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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:32 UTC
Update Date2020-06-23 16:17:23 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 is a very strong basic compound (based on its pKa). Glycineamideribotide exists in all living species, ranging from bacteria to humans. Within humans, glycineamideribotide participates in a number of enzymatic reactions. In particular, glycineamideribotide can be biosynthesized from 5-phosphoribosylamine and glycine through its interaction with the enzyme trifunctional purine biosynthetic protein adenosine-3. In addition, 10-formyltetrahydrofolate and glycineamideribotide can be converted into tetrahydrofolic acid and 5'-phosphoribosyl-N-formylglycinamide through its interaction with the enzyme trifunctional purine biosynthetic protein adenosine-3. In humans, glycineamideribotide is involved in the metabolic disorder called the gout or kelley-seegmiller syndrome pathway.
Structure
Data?1592929043
Synonyms
ValueSource
GARKegg
N1-(5-Phospho-D-ribosyl)glycinamideKegg
Glycinamide ribonucleotideKegg
5'-Phosphoribosyl-glycineamideHMDB
5'-PhosphoribosylglycinamideHMDB
5'-PhosphoribosylglycineamideHMDB
Glycineamide ribonucleotideHMDB
N(1)-(5-Phospho-D-ribosyl)glycinamideHMDB
N-Glycyl-5-O-phosphono-D-ribofuranosylamineHMDB
2-Amino-N-(5-O-phosphono-beta-D-ribofuranosyl)acetamideHMDB
2-Amino-N-(5-O-phosphono-β-D-ribofuranosyl)acetamideHMDB
5-Phospho-beta-D-ribosyl-glycineamideHMDB
5-Phospho-β-D-ribosyl-glycineamideHMDB
5’-PhosphoribosylglycinamideHMDB
5’-PhosphoribosylglycineamideHMDB
N1-(5-Phospho-beta-D-ribosyl)glycinamideHMDB
N1-(5-Phospho-β-D-ribosyl)glycinamideHMDB
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
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility14.6 g/LALOGPS
logP-2.4ALOGPS
logP-4.7ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)1.23ChemAxon
pKa (Strongest Basic)8.14ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area171.57 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity55.29 m³·mol⁻¹ChemAxon
Polarizability23.68 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000t-9420000000-d7fee78dd4657e2eba28Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00si-9541200000-4a23e3091baf72b01dc2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-053i-9460000000-f71dc4d8ec0f4da03819Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0560-9120000000-4770933b45387be6728cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a59-9200000000-a6f2b9ab201fd0e69ee8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0170-9550000000-99520656892b8c415efbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-d6c860661b01956c80acSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-c2f2b85e6ec9caaa4408Spectrum
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
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