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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:32 UTC
Update Date2017-12-07 01:46:53 UTC
HMDB IDHMDB0002022
Secondary Accession Numbers
  • HMDB02022
Metabolite Identification
Common NameGlycineamideribotide
DescriptionGlycinamidoribotide conversion to N-formylglycinamide ribonucleotide is the third reaction of the de novo purine biosynthesis, a reaction catalyzed by the enzyme Glycinamide ribonucleotide transformylase (EC 2.1.2.2), with concomitant conversion of 10-formyltetrahydrofolate to tetrahydrofolate. (PMID: 9143358 ). Glycineamideribotide formation is stimulated by Luteinizing hormone (LH) and Chorionic gonadotropin (HCG) via activation of Glc-6-P-dehydrogenase (EC 1.1.1.49). (PMID: 4366083 ).
Structure
Thumb
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
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
DescriptionThis compound belongs to the class of chemical entities known as glycinamide ribonucleotides. These 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassNucleosides, nucleotides, and analogues
Sub ClassGlycinamide ribonucleotides
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
  • Alkyl phosphate
  • Phosphoric acid ester
  • Oxolane
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • 1,2-diol
  • Amino acid or derivatives
  • Carboxamide group
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid derivative
  • Primary amine
  • Organic oxide
  • Primary aliphatic amine
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Carbonyl group
  • Organooxygen compound
  • Amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

Source:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

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
Polarizability23.71 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000t-9420000000-d7fee78dd4657e2eba28View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00si-9541200000-4a23e3091baf72b01dc2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-053i-9460000000-f71dc4d8ec0f4da03819View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0560-9120000000-4770933b45387be6728cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a59-9200000000-a6f2b9ab201fd0e69ee8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0170-9550000000-99520656892b8c415efbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-d6c860661b01956c80acView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-c2f2b85e6ec9caaa4408View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
AICA-RibosiduriaPw000082Pw000082 greyscalePw000082 simpleNot Available
Adenine phosphoribosyltransferase deficiency (APRT)Pw000511Pw000511 greyscalePw000511 simpleNot Available
Adenosine Deaminase DeficiencyPw000075Pw000075 greyscalePw000075 simpleNot Available
Adenylosuccinate Lyase DeficiencyPw000076Pw000076 greyscalePw000076 simpleNot Available
Azathioprine PathwayPw000266Pw000266 greyscalePw000266 simpleNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022801
KNApSAcK IDNot Available
Chemspider ID141370
KEGG Compound IDC03838
BioCyc ID5-PHOSPHO-RIBOSYL-GLYCINEAMIDE
BiGG ID42621
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound160913
PDB IDNot Available
ChEBI ID18349
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 + Phosphoric acid + Glycineamideribotidedetails
10-Formyltetrahydrofolate + Glycineamideribotide → Tetrahydrofolic acid + N(2)-formyl-N(1)-(5-phospho-D-ribosyl)glycinamidedetails
Adenosine triphosphate + 5-Phosphoribosylamine + Glycine → ADP + Phosphoric acid + Glycineamideribotidedetails
10-Formyltetrahydrofolate + Glycineamideribotide → Tetrahydrofolic acid + 5'-Phosphoribosyl-N-formylglycinamidedetails
Glycineamideribotide + 5,10-Methenyltetrahydrofolic acid + Water → 5'-Phosphoribosyl-N-formylglycinamide + Tetrahydrofolic aciddetails