ChemFOnt: Showing chemical card for 5beta-Cholestane-3alpha,7alpha,12alpha-triol (CFc000001125)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:41 UTC

Chemfont ID

CFc000001125

Molecule Identification

Common Name

5beta-Cholestane-3alpha,7alpha,12alpha-triol

Definition

5beta-Cholestane-3alpha,7alpha,12alpha-triol is an intermediate in bile acid biosynthesis. 5beta-Cholestane-3alpha,7alpha,12alpha-triol is the second to last step in the synthesis of 5beta-cyprinolsulfate. It is converted from 7alpha,12alpha-dihydroxy-5beta-cholestan-3-one via enzymatic reaction, and then it is converted into 3alpha,7alpha,12alpha,26-tetrahydroxy-5beta-cholestane via the enzyme cytochrome P450 (EC 1.14.13.15). This compound inhibits la-hydroxylation (PMID: 7937829 ). It is the byproduct of cholestanetetraol 26-dehydrogenase (EC 1.1.1.161) and the reaction that catalyzes it is classified as a small molecule reaction (BioCyc).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestane	ChEBI
3alpha,7alpha,12alpha-Trihydroxycoprostane	ChEBI
3a,7a,12a-Trihydroxy-5b-cholestane	Generator
3Α,7α,12α-trihydroxy-5β-cholestane	Generator
3a,7a,12a-Trihydroxycoprostane	Generator
3Α,7α,12α-trihydroxycoprostane	Generator
5b-Cholestane-3a,7a,12a-triol	Generator
5Β-cholestane-3α,7α,12α-triol	Generator
5-beta-Cholestane-3-alpha,7-alpha,12-alpha-triol	HMDB
3,7,12-Trihydroxycholestane	MeSH, HMDB
3,7,12-Trihydroxycoprostane	MeSH, HMDB
3,7,12-Trihydroxycoprostane, (3alpha,5alpha,7alpha,12alpha)-isomer	MeSH, HMDB
3,7,12-Trihydroxycoprostane, (3beta,5alpha,7alpha,12alpha)-isomer	MeSH, HMDB
3,7,12-Trihydroxycoprostane, (3beta,5beta,7alpha,12alpha)-isomer	MeSH, HMDB
3alpha, 7alpha,12alpha-Trihydroxy-5beta-cholestane	MeSH, HMDB
5 beta-Cholestane-3 alpha,7 alpha,12 alpha-triol	MeSH, HMDB
5beta-Cholestane-3alpha,7alpha,12alpha-triol	MeSH, KEGG
Chtriol	MeSH, HMDB
Trihydroxycoprostane	MeSH, HMDB
(3alpha,5beta,7alpha,12alpha)-Cholestane-3,7,12-triol	HMDB
(3α,5β,7α,12α)-Cholestane-3,7,12-triol	HMDB
5beta-Cholestan-3alpha,7alpha,12alpha-triol	HMDB
5β-Cholestan-3α,7α,12α-triol	HMDB

Chemical Formula

C₂₇H₄₈O₃

Average Molecular Weight

420.6682

Monoisotopic Molecular Weight

420.360345402

IUPAC Name

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

Traditional Name

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

CAS Registry Number

547-96-6

SMILES

[H][C@@]1(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)[C@H](C)CCCC(C)C

InChI Identifier

InChI=1S/C27H48O3/c1-16(2)7-6-8-17(3)20-9-10-21-25-22(15-24(30)27(20,21)5)26(4)12-11-19(28)13-18(26)14-23(25)29/h16-25,28-30H,6-15H2,1-5H3/t17-,18+,19-,20-,21+,22+,23-,24+,25+,26+,27-/m1/s1

InChI Key

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

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3alpha-hydroxy steroid (CHEBI:16496 )
7alpha-hydroxy steroid (CHEBI:16496 )
12alpha-hydroxy steroid (CHEBI:16496 )
C27 bile acids, alcohols, and derivatives (C05454 )
C27 bile acids, alcohols, and derivatives (LMST04030035 )

Functional Ontology

Physiological effect

Health effect

Metabolic disorder

Metabolic syndrome (HMDB: HMDB0001457)

Disposition

Biological location

Tissue

All Tissues (HMDB: HMDB0001457)

Connective tissue

Adipose tissue (HMDB: HMDB0001457)

Nervous tissue

Hepatic tissue (HMDB: HMDB0001457)

Cellular substructure

Organelle

Mitochondrion (HMDB: HMDB0001457)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0001457)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0001457)

Source

Endogenous

Endogenous (HMDB: HMDB0001457)

Animal

Animal (HMDB: HMDB0001457)

Exogenous

Food

Food (HMDB: HMDB0001457)

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)

Exogenous (HMDB: HMDB0001457)

Process

Naturally occurring process

Role

Biological role

Human metabolite (HMDB: HMDB0001457)
Membrane stabilizer (HMDB: HMDB0001457)

Molecular messenger

Hormone (HMDB: HMDB0001457)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0001457)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0053 g/L	ALOGPS
logP	4.78	ALOGPS
logP	4.98	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	18.3	ChemAxon
pKa (Strongest Basic)	-0.16	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	60.69 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	122.87 m³·mol⁻¹	ChemAxon
Polarizability	52.4 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