Record Information |
---|
Version | 1.0 |
---|
Creation Date | 2016-05-27 01:14:50 UTC |
---|
Update Date | 2016-11-09 01:22:24 UTC |
---|
Accession Number | CHEM041124 |
---|
Identification |
---|
Common Name | 1beta,3alpha,7beta-Trihydroxy-5beta-cholanoic acid |
---|
Class | Small Molecule |
---|
Description | 1b,3a,7b-Trihydroxy-5b-cholanoic 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 1, 3, and 7. 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 holesterol. 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). |
---|
Contaminant Sources | |
---|
Contaminant Type | Not Available |
---|
Chemical Structure | |
---|
Synonyms | Value | Source |
---|
1b,3a,7b-Trihydroxy-5b-cholanoate | Generator | 1b,3a,7b-Trihydroxy-5b-cholanate | HMDB | 1b,3a,7b-Trihydroxy-5b-cholanic acid | HMDB | 7b-Hydroxyisocholate | HMDB | 7b-Hydroxyisocholic acid | HMDB | Lagocholate | HMDB | Lagocholic acid | HMDB | (5R)-5-Hydroxy-5-[(2S,3R,5S,9S,15S)-3,5,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate | Generator |
|
---|
Chemical Formula | C24H40O6 |
---|
Average Molecular Mass | 424.571 g/mol |
---|
Monoisotopic Mass | 424.282 g/mol |
---|
CAS Registry Number | Not Available |
---|
IUPAC Name | (5R)-5-hydroxy-5-[(2S,3R,5S,9S,15S)-3,5,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid |
---|
Traditional Name | (5R)-5-hydroxy-5-[(2S,3R,5S,9S,15S)-3,5,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid |
---|
SMILES | C[C@]12CCC3C(C1CCC2[C@H](O)CCCC(O)=O)[C@@H](O)CC1C[C@H](O)C[C@@H](O)[C@]31C |
---|
InChI Identifier | InChI=1S/C24H40O6/c1-23-9-8-17-22(16(23)7-6-15(23)18(26)4-3-5-21(29)30)19(27)11-13-10-14(25)12-20(28)24(13,17)2/h13-20,22,25-28H,3-12H2,1-2H3,(H,29,30)/t13?,14-,15?,16?,17?,18+,19-,20+,22?,23+,24-/m0/s1 |
---|
InChI Key | TVLHFFLEOSSHFT-QVLZICSDSA-N |
---|
Chemical Taxonomy |
---|
Description | belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans. |
---|
Kingdom | Organic compounds |
---|
Super Class | Lipids and lipid-like molecules |
---|
Class | Steroids and steroid derivatives |
---|
Sub Class | Androstane steroids |
---|
Direct Parent | Androgens and derivatives |
---|
Alternative Parents | |
---|
Substituents | - 20-hydroxysteroid
- Androgen-skeleton
- 3-hydroxysteroid
- 1-hydroxysteroid
- 7-hydroxysteroid
- 7-alpha-hydroxysteroid
- 3-alpha-hydroxysteroid
- Hydroxysteroid
- Medium-chain fatty acid
- Hydroxy fatty acid
- Fatty acyl
- Fatty acid
- Cyclic alcohol
- Secondary alcohol
- Carboxylic acid derivative
- Carboxylic acid
- Polyol
- Monocarboxylic acid or derivatives
- Alcohol
- Organic oxygen compound
- Carbonyl group
- Hydrocarbon derivative
- Organooxygen compound
- Organic oxide
- Aliphatic homopolycyclic compound
|
---|
Molecular Framework | Aliphatic homopolycyclic compounds |
---|
External Descriptors | Not Available |
---|
Biological Properties |
---|
Status | Detected and Not Quantified |
---|
Origin | Not Available |
---|
Cellular Locations | Not Available |
---|
Biofluid Locations | Not Available |
---|
Tissue Locations | Not Available |
---|
Pathways | Not Available |
---|
Applications | Not Available |
---|
Biological Roles | Not Available |
---|
Chemical Roles | Not Available |
---|
Physical Properties |
---|
State | Not Available |
---|
Appearance | Not Available |
---|
Experimental Properties | Property | Value |
---|
Melting Point | Not Available | Boiling Point | Not Available | Solubility | Not Available |
|
---|
Predicted Properties | |
---|
Spectra |
---|
