(3R,5R,7R,8R,9S,10S,12S,13R,14S,17R)-17-[(2S)-5-hydroxypentan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,7,12-triol

Details

• Internal ID: 5cb995a5-44f6-44b7-af96-93411a302132
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Bile acids, alcohols and derivatives > Hydroxy bile acids, alcohols and derivatives > Tetrahydroxy bile acids, alcohols and derivatives
• IUPAC Name: (3R,5R,7R,8R,9S,10S,12S,13R,14S,17R)-17-[(2S)-5-hydroxypentan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,7,12-triol
• SMILES (Canonical): CC(CCCO)C1CCC2C1(C(CC3C2C(CC4C3(CCC(C4)O)C)O)O)C
• SMILES (Isomeric): C[C@@H](CCCO)[C@H]1CC[C@@H]2[C@@]1([C@H](C[C@H]3[C@H]2[C@@H](C[C@@H]4[C@@]3(CC[C@H](C4)O)C)O)O)C
• InChI: InChI=1S/C24H42O4/c1-14(5-4-10-25)17-6-7-18-22-19(13-21(28)24(17,18)3)23(2)9-8-16(26)11-15(23)12-20(22)27/h14-22,25-28H,4-13H2,1-3H3/t14-,15+,16+,17+,18-,19-,20+,21-,22-,23-,24+/m0/s1
• InChI Key: BMSROUVLRAQRBY-LJRDGOJWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₄₂O₄
• Molecular Weight: 394.60 g/mol
• Exact Mass: 394.30830982 g/mol
• Topological Polar Surface Area (TPSA): 80.90 Ų
• XlogP: 3.80
• Atomic LogP (AlogP): 3.36
• H-Bond Acceptor: 4
• H-Bond Donor: 4
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9890	98.90%
Caco-2	-	0.6614	66.14%
Blood Brain Barrier	-	0.5365	53.65%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.5605	56.05%
OATP2B1 inhibitior	-	0.6115	61.15%
OATP1B1 inhibitior	+	0.7586	75.86%
OATP1B3 inhibitior	+	0.9414	94.14%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6936	69.36%
BSEP inhibitior	-	0.6129	61.29%
P-glycoprotein inhibitior	-	0.6090	60.90%
P-glycoprotein substrate	+	0.5986	59.86%
CYP3A4 substrate	+	0.7266	72.66%
CYP2C9 substrate	-	0.6248	62.48%
CYP2D6 substrate	-	0.6942	69.42%
CYP3A4 inhibition	-	0.6962	69.62%
CYP2C9 inhibition	-	0.8577	85.77%
CYP2C19 inhibition	-	0.9401	94.01%
CYP2D6 inhibition	-	0.9652	96.52%
CYP1A2 inhibition	-	0.7754	77.54%
CYP2C8 inhibition	-	0.6491	64.91%
CYP inhibitory promiscuity	-	0.8855	88.55%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.7451	74.51%
Eye corrosion	-	0.9930	99.30%
Eye irritation	-	0.8820	88.20%
Skin irritation	-	0.5499	54.99%
Skin corrosion	-	0.9674	96.74%
Ames mutagenesis	-	0.5224	52.24%
Human Ether-a-go-go-Related Gene inhibition	-	0.5420	54.20%
Micronuclear	-	0.9800	98.00%
Hepatotoxicity	+	0.5702	57.02%
skin sensitisation	-	0.8708	87.08%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.5928	59.28%
Acute Oral Toxicity (c)	III	0.7512	75.12%
Estrogen receptor binding	+	0.6482	64.82%
Androgen receptor binding	+	0.6644	66.44%
Thyroid receptor binding	+	0.7198	71.98%
Glucocorticoid receptor binding	+	0.8682	86.82%
Aromatase binding	+	0.7045	70.45%
PPAR gamma	-	0.5175	51.75%
Honey bee toxicity	-	0.8010	80.10%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6655	66.55%
Fish aquatic toxicity	+	0.9211	92.11%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	870 nM	EC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.08%	97.25%
CHEMBL226	P30542	Adenosine A1 receptor	97.09%	95.93%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.09%	96.09%
CHEMBL237	P41145	Kappa opioid receptor	96.06%	98.10%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.55%	97.09%
CHEMBL4394	Q9NYA1	Sphingosine kinase 1	90.51%	96.03%
CHEMBL242	Q92731	Estrogen receptor beta	90.39%	98.35%
CHEMBL238	Q01959	Dopamine transporter	89.94%	95.88%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	89.84%	95.89%
CHEMBL233	P35372	Mu opioid receptor	89.58%	97.93%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	89.57%	97.29%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.97%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.53%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.00%	100.00%
CHEMBL2581	P07339	Cathepsin D	87.34%	98.95%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	87.20%	95.58%
CHEMBL2996	Q05655	Protein kinase C delta	86.63%	97.79%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	86.20%	92.86%
CHEMBL236	P41143	Delta opioid receptor	86.09%	99.35%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	85.67%	89.05%
CHEMBL5103	Q969S8	Histone deacetylase 10	85.50%	90.08%
CHEMBL3837	P07711	Cathepsin L	85.48%	96.61%
CHEMBL2179	P04062	Beta-glucocerebrosidase	84.52%	85.31%
CHEMBL4227	P25090	Lipoxin A4 receptor	84.45%	100.00%
CHEMBL1871	P10275	Androgen Receptor	84.35%	96.43%
CHEMBL1937	Q92769	Histone deacetylase 2	83.83%	94.75%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	83.61%	82.69%
CHEMBL221	P23219	Cyclooxygenase-1	82.41%	90.17%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.16%	90.71%
CHEMBL299	P17252	Protein kinase C alpha	82.06%	98.03%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.73%	95.89%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.72%	100.00%
CHEMBL2514	O95665	Neurotensin receptor 2	81.49%	100.00%
CHEMBL4588	P22894	Matrix metalloproteinase 8	81.13%	94.66%
CHEMBL2885	P07451	Carbonic anhydrase III	80.73%	87.45%
CHEMBL3045	P05771	Protein kinase C beta	80.62%	97.63%
CHEMBL4123	P30989	Neurotensin receptor 1	80.56%	96.67%
CHEMBL2140	P48775	Tryptophan 2,3-dioxygenase	80.46%	98.46%
CHEMBL1907594	P30926	Neuronal acetylcholine receptor; alpha3/beta4	80.15%	97.23%
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	80.10%	92.78%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 96563175
• LOTUS: LTS0036503
• wikiData: Q104938540