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5'-Phospho-ribosylglycinamide (M2MDB003431)

Record Information
Version2.0
Creation Date2012-10-10 12:13:45 -0600
Update Date2015-06-03 17:25:48 -0600
Secondary Accession Numbers
  • ECMDB23041
Identification
Name:5'-Phospho-ribosylglycinamide
Description5-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
MOLSDFPDBSMILESInChI
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
Weight:Average: 286.1764
Monoisotopic: 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
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 Descriptors
Physical Properties
State:Not Available
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
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
Polarizability23.69 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Adenosine triphosphate + 5-Phosphoribosylamine + Glycine > ADP + Inorganic phosphate + 5'-Phospho-ribosylglycinamide
N10-Formyl-THF + 5'-Phospho-ribosylglycinamide > Tetrahydrofolic acid + 5'-phosphoribosyl-N-formylglycinamide
Formic acid + Adenosine triphosphate + 5'-Phospho-ribosylglycinamide > 5'-Phosphoribosyl-N-formylglycineamide + ADP + Pyrophosphate
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000t-9420000000-d7fee78dd4657e2eba28View 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
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 IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. Phosphoribosylglycinamide formyltransferase
General function:
Involved in hydroxymethyl-, formyl- and related transferase activity
Specific function:
10-formyltetrahydrofolate + N(1)-(5-phospho-D- ribosyl)glycinamide = tetrahydrofolate + N(2)-formyl-N(1)-(5- phospho-D-ribosyl)glycinamide
Gene Name:
purN
Uniprot ID:
P08179
Molecular weight:
23238
Reactions
10-formyltetrahydrofolate + N(1)-(5-phospho-D-ribosyl)glycinamide = tetrahydrofolate + N(2)-formyl-N(1)-(5-phospho-D-ribosyl)glycinamide.
Protein Details
2. Phosphoribosylamine--glycine ligase
General function:
Involved in ATP binding
Specific function:
ATP + 5-phospho-D-ribosylamine + glycine = ADP + phosphate + N(1)-(5-phospho-D-ribosyl)glycinamide
Gene Name:
purD
Uniprot ID:
P15640
Molecular weight:
45940
Reactions
ATP + 5-phospho-D-ribosylamine + glycine = ADP + phosphate + N(1)-(5-phospho-D-ribosyl)glycinamide.
Protein Details
3. Phosphoribosylglycinamide formyltransferase 2
General function:
Involved in ATP binding
Specific function:
Catalyzes two reactions:the first one is the production of beta-formyl glycinamide ribonucleotide (GAR) from formate, ATP and beta GAR; the second, a side reaction, is the production of acetyl phosphate and ADP from acetate and ATP
Gene Name:
purT
Uniprot ID:
P33221
Molecular weight:
42433
Reactions
Formate + ATP + 5'-phospho-ribosylglycinamide = 5'-phosphoribosyl-N-formylglycinamide + ADP + diphosphate.