:16196)
1-arachidonoyl-2-oleoyl-sn-glycero-3-phosphate
(CHEBI:75141)
has functional parent
oleic acid
(CHEBI:16196)
1-arachidonoyl-2-oleoylglycerol
(CHEBI:75611)
has functional parent
oleic acid
(CHEBI:16196)
1-butyryl-2-oleoyl-sn-glycerol
(CHEBI:75443)
has functional parent
oleic acid
(CHEBI:16196)
1-capryl-2-oleoyl-sn-glycerol
(CHEBI:75505)
has functional parent
oleic acid
(CHEBI:16196)
1-decanoyl-2-oleoyl-sn-glycero-3-phosphocholine
(CHEBI:86410)
has functional parent
oleic acid
(CHEBI:16196)
1-decanoyl-2-oleoylglycerol
(CHEBI:85787)
has functional parent
oleic acid
(CHEBI:16196)
1-eicosanoyl-2-[(9Z)-octadecenoyl]-sn-glycero-3-phosphocholine
(CHEBI:86171)
has functional parent
oleic acid
(CHEBI:16196)
1-heptadecanoyl-2-oleoyl-sn-glycero-3-phosphate
(CHEBI:74841)
has functional parent
oleic acid
(CHEBI:16196)
1-heptadecanoyl-2-oleoyl-sn-glycero-3-phosphocholine
(CHEBI:133624)
has functional parent
oleic acid
(CHEBI:16196)
1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine
(CHEBI:73124)
has functional parent
oleic acid
(CHEBI:16196)
1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine
(CHEBI:73001)
has functional parent
oleic acid
(CHEBI:16196)
1-icosanoyl-2-oleoyl-sn-glycero-3-phosphate
(CHEBI:74942)
has functional parent
oleic acid
(CHEBI:16196)
1-icosanoyl-2-oleoyl-sn-glycerol
(CHEBI:75470)
has functional parent
oleic acid
(CHEBI:16196)
1-lauroyl-2-oleoylglycerol
(CHEBI:75579)
has functional parent
oleic acid
(CHEBI:16196)
1-linolenoyl-2-oleoyl-sn-glycero-3-phosphate
(CHEBI:74833)
has functional parent
oleic acid
(CHEBI:16196)
1-linoleoyl-2-oleoyl-sn-glycero-3-phosphate
(CHEBI:74830)
has functional parent
oleic acid
(CHEBI:16196)
1-linoleoyl-2-oleoylglycerol
(CHEBI:75614)
has functional parent
oleic acid
(CHEBI:16196)
1-myristoyl-2-oleoyl-sn-glycero-3-phosphate
(CHEBI:74943)
has functional parent
oleic acid
(CHEBI:16196)
1-myristoyl-2-oleoyl-sn-glycero-3-phosphoethanolamine
(CHEBI:85237)
has functional parent
oleic acid
(CHEBI:16196)
1-myristoyl-2-oleoylglycerol
(CHEBI:75582)
has functional parent
oleic acid
(CHEBI:16196)
1-octanoyl-2-oleoyl-sn-glycerol
(CHEBI:75462)
has functional parent
oleic acid
(CHEBI:16196)
1-oleoyl-2,3-di-linoleoyl-sn-glycerol
(CHEBI:84458)
has functional parent
oleic acid
(CHEBI:16196)
1-oleoyl-2-(α-linolenoyl)-sn-glycerol
(CHEBI:75475)
has functional parent
oleic acid
(CHEBI:16196)
1-oleoyl-2-(11Z)-octadecenoyl-sn-glycero-3-phosphate
(CHEBI:75357)
has functional parent
oleic acid
(CHEBI:16196)
1-oleoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycerol
(CHEBI:84439)
has functional parent
oleic acid
(CHEBI:16196)
1-oleoyl-2-(6Z)-octadecenoyl-sn-glycero-3-phosphate
(CHEBI:75363)
has functional parent
oleic acid
(CHEBI:16196)
1-oleoyl-2-(7Z,10Z,13Z,16Z-docosatetraenoyl)-sn-glycerol
(CHEBI:84438)
has functional parent
oleic acid
(CHEBI:16196)
1-oleoyl-2-(8Z,11Z,14Z-eicosatrienoyl)-sn-glycerol
(CHEBI:84437)
has functional parent
oleic acid
(CHEBI:16196)
1-oleoyl-2-O-arachidonyl-sn-glycerol
(CHEBI:75914)
has functional parent
oleic acid
(CHEBI:16196)
1-oleoyl-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl]-sn-glycero-3-phosphate
(CHEBI:139413)
has functional parent
oleic acid
(CHEBI:16196)
1-oleoyl-2-[(8Z,11Z,14Z)-icosatrienoyl]-sn-glycero-3-phosphocholine
(CHEBI:89618)
has functional parent
oleic acid
(CHEBI:16196)
1-oleoyl-2-acyl-sn-glycero-3-phosphocholine
(CHEBI:78421)
has functional parent
oleic acid
(CHEBI:16196)
1-oleoyl-2-acyl-sn-glycero-3-phosphoserine(1−)
(CHEBI:78422)
has functional parent
oleic acid
(CHEBI:16196)
1-oleoyl-2-arachidonoyl-sn-glycero-3-phosphate
(CHEBI:75118)
has functional parent
oleic acid
(CHEBI:16196)
1-oleoyl-2-arachidonoyl-sn-glycero-3-phospho-1D-myo-inositol
(CHEBI:82762)
has functional parent
oleic acid
(CHEBI:16196)
1-oleoyl-2-arachidonoyl-sn-glycero-3-phospho-L-serine
(CHEBI:75099)
has functional parent
oleic acid
(CHEBI:16196)
1-oleoyl-2-arachidonoyl-sn-glycero-3-phosphocholine
(CHEBI:74671)
has functional parent
oleic acid
(CHEBI:16196)
1-oleoyl-2-arachidonoyl-sn-glycerol
(CHEBI:75449)
has functional parent
oleic acid
(CHEBI:16196)
1-oleoyl-2-arachidonoyl-sn-glycerol-3-phosphoethanolamine
(CHEBI:75169)
has functional parent
oleic acid
(CHEBI:16196)
1-oleoyl-2-decanoyl-sn-glycerol
(CHEBI:75444)
