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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:32 UTC
Update Date2021-09-14 15:46:58 UTC
HMDB IDHMDB0002022
Secondary Accession Numbers
  • HMDB02022
Metabolite Identification
Common NameGlycineamideribotide
DescriptionGlycineamideribotide, also known as GAR, belongs to the class of organic compounds known as glycinamide ribonucleotides. Glycinamide ribonucleotides are compounds in which the amide N atom of glycineamide is linked to the C-1 of a ribosyl (or deoxyribosyl) moiety. Nucleotides have a phosphate group linked to the C5 carbon of the ribose (or deoxyribose) moiety. Glycineamideribotide exists in all living species, ranging from bacteria to plants to humans. In humans, glycineamideribotide is involved in the metabolic disorder called the gout or kelley-seegmiller syndrome pathway. Glycineamideribotide has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make glycineamideribotide a potential biomarker for the consumption of these foods. Glycineamideribotide is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on Glycineamideribotide.
Structure
Thumb
Synonyms
Chemical FormulaC7H15N2O8P
Average Molecular Weight286.1764
Monoisotopic Molecular Weight286.056601978
IUPAC Name{[(2R,3S,4R,5R)-5-(2-aminoacetamido)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
Traditional Nameglycineamide ribonucleotide
CAS Registry Number10074-18-7
SMILES
NCC(=O)N[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O
InChI Identifier
InChI=1S/C7H15N2O8P/c8-1-4(10)9-7-6(12)5(11)3(17-7)2-16-18(13,14)15/h3,5-7,11-12H,1-2,8H2,(H,9,10)(H2,13,14,15)/t3-,5-,6-,7-/m1/s1
InChI KeyOBQMLSFOUZUIOB-SHUUEZRQSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as glycinamide ribonucleotides. Glycinamide ribonucleotides are compounds in which the amide N atom of glycineamide is linked to the C-1 of a ribosyl (or deoxyribosyl) moiety. Nucleotides have a phosphate group linked to the C5 carbon of the ribose (or deoxyribose) moiety.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassGlycinamide ribonucleotides
Sub ClassNot Available
Direct ParentGlycinamide ribonucleotides
Alternative Parents
Substituents
  • Glycinamide-ribonucleotide
  • Pentose phosphate
  • Pentose-5-phosphate
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • Monosaccharide phosphate
  • Pentose monosaccharide
  • Monoalkyl phosphate
  • Monosaccharide
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Tetrahydrofuran
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Amino acid or derivatives
  • Carboxamide group
  • 1,2-diol
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxide
  • Primary aliphatic amine
  • Organopnictogen compound
  • Alcohol
  • Organonitrogen compound
  • Carbonyl group
  • Organooxygen compound
  • Amine
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary amine
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022801
KNApSAcK IDC00007395
Chemspider ID141370
KEGG Compound IDC03838
BioCyc ID5-PHOSPHO-RIBOSYL-GLYCINEAMIDE
BiGG ID42621
Wikipedia LinkGlycineamide ribonucleotide
METLIN IDNot Available
PubChem Compound160913
PDB IDNot Available
ChEBI ID18349
Food Biomarker OntologyNot Available
VMH IDGAR
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Caperelli CA, Giroux EL: The human glycinamide ribonucleotide transformylase domain: purification, characterization, and kinetic mechanism. Arch Biochem Biophys. 1997 May 1;341(1):98-103. [PubMed:9143358 ]
  2. McKerns KW: Gonadotropin regulation of nucleotide biosynthesis in corpus luteum. Biochemistry. 1973 Dec 4;12(25):5206-11. [PubMed:4366083 ]

Enzymes

General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
GART
Uniprot ID:
P22102
Molecular weight:
107766.295
Reactions
Adenosine triphosphate + 5-Phosphoribosylamine + Glycine → ADP + Phosphate + Glycineamideribotidedetails
10-Formyltetrahydrofolate + Glycineamideribotide → Tetrahydrofolic acid + N(2)-formyl-N(1)-(5-phospho-D-ribosyl)glycinamidedetails
Adenosine triphosphate + 5-Phosphoribosylamine + Glycine → ADP + Phosphate + Glycineamideribotidedetails
10-Formyltetrahydrofolate + Glycineamideribotide → Tetrahydrofolic acid + 5'-Phosphoribosyl-N-formylglycinamidedetails
Glycineamideribotide + 5,10-Methenyltetrahydrofolic acid + Water → 5'-Phosphoribosyl-N-formylglycinamide + Tetrahydrofolic aciddetails