(-)-leukotoxin B

Details

• Internal ID: 498bb76c-1a6b-44a6-b6d8-6d800e970836
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty acids and conjugates > Long-chain fatty acids
• IUPAC Name: (Z)-11-[(2R,3S)-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+/m0/s1
• InChI Key: CCPPLLJZDQAOHD-BEBBCNLGSA-N
• Popularity: 52 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
• Atomic LogP (AlogP): 5.10
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 14

Synonyms

• (-)-vernolic acid
• Vernolic acid, cis-(-)-
• Vernolic acid
• Vernolic acid (-)-form [MI]
• (-)-Vernolsaeure
• 32381-42-3
• UNII-FF156V3318
• (12R,13S)-(-)-12,13-Epoxyoleic acid
• 12,13-epoxylinoleic acid
• FF156V3318
• 9-Undecenoic acid, 11-((2R,3S)-3-pentyl-2-oxiranyl)-, (9Z)-
• (-)-12(R),13(S)-vernolic acid
• cis-12S,13R,-ep, 9c-18:1
• (9Z)-11-[(2R,3S)-3-pentyloxiran-2-yl]undec-9-enoic acid
• cis-12,13-Epoxy-cis-9-octadecenoic acid
• (12R,13S)-(9Z)-12,13-Epoxyoctadecenoic acid
• (9Z)-(12R,13S)-12,13-Epoxyoctadecenoic acid
• cis-12,13-epoxy-9(z)-octadecenoic acid
• cis-(-)-vernolic acid
• SCHEMBL2507620
• CHEBI:38300
• DTXSID001205124
• 17966-13-1
• 12R,13S-epoxy-9(Z)-octadecenoic acid
• C08368
• Q7922031
• (9Z)-11-[(2R,3S)-3-Pentyl-2-oxiranyl]-9-undecenoic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9872	98.72%
Caco-2	+	0.5914	59.14%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.4953	49.53%
OATP2B1 inhibitior	-	0.8503	85.03%
OATP1B1 inhibitior	+	0.6891	68.91%
OATP1B3 inhibitior	+	0.8947	89.47%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	-	0.7516	75.16%
P-glycoprotein inhibitior	-	0.8250	82.50%
P-glycoprotein substrate	-	0.9006	90.06%
CYP3A4 substrate	-	0.5227	52.27%
CYP2C9 substrate	+	0.6009	60.09%
CYP2D6 substrate	-	0.8720	87.20%
CYP3A4 inhibition	-	0.7256	72.56%
CYP2C9 inhibition	-	0.8240	82.40%
CYP2C19 inhibition	-	0.7613	76.13%
CYP2D6 inhibition	-	0.9390	93.90%
CYP1A2 inhibition	-	0.5957	59.57%
CYP2C8 inhibition	-	0.7983	79.83%
CYP inhibitory promiscuity	-	0.9206	92.06%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8515	85.15%
Carcinogenicity (trinary)	Non-required	0.6707	67.07%
Eye corrosion	-	0.8483	84.83%
Eye irritation	-	0.5000	50.00%
Skin irritation	+	0.6889	68.89%
Skin corrosion	-	0.7004	70.04%
Ames mutagenesis	-	0.9900	99.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7452	74.52%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.7196	71.96%
skin sensitisation	+	0.5000	50.00%
Respiratory toxicity	-	0.5889	58.89%
Reproductive toxicity	-	0.5746	57.46%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	-	0.6582	65.82%
Acute Oral Toxicity (c)	III	0.4929	49.29%
Estrogen receptor binding	-	0.6170	61.70%
Androgen receptor binding	-	0.7252	72.52%
Thyroid receptor binding	+	0.5423	54.23%
Glucocorticoid receptor binding	-	0.6874	68.74%
Aromatase binding	-	0.7895	78.95%
PPAR gamma	+	0.7853	78.53%
Honey bee toxicity	-	0.9751	97.51%
Biodegradation	+	0.7750	77.50%
Crustacea aquatic toxicity	+	0.8900	89.00%
Fish aquatic toxicity	+	0.9593	95.93%

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
• Euphorbia lagascae
• Mucuna pruriens
• Oryza sativa
• Pithecellobium dulce
• Plectranthus mollis
• Syzygium cumini
• Tabebuia aurea
• Turnera ulmifolia
• Vernonia galamensis subsp. galamensis

Cross-Links

• PubChem: 5281128
• LOTUS: LTS0159408
• wikiData: Q7922031