has functional parent
oleic acid
(CHEBI:16196)
1-oleoyl-2-gondoyl-sn-glycerol
(CHEBI:84436)
has functional parent
oleic acid
(CHEBI:16196)
1-oleoyl-2-heptadecanoyl-sn-glycero-3-phosphate
(CHEBI:74845)
has functional parent
oleic acid
(CHEBI:16196)
1-oleoyl-2-hexadecanoyl-sn-glycero-3-phospho-(1ʼ-sn-glycerol-3ʼ-phosphate)
(CHEBI:136816)
has functional parent
oleic acid
(CHEBI:16196)
1-oleoyl-2-icosanoyl-sn-glycero-3-phosphate
(CHEBI:75134)
has functional parent
oleic acid
(CHEBI:16196)
1-oleoyl-2-lauroyl-sn-glycero-3-phospho-(1ʼ-sn-glycerol)
(CHEBI:77121)
has functional parent
oleic acid
(CHEBI:16196)
1-oleoyl-2-lauroyl-sn-glycerol
(CHEBI:75445)
has functional parent
oleic acid
(CHEBI:16196)
1-oleoyl-2-linolenoyl-PAP
(CHEBI:53754)
has functional parent
oleic acid
(CHEBI:16196)
1-oleoyl-2-linoleoyl-sn-glycero-3-phosphate
(CHEBI:74849)
has functional parent
oleic acid
(CHEBI:16196)
1-oleoyl-2-linoleoyl-sn-glycero-3-phospho-L-serine
(CHEBI:75096)
has functional parent
oleic acid
(CHEBI:16196)
1-oleoyl-2-linoleoyl-sn-glycero-3-phosphocholine
(CHEBI:74670)
has functional parent
oleic acid
(CHEBI:16196)
1-oleoyl-2-linoleoyl-sn-glycerol
(CHEBI:75450)
has functional parent
oleic acid
(CHEBI:16196)
1-oleoyl-2-linoleyl-sn-glycero-3-phosphoethanolamine
(CHEBI:84543)
has functional parent
oleic acid
(CHEBI:16196)
1-oleoyl-2-myristoyl-sn-glycero-3-phosphate
(CHEBI:74930)
has functional parent
oleic acid
(CHEBI:16196)
1-oleoyl-2-myristoyl-sn-glycero-3-phosphoethanolamine
(CHEBI:82840)
has functional parent
oleic acid
(CHEBI:16196)
1-oleoyl-2-myristoyl-sn-glycerol
(CHEBI:75446)
has functional parent
oleic acid
(CHEBI:16196)
1-oleoyl-2-palmitoleoyl-sn-glycero-3-phospho-L-serine
(CHEBI:75101)
has functional parent
oleic acid
(CHEBI:16196)
1-oleoyl-2-palmitoleoyl-sn-glycero-3-phosphoethanolamine
(CHEBI:82837)
has functional parent
oleic acid
(CHEBI:16196)
1-oleoyl-2-palmitoyl-sn-glycero-3-phosphate
(CHEBI:74836)
has functional parent
oleic acid
(CHEBI:16196)
1-oleoyl-2-palmitoyl-sn-glycero-3-phospho-L-serine
(CHEBI:75106)
has functional parent
oleic acid
(CHEBI:16196)
1-oleoyl-2-palmitoyl-sn-glycero-3-phosphocholine
(CHEBI:74667)
has functional parent
oleic acid
(CHEBI:16196)
1-oleoyl-2-palmitoyl-sn-glycero-3-phosphoethanolamine
(CHEBI:82839)
has functional parent
oleic acid
(CHEBI:16196)
1-oleoyl-2-palmitoylglycerol
(CHEBI:76065)
has functional parent
oleic acid
(CHEBI:16196)
1-oleoyl-2-pentadecanoyl-sn-glycero-3-phosphate
(CHEBI:74852)
has functional parent
oleic acid
(CHEBI:16196)
1-oleoyl-2-stearoyl-sn-glycero-3-phosphate
(CHEBI:74839)
has functional parent
oleic acid
(CHEBI:16196)
1-oleoyl-2-stearoyl-sn-glycero-3-phospho-L-serine
(CHEBI:75103)
has functional parent
oleic acid
(CHEBI:16196)
1-oleoyl-2-stearoyl-sn-glycero-3-phosphocholine
(CHEBI:76073)
has functional parent
oleic acid
(CHEBI:16196)
1-oleoyl-2-stearoyl-sn-glycero-3-phosphoethanolamine
(CHEBI:85076)
has functional parent
oleic acid
(CHEBI:16196)
1-oleoyl-2-stearoyl-sn-glycerol
(CHEBI:75448)
has functional parent
oleic acid
(CHEBI:16196)
1-oleoyl-2-{6-[(7-nitro-2-1,3-benzoxadiazol-4-yl)amino]hexanoyl}-sn-glycero-3-phospho-L-serine
(CHEBI:88338)
has functional parent
oleic acid
(CHEBI:16196)
1-oleoyl-3-linoleoylglycerol
(CHEBI:133484)
has functional parent
oleic acid
(CHEBI:16196)
1-oleoyl-3-palmitoylglycerol
(CHEBI:75869)
has functional parent
oleic acid
(CHEBI:16196)
1-oleoyl-sn-glycero-3-phospho-D-myo-inositol
(CHEBI:82753)
has functional parent
oleic acid
(CHEBI:16196)
1-oleoyl-sn-glycero-3-phosphoethanolamine
(CHEBI:75168)
has functional parent
oleic acid
(CHEBI:16196)
1-oleoyl-sn-glycero-3-phosphoglycerol
(CHEBI:85410)
has functional parent
oleic acid
(CHEBI:16196)
1-oleoyl-sn-glycerol
(CHEBI:75757)
has functional parent
oleic acid
(CHEBI:16196)
1-oleoylglycerol
(CHEBI:75342)
has functional parent
oleic acid
(CHEBI:16196)
1-oleyl-2-linoleyl-PAP
(CHEBI:53752)
has functional parent
oleic acid
(CHEBI:16196)
1-palmitoyl-2-oleoyl-3-stearoyl-sn-glycerol
(CHEBI:77623)
has functional parent
oleic acid
(CHEBI:16196)
1-palmitoyl-2-oleoyl-sn-glycero-3-phosphoglycerol
(CHEBI:34080)
has functional parent
oleic acid
(CHEBI:16196)
1-palmitoyl-2-oleoylglycerol
(CHEBI:75585)
has functional parent
oleic acid
(CHEBI:16196)
