(2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-17-[(2S,5R)-2,5,6-trihydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one

Details

• Internal ID: 6d2420e3-f547-4e1f-978c-7ab5c1de58f0
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Bile acids, alcohols and derivatives > Hydroxy bile acids, alcohols and derivatives
• IUPAC Name: (2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-17-[(2S,5R)-2,5,6-trihydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
• SMILES (Canonical): CC12CCC3C(=CC(=O)C4C3(CC(C(C4)O)O)C)C1(CCC2C(C)(CCC(C(C)(C)O)O)O)O
• SMILES (Isomeric): C[C@]12CC[C@H]3C(=CC(=O)[C@H]4[C@@]3(C[C@@H]([C@@H](C4)O)O)C)[C@@]1(CC[C@@H]2[C@](C)(CC[C@H](C(C)(C)O)O)O)O
• InChI: InChI=1S/C27H44O7/c1-23(2,32)22(31)8-10-26(5,33)21-7-11-27(34)16-12-18(28)17-13-19(29)20(30)14-24(17,3)15(16)6-9-25(21,27)4/h12,15,17,19-22,29-34H,6-11,13-14H2,1-5H3/t15-,17-,19+,20-,21-,22+,24+,25+,26-,27+/m0/s1
• InChI Key: VUBCOFCCIFBERZ-QUOJMMGDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₄₄O₇
• Molecular Weight: 480.60 g/mol
• Exact Mass: 480.30870374 g/mol
• Topological Polar Surface Area (TPSA): 138.00 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): 1.85
• H-Bond Acceptor: 7
• H-Bond Donor: 6
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9938	99.38%
Caco-2	-	0.5816	58.16%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.8310	83.10%
OATP2B1 inhibitior	-	0.8587	85.87%
OATP1B1 inhibitior	+	0.9177	91.77%
OATP1B3 inhibitior	+	0.9479	94.79%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	+	0.7029	70.29%
P-glycoprotein inhibitior	-	0.6903	69.03%
P-glycoprotein substrate	+	0.5215	52.15%
CYP3A4 substrate	+	0.6805	68.05%
CYP2C9 substrate	-	0.8086	80.86%
CYP2D6 substrate	-	0.8838	88.38%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.8690	86.90%
CYP2C19 inhibition	-	0.8364	83.64%
CYP2D6 inhibition	-	0.9516	95.16%
CYP1A2 inhibition	-	0.9278	92.78%
CYP2C8 inhibition	-	0.6670	66.70%
CYP inhibitory promiscuity	-	0.8761	87.61%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6900	69.00%
Eye corrosion	-	0.9944	99.44%
Eye irritation	-	0.9486	94.86%
Skin irritation	+	0.6543	65.43%
Skin corrosion	-	0.9489	94.89%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4486	44.86%
Micronuclear	-	0.9000	90.00%
Hepatotoxicity	-	0.5930	59.30%
skin sensitisation	-	0.7034	70.34%
Respiratory toxicity	+	0.8333	83.33%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	-	0.8510	85.10%
Acute Oral Toxicity (c)	III	0.5365	53.65%
Estrogen receptor binding	+	0.7996	79.96%
Androgen receptor binding	+	0.7238	72.38%
Thyroid receptor binding	+	0.6515	65.15%
Glucocorticoid receptor binding	+	0.7806	78.06%
Aromatase binding	+	0.6983	69.83%
PPAR gamma	-	0.5571	55.71%
Honey bee toxicity	-	0.8172	81.72%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9934	99.34%

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	99.17%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	99.07%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.41%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.80%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.59%	96.09%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	95.22%	82.69%
CHEMBL2581	P07339	Cathepsin D	94.95%	98.95%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	93.82%	94.78%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.55%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.27%	100.00%
CHEMBL218	P21554	Cannabinoid CB1 receptor	87.35%	96.61%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.96%	95.89%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.82%	97.14%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	83.93%	100.00%
CHEMBL1902	P62942	FK506-binding protein 1A	83.86%	97.05%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.84%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.67%	86.33%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.25%	91.07%

Plants that contains it

• Paris polyphylla
• Vitex pinnata
• Vitex scabra

Cross-Links

• PubChem: 12020130
• LOTUS: LTS0172465
• wikiData: Q105293154