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Record Information
Version3.6
Creation Date2008-08-12 15:06:41 UTC
Update Date2016-02-11 01:07:59 UTC
HMDB IDHMDB06823
Secondary Accession NumbersNone
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 KeyInChIKey=ZJYBJXKSWQPKFW-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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 ClassOrganooxygen compounds
ClassCarbohydrates and carbohydrate conjugates
Sub ClassMonosaccharides
Direct ParentPentose phosphates
Alternative Parents
Substituents
  • Pentose-5-phosphate
  • Organic pyrophosphate
  • Monoalkyl phosphate
  • Secondary aliphatic/aromatic amine
  • Pyrimidone
  • Aminopyrimidine
  • Alkyl phosphate
  • Pyrimidine
  • Primary aromatic amine
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Hydropyrimidine
  • Beta-hydroxy ketone
  • Beta-ketoaldehyde
  • Acyloin
  • Heteroaromatic compound
  • Vinylogous amide
  • Alpha-hydroxy ketone
  • Alpha-aminoketone
  • Secondary alcohol
  • Ketone
  • 1,2-diol
  • Azacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Hydrocarbon derivative
  • Primary amine
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count12ChemAxon
Refractivity105.24 m3·mol-1ChemAxon
Polarizability38.94 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
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 LinkKEGG Link
Dopa-responsive dystoniaSMP00486Not Available
Hyperphenylalaniemia due to guanosine triphosphate cyclohydrolase deficiencySMP00487Not Available
Hyperphenylalaninemia due to 6-pyruvoyltetrahydropterin synthase deficiency (ptps)SMP00488Not Available
Hyperphenylalaninemia due to dhpr-deficiencySMP00489Not Available
Pterine BiosynthesisSMP00005map00790
Segawa syndromeSMP00490Not Available
Sepiapterin reductase deficiencySMP00491Not Available
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
NuGOwiki LinkHMDB06823
Metagene LinkHMDB06823
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