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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-16 15:27:09 UTC
HMDB IDHMDB0000631
Secondary Accession Numbers
  • HMDB0004012
  • HMDB00631
  • HMDB04012
Metabolite Identification
Common NameDeoxycholic acid glycine conjugate
DescriptionDeoxycholic acid glycine conjugate, or or Deoxyglycocholic acid or Deoxygcholylglycine is a bile salt formed in the liver by conjugation of deoxycholate with glycine. It usually exists as the sodium salt. Deoxygcholylglycine 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 acid Deoxyglycocholic acid acts as a detergent to solubilize fats for absorption and is itself absorbed. Bile acids are steroid acids found predominantly in the bile of mammals. The distinction between different bile acids is minute, and depends only on the presence or absence of hydroxyl groups on positions 3, 7, and 12. Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. Bile acids recirculate through the liver, bile ducts, small intestine, and portal vein to form an enterohepatic circuit. They exist as anions at physiological pH, and consequently require a carrier for transport across the membranes of the enterohepatic tissues. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. Bile acids have potent toxic properties (e.g. membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues (PMID: 11316487 , 16037564 , 12576301 , 11907135 ). Deoxyglycocholic acid is used as a cholagogue and choleretic.
Structure
Data?1582752145
Synonyms
ValueSource
Deoxycholate glycine conjugateGenerator
Deoxycholic acid glycine conjugic acidGenerator
Acid, glycodeoxycholicMeSH
Deoxycholate, glycineMeSH
Glycine deoxycholateMeSH
Glycodeoxycholic acidMeSH
GlycodeoxycholateMeSH
DeoxycholylglycineMeSH
DeoxyglycocholateHMDB
Deoxyglycocholic acidHMDB
GlycodesoxycholateHMDB
Glycodesoxycholic acidHMDB
GlycyldeoxycholateHMDB
Glycyldeoxycholic acidHMDB
N-(3a,12a-Dihydroxy-5b-cholan-24-oyl)-glycineHMDB
N-(Carboxymethyl)-3a,12a-dihydroxy-5b-cholan-24-amideHMDB
Chemical FormulaC26H43NO5
Average Molecular Weight449.6233
Monoisotopic Molecular Weight449.314123491
IUPAC Name2-[(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
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
CAS Registry Number360-65-6
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
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
InChI KeyWVULKSPCQVQLCU-ZMBDPXIHSA-N
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentGlycinated bile acids and derivatives
Alternative Parents
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
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0027 mg/mLNot Available
LogP2.25RODA,A ET AL. (1990)
Experimental Spectral Properties

Experimental Collision Cross Sections

PredictorAdduct TypeData SourceCCS Value (Å2)Reference
AllCCS[M-H]-Not Available197.815http://allccs.zhulab.cn/database/detail?ID=AllCCS00000203
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0078 g/LALOGPS
logP10(2.69) g/LALOGPS
logP10(2.69) g/LChemAxon
logS10(-4.8) g/LALOGPS
pKa (Strongest Acidic)3.77ChemAxon
pKa (Strongest Basic)-0.32ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area106.86 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity122 m³·mol⁻¹ChemAxon
Polarizability52.11 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+200.24731661259
DarkChem[M-H]-199.03731661259
AllCCS[M+H]+211.61932859911
AllCCS[M-H]-205.09632859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Deoxycholic acid glycine conjugate,1TMS,#1C[C@H](CCC(=O)NCC(=O)O[Si](C)(C)C)[C@H]1CCC2C3CC[C@@H]4C[C@H](O)CC[C@]4(C)C3C[C@H](O)[C@@]21C3905.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
Deoxycholic acid glycine conjugate,1TMS,#2C[C@H](CCC(=O)NCC(=O)O)[C@H]1CCC2C3CC[C@@H]4C[C@H](O)CC[C@]4(C)C3C[C@H](O[Si](C)(C)C)[C@@]21C3915.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Deoxycholic acid glycine conjugate,1TMS,#3C[C@H](CCC(=O)NCC(=O)O)[C@H]1CCC2C3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)C3C[C@H](O)[C@@]21C3963.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
Deoxycholic acid glycine conjugate,1TMS,#4C[C@H](CCC(=O)N(CC(=O)O)[Si](C)(C)C)[C@H]1CCC2C3CC[C@@H]4C[C@H](O)CC[C@]4(C)C3C[C@H](O)[C@@]21C3935.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
Deoxycholic acid glycine conjugate,2TMS,#1C[C@H](CCC(=O)NCC(=O)O[Si](C)(C)C)[C@H]1CCC2C3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)C3C[C@H](O)[C@@]21C3863.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Deoxycholic acid glycine conjugate,2TMS,#2C[C@H](CCC(=O)NCC(=O)O[Si](C)(C)C)[C@H]1CCC2C3CC[C@@H]4C[C@H](O)CC[C@]4(C)C3C[C@H](O[Si](C)(C)C)[C@@]21C3850.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
Deoxycholic acid glycine conjugate,2TMS,#3C[C@H](CCC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C)[C@H]1CCC2C3CC[C@@H]4C[C@H](O)CC[C@]4(C)C3C[C@H](O)[C@@]21C3876.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
