(25s)-5alpha-Cholestan-3beta,5,6beta,15alpha,26-pentaol

Details

• Internal ID: 5b366396-a293-48b9-b240-c7a8ef56fd3c
• 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: (3S,5R,6R,8R,9S,10R,13R,14S,15S,17R)-17-[(2R,6S)-7-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-1,2,3,4,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,5,6,15-tetrol
• SMILES (Canonical): CC(CCCC(C)C1CC(C2C1(CCC3C2CC(C4(C3(CCC(C4)O)C)O)O)C)O)CO
• SMILES (Isomeric): C[C@@H](CCC[C@@H](C)[C@H]1C[C@@H]([C@@H]2[C@@]1(CC[C@H]3[C@H]2C[C@H]([C@@]4([C@@]3(CC[C@@H](C4)O)C)O)O)C)O)CO
• InChI: InChI=1S/C27H48O5/c1-16(15-28)6-5-7-17(2)21-13-22(30)24-19-12-23(31)27(32)14-18(29)8-11-26(27,4)20(19)9-10-25(21,24)3/h16-24,28-32H,5-15H2,1-4H3/t16-,17+,18-,19+,20-,21+,22-,23+,24+,25+,26+,27-/m0/s1
• InChI Key: OVRQFVWSTBRXSY-DMSIPSRZSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₄₈O₅
• Molecular Weight: 452.70 g/mol
• Exact Mass: 452.35017463 g/mol
• Topological Polar Surface Area (TPSA): 101.00 Ų
• XlogP: 4.20
• Atomic LogP (AlogP): 3.50
• H-Bond Acceptor: 5
• H-Bond Donor: 5
• Rotatable Bonds: 6

Synonyms

• (25S)-5alpha-Cholestane-3beta,5,6beta,15alpha,26-pentaol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9288	92.88%
Caco-2	-	0.7179	71.79%
Blood Brain Barrier	+	0.5885	58.85%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.5170	51.70%
OATP2B1 inhibitior	-	0.5722	57.22%
OATP1B1 inhibitior	+	0.8943	89.43%
OATP1B3 inhibitior	+	0.9346	93.46%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7650	76.50%
BSEP inhibitior	-	0.5943	59.43%
P-glycoprotein inhibitior	-	0.6797	67.97%
P-glycoprotein substrate	+	0.6519	65.19%
CYP3A4 substrate	+	0.7340	73.40%
CYP2C9 substrate	-	0.5963	59.63%
CYP2D6 substrate	-	0.7575	75.75%
CYP3A4 inhibition	-	0.8841	88.41%
CYP2C9 inhibition	-	0.8402	84.02%
CYP2C19 inhibition	-	0.8611	86.11%
CYP2D6 inhibition	-	0.9626	96.26%
CYP1A2 inhibition	-	0.7628	76.28%
CYP2C8 inhibition	-	0.5763	57.63%
CYP inhibitory promiscuity	-	0.9575	95.75%
UGT catelyzed	+	1.0000	100.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.7440	74.40%
Eye corrosion	-	0.9934	99.34%
Eye irritation	-	0.9299	92.99%
Skin irritation	-	0.5374	53.74%
Skin corrosion	-	0.9559	95.59%
Ames mutagenesis	-	0.6315	63.15%
Human Ether-a-go-go-Related Gene inhibition	-	0.3896	38.96%
Micronuclear	-	0.9500	95.00%
Hepatotoxicity	+	0.5328	53.28%
skin sensitisation	-	0.8942	89.42%
Respiratory toxicity	+	0.7778	77.78%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	-	0.8425	84.25%
Acute Oral Toxicity (c)	III	0.6366	63.66%
Estrogen receptor binding	+	0.6775	67.75%
Androgen receptor binding	+	0.7649	76.49%
Thyroid receptor binding	+	0.6258	62.58%
Glucocorticoid receptor binding	+	0.7412	74.12%
Aromatase binding	+	0.6950	69.50%
PPAR gamma	-	0.4899	48.99%
Honey bee toxicity	-	0.7785	77.85%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5855	58.55%
Fish aquatic toxicity	+	0.8732	87.32%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.64%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.87%	97.25%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	96.55%	95.58%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	95.61%	82.69%
CHEMBL226	P30542	Adenosine A1 receptor	94.44%	95.93%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	92.46%	89.05%
CHEMBL4302	P08183	P-glycoprotein 1	92.19%	92.98%
CHEMBL2996	Q05655	Protein kinase C delta	92.19%	97.79%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.96%	97.09%
CHEMBL237	P41145	Kappa opioid receptor	91.22%	98.10%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.80%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.72%	94.45%
CHEMBL299	P17252	Protein kinase C alpha	90.24%	98.03%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	88.72%	92.86%
CHEMBL218	P21554	Cannabinoid CB1 receptor	87.70%	96.61%
CHEMBL236	P41143	Delta opioid receptor	86.70%	99.35%
CHEMBL1871	P10275	Androgen Receptor	85.97%	96.43%
CHEMBL2581	P07339	Cathepsin D	85.87%	98.95%
CHEMBL1937	Q92769	Histone deacetylase 2	85.45%	94.75%
CHEMBL242	Q92731	Estrogen receptor beta	85.41%	98.35%
CHEMBL4227	P25090	Lipoxin A4 receptor	85.24%	100.00%
CHEMBL221	P23219	Cyclooxygenase-1	84.52%	90.17%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.01%	95.89%
CHEMBL206	P03372	Estrogen receptor alpha	83.56%	97.64%
CHEMBL238	Q01959	Dopamine transporter	83.45%	95.88%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.31%	95.89%
CHEMBL2959	Q08881	Tyrosine-protein kinase ITK/TSK	82.87%	95.00%
CHEMBL2179	P04062	Beta-glucocerebrosidase	82.57%	85.31%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	82.23%	96.77%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	81.81%	95.50%
CHEMBL2001	Q9H244	Purinergic receptor P2Y12	81.76%	96.00%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	81.65%	100.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.38%	93.56%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	81.27%	97.29%
CHEMBL2885	P07451	Carbonic anhydrase III	81.03%	87.45%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.76%	90.71%
CHEMBL2514	O95665	Neurotensin receptor 2	80.20%	100.00%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.20%	96.90%

Plants that contains it

• Lippia origanoides

Cross-Links

• PubChem: 14778769
• NPASS: NPC196957
• LOTUS: LTS0192090
• wikiData: Q105201068