Spectra | Spectrum Type | Description | Splash Key | View |
---|
Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-057i-0259200000-548951fb57f423c7e4c2 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive | splash10-00b9-2120398000-13a7de5dcf35c15ffd81 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-052r-0009600000-e389ed646d1a4be3386e | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-0019200000-74f9bc6344ea79571b89 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00ks-0069000000-fc660c8de3a3fc223fd7 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-05fr-0003900000-c4d41c4ee30c6fc7f6ca | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a4i-1006900000-1a3fc4580ed27846c22f | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4i-5019000000-0f836598fa1e055939b1 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-002r-0009700000-be4306453f267fb010f6 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-1359200000-17ba93bdaa36abe7bebb | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0570-4594000000-9dd6f94bb7191e1d7768 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00di-0000900000-f2b8ea5cd784108b4f12 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-05fr-1015900000-0b15d06ac54c83e2a167 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0fkl-9023400000-c77a070b8d3c1bea8740 | Spectrum |
|
---|
Toxicity Profile |
---|
Route of Exposure | Not Available |
---|
Mechanism of Toxicity | Not Available |
---|
Metabolism | Not Available |
---|
Toxicity Values | Not Available |
---|
Lethal Dose | Not Available |
---|
Carcinogenicity (IARC Classification) | Not Available |
---|
Uses/Sources | Not Available |
---|
Minimum Risk Level | Not Available |
---|
Health Effects | Not Available |
---|
Symptoms | Not Available |
---|
Treatment | Not Available |
---|
Concentrations |
---|
| Not Available |
---|
External Links |
---|
DrugBank ID | Not Available |
---|
HMDB ID | HMDB0013158 |
---|
FooDB ID | FDB029314 |
---|
Phenol Explorer ID | Not Available |
---|
KNApSAcK ID | Not Available |
---|
BiGG ID | Not Available |
---|
BioCyc ID | Not Available |
---|
METLIN ID | Not Available |
---|
PDB ID | Not Available |
---|
Wikipedia Link | Not Available |
---|
Chemspider ID | Not Available |
---|
ChEBI ID | Not Available |
---|
PubChem Compound ID | 53481888 |
---|
Kegg Compound ID | Not Available |
---|
YMDB ID | Not Available |
---|
ECMDB ID | Not Available |
---|
References |
---|
Synthesis Reference | Not Available |
---|
MSDS | Not Available |
---|
General References | 1. St-Pierre MV, Kullak-Ublick GA, Hagenbuch B, Meier PJ: Transport of bile acids in hepatic and non-hepatic tissues. J Exp Biol. 2001 May;204(Pt 10):1673-86. | 2. Claudel T, Staels B, Kuipers F: The Farnesoid X receptor: a molecular link between bile acid and lipid and glucose metabolism. Arterioscler Thromb Vasc Biol. 2005 Oct;25(10):2020-30. Epub 2005 Jul 21. | 3. Chiang JY: Bile acid regulation of hepatic physiology: III. Bile acids and nuclear receptors. Am J Physiol Gastrointest Liver Physiol. 2003 Mar;284(3):G349-56. | 4. Davis RA, Miyake JH, Hui TY, Spann NJ: Regulation of cholesterol-7alpha-hydroxylase: BAREly missing a SHP. J Lipid Res. 2002 Apr;43(4):533-43. | 5. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. | 6. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. | 7. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. | 8. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. | 9. The lipid handbook with CD-ROM |
|
---|