Deoxycholic acid glycine conjugate,2TMS,#4C[C@H](CCC(=O)NCC(=O)O)[C@H]1CCC2C3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)C3C[C@H](O[Si](C)(C)C)[C@@]21C3844.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Deoxycholic acid glycine conjugate,2TMS,#5C[C@H](CCC(=O)N(CC(=O)O)[Si](C)(C)C)[C@H]1CCC2C3CC[C@@H]4C[C@H](O)CC[C@]4(C)C3C[C@H](O[Si](C)(C)C)[C@@]21C3847.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Deoxycholic acid glycine conjugate,2TMS,#6C[C@H](CCC(=O)N(CC(=O)O)[Si](C)(C)C)[C@H]1CCC2C3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)C3C[C@H](O)[C@@]21C3919.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Deoxycholic acid glycine conjugate,3TMS,#1C[C@H](CCC(=O)NCC(=O)O[Si](C)(C)C)[C@H]1CCC2C3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)C3C[C@H](O[Si](C)(C)C)[C@@]21C3771.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
Deoxycholic acid glycine conjugate,3TMS,#2C[C@H](CCC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C)[C@H]1CCC2C3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)C3C[C@H](O)[C@@]21C3828.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
Deoxycholic acid glycine conjugate,3TMS,#3C[C@H](CCC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C)[C@H]1CCC2C3CC[C@@H]4C[C@H](O)CC[C@]4(C)C3C[C@H](O[Si](C)(C)C)[C@@]21C3794.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
Deoxycholic acid glycine conjugate,3TMS,#4C[C@H](CCC(=O)N(CC(=O)O)[Si](C)(C)C)[C@H]1CCC2C3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)C3C[C@H](O[Si](C)(C)C)[C@@]21C3780.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
Deoxycholic acid glycine conjugate,1TBDMS,#1C[C@H](CCC(=O)NCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CCC2C3CC[C@@H]4C[C@H](O)CC[C@]4(C)C3C[C@H](O)[C@@]21C4148.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
Deoxycholic acid glycine conjugate,1TBDMS,#2C[C@H](CCC(=O)NCC(=O)O)[C@H]1CCC2C3CC[C@@H]4C[C@H](O)CC[C@]4(C)C3C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C4129.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Deoxycholic acid glycine conjugate,1TBDMS,#3C[C@H](CCC(=O)NCC(=O)O)[C@H]1CCC2C3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)C3C[C@H](O)[C@@]21C4184.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
Deoxycholic acid glycine conjugate,1TBDMS,#4C[C@H](CCC(=O)N(CC(=O)O)[Si](C)(C)C(C)(C)C)[C@H]1CCC2C3CC[C@@H]4C[C@H](O)CC[C@]4(C)C3C[C@H](O)[C@@]21C4155.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
Deoxycholic acid glycine conjugate,2TBDMS,#1C[C@H](CCC(=O)NCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CCC2C3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)C3C[C@H](O)[C@@]21C4285.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Deoxycholic acid glycine conjugate,2TBDMS,#2C[C@H](CCC(=O)NCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CCC2C3CC[C@@H]4C[C@H](O)CC[C@]4(C)C3C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C4262.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Deoxycholic acid glycine conjugate,2TBDMS,#3C[C@H](CCC(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H]1CCC2C3CC[C@@H]4C[C@H](O)CC[C@]4(C)C3C[C@H](O)[C@@]21C4324.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Deoxycholic acid glycine conjugate,2TBDMS,#4C[C@H](CCC(=O)NCC(=O)O)[C@H]1CCC2C3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)C3C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C4268.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
Deoxycholic acid glycine conjugate,2TBDMS,#5C[C@H](CCC(=O)N(CC(=O)O)[Si](C)(C)C(C)(C)C)[C@H]1CCC2C3CC[C@@H]4C[C@H](O)CC[C@]4(C)C3C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C4295.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Deoxycholic acid glycine conjugate,2TBDMS,#6C[C@H](CCC(=O)N(CC(=O)O)[Si](C)(C)C(C)(C)C)[C@H]1CCC2C3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)C3C[C@H](O)[C@@]21C4363.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
Deoxycholic acid glycine conjugate,3TBDMS,#1C[C@H](CCC(=O)NCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CCC2C3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)C3C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C4400.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Deoxycholic acid glycine conjugate,3TBDMS,#2C[C@H](CCC(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H]1CCC2C3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)C3C[C@H](O)[C@@]21C4497.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
Deoxycholic acid glycine conjugate,3TBDMS,#3C[C@H](CCC(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H]1CCC2C3CC[C@@H]4C[C@H](O)CC[C@]4(C)C3C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C4467.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
