(25S)-5alpha-cholestan-3beta,6beta,15alpha,16beta,26-pentol

Details

• Internal ID: cf2e9d6d-eed4-43e7-83a6-0b0f925eb77d
• 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,5S,6R,8R,9S,10R,13R,14S,15R,16R,17R)-17-[(2R,6S)-7-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,6,15,16-tetrol
• SMILES (Canonical): CC(CCCC(C)C1C(C(C2C1(CCC3C2CC(C4C3(CCC(C4)O)C)O)C)O)O)CO
• SMILES (Isomeric): C[C@@H](CCC[C@@H](C)[C@H]1[C@H]([C@@H]([C@@H]2[C@@]1(CC[C@H]3[C@H]2C[C@H]([C@@H]4[C@@]3(CC[C@@H](C4)O)C)O)C)O)O)CO
• InChI: InChI=1S/C27H48O5/c1-15(14-28)6-5-7-16(2)22-24(31)25(32)23-18-13-21(30)20-12-17(29)8-10-26(20,3)19(18)9-11-27(22,23)4/h15-25,28-32H,5-14H2,1-4H3/t15-,16+,17-,18+,19-,20+,21+,22-,23+,24+,25+,26+,27+/m0/s1
• InChI Key: LOHYQIICSUGJLE-ULEKDTFZSA-N
• Popularity: 0 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: 4.30
• Atomic LogP (AlogP): 3.35
• H-Bond Acceptor: 5
• H-Bond Donor: 5
• Rotatable Bonds: 6

Synonyms

• CHEBI:187418
• LMST01010323
• (25S)-5alpha-Cholestane-3beta,6beta,15alpha,16beta,26-pentaol
• (3S,5S,6R,8R,9S,10R,13R,14S,15R,16R,17R)-17-[(2R,6S)-7-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,6,15,16-tetrol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9732	97.32%
Caco-2	-	0.7357	73.57%
Blood Brain Barrier	+	0.5135	51.35%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.6341	63.41%
OATP2B1 inhibitior	-	0.5761	57.61%
OATP1B1 inhibitior	+	0.8939	89.39%
OATP1B3 inhibitior	+	0.9474	94.74%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7083	70.83%
BSEP inhibitior	-	0.7389	73.89%
P-glycoprotein inhibitior	-	0.6540	65.40%
P-glycoprotein substrate	+	0.5312	53.12%
CYP3A4 substrate	+	0.7168	71.68%
CYP2C9 substrate	-	0.6198	61.98%
CYP2D6 substrate	-	0.7208	72.08%
CYP3A4 inhibition	-	0.7700	77.00%
CYP2C9 inhibition	-	0.8541	85.41%
CYP2C19 inhibition	-	0.9008	90.08%
CYP2D6 inhibition	-	0.9676	96.76%
CYP1A2 inhibition	-	0.7681	76.81%
CYP2C8 inhibition	-	0.7027	70.27%
CYP inhibitory promiscuity	-	0.9491	94.91%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.7524	75.24%
Eye corrosion	-	0.9931	99.31%
Eye irritation	-	0.9293	92.93%
Skin irritation	-	0.5287	52.87%
Skin corrosion	-	0.9609	96.09%
Ames mutagenesis	-	0.7210	72.10%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	-	0.9700	97.00%
Hepatotoxicity	+	0.5030	50.30%
skin sensitisation	-	0.8744	87.44%
Respiratory toxicity	+	0.7778	77.78%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.6940	69.40%
Acute Oral Toxicity (c)	III	0.6226	62.26%
Estrogen receptor binding	+	0.6555	65.55%
Androgen receptor binding	+	0.6661	66.61%
Thyroid receptor binding	+	0.5884	58.84%
Glucocorticoid receptor binding	+	0.6894	68.94%
Aromatase binding	+	0.6815	68.15%
PPAR gamma	+	0.5397	53.97%
Honey bee toxicity	-	0.8507	85.07%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6255	62.55%
Fish aquatic toxicity	+	0.9057	90.57%

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	97.90%	96.09%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	95.78%	95.58%
CHEMBL226	P30542	Adenosine A1 receptor	95.05%	95.93%
CHEMBL221	P23219	Cyclooxygenase-1	92.48%	90.17%
CHEMBL238	Q01959	Dopamine transporter	91.68%	95.88%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	91.63%	97.29%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.87%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.64%	97.25%
CHEMBL237	P41145	Kappa opioid receptor	89.44%	98.10%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	89.03%	96.38%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.66%	100.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	88.63%	82.69%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.53%	97.09%
CHEMBL242	Q92731	Estrogen receptor beta	88.28%	98.35%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	88.27%	92.86%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.36%	91.11%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	87.10%	96.77%
CHEMBL2581	P07339	Cathepsin D	86.75%	98.95%
CHEMBL2996	Q05655	Protein kinase C delta	86.43%	97.79%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	86.10%	89.05%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.96%	95.89%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	85.02%	92.88%
CHEMBL4227	P25090	Lipoxin A4 receptor	84.76%	100.00%
CHEMBL2001	Q9H244	Purinergic receptor P2Y12	84.03%	96.00%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	83.51%	98.33%
CHEMBL344	Q99705	Melanin-concentrating hormone receptor 1	83.38%	92.50%
CHEMBL2534	O15530	3-phosphoinositide dependent protein kinase-1	83.18%	95.36%
CHEMBL1871	P10275	Androgen Receptor	82.68%	96.43%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.27%	95.89%
CHEMBL2094135	Q96BI3	Gamma-secretase	81.93%	98.05%
CHEMBL206	P03372	Estrogen receptor alpha	81.45%	97.64%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	80.95%	98.75%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	80.07%	97.50%

Plants that contains it

• Capsicum annuum
• Lilium lancifolium
• Lippia origanoides
• Rosa villosa

Cross-Links

• PubChem: 52931335
• NPASS: NPC179262
• LOTUS: LTS0248546
• wikiData: Q104982611