(3R,4aR,6aS,9S,10aS,10bR)-3-ethenyl-3,4a,7,7,10a-pentamethyl-2,5,6,6a,8,9,10,10b-octahydro-1H-benzo[f]chromen-9-ol

Details

• Internal ID: 58eb6f71-d86c-4b57-8118-80da537b0d53
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (3R,4aR,6aS,9S,10aS,10bR)-3-ethenyl-3,4a,7,7,10a-pentamethyl-2,5,6,6a,8,9,10,10b-octahydro-1H-benzo[f]chromen-9-ol
• SMILES (Canonical): CC1(CC(CC2(C1CCC3(C2CCC(O3)(C)C=C)C)C)O)C
• SMILES (Isomeric): C[C@@]1(CC[C@H]2[C@](O1)(CC[C@@H]3[C@@]2(C[C@H](CC3(C)C)O)C)C)C=C
• InChI: InChI=1S/C20H34O2/c1-7-18(4)10-8-16-19(5)13-14(21)12-17(2,3)15(19)9-11-20(16,6)22-18/h7,14-16,21H,1,8-13H2,2-6H3/t14-,15-,16+,18-,19-,20+/m0/s1
• InChI Key: YUPMLGNDHOQHCD-JFVPRCSHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₄O₂
• Molecular Weight: 306.50 g/mol
• Exact Mass: 306.255880323 g/mol
• Topological Polar Surface Area (TPSA): 29.50 Ų
• XlogP: 4.40
• Atomic LogP (AlogP): 4.71
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9935	99.35%
Caco-2	+	0.7208	72.08%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Lysosomes	0.4012	40.12%
OATP2B1 inhibitior	-	0.8553	85.53%
OATP1B1 inhibitior	+	0.9246	92.46%
OATP1B3 inhibitior	+	0.9400	94.00%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	-	0.6982	69.82%
P-glycoprotein inhibitior	-	0.8276	82.76%
P-glycoprotein substrate	-	0.8910	89.10%
CYP3A4 substrate	+	0.6030	60.30%
CYP2C9 substrate	-	0.6262	62.62%
CYP2D6 substrate	-	0.6909	69.09%
CYP3A4 inhibition	-	0.7827	78.27%
CYP2C9 inhibition	-	0.8707	87.07%
CYP2C19 inhibition	-	0.6447	64.47%
CYP2D6 inhibition	-	0.9478	94.78%
CYP1A2 inhibition	-	0.7715	77.15%
CYP2C8 inhibition	-	0.7434	74.34%
CYP inhibitory promiscuity	-	0.9646	96.46%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.7022	70.22%
Eye corrosion	-	0.9626	96.26%
Eye irritation	-	0.8497	84.97%
Skin irritation	-	0.6048	60.48%
Skin corrosion	-	0.9347	93.47%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5684	56.84%
Micronuclear	-	0.9600	96.00%
Hepatotoxicity	-	0.6375	63.75%
skin sensitisation	+	0.5812	58.12%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	+	0.5333	53.33%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	+	0.6863	68.63%
Acute Oral Toxicity (c)	III	0.8453	84.53%
Estrogen receptor binding	+	0.6670	66.70%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	+	0.6702	67.02%
Glucocorticoid receptor binding	+	0.7433	74.33%
Aromatase binding	+	0.5701	57.01%
PPAR gamma	-	0.5413	54.13%
Honey bee toxicity	-	0.7511	75.11%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.8801	88.01%

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	94.50%	91.11%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.10%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.62%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.61%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.24%	96.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.19%	92.94%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.50%	95.89%
CHEMBL259	P32245	Melanocortin receptor 4	81.35%	95.38%
CHEMBL5600	P27448	Serine/threonine-protein kinase c-TAK1	80.93%	88.81%
CHEMBL1907601	P11802	Cyclin-dependent kinase 4/cyclin D1	80.62%	98.99%

Plants that contains it

• Manoao colensoi
• Sideritis perfoliata

Cross-Links

• PubChem: 21593578
• LOTUS: LTS0097539
• wikiData: Q105364296