Record Information |
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Version | 1.0 |
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Creation Date | 2016-05-26 05:16:46 UTC |
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Update Date | 2016-11-09 01:21:12 UTC |
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Accession Number | CHEM034855 |
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Identification |
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Common Name | 3a,6b,7b-Trihydroxy-5b-cholanoic acid |
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Class | Small Molecule |
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Description | |
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Contaminant Sources | |
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Contaminant Type | Not Available |
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Chemical Structure | |
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Synonyms | Value | Source |
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(3alpha,5beta,6beta,7beta)-3,6,7-Trihydroxycholan-24-Oic acid | ChEBI | 3,6,7-Trihydroxy-5beta-cholan-24-Oic acid | ChEBI | 5beta-Cholanic acid-3alpha,6beta,7beta-triol | ChEBI | beta-MCA | ChEBI | beta-Muricholic acid | Kegg | 3alpha,6beta,7beta-Trihydroxy-5beta-cholan-24-Oic acid | Kegg | (3a,5b,6b,7b)-3,6,7-Trihydroxycholan-24-Oate | Generator | (3a,5b,6b,7b)-3,6,7-Trihydroxycholan-24-Oic acid | Generator | (3alpha,5beta,6beta,7beta)-3,6,7-Trihydroxycholan-24-Oate | Generator | (3Α,5β,6β,7β)-3,6,7-trihydroxycholan-24-Oate | Generator | (3Α,5β,6β,7β)-3,6,7-trihydroxycholan-24-Oic acid | Generator | 3,6,7-Trihydroxy-5b-cholan-24-Oate | Generator | 3,6,7-Trihydroxy-5b-cholan-24-Oic acid | Generator | 3,6,7-Trihydroxy-5beta-cholan-24-Oate | Generator | 3,6,7-Trihydroxy-5β-cholan-24-Oate | Generator | 3,6,7-Trihydroxy-5β-cholan-24-Oic acid | Generator | 5b-Cholanate-3a,6b,7b-triol | Generator | 5b-Cholanic acid-3a,6b,7b-triol | Generator | 5beta-Cholanate-3alpha,6beta,7beta-triol | Generator | 5Β-cholanate-3α,6β,7β-triol | Generator | 5Β-cholanic acid-3α,6β,7β-triol | Generator | b-MCA | Generator | Β-mca | Generator | b-Muricholate | Generator | b-Muricholic acid | Generator | beta-Muricholate | Generator | Β-muricholate | Generator | Β-muricholic acid | Generator | 3a,6b,7b-Trihydroxy-5b-cholan-24-Oate | Generator | 3a,6b,7b-Trihydroxy-5b-cholan-24-Oic acid | Generator | 3alpha,6beta,7beta-Trihydroxy-5beta-cholan-24-Oate | Generator | 3Α,6β,7β-trihydroxy-5β-cholan-24-Oate | Generator | 3Α,6β,7β-trihydroxy-5β-cholan-24-Oic acid | Generator | 3a,6b,7b-Trihydroxy-5b-cholanoate | Generator | 3a,6b,7b-Trihydroxy-5b-cholanate | HMDB | 3a,6b,7b-Trihydroxy-5b-cholanic acid | HMDB | 3 alpha,6 alpha,7 beta-Trihydroxy-5 beta-cholanoic acid | HMDB | 3,6,7-Trihydroxy-5-cholanoic acid | HMDB | alpha-Muricholic acid | HMDB | Hyocholic acid | HMDB | Muricholic acid | HMDB | Muricholic acid, (3alpha,5alpha,6alpha,7alpha)-isomer | HMDB | Muricholic acid, (3alpha,5beta,6alpha,7alpha)-isomer | HMDB | Muricholic acid, (3alpha,5beta,6alpha,7beta)-isomer | HMDB | Muricholic acid, (3alpha,5beta,6beta,7alpha)-isomer | HMDB | Muricholic acid, (3alpha,5beta,6beta,7beta)-isomer | HMDB | Muricholic acid, sodium salt | HMDB | Omega-muricholic acid | HMDB | Trihydroxy-5 alpha-cholanoic acid | HMDB |
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Chemical Formula | C24H40O5 |
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Average Molecular Mass | 408.571 g/mol |
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Monoisotopic Mass | 408.288 g/mol |
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CAS Registry Number | 2393-59-1 |
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IUPAC Name | (4R)-4-[(1S,2R,5R,7R,8S,9R,10S,11S,14R,15R)-5,8,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid |
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Traditional Name | (4R)-4-[(1S,2R,5R,7R,8S,9R,10S,11S,14R,15R)-5,8,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid |
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SMILES | [H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@@H](O)[C@@H](O)[C@]2([H])C[C@H](O)CC[C@]12C |
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InChI Identifier | InChI=1S/C24H40O5/c1-13(4-7-19(26)27)15-5-6-16-20-17(9-11-23(15,16)2)24(3)10-8-14(25)12-18(24)21(28)22(20)29/h13-18,20-22,25,28-29H,4-12H2,1-3H3,(H,26,27)/t13-,14-,15-,16+,17+,18+,20+,21+,22-,23-,24-/m1/s1 |
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InChI Key | DKPMWHFRUGMUKF-CRKPLTDNSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Steroids and steroid derivatives |
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Sub Class | Bile acids, alcohols and derivatives |
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Direct Parent | Trihydroxy bile acids, alcohols and derivatives |
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Alternative Parents | |
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Substituents | - Trihydroxy bile acid, alcohol, or derivatives
- 3-hydroxysteroid
- 6-hydroxysteroid
- 7-hydroxysteroid
- 7-alpha-hydroxysteroid
- 3-alpha-hydroxysteroid
- Hydroxysteroid
- Cyclic alcohol
- Secondary alcohol
- Carboxylic acid derivative
- Carboxylic acid
- Polyol
- Monocarboxylic acid or derivatives
- Organic oxide
- Alcohol
- Organic oxygen compound
- Hydrocarbon derivative
- Carbonyl group
- Organooxygen compound
- Aliphatic homopolycyclic compound
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Molecular Framework | Aliphatic homopolycyclic compounds |
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External Descriptors | |
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Biological Properties |
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Status | Detected and Not Quantified |
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Origin | Not Available |
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Cellular Locations | Not Available |
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Biofluid Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | Not Available |
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Applications | Not Available |
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Biological Roles | Not Available |
