ChemFOnt: Showing chemical card for 3-Oxocholic acid (CFc000000384)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:44:45 UTC

Chemfont ID

CFc000000384

Molecule Identification

Common Name

3-Oxocholic acid

Definition

3-Oxocholic acid, also known as 7alpha,12alpha-dihydroxy-3-oxo-5beta-cholan-24-oic acid, is a bile acid. Bile acids are steroid acids found predominantly in the bile of mammals. The distinction between different bile acids is minute, depending only on the presence or absence of hydroxyl groups on positions 3, 7, and 12. 3-Oxocholic acid is considered to be practically insoluble (in water) and acidic.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-Oxocholate	Generator
(5beta,7alpha,12alpha)-7,12-Dihydroxy-3-oxo-cholan-24-Oate	HMDB
(5beta,7alpha,12alpha)-7,12-Dihydroxy-3-oxo-cholan-24-Oic acid	HMDB
7,12-Dihydroxy-3-oxocholanate	HMDB
7,12-Dihydroxy-3-oxocholanic acid	HMDB
7a,12a-Dihydroxy-3-oxo-5b-cholan-24-Oate	HMDB
7a,12a-Dihydroxy-3-oxo-5b-cholan-24-Oic acid	HMDB
7alpha,12alpha-Dihydroxy-3-oxo-cholanoate	HMDB
7alpha,12alpha-Dihydroxy-3-oxo-cholanoic acid	HMDB

Chemical Formula

C₂₄H₃₈O₅

Average Molecular Weight

406.5555

Monoisotopic Molecular Weight

406.271924326

IUPAC Name

(4R)-4-[(1S,2S,7R,9R,10R,11S,14S,15R,16R)-9,16-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid

Traditional Name

(4R)-4-[(1S,2S,7R,9R,10R,11S,14S,15R,16R)-9,16-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid

CAS Registry Number

2304-89-4

SMILES

[H][C@@](C)(CCC(O)=O)[C@]1([H])CC[C@@]2([H])[C@]3([H])[C@]([H])(O)C[C@]4([H])CC(=O)CC[C@]4(C)[C@@]3([H])C[C@@]([H])(O)[C@]12C

InChI Identifier

InChI=1S/C24H38O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-14,16-20,22,26-27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,16+,17+,18+,19-,20-,22+,23+,24-/m1/s1

InChI Key

OEKUSRBIIZNLHZ-ZHDFXGGTSA-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

Dihydroxy bile acid, alcohol, or derivatives
3-oxosteroid
12-hydroxysteroid
3-oxo-5-beta-steroid
7-hydroxysteroid
Hydroxysteroid
Oxosteroid
Cyclic alcohol
Cyclic ketone
Secondary alcohol
Ketone
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Feces (PMID: 27275383)
Urine (PMID: 1112456)

Cellular substructure

Extracellular (HMDB: HMDB0000502)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31643938)
Bile (PMID: 31643938)

Source

Exogenous

Exogenous (HMDB: HMDB0000502)

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: HMDB0000502)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Biomarker

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.041 g/L	ALOGPS
logP	2.24	ALOGPS
logP	2.69	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	4.48	ChemAxon
pKa (Strongest Basic)	-0.18	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	109.76 m³·mol⁻¹	ChemAxon
Polarizability	46.19 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

FDB022080

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

53477697

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Production of 7a,12a-dihydroxy-3-keto-5b-cholanic acid. Jpn. Kokai Tokkyo Koho (1981), 12 pp.

Showing chemical card for 3-Oxocholic acid (CFc000000384)

MOL for CFc000000384 (3-Oxocholic acid)

3D MOL for CFc000000384 (3-Oxocholic acid)

3D SDF for CFc000000384 (3-Oxocholic acid)

3D-SDF for CFc000000384 (3-Oxocholic acid)

PDB for CFc000000384 (3-Oxocholic acid)

3D PDB for CFc000000384 (3-Oxocholic acid)

SMILES for CFc000000384 (3-Oxocholic acid)

INCHI for CFc000000384 (3-Oxocholic acid)

Structure for CFc000000384 (3-Oxocholic acid)

3D Structure for CFc000000384 (3-Oxocholic acid)