Deoxycholic acid glycine conjugate,3TBDMS,#4C[C@H](CCC(=O)N(CC(=O)O)[Si](C)(C)C(C)(C)C)[C@H]1CCC2C3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)C3C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C4473.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Deoxycholic acid glycine conjugate GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-0124900000-9935025b691abf76f8372017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Deoxycholic acid glycine conjugate GC-MS (3 TMS) - 70eV, Positivesplash10-0udj-2101139000-a160ba76c005cfc50ac72017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Deoxycholic acid glycine conjugate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Deoxycholic acid glycine conjugate Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-0ik9-0000900000-4a3e850d7237d0106c352012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Deoxycholic acid glycine conjugate Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-01ti-3894300000-fa0e7861362d7bf348bb2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Deoxycholic acid glycine conjugate Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0a7i-5910000000-17134bf01487bc71d3732012-07-24HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deoxycholic acid glycine conjugate 10V, Positive-QTOFsplash10-0gz9-2002900000-02545f99732b7619c59d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deoxycholic acid glycine conjugate 20V, Positive-QTOFsplash10-056r-9005400000-282d54d2414239340bc62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deoxycholic acid glycine conjugate 40V, Positive-QTOFsplash10-004i-9104100000-4eb16c3c40c7f98e37882017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deoxycholic acid glycine conjugate 10V, Negative-QTOFsplash10-0002-0000900000-9e4d382267acd7d0da8c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deoxycholic acid glycine conjugate 20V, Negative-QTOFsplash10-00ea-4103900000-d0ad37cdb8c4ebcc8b3f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deoxycholic acid glycine conjugate 40V, Negative-QTOFsplash10-05fr-9001000000-23d56965528e66b241e72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deoxycholic acid glycine conjugate 10V, Negative-QTOFsplash10-0002-0000900000-1659120ddaaa97329ed42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deoxycholic acid glycine conjugate 20V, Negative-QTOFsplash10-0002-1001900000-74add9101b276384e02f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deoxycholic acid glycine conjugate 40V, Negative-QTOFsplash10-00dj-9003300000-7b2d9962126a043e24442021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deoxycholic acid glycine conjugate 10V, Positive-QTOFsplash10-0ue9-0001900000-e79d7064b1c912d327742021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deoxycholic acid glycine conjugate 20V, Positive-QTOFsplash10-0kuu-4855900000-7091abc8f240404bf1592021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deoxycholic acid glycine conjugate 40V, Positive-QTOFsplash10-0avi-9730300000-e569a38323705f9cdfc62021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen Locations
  • Bile
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Prostate
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BileDetected and Quantified>0.01 uMAdult (>18 years old)BothNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified19.19 +/- 13.69 nmol/g dry fecesNot SpecifiedNot Specified
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Pancreatic ductal adenocarcinoma
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Hepatocellular carcinoma
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Liver Cirrhosis
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)FemaleEpithelial ovarian cancer details
Associated Disorders and Diseases
Disease References
Hepatocellular carcinoma
  1. 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
  1. 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
  1. 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 ]
  2. 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 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022152
KNApSAcK IDC00030411
Chemspider ID17215983
KEGG Compound IDC05464
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5604
PubChem Compound22833539
PDB IDNot Available
ChEBI ID27471
Food Biomarker OntologyNot Available
VMH IDM01989
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceParmentier 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)Download (PDF)
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. Demers LM, Hepner G: Radioimmunoassay of bile acids in serum. Clin Chem. 1976 May;22(5):602-6. [PubMed:1261008 ]
  6. 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 ]
  7. St-Pierre MV, Kullak-Ublick GA, Hagenbuch B, Meier PJ: Transport of bile acids in hepatic and non-hepatic tissues. J Exp Biol. 2001 May;204(Pt 10):1673-86. [PubMed:11316487 ]
  8. Claudel T, Staels B, Kuipers F: The Farnesoid X receptor: a molecular link between bile acid and lipid and glucose metabolism. Arterioscler Thromb Vasc Biol. 2005 Oct;25(10):2020-30. Epub 2005 Jul 21. [PubMed:16037564 ]
  9. Chiang JY: Bile acid regulation of hepatic physiology: III. Bile acids and nuclear receptors. Am J Physiol Gastrointest Liver Physiol. 2003 Mar;284(3):G349-56. [PubMed:12576301 ]
  10. Davis RA, Miyake JH, Hui TY, Spann NJ: Regulation of cholesterol-7alpha-hydroxylase: BAREly missing a SHP. J Lipid Res. 2002 Apr;43(4):533-43. [PubMed:11907135 ]

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