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

Details

• Internal ID: 4f1d3aa1-d682-4d95-8cf9-402b2f45d51b
• 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-[(2R,3R,5S)-2,3,5,6-tetrahydroxy-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)(C(CC(C(C)(C)O)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)([C@@H](C[C@@H](C(C)(C)O)O)O)O)O
• InChI: InChI=1S/C27H44O8/c1-23(2,33)21(31)12-22(32)26(5,34)20-7-9-27(35)15-10-17(28)16-11-18(29)19(30)13-24(16,3)14(15)6-8-25(20,27)4/h10,14,16,18-22,29-35H,6-9,11-13H2,1-5H3/t14-,16-,18+,19-,20-,21-,22+,24+,25+,26+,27+/m0/s1
• InChI Key: NXKBQUXBPMOHPK-MLXSIWSOSA-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: -0.50
• Atomic LogP (AlogP): 0.82
• H-Bond Acceptor: 8
• H-Bond Donor: 7
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9876	98.76%
Caco-2	-	0.6163	61.63%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7639	76.39%
OATP2B1 inhibitior	-	0.8578	85.78%
OATP1B1 inhibitior	+	0.9197	91.97%
OATP1B3 inhibitior	+	0.8829	88.29%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.7237	72.37%
P-glycoprotein inhibitior	-	0.6637	66.37%
P-glycoprotein substrate	+	0.5129	51.29%
CYP3A4 substrate	+	0.6790	67.90%
CYP2C9 substrate	-	0.8086	80.86%
CYP2D6 substrate	-	0.8838	88.38%
CYP3A4 inhibition	-	0.8669	86.69%
CYP2C9 inhibition	-	0.8366	83.66%
CYP2C19 inhibition	-	0.7655	76.55%
CYP2D6 inhibition	-	0.9506	95.06%
CYP1A2 inhibition	-	0.9041	90.41%
CYP2C8 inhibition	-	0.6451	64.51%
CYP inhibitory promiscuity	-	0.8821	88.21%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6704	67.04%
Eye corrosion	-	0.9933	99.33%
Eye irritation	-	0.9429	94.29%
Skin irritation	+	0.6255	62.55%
Skin corrosion	-	0.9392	93.92%
Ames mutagenesis	-	0.7070	70.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.4573	45.73%
Micronuclear	-	0.9100	91.00%
Hepatotoxicity	+	0.5048	50.48%
skin sensitisation	-	0.7756	77.56%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	-	0.8643	86.43%
Acute Oral Toxicity (c)	I	0.5472	54.72%
Estrogen receptor binding	+	0.7710	77.10%
Androgen receptor binding	+	0.7253	72.53%
Thyroid receptor binding	+	0.6277	62.77%
Glucocorticoid receptor binding	+	0.7524	75.24%
Aromatase binding	+	0.6744	67.44%
PPAR gamma	-	0.5287	52.87%
Honey bee toxicity	-	0.8238	82.38%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9906	99.06%

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	99.47%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.73%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.52%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.04%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.73%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.80%	96.09%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	92.80%	82.69%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.95%	95.56%
CHEMBL218	P21554	Cannabinoid CB1 receptor	91.23%	96.61%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	90.35%	94.78%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.31%	100.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	87.09%	91.07%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.02%	95.89%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.58%	97.14%
CHEMBL1871	P10275	Androgen Receptor	84.55%	96.43%
CHEMBL221	P23219	Cyclooxygenase-1	83.10%	90.17%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	83.06%	93.04%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.63%	100.00%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	80.76%	90.24%
CHEMBL1902	P62942	FK506-binding protein 1A	80.39%	97.05%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.01%	86.33%

Plants that contains it

• Abuta velutina
• Polypodium virginianum
• Polypodium vulgare
• Vitex canescens
• Vitex strickeri

Cross-Links

• PubChem: 11016518
• LOTUS: LTS0162589
• wikiData: Q104398719