| Record Information |
|---|
| Version |
3.5 |
| Creation Date |
2005-11-16 08:48:42 -0700 |
| Update Date |
2013-02-08 17:08:43 -0700 |
| HMDB ID |
HMDB00502 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
|---|
| Common Name |
3-Oxocholic acid |
| Description |
3-Oxocholic acid is a bile acid. Bile acids are steroid acids found predominantly in bile of mammals. The distinction between different bile acids is minute, depends only on presence or absence of hydroxyl groups on positions 3, 7, and 12. |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
|
| Synonyms |
- (5beta,7alpha,12alpha)-7,12-dihydroxy-3-oxo-Cholan-24-oate
- (5beta,7alpha,12alpha)-7,12-dihydroxy-3-oxo-Cholan-24-oic acid
- 3-Oxocholate
- 3-Oxocholic acid
- 7,12-Dihydroxy-3-oxocholanate
- 7,12-Dihydroxy-3-oxocholanic acid
- 7a,12a-Dihydroxy-3-oxo-5b-cholan-24-oate
- 7a,12a-Dihydroxy-3-oxo-5b-cholan-24-oic acid
- 7alpha,12alpha-Dihydroxy-3-oxo-cholanoate
- 7alpha,12alpha-Dihydroxy-3-oxo-cholanoic acid
|
| 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 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 |
| CAS Registry Number |
2304-89-4 |
| SMILES |
[H][C@]1(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)[C@H](C)CCC(O)=O |
| 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 |
|---|
| Kingdom |
Organic Compounds |
| Super Class |
Lipids |
| Class |
Steroids and Steroid Derivatives |
| Sub Class |
Bile Acids, Alcohols and Derivatives |
| Other Descriptors |
- Aliphatic Homopolycyclic Compounds
- Bile Acids, Alcohols and Derivatives
|
| Substituents |
- 12 Hydroxy Steroid
- 3 Keto Steroid
- 7 Hydroxy Steroid
- Bicyclohexane
- Carboxylic Acid
- Cyclic Alcohol
- Cyclohexane
- Decaline
- Ketone
- Secondary Alcohol
|
| Direct Parent |
Dihydroxy Bile Acids, Alcohols and Derivatives |
| Ontology |
|---|
| Status |
Expected and Not Quantified |
| Origin |
|
| Biofunction |
- Cell signaling
- Fat solubilization and Waste products
- Fuel and energy storage
- Fuel or energy source
- Membrane integrity/stability
|
| Application |
- Nutrients
- Stabilizers
- Surfactants and Emulsifiers
|
| Cellular locations |
|
| Physical Properties |
|---|
| State |
Solid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
218 - 220 °C |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
Not Available |
Not Available |
| LogP |
Not Available |
Not Available |
|
| Predicted Properties |
|
| Spectra |
|---|
|
Not Available
|
| Biological Properties |
|---|
| Cellular Locations |
|
| Biofluid Locations |
Not Available
|
| Tissue Location |
- Intestine
- Kidney
- Liver
- Gall Bladder
|
| Pathways |
Not Available
|
| Normal Concentrations |
|---|
|
Not Available |
| Abnormal Concentrations |
|---|
|
Not Available |
| Associated Disorders and Diseases |
|---|
| Disease References |
None |
| Associated OMIM IDs |
None |
| External Links |
|---|
| DrugBank ID |
Not Available |
| DrugBank Metabolite ID |
Not Available |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB 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 |
| NuGOwiki Link |
HMDB00502  |
| Metagene Link |
HMDB00502 |
| METLIN ID |
5488 |
| PubChem Compound |
53477697 |
| PDB ID |
Not Available |
| ChEBI ID |
Not Available |
| References |
|---|
| Synthesis Reference |
Production of 7a,12a-dihydroxy-3-keto-5b-cholanic acid. Jpn. Kokai Tokkyo Koho (1981), 12 pp. |
| Material Safety Data Sheet (MSDS) |
Not Available
|
| General References |
- Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30.
Pubmed: 12829005
- Kimura A, Mahara R, Inoue T, Nomura Y, Murai T, Kurosawa T, Tohma M, Noguchi K, Hoshiyama A, Fujisawa T, Kato H: Profile of urinary bile acids in infants and children: developmental pattern of excretion of unsaturated ketonic bile acids and 7beta-hydroxylated bile acids. Pediatr Res. 1999 Apr;45(4 Pt 1):603-9.
Pubmed: 10203155
|