1-palmityl-2-acetyl-3-oleoyl-sn-glycerol
(CHEBI:76055)
has functional parent
oleic acid
(CHEBI:16196)
1-palmityl-2-methyl-3-oleoyl-sn-glycerol
(CHEBI:76064)
has functional parent
oleic acid
(CHEBI:16196)
1-palmityl-2-oleoyl-sn-glycero-3-phosphate
(CHEBI:77357)
has functional parent
oleic acid
(CHEBI:16196)
1-palmityl-2-oleoyl-sn-glycerol
(CHEBI:77185)
has functional parent
oleic acid
(CHEBI:16196)
1-pentadecanoyl-2-oleoyl-sn-glycero-3-phosphocholine
(CHEBI:133623)
has functional parent
oleic acid
(CHEBI:16196)
1-stearoyl-2-arachidonoyl-3-oleoyl-sn-glycerol
(CHEBI:75729)
has functional parent
oleic acid
(CHEBI:16196)
1-stearoyl-2-oleoyl-sn-glycero-3-phosphate
(CHEBI:74847)
has functional parent
oleic acid
(CHEBI:16196)
1-stearoyl-2-oleoyl-sn-glycero-3-phospho-1D-myo-inositol
(CHEBI:77346)
has functional parent
oleic acid
(CHEBI:16196)
1-stearoyl-2-oleoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-biphosphate
(CHEBI:77279)
has functional parent
oleic acid
(CHEBI:16196)
1-stearoyl-2-oleoyl-sn-glycero-3-phospho-1D-myo-inositol 4-phosphate
(CHEBI:77277)
has functional parent
oleic acid
(CHEBI:16196)
1-stearoyl-2-oleoyl-sn-glycero-3-phospho-1D-myo-inositol 5-phosphate
(CHEBI:77347)
has functional parent
oleic acid
(CHEBI:16196)
1-stearoyl-2-oleoyl-sn-glycero-3-phosphoserine
(CHEBI:79096)
has functional parent
oleic acid
(CHEBI:16196)
1-stearoyl-2-oleoylglycerol
(CHEBI:75590)
has functional parent
oleic acid
(CHEBI:16196)
1-tetracosanoyl-2-[(9Z)-octadecenoyl]-sn-glycero-3-phosphocholine
(CHEBI:86213)
has functional parent
oleic acid
(CHEBI:16196)
1-tetradecanoyl-2-[(9Z)-octadecenoyl]-sn-glycero-3-phosphocholine
(CHEBI:84808)
has functional parent
oleic acid
(CHEBI:16196)
1-tetradecyl-2-[(9Z)-octadecenoyl]-sn-glycero-3-phosphocholine
(CHEBI:86424)
has functional parent
oleic acid
(CHEBI:16196)
10-hydroperoxy-8E-octadecenoic acid
(CHEBI:85589)
has functional parent
oleic acid
(CHEBI:16196)
12-[(9Z)-octadecenoyloxy]octadecanoic acid
(CHEBI:137082)
has functional parent
oleic acid
(CHEBI:16196)
13-[(9Z)-octadecenoyloxy]octadecanoic acid
(CHEBI:137083)
has functional parent
oleic acid
(CHEBI:16196)
18-hydroxyoleic acid
(CHEBI:79312)
has functional parent
oleic acid
(CHEBI:16196)
18-hydroxyoleoyl-CoA
(CHEBI:86053)
has functional parent
oleic acid
(CHEBI:16196)
18-oxooleic acid
(CHEBI:133357)
has functional parent
oleic acid
(CHEBI:16196)
2,3-dioleoyl-sn-glycerol
(CHEBI:75824)
has functional parent
oleic acid
(CHEBI:16196)
2-hydroxyoleic acid
(CHEBI:143096)
has functional parent
oleic acid
(CHEBI:16196)
2-oleoyl-sn-glycero-3-phosphate
(CHEBI:78270)
has functional parent
oleic acid
(CHEBI:16196)
2-oleoyl-sn-glycero-3-phosphocholine
(CHEBI:76071)
has functional parent
oleic acid
(CHEBI:16196)
2-oleoyl-sn-glycero-3-phosphoethanolamine
(CHEBI:76231)
has functional parent
oleic acid
(CHEBI:16196)
2-oleoyl-sn-glycero-3-phosphoethanolamine zwitterion
(CHEBI:76088)
has functional parent
oleic acid
(CHEBI:16196)
2-oleoyl-sn-glycero-3-phosphoserine
(CHEBI:77646)
has functional parent
oleic acid
(CHEBI:16196)
2-oleoylglycerol
(CHEBI:73990)
has functional parent
oleic acid
(CHEBI:16196)
2-palmitoyl-3-oleoyl-sn-glycerol
(CHEBI:75870)
has functional parent
oleic acid
(CHEBI:16196)
3-oleoyl-sn-glycerol
(CHEBI:75938)
has functional parent
oleic acid
(CHEBI:16196)
3-oxooleoyl-CoA
(CHEBI:88007)
has functional parent
oleic acid
(CHEBI:16196)
5-[(9Z)-octadecenoyloxy]octadecanoic acid
(CHEBI:137106)
has functional parent
oleic acid
(CHEBI:16196)
9-[(9Z)-octadecenoyloxy]octadecanoic acid
(CHEBI:136996)
has functional parent
oleic acid
(CHEBI:16196)
9-hydroperoxy-10E-octadecenoic acid
(CHEBI:85587)
has functional parent
oleic acid
(CHEBI:16196)
all-trans-retinyl oleate
(CHEBI:70760)
has functional parent
oleic acid
(CHEBI:16196)
N,1,2-trioleoyl-sn-glycero-3-phosphoethanolamine
(CHEBI:85790)
has functional parent
oleic acid
(CHEBI:16196)
N,1-dioleoyl-sn-glycero-3-phosphoethanolamine
(CHEBI:85664)
has functional parent
oleic acid
(CHEBI:16196)
N,O-dioleoylethanolamine
(CHEBI:76068)
has functional parent
oleic acid
(CHEBI:16196)
N-(9Z-octadecenoyl)-(2S)-hydroxyglycine
(CHEBI:142737)
has functional parent
oleic acid
(CHEBI:16196)
N-[(9Z)-octadecenoyl]sphinganine
(CHEBI:74100)
has functional parent
oleic acid
(CHEBI:16196)