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Chemical Roles | Not Available |
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Physical Properties |
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State | Not Available |
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Appearance | Not Available |
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Experimental Properties | Property | Value |
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Melting Point | Not Available | Boiling Point | Not Available | Solubility | Not Available |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-004l-0329000000-fed34af3d93baa3f7367 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive | splash10-001i-1010029000-e5824ce563bff12a309c | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_3_1) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_3_2) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_3_3) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_3_4) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_2_4) - 70eV, Positive | Not Available | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-006x-0009100000-aeaf5bcdde74fe1ddf76 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00dm-0009000000-4af1ebd01d1d670d4f42 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-003u-2209000000-454d741b691e592d251a | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0007900000-e501198616f74730538f | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-052r-1009300000-9efc23876fa89e243bc6 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4l-9007000000-e5bd870e3f9870c89a14 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0ab9-0009600000-56beda528763ce5ae6df | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-059j-3449200000-98d256091462f2bbd882 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-052u-4951000000-c203ad5efbf5e653aa09 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0001900000-68e3200734e1d0985f37 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a4r-0009800000-a11781ffcf06d8bb288c | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4j-3009300000-d354f18e540a94d7dfe1 | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | Spectrum |
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Toxicity Profile |
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Route of Exposure | Not Available |
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Mechanism of Toxicity | Not Available |
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Metabolism | Not Available |
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Toxicity Values | Not Available |
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Lethal Dose | Not Available |
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Carcinogenicity (IARC Classification) | Not Available |
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Uses/Sources | Not Available |
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Minimum Risk Level | Not Available |
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Health Effects | Not Available |
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Symptoms | Not Available |
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Treatment | Not Available |
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Concentrations |
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| Not Available |
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External Links |
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DrugBank ID | Not Available |
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HMDB ID | HMDB0000415 |
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FooDB ID | FDB022031 |
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Phenol Explorer ID | Not Available |
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KNApSAcK ID | Not Available |
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BiGG ID | Not Available |
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BioCyc ID | CPD-16583 |
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METLIN ID | 5404 |
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PDB ID | Not Available |
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Wikipedia Link | Not Available |
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Chemspider ID | 4446941 |
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ChEBI ID | 81298 |
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PubChem Compound ID | 5283853 |
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Kegg Compound ID | C17726 |
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YMDB ID | Not Available |
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ECMDB ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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MSDS | Not Available |
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General References | 1. Hsia, S. L.; Matschiner, John T.; Mahowald, Theodore A.; Elliott, Wm. H.; Doisy, E. A., Jr.; Thayer, Sidney A.; Doisy, Edward A. Bile acids. VII. Structure of acid I. Journal of Biological Chemistry (1958), 230 573-80. | 2. Sacquet E, Parquet M, Riottot M, Raizman A, Nordlinger B, Infante R: Metabolism of beta-muricholic acid in man. Steroids. 1985 May;45(5):411-26. | 3. 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. | 4. 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. | 5. 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. | 6. 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. | 7. https://www.ncbi.nlm.nih.gov/pubmed/?term=12401895 | 8. https://www.ncbi.nlm.nih.gov/pubmed/?term=1519265 | 9. https://www.ncbi.nlm.nih.gov/pubmed/?term=1568576 | 10. https://www.ncbi.nlm.nih.gov/pubmed/?term=16413764 | 11. https://www.ncbi.nlm.nih.gov/pubmed/?term=20671298 | 12. https://www.ncbi.nlm.nih.gov/pubmed/?term=2815149 | 13. https://www.ncbi.nlm.nih.gov/pubmed/?term=3828364 | 14. https://www.ncbi.nlm.nih.gov/pubmed/?term=3834660 | 15. https://www.ncbi.nlm.nih.gov/pubmed/?term=4210666 | 16. https://www.ncbi.nlm.nih.gov/pubmed/?term=4462033 | 17. https://www.ncbi.nlm.nih.gov/pubmed/?term=6047622 | 18. https://www.ncbi.nlm.nih.gov/pubmed/?term=8245721 |
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