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Human Metabolome Database Version 2.5

 

Showing metabocard for Deoxycholic acid glycine conjugate (HMDB00631)

Legend: metabolite field enzyme field

Version 2.5
Creation Date 2005-11-16 15:48:42
Update Date 2010-07-13 12:13:22
Accession Number HMDB00631
Secondary Accession Numbers HMDB04012
Common Name Deoxycholic acid glycine conjugate
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.
Synonyms
  1. Deoxycholic acid glycine conjugate
  2. Deoxycholylglycine
  3. Deoxyglycocholate
  4. Deoxyglycocholic acid
  5. Glycodeoxycholate
  6. Glycodeoxycholic acid
  7. Glycodesoxycholate
  8. Glycodesoxycholic acid
  9. Glycyldeoxycholate
  10. Glycyldeoxycholic acid
  11. N-(3a,12a-dihydroxy-5b-cholan-24-oyl)-Glycine
  12. N-(carboxymethyl)-3a,12a-dihydroxy-5b-Cholan-24-amide
Chemical IUPAC Name N-[(3a,5b,12a)-3,12-dihydroxy-24-oxocholan-24-yl]-Glycine
Chemical Formula C26H43NO5
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Amino acids and Amino Acid conjugates
Class
  • Bile Acids
  • Acyl Glycines
Sub Class
  • Bile-acid glycine conjugates
Family
  • Mammalian Metabolite
Species
  • secondary alcohol
  • carboxylic acid
  • secondary carboxylic acid amide
Biofunction
—
Application
—
Source
  • Endogenous
Average Molecular Weight 449.623
Monoisotopic Molecular Weight 449.314117
Isomeric SMILES C[C@H](CCC(=O)NCC(O)=O)[C@H]1CCC2C3CC[C@@H]4C[C@H](O)CC[C@]4(C)C3C[C@H](O)[C@]12C
Canonical SMILES CC(CCC(=O)NCC(O)=O)C1CCC2C3CCC4CC(O)CCC4(C)C3CC(O)C12C
KEGG Compound ID C05464 Link Image
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB00631 Link Image
Metagene Link HMDB00631 Link Image
METLIN ID 5604 Link Image
PubChem Compound 440688 Link Image
PubChem Substance 152887 Link Image
ChEBI ID 27471 Link Image
CAS Registry Number 360-65-6
InChI Identifier InChI=1/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
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.
Melting Point (Experimental) Not Available
Experimental Water Solubility 0.0027 mg/mL [RODA,A et al. (1990)] Source: PhysProp
Predicted Water Solubility 7.85e-03 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge -1
State Solid
Experimental LogP/Hydrophobicity 2.25 [RODA,A ET AL. (1990)] Source: PhysProp
Predicted LogP/Hydrophobicity 2.69 [Predicted by ALOGPS]; 3.4 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Download Spectrum
Download FID (Varian)
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Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Download Spectrum
Download FID (Bruker)
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Predicted 1H NMR Spectrum Show Image
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Predicted 13C NMR Spectrum Show Image
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Mass Spectrum
Low Energy
Download File
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Medium Energy
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High Energy
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Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Membrane (Predicted from LogP)
Biofluid Location
  • Bile
Tissue Location Not Available
Concentrations (Normal)
Biofluid Bile
Value >0.01 uM
Age Adult:>18 yrs old
Sex Both
Patient information Normal
Comments Not Available
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 Link Image]
Concentrations (Abnormal) Not Available
Associated Disorders Not Available
OMIM ID Not Available
Pathways
Name SMPDB Link KEGG Link
Bile Acid Biosynthesis SMP00035 Link Image map00120 Link Image
General References
  1. 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 Link Image]
  2. 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 Link Image]
