ChemFOnt: Showing chemical card for 7 alpha,26-Dihydroxy-4-cholesten-3-one (CFc000007984)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:54:35 UTC

Chemfont ID

CFc000007984

Molecule Identification

Common Name

7 alpha,26-Dihydroxy-4-cholesten-3-one

Definition

7 alpha,26-Dihydroxy-4-cholesten-3-one is involved in primary bile acid biosynthesis. 7 alpha,26-Dihydroxy-4-cholesten-3-one is produced from 7 alpha,27-Dihydroxycholesterol through the action of HSD3B7 (EC:1.1.1.181). 7 alpha,26-Dihydroxy-4-cholesten-3-one can then be converted to 7 alpha-Hydroxy-3-oxo-4-cholestenoate by CYP27A (EC:1.14.13.15).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
7 a,26-Dihydroxy-4-cholesten-3-one	Generator
7 Α,26-dihydroxy-4-cholesten-3-one	Generator
(7alpha)-7,26-Dihydroxy-cholest-4-en-3-one	HMDB
4-Cholesten-7alpha,26-diol-3-one	HMDB
7,26-Dhxyclso	HMDB, MeSH
7alpha,26-Dihydroxy-4-cholesten-3-one	HMDB
7alpha,26-Dihydroxycholest-4-en-3-one	HMDB

Chemical Formula

C₂₇H₄₄O₃

Average Molecular Weight

416.6365

Monoisotopic Molecular Weight

416.329045274

IUPAC Name

(2R,9R,15R)-9-hydroxy-14-[(2R)-7-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one

Traditional Name

(2R,9R,15R)-9-hydroxy-14-[(2R)-7-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one

CAS Registry Number

4675-38-1

SMILES

CC(CO)CCC[C@@H](C)C1CCC2C3[C@H](O)CC4=CC(=O)CC[C@]4(C)C3CC[C@]12C

InChI Identifier

InChI=1S/C27H44O3/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/h14,17-18,21-25,28,30H,5-13,15-16H2,1-4H3/t17?,18-,21?,22?,23?,24-,25?,26+,27-/m1/s1

InChI Key

KVJVJJWIEXCECB-JZGXDVPNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid 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

Dihydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

26-hydroxysteroid
Dihydroxy bile acid, alcohol, or derivatives
3-oxo-delta-4-steroid
3-oxosteroid
7-hydroxysteroid
Oxosteroid
Hydroxysteroid
Delta-4-steroid
Fatty alcohol
Cyclohexenone
Fatty acyl
Cyclic alcohol
Secondary alcohol
Cyclic ketone
Ketone
Organooxygen compound
Primary alcohol
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Alcohol
Organic oxide
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: HMDB0012459)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0012459)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0012459)

Source

Endogenous

Endogenous (HMDB: HMDB0012459)

Animal

Animal (HMDB: HMDB0012459)

Exogenous

Food

Food (HMDB: HMDB0012459)

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: HMDB0012459)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0012459)

Biochemical pathway

Disease pathway

Congenital Bile Acid Synthesis Defect Type II (HMDB: HMDB0012459)
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: HMDB0012459)
Bile Acid Biosynthesis (PathBank: SMP0087329)

Lipid metabolism pathway (HMDB: HMDB0012459)

Cellular process

Cell signaling (HMDB: HMDB0012459)

Biochemical process

Lipid transport (HMDB: HMDB0012459)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0012459)

Molecular messenger

Signaling molecule (HMDB: HMDB0012459)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0012459)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0029 g/L	ALOGPS
logP	4.6	ALOGPS
logP	5.01	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	17.14	ChemAxon
pKa (Strongest Basic)	-0.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	123.01 m³·mol⁻¹	ChemAxon
Polarizability	50.79 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0012459

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029075

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C17336

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53481412

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 7 alpha,26-Dihydroxy-4-cholesten-3-one (CFc000007984)

MOL for CFc000007984 (7 alpha,26-Dihydroxy-4-cholesten-3-one)

3D MOL for CFc000007984 (7 alpha,26-Dihydroxy-4-cholesten-3-one)

3D SDF for CFc000007984 (7 alpha,26-Dihydroxy-4-cholesten-3-one)

3D-SDF for CFc000007984 (7 alpha,26-Dihydroxy-4-cholesten-3-one)

PDB for CFc000007984 (7 alpha,26-Dihydroxy-4-cholesten-3-one)

3D PDB for CFc000007984 (7 alpha,26-Dihydroxy-4-cholesten-3-one)

SMILES for CFc000007984 (7 alpha,26-Dihydroxy-4-cholesten-3-one)

INCHI for CFc000007984 (7 alpha,26-Dihydroxy-4-cholesten-3-one)

Structure for CFc000007984 (7 alpha,26-Dihydroxy-4-cholesten-3-one)

3D Structure for CFc000007984 (7 alpha,26-Dihydroxy-4-cholesten-3-one)