N-arachidonoyl-1,2-dioleoyl-sn-glycero-3-phosphoethanolamine
(CHEBI:85784)
has functional parent
oleic acid
(CHEBI:16196)
N-arachidonoyl-1-oleoyl-sn-glycero-3-phosphoethanolamine
(CHEBI:85666)
has functional parent
oleic acid
(CHEBI:16196)
n-butyl oleate
(CHEBI:82946)
has functional parent
oleic acid
(CHEBI:16196)
N-icosanoyl-1-oleoyl-sn-glycero-3-phosphoethanolamine
(CHEBI:85667)
has functional parent
oleic acid
(CHEBI:16196)
N-lauroyl-1,2-dioleoyl-sn-glycero-3-phosphoethanolamine
(CHEBI:85794)
has functional parent
oleic acid
(CHEBI:16196)
N-myristoyl-1,2-dioleoyl-sn-glycero-3-phosphoethanolamine
(CHEBI:85793)
has functional parent
oleic acid
(CHEBI:16196)
N-oleoyl-(4E,14Z)-sphingadienine-1-phosphocholine
(CHEBI:105799)
has functional parent
oleic acid
(CHEBI:16196)
N-oleoyl-1,2-diacyl-sn-glycero-3-phosphoethanolamine
(CHEBI:138239)
has functional parent
oleic acid
(CHEBI:16196)
N-oleoyl-sn-glycero-3-phosphoethanolamine
(CHEBI:85670)
has functional parent
oleic acid
(CHEBI:16196)
N-oleoyl-L-glutamic acid
(CHEBI:136713)
has functional parent
oleic acid
(CHEBI:16196)
N-oleoyl-L-glutamine
(CHEBI:136615)
has functional parent
oleic acid
(CHEBI:16196)
N-oleoyl-L-isoleucine
(CHEBI:136711)
has functional parent
oleic acid
(CHEBI:16196)
N-oleoyl-L-leucine
(CHEBI:136616)
has functional parent
oleic acid
(CHEBI:16196)
N-oleoyl-L-phenylalanine
(CHEBI:134021)
has functional parent
oleic acid
(CHEBI:16196)
N-oleoyl-L-serine
(CHEBI:136614)
has functional parent
oleic acid
(CHEBI:16196)
N-oleoyldopamine
(CHEBI:31883)
has functional parent
oleic acid
(CHEBI:16196)
N-oleoylethanolamine phosphate
(CHEBI:145794)
has functional parent
oleic acid
(CHEBI:16196)
N-oleoylglycine
(CHEBI:73723)
has functional parent
oleic acid
(CHEBI:16196)
N-oleoylphytosphingosine
(CHEBI:85204)
has functional parent
oleic acid
(CHEBI:16196)
N-oleoylserotonin
(CHEBI:134064)
has functional parent
oleic acid
(CHEBI:16196)
N-oleoylsphinganine-1-phosphocholine
(CHEBI:134074)
has functional parent
oleic acid
(CHEBI:16196)
N-oleoylsphingosine
(CHEBI:77996)
has functional parent
oleic acid
(CHEBI:16196)
N-oleoylsphingosine 1-phosphate
(CHEBI:85882)
has functional parent
oleic acid
(CHEBI:16196)
N-oleoylsphingosine-1-phosphocholine
(CHEBI:84487)
has functional parent
oleic acid
(CHEBI:16196)
N-oleoyltaurine
(CHEBI:146206)
has functional parent
oleic acid
(CHEBI:16196)
N-oleoylthreonine
(CHEBI:131695)
has functional parent
oleic acid
(CHEBI:16196)
N-palmitoyl-1,2-dioleoyl-sn-glycero-3-phosphoethanolamine
(CHEBI:78940)
has functional parent
oleic acid
(CHEBI:16196)
N-palmitoyl-1-oleoyl-sn-glycero-3-phosphoethanolamine
(CHEBI:85654)
has functional parent
oleic acid
(CHEBI:16196)
N-stearoyl-1,2-dioleoyl-sn-glycero-3-phosphoethanolamine
(CHEBI:85791)
has functional parent
oleic acid
(CHEBI:16196)
N-stearoyl-1-oleoyl-sn-glycero-3-phosphoethanolamine
(CHEBI:85660)
has functional parent
oleic acid
(CHEBI:16196)
O-oleoylanandamide
(CHEBI:76070)
has functional parent
oleic acid
(CHEBI:16196)
arachidyl oleate
(CHEBI:75628)
has functional parent
oleic acid
(CHEBI:16196)
CDP-1,2-dioleoyl-sn-glycerol
(CHEBI:85856)
has functional parent
oleic acid
(CHEBI:16196)
CDP-1-stearoyl-2-oleoyl-sn-glycerol
(CHEBI:85841)
has functional parent
oleic acid
(CHEBI:16196)
cholesteryl oleate
(CHEBI:46898)
has functional parent
oleic acid
(CHEBI:16196)
decyl oleate
(CHEBI:75620)
has functional parent
oleic acid
(CHEBI:16196)
egonol oleate
(CHEBI:69548)
has functional parent
oleic acid
(CHEBI:16196)
ethyl oleate
(CHEBI:84940)
has functional parent
oleic acid
(CHEBI:16196)
methyl oleate
(CHEBI:27542)
has functional parent
oleic acid
(CHEBI:16196)
monooleoylglycerol
(CHEBI:75937)
has functional parent
oleic acid
(CHEBI:16196)
oleonitrile
(CHEBI:133637)
has functional parent
oleic acid
(CHEBI:16196)
oleoyl danshenxinkun A
(CHEBI:66819)
has functional parent
oleic acid
(CHEBI:16196)
oleoyl ethanolamide
(CHEBI:71466)
has functional parent
oleic acid
(CHEBI:16196)
oleoyl neocryptotanshinone
(CHEBI:66820)
has functional parent
oleic acid
(CHEBI:16196)
oleoyl-containing glycerolipid
(CHEBI:88240)
has functional parent
oleic acid
(CHEBI:16196)
oleoylcholine
(CHEBI:133693)
has functional parent
oleic acid
(CHEBI:16196)
oleyl oleate
(CHEBI:75626)
has functional parent
oleic acid
