(3R,4aS,6aR,10aR,10bR)-3-ethenyl-3-(hydroxymethyl)-4a,7,7,10a-tetramethyl-1,2,5,6,6a,9,10,10b-octahydrobenzo[f]chromen-8-one

Details

• Internal ID: df848e76-9082-4fe9-b99c-f87cadd9fc35
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (3R,4aS,6aR,10aR,10bR)-3-ethenyl-3-(hydroxymethyl)-4a,7,7,10a-tetramethyl-1,2,5,6,6a,9,10,10b-octahydrobenzo[f]chromen-8-one
• SMILES (Canonical): CC1(C2CCC3(C(C2(CCC1=O)C)CCC(O3)(CO)C=C)C)C
• SMILES (Isomeric): C[C@@]12CCC(=O)C([C@@H]1CC[C@]3([C@@H]2CC[C@](O3)(CO)C=C)C)(C)C
• InChI: InChI=1S/C20H32O3/c1-6-20(13-21)12-8-15-18(4)10-9-16(22)17(2,3)14(18)7-11-19(15,5)23-20/h6,14-15,21H,1,7-13H2,2-5H3/t14-,15+,18+,19-,20-/m0/s1
• InChI Key: VGHBPRLIBBSXGG-OGIZJXODSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₂O₃
• Molecular Weight: 320.50 g/mol
• Exact Mass: 320.23514488 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 3.89
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9817	98.17%
Caco-2	+	0.7475	74.75%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7633	76.33%
OATP2B1 inhibitior	-	0.8611	86.11%
OATP1B1 inhibitior	+	0.9027	90.27%
OATP1B3 inhibitior	+	0.9198	91.98%
MATE1 inhibitior	-	0.9812	98.12%
OCT2 inhibitior	+	0.5500	55.00%
BSEP inhibitior	+	0.7495	74.95%
P-glycoprotein inhibitior	-	0.7795	77.95%
P-glycoprotein substrate	-	0.9043	90.43%
CYP3A4 substrate	+	0.5674	56.74%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8025	80.25%
CYP3A4 inhibition	-	0.5482	54.82%
CYP2C9 inhibition	-	0.7339	73.39%
CYP2C19 inhibition	-	0.7376	73.76%
CYP2D6 inhibition	-	0.9478	94.78%
CYP1A2 inhibition	-	0.7544	75.44%
CYP2C8 inhibition	-	0.7919	79.19%
CYP inhibitory promiscuity	-	0.9130	91.30%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.7297	72.97%
Eye corrosion	-	0.9857	98.57%
Eye irritation	-	0.9152	91.52%
Skin irritation	-	0.6984	69.84%
Skin corrosion	-	0.9447	94.47%
Ames mutagenesis	-	0.6070	60.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.5415	54.15%
Micronuclear	-	0.9400	94.00%
Hepatotoxicity	-	0.7449	74.49%
skin sensitisation	-	0.7756	77.56%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.5711	57.11%
Acute Oral Toxicity (c)	III	0.7265	72.65%
Estrogen receptor binding	+	0.6337	63.37%
Androgen receptor binding	-	0.4818	48.18%
Thyroid receptor binding	+	0.6394	63.94%
Glucocorticoid receptor binding	+	0.8008	80.08%
Aromatase binding	+	0.7367	73.67%
PPAR gamma	-	0.5304	53.04%
Honey bee toxicity	-	0.8549	85.49%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9572	95.72%

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	94.48%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.29%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.16%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.45%	95.56%
CHEMBL1937	Q92769	Histone deacetylase 2	83.64%	94.75%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.75%	96.09%
CHEMBL2581	P07339	Cathepsin D	82.59%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.43%	97.25%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.46%	99.23%

Plants that contains it

• Excoecaria agallocha

Cross-Links

• PubChem: 15213872
• LOTUS: LTS0264294
• wikiData: Q105285807