You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
| Record Information |
|---|
| Version | 3.6 |
|---|
| Creation Date | 2005-11-16 15:48:42 UTC |
|---|
| Update Date | 2017-03-02 21:26:02 UTC |
|---|
| HMDB ID | HMDB00637 |
|---|
| Secondary Accession Numbers | |
|---|
| Metabolite Identification |
|---|
| Common Name | Chenodeoxycholic acid glycine conjugate |
|---|
| Description | Chenodeoxycholic acid glycine conjugate is an acyl glycine and a bile acid-glycine conugate. It is a secondary bile acid produced by the action of enzymes existing in the microbial flora of the colonic environment. In hepatocytes, both primary and secondary bile acids undergo amino acid conjugation at the C-24 carboxylic acid on the side chain, and almost all bile acids in the bile duct therefore exist in a glycine conjugated form (PMID:16949895 ). This compound usually exists as the sodium salt and acts as a detergent to solubilize fats for absorption and is itself absorbed. It is a cholagogue and choleretic. |
|---|
| Structure | |
|---|
| Synonyms | | Value | Source |
|---|
| (23R)-Hydroxychenodeoxycholylglycine | HMDB | | 12-Deoxycholylglycine | HMDB | | 12-Desoxycholylglycine | HMDB | | 3a,7a-Dihydroxy-N-(carboxymethyl)-5b-cholan-24-amide | HMDB | | Chenodeoxycholylglycine | HMDB | | Glycine chenodeoxycholate | HMDB | | Glycochenodeoxycholate | HMDB | | Glycochenodeoxycholic acid | HMDB | | Glycylchenodeoxycholate | HMDB | | Glycylchenodeoxycholic acid | HMDB | | N-(3a,7a-Dihydroxy-5b-cholan-24-oyl)-glycine | HMDB | | N-(Carboxymethyl)-3a,7a-dihydroxy-5b-cholan-24-amide | HMDB | | Acid, glycochenodeoxycholic | MeSH | | Chenodeoxycholate, glycine | MeSH |
|
|---|
| Chemical Formula | C26H43NO5 |
|---|
| Average Molecular Weight | 449.6233 |
|---|
| Monoisotopic Molecular Weight | 449.314123491 |
|---|
| IUPAC Name | 2-[(4R)-4-[(2S,5R,7S,9R,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanamido]acetic acid |
|---|
| Traditional Name | [(4R)-4-[(2S,5R,7S,9R,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanamido]acetic acid |
|---|
| CAS Registry Number | 640-79-9 |
|---|
| SMILES | [H][C@@]12C[C@H](O)CC[C@]1(C)C1CC[C@]3(C)[C@H](CCC3C1[C@H](O)C2)[C@H](C)CCC(=O)NCC(O)=O |
|---|
| InChI Identifier | InChI=1S/C26H43NO5/c1-15(4-7-22(30)27-14-23(31)32)18-5-6-19-24-20(9-11-26(18,19)3)25(2)10-8-17(28)12-16(25)13-21(24)29/h15-21,24,28-29H,4-14H2,1-3H3,(H,27,30)(H,31,32)/t15-,16+,17-,18-,19?,20?,21-,24?,25+,26-/m1/s1 |
|---|
| InChI Key | GHCZAUBVMUEKKP-AHBZRTSYSA-N |
|---|
| Chemical Taxonomy |
|---|
| Classification | Not classified |
|---|
| Ontology |
|---|
| Status | Detected and Quantified |
|---|
| Origin | |
|---|
| Biofunction | - Cell signaling
- Fuel and energy storage
- Fuel or energy source
- Membrane integrity/stability
|
|---|
| Application | - Nutrients
- Stabilizers
- Surfactants and Emulsifiers
|
|---|
| 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 | 0.00315 mg/mL | Not Available | | LogP | 2.12 | RODA,A ET AL. (1990) |
|
|---|
| Predicted Properties | |
|---|
| Spectra |
|---|
| Spectra | |
|---|
| Biological Properties |
|---|
| Cellular Locations | |
|---|
| Biofluid Locations | |
|---|
| Tissue Location | |
|---|
| Pathways | | Name | SMPDB Link | KEGG Link |
|---|
| 27-Hydroxylase Deficiency | SMP00720 | Not Available | | Bile Acid Biosynthesis | SMP00035 | map00120 | | Cerebrotendinous Xanthomatosis (CTX) | SMP00315 | Not Available | | Congenital Bile Acid Synthesis Defect Type II | SMP00314 | Not Available | | Congenital Bile Acid Synthesis Defect Type III | SMP00318 | Not Available | | Familial Hypercholanemia (FHCA) | SMP00317 | Not Available | | Zellweger Syndrome | SMP00316 | Not Available |
|
|---|
| Normal Concentrations |
|---|
| |
| Bile | Detected and Quantified | >0.01 uM | Adult (>18 years old) | Both | Normal | | details | | Blood | Detected and Quantified | 0.06 +/- 0.01 uM | Adult (>18 years old) | Both | Normal | - Geigy Scientific ...
