2-[(1R,2S,3S)-3-[(2S,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexoxy]-2-[(E)-pent-2-enyl]cyclopentyl]acetic acid

Details

• Internal ID: a581b7da-f09a-44af-9094-3d2ee2be1411
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Lineolic acids and derivatives > Jasmonic acids
• IUPAC Name: 2-[(1R,2S,3S)-3-[(2S,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexoxy]-2-[(E)-pent-2-enyl]cyclopentyl]acetic acid
• SMILES (Canonical): CCC=CCC1C(CCC1OCC(C(C(C(CO)O)O)O)O)CC(=O)O
• SMILES (Isomeric): CC/C=C/C[C@H]1[C@H](CC[C@@H]1OC[C@@H]([C@@H]([C@@H]([C@@H](CO)O)O)O)O)CC(=O)O
• InChI: InChI=1S/C18H32O8/c1-2-3-4-5-12-11(8-16(22)23)6-7-15(12)26-10-14(21)18(25)17(24)13(20)9-19/h3-4,11-15,17-21,24-25H,2,5-10H2,1H3,(H,22,23)/b4-3+/t11-,12+,13-,14+,15+,17-,18+/m1/s1
• InChI Key: LUKIHEAXSOXOMC-GSXBPAGWSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₃₂O₈
• Molecular Weight: 376.40 g/mol
• Exact Mass: 376.20971797 g/mol
• Topological Polar Surface Area (TPSA): 148.00 Ų
• XlogP: -0.70
• Atomic LogP (AlogP): -0.34
• H-Bond Acceptor: 7
• H-Bond Donor: 6
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6950	69.50%
Caco-2	-	0.8233	82.33%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.8333	83.33%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9069	90.69%
OATP1B3 inhibitior	+	0.9423	94.23%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7588	75.88%
BSEP inhibitior	-	0.9039	90.39%
P-glycoprotein inhibitior	-	0.8429	84.29%
P-glycoprotein substrate	-	0.6404	64.04%
CYP3A4 substrate	+	0.5409	54.09%
CYP2C9 substrate	-	0.5894	58.94%
CYP2D6 substrate	-	0.8704	87.04%
CYP3A4 inhibition	-	0.9517	95.17%
CYP2C9 inhibition	-	0.9106	91.06%
CYP2C19 inhibition	-	0.8565	85.65%
CYP2D6 inhibition	-	0.8960	89.60%
CYP1A2 inhibition	-	0.7729	77.29%
CYP2C8 inhibition	-	0.8512	85.12%
CYP inhibitory promiscuity	-	0.9553	95.53%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.7723	77.23%
Eye corrosion	-	0.9947	99.47%
Eye irritation	-	0.9826	98.26%
Skin irritation	-	0.7595	75.95%
Skin corrosion	-	0.9620	96.20%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6599	65.99%
Micronuclear	-	0.9400	94.00%
Hepatotoxicity	-	0.7375	73.75%
skin sensitisation	-	0.8602	86.02%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.8288	82.88%
Acute Oral Toxicity (c)	III	0.6115	61.15%
Estrogen receptor binding	+	0.6999	69.99%
Androgen receptor binding	-	0.5900	59.00%
Thyroid receptor binding	-	0.5192	51.92%
Glucocorticoid receptor binding	-	0.4912	49.12%
Aromatase binding	-	0.5356	53.56%
PPAR gamma	+	0.5758	57.58%
Honey bee toxicity	-	0.9281	92.81%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.7900	79.00%
Fish aquatic toxicity	+	0.7259	72.59%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.58%	96.09%
CHEMBL2581	P07339	Cathepsin D	94.19%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	91.17%	90.17%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.05%	99.17%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.88%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.68%	97.09%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	85.66%	96.47%
CHEMBL340	P08684	Cytochrome P450 3A4	83.45%	91.19%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	81.84%	97.29%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	81.31%	96.38%
CHEMBL2664	P23526	Adenosylhomocysteinase	80.83%	86.67%

Plants that contains it

• Cucurbita pepo

Cross-Links

• PubChem: 163193439
• LOTUS: LTS0140116
• wikiData: Q105157508