Record Information
Version2.0
Creation Date2015-09-08 17:50:23 -0600
Update Date2015-09-14 16:46:45 -0600
Secondary Accession Numbers
  • ECMDB24246
Identification
Name:N1-(5-phospho-β-D-ribosyl)glycinamide
DescriptionN1-(5-phospho-beta-D-ribosyl)glycinamide is an intermediate in 5-aminoimidazole ribonucleotide biosynthesis I pathway in E.coli. It is a substrate for the enzyme phosphoribosylglycinamide formyltransferase 1 which catalyzes the reaction an N10-formyl-tetrahydrofolate + N1-(5-phospho-beta-D-ribosyl)glycinamide -> a tetrahydrofolate + N2-formyl-N1-(5-phospho-beta-D-ribosyl)glycinamide + H+. It is also a product for enzyme phosphoribosylamine-glycine ligase which catalyzes reaction ATP + 5-phospho-beta-D-ribosylamine + glycine -> ADP + N1-(5-phospho-beta-D-ribosyl)glycinamide + phosphate + H+ (BioCYc: 5-PHOSPHO-RIBOSYL-GLYCINEAMIDE).
Structure
Thumb
Synonyms:Not Available
Chemical Formula:C7H14N2O8P
Weight:Average: 285.169
Monoisotopic: 285.049325997
InChI Key:OBQMLSFOUZUIOB-UHFFFAOYSA-M
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)/p-1
CAS number:Not Available
IUPAC Name:[5-(2-azaniumylacetamido)-3,4-dihydroxyoxolan-2-yl]methyl phosphate
Traditional IUPAC Name:[5-(2-ammonioacetamido)-3,4-dihydroxyoxolan-2-yl]methyl phosphate
SMILES:[NH3+]CC(=O)NC1OC(COP([O-])([O-])=O)C(O)C1O
Chemical Taxonomy
Description belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPentose phosphates
Alternative Parents
Substituents
  • Pentose-5-phosphate
  • Pentose phosphate
  • N-glycosyl compound
  • Glycosyl compound
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Tetrahydrofuran
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Carboximidic acid derivative
  • Carboximidic acid
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary amine
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Alcohol
  • Organic anion
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility45.1 g/LALOGPS
logP-1.9ALOGPS
logP-4.7ChemAxon
logS-0.9ALOGPS
pKa (Strongest Acidic)1.23ChemAxon
pKa (Strongest Basic)8.14ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area178.85 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity64.34 m³·mol⁻¹ChemAxon
Polarizability23.92 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Thiamin diphosphate biosynthesisPW002028 ThumbThumb?image type=greyscaleThumb?image type=simple
purine nucleotides de novo biosynthesisPW000910 ThumbThumb?image type=greyscaleThumb?image type=simple
purine nucleotides de novo biosynthesis 1435709748PW000960 ThumbThumb?image type=greyscaleThumb?image type=simple
purine nucleotides de novo biosynthesis 2PW002033 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-9230000000-1055514d142206e7d587View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-9110000000-04d0f5553abcbd0fd252View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-003r-9200000000-9507b88a161e6ec8fdfaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-3900000000-cf08513f99d80344c5f1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004r-9010000000-7f863cfb14b9195d2f64View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00fr-9000000000-ce632b84eee06368c6b2View in MoNA
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound IDNot Available
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

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.
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.
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.