Deoxycholic acid glycine conjugate
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.
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Structure for HMDB00631 (Deoxycholic acid glycine conjugate)
C26H43NO5
449.6233
449.314123491
2-[(4R)-4-[(2S,5R,7R,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanamido]acetic acid
[(4R)-4-[(2S,5R,7R,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanamido]acetic acid
360-65-6
[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
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
WVULKSPCQVQLCU-ZMBDPXIHSA-N
Not classified
Detected and Quantified
Solid
LC-MS/MS Spectrum – Quattro_QQQ 10V, Positive (Annotated)splash10-0ik9-0000900000-4a3e850d7237d0106c35View in MoNA
LC-MS/MS Spectrum – Quattro_QQQ 25V, Positive (Annotated)splash10-01ti-3894300000-fa0e7861362d7bf348bbView in MoNA
LC-MS/MS Spectrum – Quattro_QQQ 40V, Positive (Annotated)splash10-0a7i-5910000000-17134bf01487bc71d373View in MoNA
1H NMR SpectrumNot Available
[1H,13C] 2D NMR SpectrumNot Available
Normal
Normal
Pancreatic ductal adenocarcinoma
Hepatocellliar carcinoma
Liver Cirrhosis
None
None
Not Available
Not Available
Not Available
Not Available
FDB022152
Not Available
17215983
C05464
Not Available
Not Available
Not Available
HMDB00631
HMDB00631
5604
22833539
Not Available
27471
- 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 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 ]
- 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 ]
Enzymes
- General function:
- Involved in glycine N-acyltransferase activity
- Specific function:
- Mitochondrial acyltransferase which transfers an acyl group to the N-terminus of glycine and glutamine, although much less efficiently. Can conjugate numerous substrates to form a variety of N-acylglycines, with a preference for benzoyl-CoA over phenylacetyl-CoA as acyl donors. Thereby detoxify xenobiotics, such as benzoic acid or salicylic acid, and endogenous organic acids, such as isovaleric acid.
- Gene Name:
- GLYAT
- Uniprot ID:
- Q6IB77
- Molecular weight:
- 18506.33
- General function:
- Involved in glycine N-acyltransferase activity
- Specific function:
- Acyltransferase which transfers an acyl group to the N-terminus of glutamine. Can use phenylacetyl-CoA as an acyl donor.
- Gene Name:
- GLYATL1
- Uniprot ID:
- Q969I3
- Molecular weight:
- 35100.895
- General function:
- Involved in glycine N-acyltransferase activity
- Specific function:
- Mitochondrial acyltransferase which transfers the acyl group to the N-terminus of glycine. Conjugates numerous substrates, such as arachidonoyl-CoA and saturated medium and long-chain acyl-CoAs ranging from chain-length C8:0-CoA to C18:0-CoA, to form a variety of N-acylglycines. Shows a preference for monounsaturated fatty acid oleoyl-CoA (C18:1-CoA) as an acyl donor. Does not exhibit any activity toward C22:6-CoA and chenodeoxycholoyl-CoA, nor toward serine or alanine.
- Gene Name:
- GLYATL2
- Uniprot ID:
- Q8WU03
- Molecular weight:
- 34277.055
- General function:
- Involved in glycine N-acyltransferase activity
- Specific function:
- Acyltransferase which transfers the acyl group to the N- terminus of glycine
- Gene Name:
- GLYATL3
- Uniprot ID:
- Q5SZD4
- Molecular weight:
- 32703.3