(3R,4aR,6aR,8S,9aS,9bR)-3-ethenyl-8-hydroxy-3,4a,7,7,9a-pentamethyl-2,5,6,6a,9,9b-hexahydro-1H-cyclopenta[f]chromene-8-carboxylic acid

Details

• Internal ID: fc96b31e-af98-4a08-b129-bb1cb1e2f382
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (3R,4aR,6aR,8S,9aS,9bR)-3-ethenyl-8-hydroxy-3,4a,7,7,9a-pentamethyl-2,5,6,6a,9,9b-hexahydro-1H-cyclopenta[f]chromene-8-carboxylic acid
• SMILES (Canonical): CC1(C2CCC3(C(C2(CC1(C(=O)O)O)C)CCC(O3)(C)C=C)C)C
• SMILES (Isomeric): C[C@@]1(CC[C@H]2[C@](O1)(CC[C@@H]3[C@@]2(C[C@](C3(C)C)(C(=O)O)O)C)C)C=C
• InChI: InChI=1S/C20H32O4/c1-7-17(4)10-8-14-18(5)12-20(23,15(21)22)16(2,3)13(18)9-11-19(14,6)24-17/h7,13-14,23H,1,8-12H2,2-6H3,(H,21,22)/t13-,14+,17-,18-,19+,20+/m0/s1
• InChI Key: KIGVAOKEQFQUJB-AFVQWYAQSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₂O₄
• Molecular Weight: 336.50 g/mol
• Exact Mass: 336.23005950 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 3.40
• Atomic LogP (AlogP): 3.78
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9424	94.24%
Caco-2	+	0.6707	67.07%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7351	73.51%
OATP2B1 inhibitior	-	0.8590	85.90%
OATP1B1 inhibitior	+	0.9234	92.34%
OATP1B3 inhibitior	+	0.8307	83.07%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7571	75.71%
BSEP inhibitior	-	0.4943	49.43%
P-glycoprotein inhibitior	-	0.7962	79.62%
P-glycoprotein substrate	-	0.8714	87.14%
CYP3A4 substrate	+	0.6065	60.65%
CYP2C9 substrate	-	0.7953	79.53%
CYP2D6 substrate	-	0.8700	87.00%
CYP3A4 inhibition	-	0.7107	71.07%
CYP2C9 inhibition	-	0.9217	92.17%
CYP2C19 inhibition	-	0.8339	83.39%
CYP2D6 inhibition	-	0.9572	95.72%
CYP1A2 inhibition	-	0.7988	79.88%
CYP2C8 inhibition	-	0.6671	66.71%
CYP inhibitory promiscuity	-	0.9811	98.11%
UGT catelyzed	-	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7021	70.21%
Eye corrosion	-	0.9911	99.11%
Eye irritation	-	0.9053	90.53%
Skin irritation	+	0.5862	58.62%
Skin corrosion	-	0.9032	90.32%
Ames mutagenesis	-	0.7600	76.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	-	0.8900	89.00%
Hepatotoxicity	+	0.5001	50.01%
skin sensitisation	-	0.7781	77.81%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	+	0.6257	62.57%
Acute Oral Toxicity (c)	III	0.5951	59.51%
Estrogen receptor binding	+	0.7221	72.21%
Androgen receptor binding	+	0.6466	64.66%
Thyroid receptor binding	+	0.6645	66.45%
Glucocorticoid receptor binding	+	0.7555	75.55%
Aromatase binding	+	0.7023	70.23%
PPAR gamma	-	0.5268	52.68%
Honey bee toxicity	-	0.8944	89.44%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	+	0.9888	98.88%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.67%	91.11%
CHEMBL4246	P42680	Tyrosine-protein kinase TEC	90.25%	82.05%
CHEMBL340	P08684	Cytochrome P450 3A4	88.90%	91.19%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.20%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.75%	96.09%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	84.01%	96.38%
CHEMBL5028	O14672	ADAM10	82.54%	97.50%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	82.14%	93.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.95%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.84%	86.33%

Plants that contains it

• Manoao colensoi

Cross-Links

• PubChem: 101600189
• LOTUS: LTS0065241
• wikiData: Q105141506