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Record Information
Version4.0
Creation Date2008-08-12 15:06:41 UTC
Update Date2017-09-27 08:24:48 UTC
HMDB IDHMDB0006823
Secondary Accession Numbers
  • HMDB06823
Metabolite Identification
Common Name2,5-Diamino-6-(5'-triphosphoryl-3',4'-trihydroxy-2'-oxopentyl)-amino-4-oxopyrimidine
Description2,5-Diamino-6-(5'-triphosphoryl-3',4'-trihydroxy-2'-oxopentyl)-amino-4-oxopyrimidine is involved in folate biosynthesis. 2,5-Diamino-6-(5'-triphosphoryl-3',4'-trihydroxy-2'-oxopentyl)-amino-4-oxopyrimidine is created from 2,5-Diaminopyrimidine nucleoside triphosphate by GTP cyclohydrolase I [EC:3.5.4.16]. 2,5-Diamino-6-(5'-triphosphoryl-3',4'-trihydroxy-2'-oxopentyl)-amino-4-oxopyrimidine can be converted into 2-Amino-4-hydroxy-6-(erythro-1,2,3-trihydroxypropyl)dihydropteridine. triphosphate by GTP cyclohydrolase I [EC:3.5.4.16]. GTP cyclohydrolase I [EC:3.5.4.16] can also be converted to 6-(3'-Triphosphoryl-1'-methylglyceryl)-7-methyl-7,8-dihydrobiopterin.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC9H18N5O14P3
Average Molecular Weight513.1856
Monoisotopic Molecular Weight513.006309845
IUPAC Name[({[({5-[(2,5-diamino-6-oxo-3,6-dihydropyrimidin-4-yl)amino]-2,3-dihydroxy-4-oxopentyl}oxy)(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl)oxy]phosphonic acid
Traditional Name[({5-[(2,5-diamino-6-oxo-3H-pyrimidin-4-yl)amino]-2,3-dihydroxy-4-oxopentyl}oxy(hydroxy)phosphoryl)oxy(hydroxy)phosphoryl]oxyphosphonic acid
CAS Registry NumberNot Available
SMILES
NC1=NC(=O)C(N)=C(NCC(=O)C(O)C(O)COP(O)(=O)OP(O)(=O)OP(O)(O)=O)N1
InChI Identifier
InChI=1S/C9H18N5O14P3/c10-5-7(13-9(11)14-8(5)18)12-1-3(15)6(17)4(16)2-26-30(22,23)28-31(24,25)27-29(19,20)21/h4,6,16-17H,1-2,10H2,(H,22,23)(H,24,25)(H2,19,20,21)(H4,11,12,13,14,18)
InChI KeyZJYBJXKSWQPKFW-UHFFFAOYSA-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-5-phosphate
  • Monosaccharide phosphate
  • Pyrimidone
  • Aminopyrimidine
  • Secondary aliphatic/aromatic amine
  • Monoalkyl phosphate
  • Organic phosphoric acid derivative
  • Hydropyrimidine
  • Acyloin
  • Phosphoric acid ester
  • Beta-hydroxy ketone
  • Primary aromatic amine
  • Pyrimidine
  • Alkyl phosphate
  • Alpha-hydroxy ketone
  • Heteroaromatic compound
  • Vinylogous amide
  • Ketone
  • Secondary alcohol
  • 1,2-diol
  • Azacycle
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Carbonyl group
  • Primary amine
  • Hydrocarbon derivative
  • Amine
  • Organic oxide
  • Alcohol
  • Organopnictogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
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 Solubility6.42 g/LALOGPS
logP-0.86ALOGPS
logP-6.2ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)0.89ChemAxon
pKa (Strongest Basic)3.72ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area322.88 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity105.24 m³·mol⁻¹ChemAxon
Polarizability38.94 ųChemAxon
Number of Rings1ChemAxon
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, Positivesplash10-0kaj-3695200000-3a55935f0cd1e0f2f9efView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-004i-2194102000-c52d41bf51dcab1f48f4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-1442920000-fe5a369793012336651cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0w2c-1941200000-110e7623a57abfccc156View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udj-5910000000-57cceddb7b071bdbb766View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0492220000-7b3e1f682e2fbbb3c9a5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-057l-9560000000-056e90117fa787c6136eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-9620000000-81675245a86543331ea4View 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
Displaying entries 1 - 5 of 7 in total
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 IDFDB024103
KNApSAcK IDNot Available
Chemspider ID389753
KEGG Compound IDC06148
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440923
PDB IDNot Available
ChEBI 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
Dihydroneopterin triphosphate + Water → 2,5-Diamino-6-(5'-triphosphoryl-3',4'-trihydroxy-2'-oxopentyl)-amino-4-oxopyrimidinedetails
2,5-Diaminopyrimidine nucleoside triphosphate → 2,5-Diamino-6-(5'-triphosphoryl-3',4'-trihydroxy-2'-oxopentyl)-amino-4-oxopyrimidinedetails