  3. Demers LM, Hepner G: Radioimmunoassay of bile acids in serum. Clin Chem. 1976 May;22(5):602-6. [PubMed Link Image]
  4. 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 Link Image]
Metabolic Enzymes
  1. Glycine N-acyltransferase
  2. Glycine N-acyltransferase-like protein 1
  3. Glycine N-acyltransferase-like protein 2
  4. Glycine N-acyltransferase-like protein 3
Enzyme 1 [top]
Enzyme 1 ID 12971
Enzyme 1 Name Glycine N-acyltransferase
Enzyme 1 Synonyms
  1. Acyl-CoA:glycine N-acyltransferase
  2. AAc
  3. Aralkyl acyl-CoA N-acyltransferase
  4. Aralkyl acyl-CoA:amino acid N-acyltransferase
  5. HRP-1(CLP)
Enzyme 1 Gene Name GLYAT
Enzyme 1 Protein Sequence >Glycine N-acyltransferase 
MMLPLQGAQMLQMLEKSLRKSLPASLKVYGTVFHINHGNPFNLKAVVDKWPDFNTVVVCP
QEQDMTDDLDHYTNTYQIYSKDPQNCQEFLGSPELINWKQHLQIQSSQPSLNEAIQNLAA
IKSFKVKQTQRILYMAAETAKELTPFLLKSKILSPSGGKPKAINQEMFKLSSMDVTHAHL
VNKFWHFGGNERSQRFIERCIQTFPTCCLLGPEGTPVCWDLMDQTGEMRMAGTLPEYRLH
GLVTYVIYSHAQKLGKLGFPVYSHVDYSNEAMQKMSYTLQHVPIPRSWNQWNCVPL
Enzyme 1 Number of Residues 296
Enzyme 1 Molecular Weight 33898
Enzyme 1 Theoretical pI 8.28
Enzyme 1 GO Classification Not Available
Enzyme 1 General Function Not Available
Enzyme 1 Specific Function Mitochondrial acyltransferase which transfers the acyl group to the N-terminus of glycine. Can conjugate a multitude of substrates to form a variety of N-acylglycines
Enzyme 1 Pathways Not Available
Enzyme 1 Reactions
  • Acyl-CoA + glycine = CoA + N-acylglycine
Enzyme 1 Pfam Domain Function
Enzyme 1 Signals
  • None
Enzyme 1 Transmembrane Regions
  • None
Enzyme 1 Essentiality Not Available
Enzyme 1 GenBank ID Protein 2554941 Link Image
Enzyme 1 UniProtKB/Swiss-Prot ID Q6IB77 Link Image
Enzyme 1 UniProtKB/Swiss-Prot Entry Name GLYAT_HUMAN Link Image
Enzyme 1 PDB ID Not Available
Enzyme 1 Cellular Location Not Available
Enzyme 1 Gene Sequence Not Available
Enzyme 1 GenBank Gene ID AF023466 Link Image
Enzyme 1 GeneCard ID Q6IB77 Link Image
Enzyme 1 GenAtlas ID GLYAT Link Image
Enzyme 1 HGNC ID HGNC:13734 Link Image
Enzyme 1 Chromosome Location Not Available
Enzyme 1 Locus Not Available
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 General References Not Available
Enzyme 1 Metabolite References Not Available
Enzyme 2 [top]
Enzyme 2 ID 12972
Enzyme 2 Name Glycine N-acyltransferase-like protein 1
Enzyme 2 Synonyms
  1. Acyl-CoA:glycine N-acyltransferase-like protein 1
Enzyme 2 Gene Name GLYATL1
Enzyme 2 Protein Sequence >Glycine N-acyltransferase-like protein 1 
MILLNNSHKLLALYKSLARSIPESLKVYGSVYHINHGNPFNMEVLVDSWPEYQMVIIRPQ
KQEMTDDMDSYTNVYRMFSKEPQKSEEVLKNCEIVNWKQRLQIQGLQESLGEGIRVATFS
KSVKVEHSRALLLVTEDILKLNASSKSKLGSWAETGHPDDEFESETPNFKYAQLDVSYSG
LVNDNWKRGKNERSLHYIKRCIEDLPAACMLGPEGVPVSWVTMDPSCEVGMAYSMEKYRR
TGNMARVMVRYMKYLRQKNIPFYISVLEENEDSRRFVGQFGFFEASCEWHQWTCYPQNLV
PF
Enzyme 2 Number of Residues 302
Enzyme 2 Molecular Weight 35102
Enzyme 2 Theoretical pI 6.86
Enzyme 2 GO Classification Not Available
Enzyme 2 General Function Not Available
Enzyme 2 Specific Function Mitochondrial acyltransferase which transfers the acyl group to the N-terminus of glycine. Can conjugate a multitude of substrates to form a variety of N-acylglycines
Enzyme 2 Pathways Not Available
Enzyme 2 Reactions
  • Acyl-CoA + glycine = CoA + N-acylglycine
Enzyme 2 Pfam Domain Function
Enzyme 2 Signals
  • None
Enzyme 2 Transmembrane Regions
  • None
Enzyme 2 Essentiality Not Available
Enzyme 2 GenBank ID Protein 71384826 Link Image
Enzyme 2 UniProtKB/Swiss-Prot ID Q969I3 Link Image
Enzyme 2 UniProtKB/Swiss-Prot Entry Name GLYL1_HUMAN Link Image
Enzyme 2 PDB ID Not Available
Enzyme 2 Cellular Location Not Available
Enzyme 2 Gene Sequence Not Available
Enzyme 2 GenBank Gene ID DQ084381 Link Image
