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

Details

• Internal ID: f047b35f-f521-4381-b98e-2fa4425c661f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (3R,4aR,6aS,8R,9S,10aS,10bR)-3-ethenyl-3,4a,7,7,10a-pentamethyl-2,5,6,6a,8,9,10,10b-octahydro-1H-benzo[f]chromene-8,9-diol
• SMILES (Canonical): CC1(C2CCC3(C(C2(CC(C1O)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@@H]([C@@H](C3(C)C)O)O)C)C)C=C
• InChI: InChI=1S/C20H34O3/c1-7-18(4)10-8-15-19(5)12-13(21)16(22)17(2,3)14(19)9-11-20(15,6)23-18/h7,13-16,21-22H,1,8-12H2,2-6H3/t13-,14+,15+,16-,18-,19-,20+/m0/s1
• InChI Key: KELRYOHCDUVSFH-WACYPHKTSA-N
• Popularity: 0 references 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	+	0.9708	97.08%
Caco-2	+	0.5353	53.53%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6242	62.42%
OATP2B1 inhibitior	-	0.8560	85.60%
OATP1B1 inhibitior	+	0.9229	92.29%
OATP1B3 inhibitior	+	0.9444	94.44%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	-	0.6617	66.17%
P-glycoprotein inhibitior	-	0.8557	85.57%
P-glycoprotein substrate	-	0.8990	89.90%
CYP3A4 substrate	+	0.6005	60.05%
CYP2C9 substrate	-	0.6206	62.06%
CYP2D6 substrate	-	0.7190	71.90%
CYP3A4 inhibition	-	0.7786	77.86%
CYP2C9 inhibition	-	0.8988	89.88%
CYP2C19 inhibition	-	0.7098	70.98%
CYP2D6 inhibition	-	0.9479	94.79%
CYP1A2 inhibition	-	0.8089	80.89%
CYP2C8 inhibition	-	0.8007	80.07%
CYP inhibitory promiscuity	-	0.9623	96.23%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.7040	70.40%
Eye corrosion	-	0.9852	98.52%
Eye irritation	-	0.9332	93.32%
Skin irritation	-	0.5743	57.43%
Skin corrosion	-	0.9063	90.63%
Ames mutagenesis	-	0.8000	80.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4555	45.55%
Micronuclear	-	0.9600	96.00%
Hepatotoxicity	-	0.6758	67.58%
skin sensitisation	-	0.6700	67.00%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	+	0.5748	57.48%
Acute Oral Toxicity (c)	III	0.6870	68.70%
Estrogen receptor binding	+	0.6445	64.45%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	+	0.6989	69.89%
Glucocorticoid receptor binding	+	0.8132	81.32%
Aromatase binding	+	0.6520	65.20%
PPAR gamma	+	0.5621	56.21%
Honey bee toxicity	-	0.8105	81.05%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.6000	60.00%
Fish aquatic toxicity	+	0.9637	96.37%

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	96.72%	91.11%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.60%	100.00%
CHEMBL4040	P28482	MAP kinase ERK2	87.40%	83.82%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.02%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.83%	96.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.15%	92.94%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.98%	95.89%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	82.29%	82.69%
CHEMBL259	P32245	Melanocortin receptor 4	80.34%	95.38%
CHEMBL221	P23219	Cyclooxygenase-1	80.15%	90.17%

Plants that contains it

• Halocarpus kirkii

Cross-Links

• PubChem: 163020559
• LOTUS: LTS0143254
• wikiData: Q105140031