(CHEBI:16196)
oleylanilide
(CHEBI:53721)
has functional parent
oleic acid
(CHEBI:16196)
palmitoleyl oleate
(CHEBI:75624)
has functional parent
oleic acid
(CHEBI:16196)
palmityl oleate
(CHEBI:75622)
has functional parent
oleic acid
(CHEBI:16196)
stearyl oleate
(CHEBI:75625)
has functional parent
oleic acid
(CHEBI:16196)
triolein
(CHEBI:53753)
has functional parent
oleic acid
(CHEBI:16196)
trioleoyl 2-monolysocardiolipin
(CHEBI:77561)
has functional parent
oleic acid
(CHEBI:16196)
corn oil
(CHEBI:195250)
has part
oleic acid
(CHEBI:16196)
soybean oil
(CHEBI:166975)
has part
oleic acid
(CHEBI:16196)
1-(γ-linolenoyl)-2-oleoyl-sn-glycero-3-phosphate
(CHEBI:74936)
is a
oleic acid
(CHEBI:16196)
oleate
(CHEBI:30823)
is conjugate base of
oleic acid
(CHEBI:16196)
oleoyl group
(CHEBI:25667)
is substituent group from
oleic acid
(CHEBI:16196)
|
|
(9Z)-octadec-9-enoic acid
|
|
(9Z)-Octadecenoic acid
|
KEGG COMPOUND
|
|
(Z)-Octadec-9-enoic acid
|
KEGG COMPOUND
|
|
18:1 n-9
|
ChEBI
|
|
18:1Δ9cis
|
ChEBI
|
|
C18:1 n-9
|
ChEBI
|
|
cis-9-octadecenoic acid
|
NIST Chemistry WebBook
|
|
cis-Δ9-octadecenoic acid
|
ChemIDplus
|
|
cis-oleic acid
|
ChEBI
|
|
FA 18:1
|
ChEBI
|
|
Octadec-9-enoic acid
|
ChEMBL
|
Oelsäure
|
ChEBI
|
|
Oleate
|
KEGG COMPOUND
|
|
Oleic acid
|
KEGG COMPOUND
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OLEIC ACID
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PDBeChem
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Ölsäure
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ChEBI
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3400
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DrugCentral
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C00001232
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KNApSAcK
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C00712
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KEGG COMPOUND
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D02315
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KEGG DRUG
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DB04224
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DrugBank
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ECMDB21348
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ECMDB
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HMDB0000207
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HMDB
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LMFA01030002
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LIPID MAPS
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OLA
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PDBeChem
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Oleic_acid
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Wikipedia
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| View more database links |
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109551
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Gmelin Registry Number
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Gmelin
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112-80-1
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CAS Registry Number
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KEGG COMPOUND
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112-80-1
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CAS Registry Number
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NIST Chemistry WebBook
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112-80-1
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CAS Registry Number
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ChemIDplus
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1726542
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Reaxys Registry Number
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Reaxys
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57556
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Gmelin Registry Number
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Gmelin
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Prokopovich P, Köbrick M, Brousseau E, Perni S (2015)
Potent antimicrobial activity of bone cement encapsulating silver nanoparticles capped with oleic acid.
