ChemFOnt: Showing chemical card for 3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane (CFc000007980)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:54:34 UTC

Chemfont ID

CFc000007980

Molecule Identification

Common Name

3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane

Definition

3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane is found in the primary bile acid biosynthesis pathway. 3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane is produced from 3 alpha,7 alpha-Dihydroxy-5beta-cholestane through the action of CYP27A (E1.14.13.15). 3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane is then converted to 3 alpha,7 alpha-Dihydroxy-5beta-cholestan-26-al by CYP27A (E1.14.13.15).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3 a,7 a,26-Trihydroxy-5b-cholestane	Generator
3 Α,7 α,26-trihydroxy-5β-cholestane	Generator
5 beta-Cholestane-3 alpha,7 alpha,26-triol	MeSH
Cholestane-3,7,26-triol	MeSH
(25R)-5beta-Cholestane-3alpha,7alpha,26-triol	HMDB
(3alpha,5beta,7alpha)-Cholestane-3,7,26-triol	HMDB
3alpha,7alpha,26-Trihydroxy-5beta-cholestane	HMDB
5beta-Cholestan-3alpha,7alpha,26-triol	HMDB
5beta-Cholestane-3alpha,7alpha,26-triol	HMDB

Chemical Formula

C₂₇H₄₈O₃

Average Molecular Weight

420.6682

Monoisotopic Molecular Weight

420.360345402

IUPAC Name

(2S,5R,9R,15R)-14-[(2R)-7-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,9-diol

Traditional Name

(2S,5R,9R,15R)-14-[(2R)-7-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,9-diol

CAS Registry Number

15313-69-6

SMILES

CC(CO)CCC[C@@H](C)C1CCC2C3[C@H](O)CC4C[C@H](O)CC[C@]4(C)C3CC[C@]12C

InChI Identifier

InChI=1S/C27H48O3/c1-17(16-28)6-5-7-18(2)21-8-9-22-25-23(11-13-27(21,22)4)26(3)12-10-20(29)14-19(26)15-24(25)30/h17-25,28-30H,5-16H2,1-4H3/t17?,18-,19?,20-,21?,22?,23?,24-,25?,26+,27-/m1/s1

InChI Key

OQIJRBFRXGIHMI-KZQGXEQDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Trihydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

26-hydroxysteroid
Trihydroxy bile acid, alcohol, or derivatives
3-hydroxysteroid
Hydroxysteroid
7-hydroxysteroid
3-alpha-hydroxysteroid
Fatty alcohol
Fatty acyl
Cyclic alcohol
Secondary alcohol
Primary alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0012455)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0012455)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0012455)

Source

Endogenous

Endogenous (HMDB: HMDB0012455)

Animal

Animal (HMDB: HMDB0012455)

Exogenous

Food

Food (HMDB: HMDB0012455)

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: HMDB0012455)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0012455)

Biochemical pathway

Disease pathway

Congenital Bile Acid Synthesis Defect Type II (HMDB: HMDB0012455)
27-Hydroxylase Deficiency (PathBank: SMP0120652)
Cerebrotendinous Xanthomatosis (CTX) (PathBank: SMP0120683)
Familial Hypercholanemia (FHCA) (PathBank: SMP0120697)
Zellweger Syndrome (PathBank: SMP0120715)
Congenital Bile Acid Synthesis Defect Type II (PathBank: SMP0120687)
Congenital Bile Acid Synthesis Defect Type III (PathBank: SMP0120688)

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0012455)
Bile Acid Biosynthesis (PathBank: SMP0087329)

Lipid metabolism pathway (HMDB: HMDB0012455)

Cellular process

Cell signaling (HMDB: HMDB0012455)

Biochemical process

Lipid transport (HMDB: HMDB0012455)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0012455)

Molecular messenger

Signaling molecule (HMDB: HMDB0012455)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0012455)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.002 g/L	ALOGPS
logP	4.95	ALOGPS
logP	4.85	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	17.42	ChemAxon
pKa (Strongest Basic)	-0.51	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	6	ChemAxon
Refractivity	123.21 m³·mol⁻¹	ChemAxon
Polarizability	52.35 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	Yes	ChemAxon

External Links

HMDB ID

HMDB0012455

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029071

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C05444

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53481409

PDB ID

Not Available

ChEBI ID

28540

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane (CFc000007980)

MOL for CFc000007980 (3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane)

3D MOL for CFc000007980 (3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane)

3D SDF for CFc000007980 (3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane)

3D-SDF for CFc000007980 (3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane)

PDB for CFc000007980 (3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane)

3D PDB for CFc000007980 (3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane)

SMILES for CFc000007980 (3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane)

INCHI for CFc000007980 (3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane)

Structure for CFc000007980 (3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane)

3D Structure for CFc000007980 (3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane)