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

Details

• Internal ID: 59a59df2-786a-4fb4-9046-fbfa59e14cb8
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Bile acids, alcohols and derivatives > Hydroxy bile acids, alcohols and derivatives > Pentahydroxy bile acids, alcohols and derivatives
• IUPAC Name: (2R,3R,5S,9R,10R,13R,14S,17S)-17-[(2R,3R)-2,6-dihydroxy-6-methyl-3-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyheptan-2-yl]-2,3,14-trihydroxy-10,13-dimethyl-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(CCC(C)(C)O)OC5C(C(C(C(O5)CO)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](CCC(C)(C)O)O[C@@H]5[C@@H]([C@H]([C@H]([C@H](O5)CO)O)O)O)O)O
• InChI: InChI=1S/C33H54O12/c1-29(2,41)9-8-24(45-28-27(40)26(39)25(38)22(15-34)44-28)32(5,42)23-7-11-33(43)17-12-19(35)18-13-20(36)21(37)14-30(18,3)16(17)6-10-31(23,33)4/h12,16,18,20-28,34,36-43H,6-11,13-15H2,1-5H3/t16-,18+,20+,21+,22+,23-,24+,25-,26-,27+,28+,30+,31+,32+,33+/m0/s1
• InChI Key: OYLAWXRQIJWVHG-OLFGWIRKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₅₄O₁₂
• Molecular Weight: 642.80 g/mol
• Exact Mass: 642.36152715 g/mol
• Topological Polar Surface Area (TPSA): 218.00 Ų
• XlogP: -1.10
• Atomic LogP (AlogP): -0.32
• H-Bond Acceptor: 12
• H-Bond Donor: 9
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9026	90.26%
Caco-2	-	0.8122	81.22%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.8474	84.74%
OATP2B1 inhibitior	-	0.5834	58.34%
OATP1B1 inhibitior	+	0.8842	88.42%
OATP1B3 inhibitior	-	0.2724	27.24%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6568	65.68%
BSEP inhibitior	-	0.4921	49.21%
P-glycoprotein inhibitior	+	0.6467	64.67%
P-glycoprotein substrate	-	0.5068	50.68%
CYP3A4 substrate	+	0.7211	72.11%
CYP2C9 substrate	-	0.8067	80.67%
CYP2D6 substrate	-	0.8910	89.10%
CYP3A4 inhibition	-	0.8752	87.52%
CYP2C9 inhibition	-	0.8084	80.84%
CYP2C19 inhibition	-	0.9022	90.22%
CYP2D6 inhibition	-	0.9331	93.31%
CYP1A2 inhibition	-	0.8266	82.66%
CYP2C8 inhibition	+	0.5323	53.23%
CYP inhibitory promiscuity	-	0.9107	91.07%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6947	69.47%
Eye corrosion	-	0.9912	99.12%
Eye irritation	-	0.9234	92.34%
Skin irritation	+	0.5185	51.85%
Skin corrosion	-	0.9448	94.48%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7331	73.31%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	+	0.5041	50.41%
skin sensitisation	-	0.9059	90.59%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.7642	76.42%
Acute Oral Toxicity (c)	III	0.6684	66.84%
Estrogen receptor binding	+	0.6796	67.96%
Androgen receptor binding	+	0.7506	75.06%
Thyroid receptor binding	-	0.5384	53.84%
Glucocorticoid receptor binding	+	0.6281	62.81%
Aromatase binding	+	0.6532	65.32%
PPAR gamma	+	0.6131	61.31%
Honey bee toxicity	-	0.7086	70.86%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9645	96.45%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.53%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	99.36%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	97.49%	97.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	96.81%	96.61%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.98%	96.09%
CHEMBL2581	P07339	Cathepsin D	93.45%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.03%	85.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	91.76%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.64%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	91.06%	100.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	89.65%	82.69%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	89.39%	97.14%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	88.45%	94.78%
CHEMBL220	P22303	Acetylcholinesterase	88.37%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.71%	86.33%
CHEMBL226	P30542	Adenosine A1 receptor	86.58%	95.93%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	86.07%	94.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.10%	89.00%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	84.85%	85.94%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.68%	94.00%
CHEMBL3922	P50579	Methionine aminopeptidase 2	84.22%	97.28%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	83.41%	100.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.37%	86.92%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	83.02%	93.04%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	83.02%	100.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.21%	91.07%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	82.12%	96.21%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	81.85%	100.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.79%	95.89%
CHEMBL5255	O00206	Toll-like receptor 4	81.57%	92.50%
CHEMBL4581	P52732	Kinesin-like protein 1	81.34%	93.18%

Plants that contains it

• Silene brahuica

Cross-Links

• PubChem: 162914957
• LOTUS: LTS0096035
• wikiData: Q105203376