Journal of biomedical materials research. Part B, Applied biomaterials 103, 273-281 [PubMed:24819471]
[show Abstract]
Bone cement is widely used in surgical treatments for the fixation for orthopaedic devices. Subsequently, 2-3% of patients undergoing these procedures develop infections that are both a major health risk for patients and a cost for the health service providers; this is also aggravated by the fact that antibiotics are losing efficacy because of the rising resistance of microorganisms to these substances. In this study, oleic acid capped silver nanoparticles (NP) were encapsulated into Poly(methyl methacrylate) (PMMA)-based bone cement samples at various ratios. Antimicrobial activity against Methicillin Resistant Staphylococcus aureus, S. aureus, Staphylococcus epidermidis, Acinetobacter baumannii was exhibited at NP concentrations as low as 0.05% (w/w). Furthermore, the mechanical properties and cytotoxicity of the bone cement containing these NP were assessed to guarantee that such material is safe to be used in orthopaedic surgical practice. | Novak M, Lah L, Šala M, Stojan J, Bohlmann J, Komel R (2015)
Oleic acid metabolism via a conserved cytochrome P450 system-mediated ω-hydroxylation in the bark beetle-associated fungus Grosmannia clavigera.
PloS one 10, e0120119 [PubMed:25794012]
[show Abstract]
The bark beetle-associated fungus Grosmannia clavigera participates in the large-scale destruction of pine forests. In the tree, it must tolerate saturating levels of toxic conifer defense chemicals (e.g. monoterpenes). The fungus can metabolize some of these compounds through the ß-oxidation pathway and use them as a source of carbon. It also uses carbon from pine triglycerides, where oleic acid is the most common fatty acid. High levels of free fatty acids, however, are toxic and can cause additional stress during host colonization. Fatty acids induce expression of neighboring genes encoding a cytochrome P450 (CYP630B18) and its redox partner, cytochrome P450 reductase (CPR2). The aim of this work was to study the function of this novel P450 system. Using LC/MS, we biochemically characterized CYP630 as a highly specific oleic acid ω-hydroxylase. We explain oleic acid specificity using protein interaction modeling. Our results underscore the importance of ω-oxidation when the main ß-oxidation pathway may be overwhelmed by other substrates such as host terpenoid compounds. Because this CYP-CPR gene cluster is evolutionarily conserved, our work has implications for metabolism studies in other fungi. | Bourgeois EA, Subramaniam S, Cheng TY, De Jong A, Layre E, Ly D, Salimi M, Legaspi A, Modlin RL, Salio M, Cerundolo V, Moody DB, Ogg G (2015)
Bee venom processes human skin lipids for presentation by CD1a.
The Journal of experimental medicine 212, 149-163 [PubMed:25584012]
[show Abstract]
Venoms frequently co-opt host immune responses, so study of their mode of action can provide insight into novel inflammatory pathways. Using bee and wasp venom responses as a model system, we investigated whether venoms contain CD1-presented antigens. Here, we show that venoms activate human T cells via CD1a proteins. Whereas CD1 proteins typically present lipids, chromatographic separation of venoms unexpectedly showed that stimulatory factors partition into protein-containing fractions. This finding was explained by demonstrating that bee venom-derived phospholipase A2 (PLA2) activates T cells through generation of small neoantigens, such as free fatty acids and lysophospholipids, from common phosphodiacylglycerides. Patient studies showed that injected PLA2 generates lysophospholipids within human skin in vivo, and polyclonal T cell responses are dependent on CD1a protein and PLA2. These findings support a previously unknown skin immune response based on T cell recognition of CD1a proteins and lipid neoantigen generated in vivo by phospholipases. The findings have implications for skin barrier sensing by T cells and mechanisms underlying phospholipase-dependent inflammatory skin disease. | Singh VK, Kavita K, Prabhakaran R, Jha B (2013)
Cis-9-octadecenoic acid from the rhizospheric bacterium Stenotrophomonas maltophilia BJ01 shows quorum quenching and anti-biofilm activities.
