Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB003431
Identification
Name: 5'-Phospho-ribosylglycinamide
Description:5-Phospho-ribosylglycinamide is an intermediate in puriine biosynthesis. It is a substrate for the enzyme Phosphoribosylglycinamide synthetase (EC:6.3.4.13) (GARS) which catalyses the second step in the de novo biosynthesis of purine. The reaction catalysed by phosphoribosylglycinamide synthetase is the ATP-dependent addition of 5-phosphoribosylamine to glycine to form 5'-phosphoribosylglycinamide.
Structure
Thumb
Synonyms:
  • (2R,3S,4R)-5-(2-aminoacetyl)amino-3,4-dihydroxyoxolan-2-ylmethyl dihydrogen phosphate
  • (2R,3S,4R)-5-(2-Aminoacetyl)amino-3,4-dihydroxyoxolan-2-ylmethyl dihydrogen phosphoric acid
  • 5'-Phosphoribosylglycinamide
  • 5'-Phosphoribosylglycineamide
  • GAR
  • Glycinamide ribonucleotide
  • Glycineamide ribonucleotide
  • Glycineamideribotide
  • N-glycyl-5-O-phosphono-D-ribofuranosylamine
  • N1-(5-Phospho-D-ribosyl)glycinamide
Chemical Formula: C7H15N2O8P
Average Molecular Weight: 286.1764
Monoisotopic Molecular Weight: 286.056601978
InChI Key: OBQMLSFOUZUIOB-HJZCUYRDSA-N
InChI: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
CAS number: Not Available
IUPAC Name:{[(2R,3S,4R)-5-(2-aminoacetamido)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
Traditional IUPAC Name: 5'-phosphoribosylglycinamide
SMILES:NCC(=O)NC1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as glycosylamines. These are compounds consisting of an?amine?with a?beta-N-glycosidic bond?to a carbohydrate, thus forming a cyclic?hemiaminal ether?bond (alpha-amino ether).
Kingdom Organic compounds
Super ClassOrganooxygen compounds
Class Carbohydrates and carbohydrate conjugates
Sub ClassGlycosyl compounds
Direct Parent Glycosylamines
Alternative Parents
Substituents
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Monosaccharide
  • Oxolane
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidic acid derivative
  • Carboximidic acid
  • Hydrocarbon derivative
  • Primary amine
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular Framework Aliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State: Not Available
Charge:-1
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility14.6 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity55.29 m3·mol-1ChemAxon
Polarizability23.69 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Pathways: Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
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
References
References: Not Available
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID18349
HMDB IDNot Available
Pubchem Compound ID5459918
Kegg IDNot Available
ChemSpider ID4573646
Wikipedia IDNot Available
BioCyc IDNot Available