Record Information
Version2.0
Creation Date2012-05-31 14:30:00 -0600
Update Date2015-06-03 17:19:24 -0600
Secondary Accession Numbers
  • ECMDB20148
Identification
Name:Formamidopyrimidine nucleoside triphosphate
DescriptionFormamidopyrimidine nucleoside triphosphate is a member of the chemical class known as Pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms.
Structure
Thumb
Synonyms:
  • (2R,3S,4R,5R)-5-(2-amino-5-formamido-4-oxo-1H-pyrimidin-6-yl)amino-3,4-dihydroxyoxolan-2-ylmethoxy-hydroxyphosphoryl phosphono hydrogen phosphate
  • (2R,3S,4R,5R)-5-(2-amino-5-formamido-4-oxo-1H-Pyrimidin-6-yl)amino-3,4-dihydroxyoxolan-2-ylmethoxy-hydroxyphosphoryl phosphono hydrogen phosphoric acid
  • Formamidopyrimidine nucleoside triphosphoric acid
  • N-(2-amino-5-formamido-6-oxo-3,6-dihydro-4-Pyrimidinyl)-5-O-(hydroxy{hydroxy(phosphonooxy)phosphoryloxy}phosphoryl)-b-D-ribofuranosylamine
  • N-(2-Amino-5-formamido-6-oxo-3,6-dihydro-4-pyrimidinyl)-5-O-(hydroxy{hydroxy(phosphonooxy)phosphoryloxy}phosphoryl)-beta-D-ribofuranosylamine
  • N-(2-amino-5-formamido-6-oxo-3,6-dihydro-4-Pyrimidinyl)-5-O-(hydroxy{hydroxy(phosphonooxy)phosphoryloxy}phosphoryl)-β-D-ribofuranosylamine
Chemical Formula:C10H18N5O15P3
Weight:Average: 541.1957
Monoisotopic: 541.001224467
InChI Key:NDXMRXXKCCKQQV-UUOKFMHZSA-N
InChI:InChI=1S/C10H18N5O15P3/c11-10-14-7(4(12-2-16)8(19)15-10)13-9-6(18)5(17)3(28-9)1-27-32(23,24)30-33(25,26)29-31(20,21)22/h2-3,5-6,9,17-18H,1H2,(H,12,16)(H,23,24)(H,25,26)(H2,20,21,22)(H4,11,13,14,15,19)/t3-,5-,6-,9-/m1/s1
CAS number:Not Available
IUPAC Name:({[({[(2R,3S,4R,5R)-5-[(2-amino-5-formamido-6-oxo-1,6-dihydropyrimidin-4-yl)amino]-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid
Traditional IUPAC Name:({[(2R,3S,4R,5R)-5-[(2-amino-5-formamido-6-oxo-1H-pyrimidin-4-yl)amino]-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxyphosphonic acid
SMILES:NC1=NC(N[C@@H]2O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]2O)=C(NC=O)C(=O)N1
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 phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • N-arylamide
  • Aminopyrimidine
  • Pyrimidone
  • Secondary aliphatic/aromatic amine
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Hydropyrimidine
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Pyrimidine
  • Vinylogous amide
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Amino acid or derivatives
  • 1,2-diol
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Secondary amine
  • Azacycle
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Amine
  • Primary amine
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-3
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility6.05 g/LALOGPS
logP-0.82ALOGPS
logP-5.3ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)0.89ChemAxon
pKa (Strongest Basic)3.99ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area318.12 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity108.76 m³·mol⁻¹ChemAxon
Polarizability40.45 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Folate biosynthesisPW000908 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03dj-6496140000-aad5ec3b4b7957d585bbView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-3025009000-fcacb0576bb63da06b26View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dl-0911230000-2740f382fa6662a3aaa2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0900000000-abf8656c4f6736ab3f89View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-3900000000-98e38554d2fe8f6cb8f0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-02ti-0960050000-9795e309994549a74a15View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9740010000-17fea225289c74811296View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-9610000000-194c76e9de5cd6054fdcView in MoNA
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID58104
HMDB IDHMDB06822
Pubchem Compound ID440840
Kegg IDC05922
ChemSpider ID389682
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

General function:
Involved in GTP cyclohydrolase I activity
Specific function:
GTP + H(2)O = formate + 2-amino-4-hydroxy-6- (erythro-1,2,3-trihydroxypropyl)-dihydropteridine triphosphate
Gene Name:
folE
Uniprot ID:
P0A6T5
Molecular weight:
24830
Reactions
GTP + H(2)O = formate + 2-amino-4-hydroxy-6-(erythro-1,2,3-trihydroxypropyl)-dihydropteridine triphosphate.