[(3R,4S,5S,8S,9S,10S,11S,13S,14S,17R)-4,11-dihydroxy-10,13-dimethyl-17-[(1R)-5-methyl-1-(sulfooxymethyl)hexyl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] hydrogen sulfate

Details

• Internal ID: 8c73fc9c-3569-417c-97f3-321867b54e49
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Bile acids, alcohols and derivatives > Hydroxy bile acids, alcohols and derivatives > Dihydroxy bile acids, alcohols and derivatives
• IUPAC Name: [(3R,4S,5S,8S,9S,10S,11S,13S,14S,17R)-4,11-dihydroxy-10,13-dimethyl-17-[(2R)-6-methyl-1-sulfooxyheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] hydrogen sulfate
• SMILES (Canonical): CC(C)CCCC(COS(=O)(=O)O)C1CCC2C1(CC(C3C2CCC4C3(CCC(C4O)OS(=O)(=O)O)C)O)C
• SMILES (Isomeric): CC(C)CCC[C@@H](COS(=O)(=O)O)[C@H]1CC[C@@H]2[C@@]1(C[C@@H]([C@H]3[C@H]2CC[C@H]4[C@@]3(CC[C@H]([C@H]4O)OS(=O)(=O)O)C)O)C
• InChI: InChI=1S/C27H48O10S2/c1-16(2)6-5-7-17(15-36-38(30,31)32)19-10-11-20-18-8-9-21-25(29)23(37-39(33,34)35)12-13-26(21,3)24(18)22(28)14-27(19,20)4/h16-25,28-29H,5-15H2,1-4H3,(H,30,31,32)(H,33,34,35)/t17-,18-,19+,20-,21+,22-,23+,24+,25-,26-,27+/m0/s1
• InChI Key: LJWULEVZMGYCEI-HJBWBOOXSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₄₈O₁₀S₂
• Molecular Weight: 596.80 g/mol
• Exact Mass: 596.26889007 g/mol
• Topological Polar Surface Area (TPSA): 184.00 Ų
• XlogP: 4.70
• Atomic LogP (AlogP): 4.04
• H-Bond Acceptor: 8
• H-Bond Donor: 4
• Rotatable Bonds: 10

Synonyms

• (3alpha,4alpha, 5beta,11beta)-4,11-dihydroxycholestane-3,21-diyl bis(hydrogen sulfate)
• [(3R,4S,5S,8S,9S,10S,11S,13S,14S,17R)-4,11-dihydroxy-10,13-dimethyl-17-[(1R)-5-methyl-1-(sulfooxymethyl)hexyl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] hydrogen sulfate
• 5beta-Cholestane-3,4,21-triol, 3,21-bis(hydrogen sulfate), disodium salt, ((3alpha,4alpha,11beta)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9666	96.66%
Caco-2	-	0.8415	84.15%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.5416	54.16%
OATP2B1 inhibitior	-	0.5580	55.80%
OATP1B1 inhibitior	+	0.9125	91.25%
OATP1B3 inhibitior	+	0.9231	92.31%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.6421	64.21%
P-glycoprotein inhibitior	+	0.6366	63.66%
P-glycoprotein substrate	+	0.6506	65.06%
CYP3A4 substrate	+	0.7381	73.81%
CYP2C9 substrate	-	0.8120	81.20%
CYP2D6 substrate	-	0.7563	75.63%
CYP3A4 inhibition	-	0.9216	92.16%
CYP2C9 inhibition	-	0.8518	85.18%
CYP2C19 inhibition	-	0.7955	79.55%
CYP2D6 inhibition	-	0.9048	90.48%
CYP1A2 inhibition	-	0.8099	80.99%
CYP2C8 inhibition	-	0.6685	66.85%
CYP inhibitory promiscuity	-	0.8342	83.42%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	+	0.5061	50.61%
Carcinogenicity (trinary)	Non-required	0.6528	65.28%
Eye corrosion	-	0.9366	93.66%
Eye irritation	-	0.9193	91.93%
Skin irritation	-	0.7616	76.16%
Skin corrosion	-	0.7836	78.36%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5406	54.06%
Micronuclear	+	0.5200	52.00%
Hepatotoxicity	-	0.6135	61.35%
skin sensitisation	-	0.8313	83.13%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.7726	77.26%
Acute Oral Toxicity (c)	III	0.6480	64.80%
Estrogen receptor binding	+	0.6378	63.78%
Androgen receptor binding	+	0.6891	68.91%
Thyroid receptor binding	-	0.6323	63.23%
Glucocorticoid receptor binding	+	0.6308	63.08%
Aromatase binding	+	0.6040	60.40%
PPAR gamma	+	0.5283	52.83%
Honey bee toxicity	-	0.7118	71.18%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9920	99.20%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	99.51%	96.38%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.71%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	97.73%	95.93%
CHEMBL2179	P04062	Beta-glucocerebrosidase	96.61%	85.31%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	94.85%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.21%	94.45%
CHEMBL2581	P07339	Cathepsin D	94.07%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	92.27%	100.00%
CHEMBL2094135	Q96BI3	Gamma-secretase	90.89%	98.05%
CHEMBL4302	P08183	P-glycoprotein 1	90.72%	92.98%
CHEMBL204	P00734	Thrombin	90.23%	96.01%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	90.11%	92.86%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	89.52%	82.69%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.77%	97.09%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	87.81%	90.71%
CHEMBL284	P27487	Dipeptidyl peptidase IV	87.70%	95.69%
CHEMBL4227	P25090	Lipoxin A4 receptor	87.09%	100.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	86.82%	93.56%
CHEMBL5203	P33316	dUTP pyrophosphatase	86.43%	99.18%
CHEMBL4835	P00338	L-lactate dehydrogenase A chain	85.91%	95.34%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.65%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.90%	95.56%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.64%	94.33%
CHEMBL221	P23219	Cyclooxygenase-1	84.61%	90.17%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	84.49%	93.03%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	83.69%	95.50%
CHEMBL4588	P22894	Matrix metalloproteinase 8	83.63%	94.66%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	83.58%	91.11%
CHEMBL1871	P10275	Androgen Receptor	83.23%	96.43%
CHEMBL2095194	P08709	Coagulation factor VII/tissue factor	83.12%	99.17%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	82.97%	97.29%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	82.60%	95.83%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.14%	95.89%
CHEMBL4581	P52732	Kinesin-like protein 1	82.02%	93.18%
CHEMBL2959	Q08881	Tyrosine-protein kinase ITK/TSK	81.73%	95.00%
CHEMBL237	P41145	Kappa opioid receptor	81.66%	98.10%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	81.09%	91.03%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.07%	100.00%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	80.97%	98.75%

Plants that contains it

• Pentadesma butyracea

Cross-Links

• PubChem: 5479475
• LOTUS: LTS0109363
• wikiData: Q105291260