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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2008-08-12 14:59:25 UTC
Update Date2020-02-26 21:26:48 UTC
HMDB IDHMDB0006821
Secondary Accession Numbers
  • HMDB06821
Metabolite Identification
Common Name2,5-Diaminopyrimidine nucleoside triphosphate
Description2,5-Diaminopyrimidine 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. 2,5-Diaminopyrimidine nucleoside triphosphate is a strong basic compound (based on its pKa). 2,5-Diaminopyrimidine nucleoside triphosphate exists in all living organisms, ranging from bacteria to humans. 2,5-Diaminopyrimidine nucleoside triphosphate is created from 2,5-Diaminopyrimidine nucleoside triphosphate by GTP cyclohydrolase I . In humans, 2,5-diaminopyrimidine nucleoside triphosphate is involved in the metabolic disorder called hyperphenylalaninemia due to dhpr-deficiency.
Structure
Data?1582752408
Synonyms
ValueSource
2,5-Diamino-3,4-dihydro-4-oxo-6-(5-triphosphoribosylamino)pyrimidineChEBI
2,5-Diaminopyrimidine nucleoside triphosphoric acidGenerator
2,5-Diaminopyrimidine nucleoside triphosphateChEBI
Chemical FormulaC9H18N5O14P3
Average Molecular Weight513.1856
Monoisotopic Molecular Weight513.006309845
IUPAC Name({[({[(2R,3S,4R,5R)-5-[(2,5-diamino-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-[(2,5-diamino-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(N)C(=O)N1
InChI Identifier
InChI=1S/C9H18N5O14P3/c10-3-6(13-9(11)14-7(3)17)12-8-5(16)4(15)2(26-8)1-25-30(21,22)28-31(23,24)27-29(18,19)20/h2,4-5,8,15-16H,1,10H2,(H,21,22)(H,23,24)(H2,18,19,20)(H4,11,12,13,14,17)/t2-,4-,5-,8-/m1/s1
InChI KeyCRXOALRUOMUPMC-UMMCILCDSA-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
  • Aminopyrimidine
  • Pyrimidone
  • Secondary aliphatic/aromatic amine
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Pyrimidine
  • Phosphoric acid ester
  • Hydropyrimidine
  • Organic phosphoric acid derivative
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Vinylogous amide
  • 1,2-diol
  • Secondary alcohol
  • Secondary amine
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Amine
  • Organic oxide
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Process

Naturally occurring process:

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 Solubility7.65 g/LALOGPS
logP-1ALOGPS
logP-5ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)0.89ChemAxon
pKa (Strongest Basic)4.34ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area315.04 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity103.8 m³·mol⁻¹ChemAxon
Polarizability38.53 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000t-8976500000-fc74ac469e1bfdc52754Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-01wf-4149225000-9b519bd8b351ee01e7e5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0911410000-3fe6a62736feeecaf0d8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-1900000000-96cf76746a620dbd2dd3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-3900000000-818a00c0207cb46c6c25Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01po-1910130000-87b06c4e5468ba593493Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002f-9430100000-349078d69c21dd6055d9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-9610000000-d08645bd83668ca53ce6Spectrum
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 IDFDB024101
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC05923
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440841
PDB IDNot Available
ChEBI ID929
Food Biomarker OntologyNot Available
VMH IDHC01652
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
Formamidopyrimidine nucleoside triphosphate + Water → 2,5-Diaminopyrimidine nucleoside triphosphate + Formic aciddetails
2,5-Diaminopyrimidine nucleoside triphosphate → 2,5-Diamino-6-(5'-triphosphoryl-3',4'-trihydroxy-2'-oxopentyl)-amino-4-oxopyrimidinedetails