Showing metabocard for Formamidopyrimidine nucleoside triphosphate (BMDB0095943)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2020-03-10 16:58:36 UTC
Update Date2020-05-21 16:29:03 UTC
BMDB IDBMDB0095943
Secondary Accession Numbers
  • BMDB95943
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
MOLSDFPDBSMILESInChI
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
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.82ALOGPS
logP-4.7ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)0.9ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area318.12 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity108.76 m³·mol⁻¹ChemAxon
Polarizability40.47 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0006822
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
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. GTP cyclohydrolase 1 feedback regulatory protein
General function:
Involved in protein binding
Specific function:
Mediates tetrahydrobiopterin inhibition of GTP cyclohydrolase 1. This inhibition is reversed by L-phenylalanine (By similarity).
Gene Name:
GCHFR
Uniprot ID:
Q32L41
Molecular weight:
9557.0
Reactions
Formamidopyrimidine nucleoside triphosphate + Water → 2,5-Diaminopyrimidine nucleoside triphosphate + Formic aciddetails
Guanosine triphosphate + Water → Formamidopyrimidine nucleoside triphosphate + Formic aciddetails
Enzyme Details
2. GTP cyclohydrolase 1
General function:
Not Available
Specific function:
Not Available
Gene Name:
GCH1
Uniprot ID:
F1MZ14
Molecular weight:
27726.0
Reactions
Formamidopyrimidine nucleoside triphosphate + Water → 2,5-Diaminopyrimidine nucleoside triphosphate + Formic aciddetails
Guanosine triphosphate + Water → Formamidopyrimidine nucleoside triphosphate + Formic aciddetails