(9Z)-(12S,13R)-12,13-Epoxyoctadecenoic acid

Details

• Internal ID: af16447e-c178-41f5-b771-85d372cf29f7
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty acids and conjugates > Long-chain fatty acids
• IUPAC Name: (Z)-11-[(2S,3R)-3-pentyloxiran-2-yl]undec-9-enoic acid
• SMILES (Canonical): CCCCCC1C(O1)CC=CCCCCCCCC(=O)O
• SMILES (Isomeric): CCCCC[C@@H]1[C@@H](O1)C/C=C\CCCCCCCC(=O)O
• InChI: InChI=1S/C18H32O3/c1-2-3-10-13-16-17(21-16)14-11-8-6-4-5-7-9-12-15-18(19)20/h8,11,16-17H,2-7,9-10,12-15H2,1H3,(H,19,20)/b11-8-/t16-,17+/m1/s1
• InChI Key: CCPPLLJZDQAOHD-GJGKEFFFSA-N
• Popularity: 268 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₃₂O₃
• Molecular Weight: 296.40 g/mol
• Exact Mass: 296.23514488 g/mol
• Topological Polar Surface Area (TPSA): 49.80 Ų
• XlogP: 5.60

Synonyms

• 503-07-1
• (+)-vernolic acid
• Vernoleate
• Leukotoxin B
• Vernolic acid (+)-form
• isoleukotoxin
• UNII-FR42854EPW
• 12S,13R-EpOME
• cis-12,13-Epoxyoleic acid
• cis-12-Epoxyoctadeca-cis-9-enoic acid
• FR42854EPW
• Vernolic acid, cis-(+/-)-
• (9Z)-(12S,13R)-12,13-Epoxyoctadecenoic acid
• cis-12-Epoxyoctadeca-cis-9-enoate
• (+/-)12(13)-EpOME
• 4S5JF40ZOQ
• 17966-13-1
• 12S,13R-epoxy-9Z-octadecenoic acid
• (Z)-11-[(2S,3R)-3-pentyloxiran-2-yl]undec-9-enoic acid
• 9-Undecenoic acid, 11-((2R,3S)-3-pentyl-2-oxiranyl)-, (9Z)-rel-
• 9-Undecenoic acid, 11-(3-pentyloxiranyl)-, (2S-(2alpha(Z),3alpha))-
• UNII-4S5JF40ZOQ
• Vernolic acid, cis-(+)-
• iso-Leukotoxin
• (+)-Vernolsaeure
• cis-12,13-epoxy-9(z)-octadecenoic acid
• (+)-leukotoxin B
• VERNOLEIC ACID
• cis-(+)-vernolic acid
• (+/-)-Vernolic Acid
• SCHEMBL55116
• CHEBI:27706
• DTXSID40895851
• CCPPLLJZDQAOHD-GJGKEFFFSA-N
• 9-Undecenoic acid, 11-(3-pentyloxiranyl)-, (2alpha(Z),3alpha)-
• LMFA02000282
• (+)-12(S),13(R)-vernolic acid
• VERNOLIC ACID (+)-FORM [MI]
• SR-01000946972
• (+)-12,13-EPOXY-9-CIS-OCTADECENOIC ACID
• SR-01000946972-1
• Q28530676
• CIS-(+)-12,13-EPOXYOCTADEC-CIS-9-ENOIC ACID
• OCTADEC-CIS-(+)-12,13-EPOXY-CIS-9-ENOIC ACID
• OLEIC ACID, 12,13-EPOXY-, (12S,13R)-(+)-
• (9Z)-11-[(2S,3R)-3-pentyloxiran-2-yl]undec-9-enoic acid
• 9-UNDECENOIC ACID, 11-((2S,3R)-3-PENTYL-2-OXIRANYL)-, (9Z)-
• 9-UNDECENOIC ACID, 11-(3-PENTYLOXIRANYL)-, (2.ALPHA.(Z),3.ALPHA.)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3060	Q9Y345	Glycine transporter 2	98.13%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.49%	96.09%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	93.26%	92.08%
CHEMBL2581	P07339	Cathepsin D	93.13%	98.95%
CHEMBL1781	P11387	DNA topoisomerase I	92.42%	97.00%
CHEMBL230	P35354	Cyclooxygenase-2	92.04%	89.63%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	88.86%	96.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.15%	91.11%
CHEMBL5255	O00206	Toll-like receptor 4	87.92%	92.50%
CHEMBL3401	O75469	Pregnane X receptor	86.25%	94.73%
CHEMBL2001	Q9H244	Purinergic receptor P2Y12	84.97%	96.00%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	82.94%	89.34%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	82.31%	97.29%
CHEMBL221	P23219	Cyclooxygenase-1	81.26%	90.17%

Plants that contains it

• Abelmoschus esculentus
• Amaranthus cruentus
• Baccharoides anthelmintica
• Euphorbia lagascae
• Galeopsis bifida
• Mucuna pruriens
• Oryza sativa
• Pithecellobium dulce
• Plectranthus mollis
• Syzygium cumini
• Tabebuia aurea
• Turnera ulmifolia
• Vernonia galamensis subsp. galamensis

Cross-Links

• PubChem: 6449780
• LOTUS: LTS0163877
• wikiData: Q28530676