Biofouling 29, 855-867 [PubMed:23844805]
[show Abstract]
Quorum quenching (QQ) is an effective approach for the prevention of bacterial infections involving biofilms. This study reports the QQ and anti-biofilm activities of a rhizospheric bacterium identified as Stenotrophomonas maltophilia BJ01. The QQ activity was demonstrated using Chromobacterium violaceum CV026 as a biosensor. A maximum of 95% reduction in violacein production, a quorum sensing-regulated behavior, was observed. Gas chromatography-mass spectroscopy of the extract showed that the active compound was cis-9-octadecenoic acid, which was confirmed by electronspray ionization-mass spectroscopy data. The extract also inhibited biofilm formation of Pseudomonas aeruginosa ATCC 9027 without affecting its growth. Scanning electron and atomic force microscopy showed architectural disruption of the biofilm when treated with the extract. This is the first report of the QQ and anti-biofilm activities of cis-9-octadecenoic acid isolated from any bacterium. It may have the potential to combat detrimental infections with P. aeruginosa. Further validation is required for any possible medical application. | Crow JA, Herring KL, Xie S, Borazjani A, Potter PM, Ross MK (2010)
Inhibition of carboxylesterase activity of THP1 monocytes/macrophages and recombinant human carboxylesterase 1 by oxysterols and fatty acids.
Biochimica et biophysica acta 1801, 31-41 [PubMed:19761868]
[show Abstract]
Two major isoforms of human carboxylesterases (CEs) are found in metabolically active tissues, CES1 and CES2. These hydrolytic enzymes are involved in xenobiotic and endobiotic metabolism. CES1 is abundantly expressed in human liver and monocytes/macrophages, including the THP1 cell line; CES2 is expressed in liver but not in monocytes/macrophages. The cholesteryl ester hydrolysis activity in human macrophages has been attributed to CES1. Here, we report the direct inhibitory effects of several endogenous oxysterols and fatty acids on the CE activity of THP1 monocytes/macrophages and recombinant human CES1 and CES2. Using THP1 whole-cell lysates we found: (1) 27-hydroxycholesterol (27-HC) is a potent inhibitor of carboxylesterase activity (IC50=33 nM); (2) 24(S),25-epoxycholesterol had moderate inhibitory activity (IC(50)=8.1 microM); and (3) cholesterol, 7-ketocholesterol, 22(R)-hydroxycholesterol, 24(S)-hydroxycholesterol, and 25-hydroxycholesterol each had little inhibitory activity. 27-HC was a partially noncompetitive inhibitor of recombinant CES1 (K(iapp)=10 nM) and impaired intracellular CES1 activity following treatment of intact THP1 cells. In contrast, recombinant CES2 activity was not inhibited by 27-HC, suggesting isoform-selective inhibition by 27-HC. Furthermore, unsaturated fatty acids were better inhibitors of CES1 activity than saturated fatty acids, while CES2 activity was unaffected by any fatty acid. Arachidonic acid (AA) was the most potent fatty acid inhibitor of recombinant CES1 and acted by a noncompetitive mechanism (K(iapp)=1.7 microM); when not complexed to albumin, exogenous AA penetrated intact THP1 cells and inhibited CES1. Inhibition results are discussed in light of recent structural models for CES1 that describe ligand binding sites separate from the active site. In addition, oxysterol-mediated inhibition of CES1 activity was demonstrated by pretreatment of human liver homogenates or intact THP1 cells with exogenous 27-HC, which resulted in significantly reduced hydrolysis of the pyrethroid insecticide bioresmethrin, a CES1-specific xenobiotic substrate. Collectively, these findings suggest that CE activity of recombinant CES1, cell lysates, and intact cells can be impaired by naturally occurring lipids, which may compromise the ability of CES1 to both detoxify environmental pollutants and metabolize endogenous compounds in vivo. | Terés S, Barceló-Coblijn G, Benet M, Alvarez R, Bressani R, Halver JE, Escribá PV (2008)
Oleic acid content is responsible for the reduction in blood pressure induced by olive oil.
Proceedings of the National Academy of Sciences of the United States of America 105, 13811-13816 [PubMed:18772370]
[show Abstract]
Numerous studies have shown that high olive oil intake reduces blood pressure (BP). These positive effects of olive oil have frequently been ascribed to its minor components, such as alpha-tocopherol, polyphenols, and other phenolic compounds that are not present in other oils. However, in this study we demonstrate that the hypotensive effect of olive oil is caused by its high oleic acid (OA) content (approximately 70-80%). We propose that olive oil intake increases OA levels in membranes, which regulates membrane lipid structure (H(II) phase propensity) in such a way as to control G protein-mediated signaling, causing a reduction in BP. This effect is in part caused by its regulatory action on G protein-associated cascades that regulate adenylyl cyclase and phospholipase C. In turn, the OA analogues, elaidic and stearic acids, had no hypotensive activity, indicating that the molecular mechanisms that link membrane lipid structure and BP regulation are very specific. Similarly, soybean oil (with low OA content) did not reduce BP. This study demonstrates that olive oil induces its hypotensive effects through the action of OA. | Lisitsyn DM, Razumovskii SD, Tishenin MA, Titov VN (2004)
Kinetic parameters of oxidation of individual fatty acids with ozone.
