ChemFOnt: Showing chemical card for 5beta-Cholestane-3alpha,7alpha,12alpha,25-tetrol (CFc000000402)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:44:47 UTC

Chemfont ID

CFc000000402

Molecule Identification

Common Name

5beta-Cholestane-3alpha,7alpha,12alpha,25-tetrol

Definition

5β-Cholestane-3α,7α,12α,25-tetrol is an intermediate in the bile acid synthetic pathway, and is secreted into the bile and urine following glucuronidation. It does not undergo enterohepatic circulation. In cerebrotendinous xanthomatosis (CTX), a bile acid synthesis disorder caused by sterol 27-hydroxylase (CYP27) deficiency, early intermediates and cholestanol accumulate in a variety of tissues, and glucuronides of 25-hydroxylated bile alcohols are released in bile, blood, and urine (PMID: 11181760 ). Bile acid synthesis from cholesterol is tightly regulated via a feedback mechanism mediated by the farnesoid X receptor (FXR), a nuclear receptor activated by bile acids. Synthesis via the classic pathway is initiated by a series of cholesterol ring modifications and followed by the side chain cleavage. The enhanced cholesterol 7 alpha-hydroxylase (CYP7A1) expression in CYP27 deficiency may be the result of a decreased flux of bile acids and bile alcohols into the liver, while production of FXR-activating 5β-cholestane-3α,7α,12α,25-tetrol is increased (PMID: 15145977 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
5 beta-Cholestane-3 beta,7 alpha,12 alpha,25-tetrol	MeSH
Cholestane-3,7,12,25-tetrol	MeSH
5 beta Cholestane-3 alpha,7 alpha,12 alpha,25-tetrol	MeSH
5b-Cholestan-3a,7a,12a,25-tetrol	HMDB

Chemical Formula

C₂₇H₄₈O₄

Average Molecular Weight

436.6676

Monoisotopic Molecular Weight

436.355260024

IUPAC Name

(1S,2S,5R,7S,9R,10R,11S,15R,16S)-14-[(2R)-6-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,9,16-triol

Traditional Name

(1S,2S,5R,7S,9R,10R,11S,15R,16S)-14-[(2R)-6-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,9,16-triol

CAS Registry Number

18866-87-0

SMILES

[H][C@@](C)(CCCC(C)(C)O)C1([H])CC[C@@]2([H])[C@]3([H])[C@]([H])(O)C[C@]4([H])C[C@]([H])(O)CC[C@]4(C)[C@@]3([H])C[C@]([H])(O)[C@]12C

InChI Identifier

InChI=1S/C27H48O4/c1-16(7-6-11-25(2,3)31)19-8-9-20-24-21(15-23(30)27(19,20)5)26(4)12-10-18(28)13-17(26)14-22(24)29/h16-24,28-31H,6-15H2,1-5H3/t16-,17+,18-,19?,20+,21+,22-,23+,24+,26+,27-/m1/s1

InChI Key

NTIXPPFPXLYJCT-RUYUEJGQSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Cholestane steroids

Direct Parent

Cholesterols and derivatives

Alternative Parents

Substituents

Cholesterol
Cholesterol-skeleton
25-hydroxysteroid
3-hydroxysteroid
12-hydroxysteroid
7-hydroxysteroid
Hydroxysteroid
3-alpha-hydroxysteroid
Cyclic alcohol
Tertiary alcohol
Secondary alcohol
Polyol
Organic oxygen compound
Alcohol
Organooxygen compound
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0000524)
Extracellular (HMDB: HMDB0000524)

Source

Exogenous

Exogenous (HMDB: HMDB0000524)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0000524)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.021 g/L	ALOGPS
logP	3.64	ALOGPS
logP	3.51	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	18.3	ChemAxon
pKa (Strongest Basic)	-0.13	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	80.92 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	124.71 m³·mol⁻¹	ChemAxon
Polarizability	52.52 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022092

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

167758

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Dayal B; Bagan E; Speck J; Salen G A facile synthesis of 5 beta-cholestane-3 alpha,7 alpha,12 alpha,25-tetrol. Steroids (1980), 35(4), 439-44.

Showing chemical card for 5beta-Cholestane-3alpha,7alpha,12alpha,25-tetrol (CFc000000402)

MOL for CFc000000402 (5beta-Cholestane-3alpha,7alpha,12alpha,25-tetrol)

3D MOL for CFc000000402 (5beta-Cholestane-3alpha,7alpha,12alpha,25-tetrol)

3D SDF for CFc000000402 (5beta-Cholestane-3alpha,7alpha,12alpha,25-tetrol)

3D-SDF for CFc000000402 (5beta-Cholestane-3alpha,7alpha,12alpha,25-tetrol)

PDB for CFc000000402 (5beta-Cholestane-3alpha,7alpha,12alpha,25-tetrol)

3D PDB for CFc000000402 (5beta-Cholestane-3alpha,7alpha,12alpha,25-tetrol)

SMILES for CFc000000402 (5beta-Cholestane-3alpha,7alpha,12alpha,25-tetrol)

INCHI for CFc000000402 (5beta-Cholestane-3alpha,7alpha,12alpha,25-tetrol)

Structure for CFc000000402 (5beta-Cholestane-3alpha,7alpha,12alpha,25-tetrol)

3D Structure for CFc000000402 (5beta-Cholestane-3alpha,7alpha,12alpha,25-tetrol)