(1S,4aS,4bR,8aR,10aR)-8a-hydroxy-7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-3,4,4b,5,6,9,10,10a-octahydro-2H-phenanthrene-1-carboxylic acid

Details

• Internal ID: dd81484e-2f06-490e-9d6a-498502df6547
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (1S,4aS,4bR,8aR,10aR)-8a-hydroxy-7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-3,4,4b,5,6,9,10,10a-octahydro-2H-phenanthrene-1-carboxylic acid
• SMILES (Canonical): CC12CCCC(C1CCC3(C2CCC(=C3)C(C)(C)O)O)(C)C(=O)O
• SMILES (Isomeric): C[C@]12CCC[C@]([C@@H]1CC[C@@]3([C@@H]2CCC(=C3)C(C)(C)O)O)(C)C(=O)O
• InChI: InChI=1S/C20H32O4/c1-17(2,23)13-6-7-15-18(3)9-5-10-19(4,16(21)22)14(18)8-11-20(15,24)12-13/h12,14-15,23-24H,5-11H2,1-4H3,(H,21,22)/t14-,15-,18+,19+,20-/m1/s1
• InChI Key: VBEKTMIFJPKWJA-PYIJOLGTSA-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): 77.80 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 3.52
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9943	99.43%
Caco-2	+	0.7996	79.96%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.8253	82.53%
OATP2B1 inhibitior	-	0.8619	86.19%
OATP1B1 inhibitior	+	0.8691	86.91%
OATP1B3 inhibitior	-	0.2654	26.54%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.5821	58.21%
BSEP inhibitior	+	0.7675	76.75%
P-glycoprotein inhibitior	-	0.8848	88.48%
P-glycoprotein substrate	-	0.7536	75.36%
CYP3A4 substrate	+	0.6122	61.22%
CYP2C9 substrate	-	0.6020	60.20%
CYP2D6 substrate	-	0.8813	88.13%
CYP3A4 inhibition	-	0.8382	83.82%
CYP2C9 inhibition	-	0.8967	89.67%
CYP2C19 inhibition	-	0.9152	91.52%
CYP2D6 inhibition	-	0.9460	94.60%
CYP1A2 inhibition	-	0.9054	90.54%
CYP2C8 inhibition	-	0.7087	70.87%
CYP inhibitory promiscuity	-	0.9420	94.20%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6644	66.44%
Eye corrosion	-	0.9930	99.30%
Eye irritation	-	0.8166	81.66%
Skin irritation	+	0.5720	57.20%
Skin corrosion	-	0.9693	96.93%
Ames mutagenesis	-	0.7170	71.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.6608	66.08%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	-	0.6297	62.97%
skin sensitisation	+	0.6067	60.67%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	-	0.6065	60.65%
Acute Oral Toxicity (c)	III	0.8343	83.43%
Estrogen receptor binding	+	0.7582	75.82%
Androgen receptor binding	+	0.5831	58.31%
Thyroid receptor binding	+	0.7322	73.22%
Glucocorticoid receptor binding	+	0.8045	80.45%
Aromatase binding	+	0.6336	63.36%
PPAR gamma	+	0.6489	64.89%
Honey bee toxicity	-	0.9183	91.83%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9930	99.30%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.93%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.66%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.36%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.42%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.66%	94.45%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	83.03%	93.04%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.12%	100.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.33%	100.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.35%	100.00%

Plants that contains it

• Pinus armandii

Cross-Links

• PubChem: 163195456
• LOTUS: LTS0264135
• wikiData: Q105283195