- Basel, Switzerlan...
- West Cadwell, N.J...
| details | | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | | Feces | Detected but not Quantified | | Children (1-13 years old) | Both | Normal | | details | | Feces | Detected and Quantified | 22.28 +/- 15.65 nmol/g of feces | Not Specified | Not Specified | Normal | | details | | Urine | Detected and Quantified | 0.0013 +/- 0.0026 umol/mmol creatinine | Infant (0-1 year old) | Both | Normal | | details |
|
|---|
| Abnormal Concentrations |
|---|
| |
| Feces | Detected but not Quantified | | Adult (>18 years old) | Both | CCD | | details | | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | ICD | | details | | Feces | Detected but not Quantified | | Not Specified | Not Specified | Recurrent Clostridium difficile infection | | details | | Feces | Detected but not Quantified | | Not Specified | Not Specified | Recurrent Clostridium difficile infection | | details | | Urine | Detected and Quantified | 0.032 +/- 0.058 umol/mmol creatinine | Adult (>18 years old) | Both | Biliary atresia | | details |
|
|---|
| Associated Disorders and Diseases |
|---|
| Disease References | | Biliary atresia |
|---|
- Nittono H, Obinata K, Nakatsu N, Watanabe T, Niijima S, Sasaki H, Arisaka O, Kato H, Yabuta K, Miyano T: Sulfated and nonsulfated bile acids in urine of patients with biliary atresia: analysis of bile acids by high-performance liquid chromatography. J Pediatr Gastroenterol Nutr. 1986 Jan;5(1):23-9. [PubMed:3944741 ]
|
|
|---|
| Associated OMIM IDs | |
|---|
| External Links |
|---|
| DrugBank ID | Not Available |
|---|
| DrugBank Metabolite ID | Not Available |
|---|
| Phenol Explorer Compound ID | Not Available |
|---|
| Phenol Explorer Metabolite ID | Not Available |
|---|
| FoodDB ID | FDB022157 |
|---|
| KNApSAcK ID | Not Available |
|---|
| Chemspider ID | 17215984 |
|---|
| KEGG Compound ID | C05466 |
|---|
| BioCyc ID | Not Available |
|---|
| BiGG ID | 45866 |
|---|
| Wikipedia Link | Not Available |
|---|
| NuGOwiki Link | HMDB00637 |
|---|
| Metagene Link | HMDB00637 |
|---|
| METLIN ID | 5610 |
|---|
| PubChem Compound | 22833540 |
|---|
| PDB ID | 1FMC |
|---|
| ChEBI ID | Not Available |
|---|
| References |
|---|
| Synthesis Reference | Parmentier G; Eyssen H Synthesis and characteristics of the specific monosulfates of chenodeoxycholate, deoxycholate and their taurine or glycine conjugates. Steroids (1977), 30(5), 583-90. |
|---|
| Material Safety Data Sheet (MSDS) | Not Available |
|---|
| General References | - Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
- Hepner GW, Demers LM: Dynamics of the enterohepatic circulation of the glycine conjugates of cholic, chenodeoxycholic, deoxycholic, and sulfolithocholic acid in man. Gastroenterology. 1977 Mar;72(3):499-501. [PubMed:832799 ]
- Bloch CA, Watkins JB: Determination of conjugated bile acids in human bile and duodenal fluid by reverse-phase high-performance liquid chromatography. J Lipid Res. 1978 May;19(4):510-3. [PubMed:659989 ]
- Demers LM, Hepner G: Radioimmunoassay of bile acids in serum. Clin Chem. 1976 May;22(5):602-6. [PubMed:1261008 ]
- Makino I, Shinozaki K, Nakagawa S, Mashimo K: Measurement of sulfated and nonsulfated bile acids in human serum and urine. J Lipid Res. 1974 Mar;15(2):132-8. [PubMed:4832755 ]
- Goto T, Myint KT, Sato K, Wada O, Kakiyama G, Iida T, Hishinuma T, Mano N, Goto J: LC/ESI-tandem mass spectrometric determination of bile acid 3-sulfates in human urine 3beta-Sulfooxy-12alpha-hydroxy-5beta-cholanoic acid is an abundant nonamidated sulfate. J Chromatogr B Analyt Technol Biomed Life Sci. 2007 Feb 1;846(1-2):69-77. Epub 2006 Sep 1. [PubMed:16949895 ]
|
|---|