| Record Information |
|---|
| Version |
3.5 |
| Creation Date |
2005-11-16 08:48:42 -0700 |
| Update Date |
2013-02-08 17:08:18 -0700 |
| HMDB ID |
HMDB00312 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
|---|
| Common Name |
3a,7a,12b-Trihydroxy-5b-cholanoic acid |
| Description |
3a,7a,12b-Trihydroxy-5b-cholanoic acid is a bile acid; bile acids with b-hydroxyl and carbonyl groups at the C-3,7 and/or 12 positions are bile acids usually found in the urine of healthy humans (PMID 8743575  ). 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. Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. Bile acids recirculate through the liver, bile ducts, small intestine and portal vein to form an enterohepatic circuit. They exist as anions at physiological pH and, consequently, require a carrier for transport across the membranes of the enterohepatic tissues. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. Bile acids have potent toxic properties (e.g., membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues. (PMID: 11316487 , 16037564 , 12576301 , 11907135 ). |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
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| Synonyms |
- 12b-Hydroxyisocholate
- 12b-Hydroxyisocholic acid
- 3a,7a,12b-Trihydroxy-5b-cholanate
- 3a,7a,12b-Trihydroxy-5b-cholanic acid
- 3a,7a,12b-Trihydroxy-5b-cholanoate
- 3a,7a,12b-Trihydroxy-5b-cholanoic acid
- Lagocholate
- Lagocholic acid
|
| Chemical Formula |
C24H40O5 |
| Average Molecular Weight |
408.5714 |
| Monoisotopic Molecular Weight |
408.28757439 |
| IUPAC Name |
(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16R)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid |
| Traditional IUPAC Name |
(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16R)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid |
| CAS Registry Number |
71883-64-2 |
| SMILES |
[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@H](O)C[C@@]1([H])[C@@]2([H])[C@H](O)C[C@]2([H])C[C@H](O)CC[C@]12C |
| InChI Identifier |
InChI=1S/C24H40O5/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/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15-,16-,17+,18+,19-,20-,22+,23+,24-/m1/s1 |
| InChI Key |
BHQCQFFYRZLCQQ-KRHHAYMPSA-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 Hydroxy Steroid
- 7 Hydroxy Steroid
- Bicyclohexane
- Carboxylic Acid
- Cyclic Alcohol
- Cyclohexane
- Decaline
- Secondary Alcohol
|
| Direct Parent |
Trihydroxy 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
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| Application |
- Nutrients
- Stabilizers
- Surfactants and Emulsifiers
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| Cellular locations |
|
| Physical Properties |
|---|
| State |
Solid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
Not Available |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
Not Available |
Not Available |
| LogP |
Not Available |
Not Available |
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| Predicted Properties |
|
| Spectra |
|---|
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Not Available
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| Biological Properties |
|---|
| Cellular Locations |
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| Biofluid Locations |
Not Available
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| Tissue Location |
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| Pathways |
Not Available
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| 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 |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB021939 |
| KNApSAcK ID |
Not Available |
| Chemspider ID |
4446957 |
| KEGG Compound ID |
Not Available |
| BioCyc ID |
Not Available |
| BiGG ID |
Not Available |
| Wikipedia Link |
Not Available |
| NuGOwiki Link |
HMDB00312 |
| Metagene Link |
HMDB00312 |
| METLIN ID |
5301 |
| PubChem Compound |
5283869 |
| PDB ID |
Not Available |
| ChEBI ID |
36240 |
| References |
|---|
| Synthesis Reference |
Batta, Ashok K.; Aggarwal, Suresht K.; Salen, Gerald; Shefer, Sarah. Selective reduction of oxo bile acids: synthesis of 3b-, 7b-, and 12b-hydroxy bile acids. Journal of Lipid Research (1991), 32(6), 977-83. |
| Material Safety Data Sheet (MSDS) |
Not Available
|
| General References |
- Borgstrom B, Krabisch L, Lindstrom M: Metabolism of cholate, 7 beta-hydroxy- and 12 beta-hydroxy-isocholates in the rat. Scand J Clin Lab Invest. 1986 Apr;46(2):177-82.
Pubmed: 3715369
- Yamaga N, Ikebuchi J, Kohara H, Ogura Y, Yamada K: Analysis of bile acids in urine specimens from healthy humans: determination of several bile acids with beta-hydroxyl and carbonyl groups. J Biochem (Tokyo). 1996 Apr;119(4):725-30.
Pubmed: 8743575
|
