Record Information |
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Version | 1.0 |
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Creation Date | 2016-05-26 05:17:10 UTC |
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Update Date | 2016-11-09 01:21:12 UTC |
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Accession Number | CHEM034864 |
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Identification |
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Common Name | 3b,12a-Dihydroxy-5b-cholanoic acid |
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Class | Small Molecule |
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Description | A dihydroxy-5beta-cholanic acid in which the two hydroxy groups are located at positions 3beta and 12alpha. The 3beta-hydroxy epimer of deoxycholic acid. |
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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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(3beta,5beta,12alpha)-3,12-Dihydroxycholan-24-Oic acid | ChEBI | 3-Epideoxycholic acid | ChEBI | 3beta-Deoxycholic acid | ChEBI | Isodeoxycholic acid | ChEBI | (3b,5b,12a)-3,12-Dihydroxycholan-24-Oate | Generator | (3b,5b,12a)-3,12-Dihydroxycholan-24-Oic acid | Generator | (3beta,5beta,12alpha)-3,12-Dihydroxycholan-24-Oate | Generator | (3Β,5β,12α)-3,12-dihydroxycholan-24-Oate | Generator | (3Β,5β,12α)-3,12-dihydroxycholan-24-Oic acid | Generator | 3-Epideoxycholate | Generator | 3b-Deoxycholate | Generator | 3b-Deoxycholic acid | Generator | 3beta-Deoxycholate | Generator | 3Β-deoxycholate | Generator | 3Β-deoxycholic acid | Generator | Isodeoxycholate | Generator | 3b,12a-Dihydroxy-5b-cholanoate | Generator | 3b,12a-Dihydroxy-5b-cholan-24-Oate | HMDB | 3b,12a-Dihydroxy-5b-cholan-24-Oic acid | HMDB | 3b,12a-Dihydroxy-5b-cholanate | HMDB | 3b,12a-Dihydroxy-5b-cholanic acid | HMDB | 3b,12a-Dihydroxycholanoate | HMDB | 3b,12a-Dihydroxycholanoic acid | HMDB | 5b-Cholanic acid-3b,12a-diol | HMDB |
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Chemical Formula | C24H40O4 |
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Average Molecular Mass | 392.572 g/mol |
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Monoisotopic Mass | 392.293 g/mol |
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CAS Registry Number | 570-63-8 |
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IUPAC Name | (4R)-4-[(1S,2S,5S,7R,10R,11S,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid |
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Traditional Name | 3-epideoxycholic acid |
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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])CC[C@]2([H])C[C@@H](O)CC[C@]12C |
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InChI Identifier | InChI=1S/C24H40O4/c1-14(4-9-22(27)28)18-7-8-19-17-6-5-15-12-16(25)10-11-23(15,2)20(17)13-21(26)24(18,19)3/h14-21,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16+,17+,18-,19+,20+,21+,23+,24-/m1/s1 |
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InChI Key | KXGVEGMKQFWNSR-OFYXWCICSA-N |
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Chemical Taxonomy |
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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. |
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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 | Dihydroxy bile acids, alcohols and derivatives |
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Alternative Parents | |
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Substituents | - Dihydroxy bile acid, alcohol, or derivatives
- 3-hydroxysteroid
- 3-beta-hydroxysteroid
- 12-hydroxysteroid
- Hydroxysteroid
- Cyclic alcohol
- Secondary alcohol
- Carboxylic acid
- Carboxylic acid derivative
- Monocarboxylic acid or derivatives
- Organooxygen compound
- Organic oxygen compound
- Hydrocarbon derivative
- Organic oxide
- Carbonyl group
- Alcohol
- 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 | splash10-00os-0119000000-ff101495d4bc6a37fc83 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive | splash10-0006-1110390000-cc7d539ad02f4039ec09 | 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_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 (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_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_3_1) - 70eV, Positive | Not Available | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-056r-0009000000-862fe061e17daf909f81 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-056r-0009000000-d2bc073ceca3e5b14c88 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-02vi-3109000000-5a4bd324fa583768a2e1 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-006x-0009000000-f969293bf286459bff3f | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00dl-0009000000-6d3e401b3a1ad3688eb2 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4l-9007000000-b74124eb1410789ddd2b | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-054o-0009000000-042c286dcf0175c346a7 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0adi-4369000000-386bba727c7c7b5bb692 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4i-8950000000-659edbcb6317b8faa9c7 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-0009000000-d1f986325aed82b811c5 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-006x-0009000000-22208ced9e4760090001 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00ts-1049000000-7c902ce3c2dd5fb3009c | 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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External Links |
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DrugBank ID | Not Available |
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HMDB ID | HMDB0000438 |
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FooDB ID | FDB022045 |
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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 | Not Available |
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METLIN ID | 5427 |
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PDB ID | Not Available |
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Wikipedia Link | Not Available |
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Chemspider ID | 141062 |
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ChEBI ID | 88098 |
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PubChem Compound ID | 160530 |
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Kegg Compound ID | Not Available |
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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. https://www.ncbi.nlm.nih.gov/pubmed/?term=10733557 | 2. https://www.ncbi.nlm.nih.gov/pubmed/?term=14680217 | 3. https://www.ncbi.nlm.nih.gov/pubmed/?term=26192599 | 4. Danielsson, Henry; Eneroth, Peter; Hellstrom, Kjell; Sjovall, Jan. Bile acids and steroids. CXXIII. Synthesis of some 3b-hydroxylated bile acids and the isolation of 3b,12a-dihydroxy-5b-cholanic acid from feces. Journal of Biological Chemistry (1962), 237 3657-9. | 5. 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. | 6. 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. | 7. 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. | 8. 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. | 9. 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. | 10. 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. |
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