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Record Information |
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Version | 4.0 |
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Status | Detected and Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2020-11-09 23:13:57 UTC |
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HMDB ID | HMDB0000631 |
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Secondary Accession Numbers | - HMDB0004012
- HMDB00631
- HMDB04012
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Metabolite Identification |
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Common Name | Deoxycholic acid glycine conjugate |
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Description | Deoxycholic acid glycine conjugate, or Deoxygcholylglycine, is an acyl glycine and a bile acid-glycine conjugate. 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 ). As a bile salt it acts as a detergent to solubilize fats for absorption and is itself absorbed. It is used as a cholagogue and choleretic. |
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Structure | |
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Synonyms | Value | Source |
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Deoxycholate glycine conjugate | Generator | Deoxycholic acid glycine conjugic acid | Generator | Deoxycholylglycine | HMDB | Deoxyglycocholate | HMDB | Deoxyglycocholic acid | HMDB | Glycodeoxycholate | HMDB | Glycodeoxycholic acid | HMDB | Glycodesoxycholate | HMDB | Glycodesoxycholic acid | HMDB | Glycyldeoxycholate | HMDB | Glycyldeoxycholic acid | HMDB | N-(3a,12a-Dihydroxy-5b-cholan-24-oyl)-glycine | HMDB | N-(Carboxymethyl)-3a,12a-dihydroxy-5b-cholan-24-amide | HMDB | Deoxycholate, glycine | HMDB | Acid, glycodeoxycholic | HMDB | Glycine deoxycholate | HMDB |
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Chemical Formula | C26H43NO5 |
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Average Molecular Weight | 449.6233 |
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Monoisotopic Molecular Weight | 449.314123491 |
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IUPAC Name | 2-[(4R)-4-[(2S,5R,7R,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid |
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Traditional Name | [(4R)-4-[(2S,5R,7R,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid |
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CAS Registry Number | 360-65-6 |
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SMILES | [H][C@]12CCC3C4CC[C@H]([C@H](C)CCC(=O)NCC(O)=O)[C@@]4(C)[C@@H](O)CC3[C@@]1(C)CC[C@@H](O)C2 |
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InChI Identifier | InChI=1S/C26H43NO5/c1-15(4-9-23(30)27-14-24(31)32)19-7-8-20-18-6-5-16-12-17(28)10-11-25(16,2)21(18)13-22(29)26(19,20)3/h15-22,28-29H,4-14H2,1-3H3,(H,27,30)(H,31,32)/t15-,16-,17-,18?,19-,20?,21?,22+,25+,26-/m1/s1 |
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InChI Key | WVULKSPCQVQLCU-ZMBDPXIHSA-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
- Dihydroxy bile acid, alcohol, or derivatives
- Hydroxy bile acid, alcohol, or derivatives
- 3-hydroxysteroid
- 12-hydroxysteroid
- Hydroxysteroid
- 3-alpha-hydroxysteroid
- N-acyl-alpha-amino acid
- N-acyl-alpha amino acid or derivatives
- Alpha-amino acid or derivatives
- Fatty amide
- Fatty acyl
- N-acyl-amine
- Cyclic alcohol
- Carboxamide group
- Secondary alcohol
- Secondary carboxylic acid amide
- Carboxylic acid derivative
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Hydrocarbon derivative
- Organic oxide
- Alcohol
- Organic nitrogen compound
- Organopnictogen compound
- Carbonyl group
- Organic oxygen compound
- Organooxygen compound
- 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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Disposition | Route of exposure: Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Industrial application: Biological role: |
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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 | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.0027 mg/mL | Not Available | LogP | 2.25 | RODA,A ET AL. (1990) |
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Predicted Properties | |
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Spectra |
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| Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-001i-0124900000-9935025b691abf76f837 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive | splash10-0udj-2101139000-a160ba76c005cfc50ac7 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-0ik9-0000900000-4a3e850d7237d0106c35 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-01ti-3894300000-fa0e7861362d7bf348bb | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-0a7i-5910000000-17134bf01487bc71d373 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0gz9-2002900000-02545f99732b7619c59d | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-056r-9005400000-282d54d2414239340bc6 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-004i-9104100000-4eb16c3c40c7f98e3788 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-0000900000-9e4d382267acd7d0da8c | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00ea-4103900000-d0ad37cdb8c4ebcc8b3f | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-05fr-9001000000-23d56965528e66b241e7 | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | Spectrum |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | |
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Tissue Locations | |
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Pathways | |
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Normal Concentrations |
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Bile | Detected and Quantified | >0.01 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Blood | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected and Quantified | 19.19 +/- 13.69 nmol/g dry feces | Not Specified | Not Specified | Normal | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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Blood | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Pancreatic ductal adenocarcinoma | | details | Blood | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Hepatocellular carcinoma | | details | Blood | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Liver Cirrhosis | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal Cancer | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal cancer | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Female | Epithelial ovarian cancer | | details |
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Associated Disorders and Diseases |
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Disease References | Hepatocellular carcinoma |
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- Ressom HW, Xiao JF, Tuli L, Varghese RS, Zhou B, Tsai TH, Ranjbar MR, Zhao Y, Wang J, Di Poto C, Cheema AK, Tadesse MG, Goldman R, Shetty K: Utilization of metabolomics to identify serum biomarkers for hepatocellular carcinoma in patients with liver cirrhosis. Anal Chim Acta. 2012 Sep 19;743:90-100. doi: 10.1016/j.aca.2012.07.013. Epub 2012 Jul 20. [PubMed:22882828 ]
| Cirrhosis |
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- Ressom HW, Xiao JF, Tuli L, Varghese RS, Zhou B, Tsai TH, Ranjbar MR, Zhao Y, Wang J, Di Poto C, Cheema AK, Tadesse MG, Goldman R, Shetty K: Utilization of metabolomics to identify serum biomarkers for hepatocellular carcinoma in patients with liver cirrhosis. Anal Chim Acta. 2012 Sep 19;743:90-100. doi: 10.1016/j.aca.2012.07.013. Epub 2012 Jul 20. [PubMed:22882828 ]
| Colorectal cancer |
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- Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
- Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
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Associated OMIM IDs | - 114550 (Hepatocellular carcinoma)
- 114500 (Colorectal cancer)
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB022152 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 17215983 |
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KEGG Compound ID | C05464 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | 5604 |
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PubChem Compound | 22833539 |
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PDB ID | Not Available |
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ChEBI ID | 27471 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | |
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References |
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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. |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - 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 GW: Levels of immunoreactive glycine-conjugated bile acids in health and hepatobiliary disease. Am J Clin Pathol. 1976 Nov;66(5):831-9. [PubMed:983991 ]
- Demers LM, Hepner G: Radioimmunoassay of bile acids in serum. Clin Chem. 1976 May;22(5):602-6. [PubMed:1261008 ]
- 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 ]
- 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 ]
- 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 ]
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