(3S,4aS,6aR,8S,10S,10aR,10bS)-3-ethenyl-3,4a,7,7,10a-pentamethyl-2,5,6,6a,8,9,10,10b-octahydro-1H-benzo[f]chromene-8,10-diol

Details

• Internal ID: 2cdab5ea-7e25-48be-be5a-6d4d84ef4218
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (3S,4aS,6aR,8S,10S,10aR,10bS)-3-ethenyl-3,4a,7,7,10a-pentamethyl-2,5,6,6a,8,9,10,10b-octahydro-1H-benzo[f]chromene-8,10-diol
• SMILES (Canonical): CC1(C2CCC3(C(C2(C(CC1O)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@H](C[C@@H](C3(C)C)O)O)C)C)C=C
• InChI: InChI=1S/C20H34O3/c1-7-18(4)10-8-14-19(5,23-18)11-9-13-17(2,3)15(21)12-16(22)20(13,14)6/h7,13-16,21-22H,1,8-12H2,2-6H3/t13-,14-,15+,16+,18-,19+,20-/m1/s1
• InChI Key: ZBTCSVYVMYCROT-RUSOHIBLSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₄O₃
• Molecular Weight: 322.50 g/mol
• Exact Mass: 322.25079494 g/mol
• Topological Polar Surface Area (TPSA): 49.70 Ų
• XlogP: 3.40
• Atomic LogP (AlogP): 3.68
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9631	96.31%
Caco-2	+	0.5848	58.48%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Lysosomes	0.5255	52.55%
OATP2B1 inhibitior	-	0.8562	85.62%
OATP1B1 inhibitior	+	0.9150	91.50%
OATP1B3 inhibitior	+	0.9538	95.38%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.5600	56.00%
P-glycoprotein inhibitior	-	0.8209	82.09%
P-glycoprotein substrate	-	0.8927	89.27%
CYP3A4 substrate	+	0.6083	60.83%
CYP2C9 substrate	-	0.6262	62.62%
CYP2D6 substrate	-	0.6909	69.09%
CYP3A4 inhibition	-	0.6190	61.90%
CYP2C9 inhibition	-	0.8636	86.36%
CYP2C19 inhibition	-	0.7742	77.42%
CYP2D6 inhibition	-	0.9427	94.27%
CYP1A2 inhibition	-	0.7408	74.08%
CYP2C8 inhibition	-	0.7489	74.89%
CYP inhibitory promiscuity	-	0.8969	89.69%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6805	68.05%
Eye corrosion	-	0.9837	98.37%
Eye irritation	-	0.8762	87.62%
Skin irritation	-	0.5623	56.23%
Skin corrosion	-	0.9006	90.06%
Ames mutagenesis	-	0.8264	82.64%
Human Ether-a-go-go-Related Gene inhibition	+	0.6517	65.17%
Micronuclear	-	0.9500	95.00%
Hepatotoxicity	-	0.5959	59.59%
skin sensitisation	-	0.6810	68.10%
Respiratory toxicity	-	0.6222	62.22%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.5227	52.27%
Acute Oral Toxicity (c)	III	0.5533	55.33%
Estrogen receptor binding	+	0.6928	69.28%
Androgen receptor binding	-	0.5560	55.60%
Thyroid receptor binding	+	0.6909	69.09%
Glucocorticoid receptor binding	+	0.7361	73.61%
Aromatase binding	+	0.6796	67.96%
PPAR gamma	+	0.5246	52.46%
Honey bee toxicity	-	0.6568	65.68%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5800	58.00%
Fish aquatic toxicity	+	0.9472	94.72%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	95.96%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.18%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.09%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.04%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.32%	100.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.84%	92.94%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	82.04%	90.24%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.11%	97.25%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.42%	95.89%

Plants that contains it

• Chrozophora oblongifolia

Cross-Links

• PubChem: 11738797
• LOTUS: LTS0027251
• wikiData: Q105370840