Bulletin of experimental biology and medicine 138, 457-459 [PubMed:15723125]
[show Abstract]
Using an original automated analyzer of double bonds we determined the rate constants for oxidation of saturated and unsaturated mono- and dienoic fatty acids (in vivo substrates for beta-oxidation in the mitochondria) by the ozone titration method. The rate constant for O(3) oxidation is maximum for oleic monoenoic acid, lower for dienoic linoleic, and very low for saturated palmitic acid. The rate constant for oxidation of oleic fatty acid, which by one order of magnitude surpasses that for oxidation of essential arachidonic acid, indicates that oleic acid is a leading in vivo acceptor of active O(2) species. By the rate of trapping active oxygen species and in the quantitative aspect, endogenously produced oleic acid can be regarded as the main biological antioxidant. | DeWitt C, Bebarta V (2004)
Botanical solvents.
Clinics in occupational and environmental medicine 4, 445-54, v-vi [PubMed:15325315]
[show Abstract]
Botanical, or plant-derived, solvents such as turpentine, pine oils, and various essential oils are used as environmentally acceptable alternatives to traditional solvents and degreasing agents. This article focuses on three lesser-known botanical solvents: limonene, oleic acid, and linoleic acid. Although data are limited, limonene, linoleic acid, and oleic acid are likely of low toxicity. Mild skin irritation may occur from exposure to these compounds, and oxidation products of limonene may produce dermal sensitization. Limonene, and possibly linoleic and oleic acids, may have irritative and bronchoconstrictive airway effects; however, data are scant and more studies are required. | Wulferink M, González J, Goebel C, Gleichmann E (2001)
T cells ignore aniline, a prohapten, but respond to its reactive metabolites generated by phagocytes: possible implications for the pathogenesis of toxic oil syndrome.
Chemical research in toxicology 14, 389-397 [PubMed:11304127]
[show Abstract]
The most basic arylamine, aniline, belongs to a class of compounds notorious for inducing allergic and autoimmune reactions. In 1981 in Spain, many people succumbed to toxic oil syndrome (TOS), a disease caused by ingestion of cooking oil contaminated with aniline. Indirect evidence points toward an immune pathogenesis of TOS driven by T lymphocytes, but it is unclear to which antigens these cells could react. Here, using the popliteal lymph node (PLN) assay in mice, we analyzed the sensitizing potential of aniline, its metabolites, and some of the aniline-coupled lipids detected in the contaminated cooking oil. Whereas aniline itself and its non-protein-reactive metabolites nitrobenzene, p-aminophenol and N-acetyl-p-aminophenol, failed to elicit PLN responses, its reactive metabolites nitrosobenzene and N-hydroxylaniline did. The aniline-coupled lipids, namely, linoleic anilide and linolenic anilide, and a mixture of fatty acid esters of 3-(N-phenylamino)-1,2-propanediol, all implicated in TOS, induced significant PLN responses, whereas the respective aniline-free lipids, linoleic acid, linolenic acid, and triolein, did not. Hence, the aniline moiety plays a crucial role in the immunogenicity of the aniline-coupled lipids of TOS. PLN responses to the reactive aniline metabolites and the one aniline-coupled lipid that was tested, linolenic anilide, were T-cell-dependent. Secondary PLN responses to nitrosobenzene were detectable not only after priming with nitrosobenzene but, in some experiments, also after priming with linolenic anilide. This suggests that the aniline moiety was cleaved from the aniline-coupled lipid and metabolized to the intermediate nitrosobenzene that generated the prospective neoantigens. Consistent with this, in lymphocyte proliferation tests in vitro, T cells primed to nitrosobenzene reacted in anamnestic fashion to white bone marrow cells (WBMCs) pulsed with aniline. Hence, we propose that aniline is a prohapten that can be metabolized by WBMCs, which form neoantigens that are recognized by T cells. The possible significance of these findings for the pathogenesis of TOS is discussed. | Marquet A, Larraga V, Diez JL, Amela C, Rodrigo J, Muñoz E, Pestaña A (1984)
Immunogenicity of fatty acid anilides in rabbits and the pathogenesis of the Spanish toxic oil syndrome.
Experientia 40, 977-980 [PubMed:6205897]
[show Abstract]
Fatty acid anilides, the major xenobiotic found in the cooking oils responsible for the Spanish toxic oil syndrome, are immunogenic for rabbits as ascertained by a skin test reaction, the characterization of specific antibodies against anilides and the immunofluorescent detection of 'anilide dependent antigens' in tissue slices from treated animals. | Weinbaum G, Panos C (1966)
Fatty acid distribution in normal and filamentous Escherichia coli.
Journal of bacteriology 92, 1576-1577 [PubMed:5332408] |
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2011-01-15