Enzyme 2 GeneCard ID Q969I3 Link Image
Enzyme 2 GenAtlas ID GLYATL1 Link Image
Enzyme 2 HGNC ID HGNC:30519 Link Image
Enzyme 2 Chromosome Location Not Available
Enzyme 2 Locus Not Available
Enzyme 2 SNPs SNPJam Report Link Image
Enzyme 2 General References Not Available
Enzyme 2 Metabolite References Not Available
Enzyme 3 [top]
Enzyme 3 ID 12973
Enzyme 3 Name Glycine N-acyltransferase-like protein 2
Enzyme 3 Synonyms
  1. Acyl-CoA:glycine N-acyltransferase-like protein 2
Enzyme 3 Gene Name GLYATL2
Enzyme 3 Protein Sequence >Glycine N-acyltransferase-like protein 2 
MLVLHNSQKLQILYKSLEKSIPESIKVYGAIFNIKDKNPFNMEVLVDAWPDYQIVITRPQ
KQEMKDDQDHYTNTYHIFTKAPDKLEEVLSYSNVISWEQTLQIQGCQEGLDEAIRKVATS
KSVQVDYMKTILFIPELPKKHKTSSNDKMELFEVDDDNKEGNFSNMFLDASHAGLVNEHW
AFGKNERSLKYIERCLQDFLGFGVLGPEGQLVSWIVMEQSCELRMGYTVPKYRHQGNMLQ
IGYHLEKYLSQKEIPFYFHVADNNEKSLQALNNLGFKICPCGWHQWKCTPKKYC
Enzyme 3 Number of Residues 294
Enzyme 3 Molecular Weight 34278
Enzyme 3 Theoretical pI 6.67
Enzyme 3 GO Classification Not Available
Enzyme 3 General Function Not Available
Enzyme 3 Specific Function Mitochondrial acyltransferase which transfers the acyl group to the N-terminus of glycine. Can conjugate a multitude of substrates to form a variety of N-acylglycines
Enzyme 3 Pathways Not Available
Enzyme 3 Reactions
  • Acyl-CoA + glycine = CoA + N-acylglycine
Enzyme 3 Pfam Domain Function
Enzyme 3 Signals
  • None
Enzyme 3 Transmembrane Regions
  • None
Enzyme 3 Essentiality Not Available
Enzyme 3 GenBank ID Protein 29243559 Link Image
Enzyme 3 UniProtKB/Swiss-Prot ID Q8WU03 Link Image
Enzyme 3 UniProtKB/Swiss-Prot Entry Name GLYL2_HUMAN Link Image
Enzyme 3 PDB ID Not Available
Enzyme 3 Cellular Location Not Available
Enzyme 3 Gene Sequence Not Available
Enzyme 3 GenBank Gene ID AF426250 Link Image
Enzyme 3 GeneCard ID Q8WU03 Link Image
Enzyme 3 GenAtlas ID GLYATL2 Link Image
Enzyme 3 HGNC ID HGNC:24178 Link Image
Enzyme 3 Chromosome Location Not Available
Enzyme 3 Locus Not Available
Enzyme 3 SNPs SNPJam Report Link Image
Enzyme 3 General References Not Available
Enzyme 3 Metabolite References Not Available
Enzyme 4 [top]
Enzyme 4 ID 12974
Enzyme 4 Name Glycine N-acyltransferase-like protein 3
Enzyme 4 Synonyms Not Available
Enzyme 4 Gene Name GLYATL3
Enzyme 4 Protein Sequence >Glycine N-acyltransferase-like protein 3 
MLVLNCSTKLLILEKMLKSCFPESLKVYGAVMNINRGNPFQKEVVLDSWPDFKAVITRRQ
REAETDNLDHYTNAYAVFYKDVRAYRQLLEECDVFNWDQVFQIKGLQSELYDVSKAVANS
KQLNIKLTSFKAVHFSPVSSLPDTSFLKGPSPRLTYLSVANADLLNRTWSRGGNEQCLRY
IANLISCFPSVCVRDEKGNPVSWSITDQFATMCHGYTLPEHRRKGYSRLVALTLARKLQS
RGFPSQGNVLDDNTASISLLKSLHAEFLPCRFHRLILTPATFSGLPHL
Enzyme 4 Number of Residues 288
Enzyme 4 Molecular Weight 32704
Enzyme 4 Theoretical pI Not Available
Enzyme 4 GO Classification Not Available
Enzyme 4 General Function Not Available
Enzyme 4 Specific Function Acyltransferase which transfers the acyl group to the N-terminus of glycine (By similarity).
Enzyme 4 Pathways Not Available
Enzyme 4 Reactions Not Available
Enzyme 4 Pfam Domain Function Not Available
Enzyme 4 Signals
  • None
Enzyme 4 Transmembrane Regions
  • None
Enzyme 4 Essentiality Not Available
Enzyme 4 GenBank ID Protein Not Available
Enzyme 4 UniProtKB/Swiss-Prot ID Q5SZD4 Link Image
Enzyme 4 UniProtKB/Swiss-Prot Entry Name GLYL3_HUMAN Link Image
Enzyme 4 PDB ID Not Available
Enzyme 4 Cellular Location Not Available
Enzyme 4 Gene Sequence Not Available
Enzyme 4 GenBank Gene ID Not Available
Enzyme 4 GeneCard ID Q5SZD4 Link Image
Enzyme 4 GenAtlas ID GLYATL3 Link Image
Enzyme 4 HGNC ID HGNC:21349 Link Image
Enzyme 4 Chromosome Location Not Available
Enzyme 4 Locus Not Available
Enzyme 4 SNPs SNPJam Report Link Image
Enzyme 4 General References Not Available
Enzyme 4 Metabolite References Not Available