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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2008-08-12 15:01:46 UTC
Update Date2021-09-14 15:46:58 UTC
HMDB IDHMDB0006822
Secondary Accession Numbers
  • HMDB06822
Metabolite Identification
Common NameFormamidopyrimidine nucleoside triphosphate
DescriptionFormamidopyrimidine nucleoside triphosphate 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. Formamidopyrimidine nucleoside triphosphate is a strong basic compound (based on its pKa). Formamidopyrimidine nucleoside triphosphate exists in all living organisms, ranging from bacteria to humans. Within humans, formamidopyrimidine nucleoside triphosphate participates in a number of enzymatic reactions. In particular, formamidopyrimidine nucleoside triphosphate can be converted into 2,5-diaminopyrimidine nucleoside triphosphate and formic acid through its interaction with the enzyme GTP cyclohydrolase. In addition, formamidopyrimidine nucleoside triphosphate and formic acid can be biosynthesized from guanosine triphosphate through its interaction with the enzyme GTP cyclohydrolase. In humans, formamidopyrimidine nucleoside triphosphate is involved in the metabolic disorder called hyperphenylalaninemia due to dhpr-deficiency.
Structure
Thumb
Synonyms
ValueSource
Formamidopyrimidine nucleoside triphosphoric acidGenerator
Chemical FormulaC10H18N5O15P3
Average Molecular Weight541.1957
Monoisotopic Molecular Weight541.001224467
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 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
CAS Registry NumberNot Available
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
InChI Identifier
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
InChI KeyNDXMRXXKCCKQQV-UUOKFMHZSA-N
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
Ontology
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024102
KNApSAcK IDNot Available
Chemspider ID389682
KEGG Compound IDC05922
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440840
PDB IDNot Available
ChEBI ID58104
Food Biomarker OntologyNot Available
VMH IDHC01651
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in GTP cyclohydrolase I activity
Specific function:
Positively regulates nitric oxide synthesis in umbilical vein endothelial cells (HUVECs). May be involved in dopamine synthesis. May modify pain sensitivity and persistence. Isoform GCH-1 is the functional enzyme, the potential function of the enzymatically inactive isoforms remains unknown.
Gene Name:
GCH1
Uniprot ID:
P30793
Molecular weight:
27902.855
Reactions
Guanosine triphosphate + Water → Formamidopyrimidine nucleoside triphosphatedetails
Formamidopyrimidine nucleoside triphosphate + Water → 2,5-Diaminopyrimidine nucleoside triphosphate + Formic aciddetails