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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2008-08-12 15:01:46 UTC
Update Date2017-10-23 19:04:25 UTC
HMDB IDHMDB0006822
Secondary Accession Numbers
  • HMDB06822
Metabolite Identification
Common NameFormamidopyrimidine nucleoside triphosphate
DescriptionFormamidopyrimidine nucleoside triphosphate is involved in folate biosynthesis. Formamidopyrimidine nucleoside triphosphat is created from 2,5-Diaminopyrimidine nucleoside triphosphate by GTP cyclohydrolase I [EC:3.5.4.16].
Structure
Thumb
SynonymsNot Available
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
DescriptionThis compound belongs to the class of chemical entities known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen compounds
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
  • Primary aromatic amine
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Vinylogous amide
  • Carboxamide group
  • Secondary carboxylic acid amide
  • 1,2-diol
  • Amino acid or derivatives
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Amine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • Carbonyl group
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Disposition

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
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
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Dopa-responsive dystoniaPw000462Pw000462 greyscalePw000462 simpleNot Available
Hyperphenylalaniemia due to guanosine triphosphate cyclohydrolase deficiencyPw000463Pw000463 greyscalePw000463 simpleNot Available
Hyperphenylalaninemia due to 6-pyruvoyltetrahydropterin synthase deficiency (ptps)Pw000464Pw000464 greyscalePw000464 simpleNot Available
Hyperphenylalaninemia due to dhpr-deficiencyPw000465Pw000465 greyscalePw000465 simpleNot Available
Pterine BiosynthesisPw000140Pw000140 greyscalePw000140 simpleMap00790
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB 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

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