(2S,3R,5R,9R,10S,13R,14S,17S)-2,3,14-trihydroxy-10-(hydroxymethyl)-13-methyl-17-[(2R,3R)-2,3,6-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: 2a269a73-39fd-4662-a07d-ea5fa9ef06fd
• 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,10S,13R,14S,17S)-2,3,14-trihydroxy-10-(hydroxymethyl)-13-methyl-17-[(2R,3R)-2,3,6-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)CO)C1(CCC2C(C)(C(CCC(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)CO)[C@@]1(CC[C@@H]2[C@](C)([C@@H](CCC(C)(C)O)O)O)O
• InChI: InChI=1S/C27H44O8/c1-23(2,33)8-7-22(32)25(4,34)21-6-10-27(35)16-11-18(29)17-12-19(30)20(31)13-26(17,14-28)15(16)5-9-24(21,27)3/h11,15,17,19-22,28,30-35H,5-10,12-14H2,1-4H3/t15-,17-,19+,20-,21-,22+,24+,25+,26-,27+/m0/s1
• InChI Key: VZAYBJKRPIYQJN-QUOJMMGDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₄₄O₈
• Molecular Weight: 496.60 g/mol
• Exact Mass: 496.30361836 g/mol
• Topological Polar Surface Area (TPSA): 159.00 Ų
• XlogP: -0.80
• Atomic LogP (AlogP): 0.83
• H-Bond Acceptor: 8
• H-Bond Donor: 7
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9922	99.22%
Caco-2	-	0.6317	63.17%
Blood Brain Barrier	+	0.6385	63.85%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.8660	86.60%
OATP2B1 inhibitior	-	0.5761	57.61%
OATP1B1 inhibitior	+	0.9150	91.50%
OATP1B3 inhibitior	+	0.9329	93.29%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.5202	52.02%
BSEP inhibitior	+	0.7555	75.55%
P-glycoprotein inhibitior	-	0.6508	65.08%
P-glycoprotein substrate	+	0.5530	55.30%
CYP3A4 substrate	+	0.6847	68.47%
CYP2C9 substrate	-	0.8204	82.04%
CYP2D6 substrate	-	0.8901	89.01%
CYP3A4 inhibition	-	0.8568	85.68%
CYP2C9 inhibition	-	0.8540	85.40%
CYP2C19 inhibition	-	0.9231	92.31%
CYP2D6 inhibition	-	0.9442	94.42%
CYP1A2 inhibition	-	0.9282	92.82%
CYP2C8 inhibition	-	0.6449	64.49%
CYP inhibitory promiscuity	-	0.9020	90.20%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.7189	71.89%
Eye corrosion	-	0.9935	99.35%
Eye irritation	-	0.9406	94.06%
Skin irritation	+	0.5518	55.18%
Skin corrosion	-	0.9581	95.81%
Ames mutagenesis	-	0.7600	76.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6741	67.41%
Micronuclear	-	0.9000	90.00%
Hepatotoxicity	-	0.6384	63.84%
skin sensitisation	-	0.8458	84.58%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	-	0.8800	88.00%
Acute Oral Toxicity (c)	III	0.7157	71.57%
Estrogen receptor binding	+	0.7877	78.77%
Androgen receptor binding	+	0.7445	74.45%
Thyroid receptor binding	+	0.6019	60.19%
Glucocorticoid receptor binding	+	0.7622	76.22%
Aromatase binding	+	0.6691	66.91%
PPAR gamma	-	0.5000	50.00%
Honey bee toxicity	-	0.8146	81.46%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9848	98.48%

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	99.40%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.49%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.20%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.91%	97.09%
CHEMBL2581	P07339	Cathepsin D	94.41%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.59%	96.09%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	92.15%	94.78%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	91.91%	82.69%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.90%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.75%	100.00%
CHEMBL218	P21554	Cannabinoid CB1 receptor	87.85%	96.61%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.29%	95.89%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	87.05%	97.14%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	86.56%	100.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	84.44%	93.99%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.09%	89.00%
CHEMBL299	P17252	Protein kinase C alpha	83.82%	98.03%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.74%	100.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.15%	91.07%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.09%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.02%	86.33%
CHEMBL2996	Q05655	Protein kinase C delta	81.72%	97.79%
CHEMBL1902	P62942	FK506-binding protein 1A	81.60%	97.05%
CHEMBL4805	Q99572	P2X purinoceptor 7	81.23%	97.50%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	81.20%	96.90%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	81.06%	100.00%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	80.56%	94.23%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.51%	93.04%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	80.31%	85.94%

Plants that contains it

• Klasea sogdiana

Cross-Links

• PubChem: 102239711
• LOTUS: LTS0071471
• wikiData: Q104251686