Record Information |
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Version | 1.0 |
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Creation Date | 2016-09-30 22:20:03 UTC |
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Update Date | 2020-05-11 20:46:36 UTC |
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BMDB ID | BMDB0000138 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Glycocholic acid |
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Description | Glycocholic acid, also known as glycocholate or N-choloyl-glycine, belongs to the class of organic compounds known as glycinated bile acids and derivatives. Glycinated bile acids and derivatives are compounds with a structure characterized by the presence of a glycine linked to a bile acid skeleton. Glycocholic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Glycocholic acid has been found to be associated with several diseases known as crohn's disease, hepatobiliary diseases, cystic fibrosis, and portal vein obstruction; also glycocholic acid has been linked to the inborn metabolic disorders including celiac disease. |
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Structure | |
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Synonyms | Value | Source |
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Glycocholate | Generator | 3a,7a,12a-Trihydroxy-5b-cholan-24-oylglycine | HMDB | 3a,7a,12a-Trihydroxy-5b-cholanic acid-24-glycine | HMDB | 3a,7a,12a-Trihydroxy-N-(carboxymethyl)-5b-cholan-24-amide | HMDB | Cholylglycine | HMDB | Glycine cholate | HMDB | Glycoreductodehydrocholic acid | HMDB | Glycylcholate | HMDB | Glycylcholic acid | HMDB | N-(Carboxymethyl)-3a,7a,12a-trihydroxy-5b-cholan-24-amide | HMDB | N-Choloyl-glycine | HMDB | N-Choloylglycine | HMDB | Glycocholic acid, sodium salt | MeSH, HMDB | Glycocholate sodium | MeSH, HMDB |
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Chemical Formula | C26H43NO6 |
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Average Molecular Weight | 465.6227 |
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Monoisotopic Molecular Weight | 465.309038113 |
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IUPAC Name | Not Available |
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Traditional Name | Not Available |
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CAS Registry Number | 475-31-0 |
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SMILES | Not Available |
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InChI Identifier | InChI=1S/C26H43NO6/c1-14(4-7-22(31)27-13-23(32)33)17-5-6-18-24-19(12-21(30)26(17,18)3)25(2)9-8-16(28)10-15(25)11-20(24)29/h14-21,24,28-30H,4-13H2,1-3H3,(H,27,31)(H,32,33)/t14-,15?,16-,17-,18+,19+,20-,21+,24+,25+,26-/m1/s1 |
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InChI Key | RFDAIACWWDREDC-MZMBZMQMSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as glycinated bile acids and derivatives. Glycinated bile acids and derivatives are compounds with a structure characterized by the presence of a glycine linked to a bile acid skeleton. |
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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 | Glycinated bile acids and derivatives |
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Alternative Parents | |
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Substituents | - Glycinated bile acid
- Trihydroxy bile acid, alcohol, or derivatives
- Hydroxy bile acid, alcohol, or derivatives
- 3-hydroxysteroid
- 12-hydroxysteroid
- Hydroxysteroid
- 7-hydroxysteroid
- 3-alpha-hydroxysteroid
- N-acyl-alpha-amino acid
- N-acyl-alpha amino acid or derivatives
- Alpha-amino acid or derivatives
- Fatty acyl
- N-acyl-amine
- Fatty amide
- Cyclic alcohol
- Secondary alcohol
- Secondary carboxylic acid amide
- Carboxamide group
- Polyol
- Monocarboxylic acid or derivatives
- Carboxylic acid derivative
- Carboxylic acid
- Organooxygen compound
- Organic oxygen compound
- Organopnictogen compound
- Organic oxide
- Hydrocarbon derivative
- Organic nitrogen compound
- Carbonyl group
- Alcohol
- Organonitrogen compound
- Aliphatic homopolycyclic compound
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Molecular Framework | Aliphatic homopolycyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Status | Detected but not Quantified |
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Origin | |
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Biofunction | Not Available |
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Application | Not Available |
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Cellular locations | |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | 170 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.0033 mg/mL | Not Available | LogP | 1.65 | RODA,A ET AL. (1990) |
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Predicted Properties | Not Available |
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Spectra |
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Spectra | |
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General References | - Qian L, Zhao A, Zhang Y, Chen T, Zeisel SH, Jia W, Cai W: Metabolomic Approaches to Explore Chemical Diversity of Human Breast-Milk, Formula Milk and Bovine Milk. Int J Mol Sci. 2016 Dec 17;17(12). pii: ijms17122128. doi: 10.3390/ijms17122128. [PubMed:27999311 ]
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