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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2010-08-17 08:28:10 UTC
Update Date2020-02-26 21:38:59 UTC
HMDB IDHMDB0013642
Secondary Accession Numbers
  • HMDB13642
Metabolite Identification
Common Name1-hydroxy-2-Oxopropyl tetrahydropterin
Description1-hydroxy-2-Oxopropyl tetrahydropterin belongs to the class of organic compounds known as pterins and derivatives. These are polycyclic aromatic compounds containing a pterin moiety, which consist of a pteridine ring bearing a ketone and an amine group to form 2-aminopteridin-4(3H)-one. 1-hydroxy-2-Oxopropyl tetrahydropterin is a strong basic compound (based on its pKa). Within humans, 1-hydroxy-2-oxopropyl tetrahydropterin participates in a number of enzymatic reactions. In particular, 1-hydroxy-2-oxopropyl tetrahydropterin can be biosynthesized from dyspropterin through its interaction with the enzyme sepiapterin reductase. In addition, 1-hydroxy-2-oxopropyl tetrahydropterin can be biosynthesized from 6-lactoyltetrahydropterin through the action of the enzyme sepiapterin reductase. 1-hydroxy-2-Oxopropyl tetrahydropterin, an intermediate formed from 6-Pyrovoyl-Tetrahydropterin in the biosynthetic pathway of tetrahydrobiopterin . In humans, 1-hydroxy-2-oxopropyl tetrahydropterin is involved in the metabolic disorder called hyperphenylalaninemia due to dhpr-deficiency.
Structure
Data?1582753139
SynonymsNot Available
Chemical FormulaC9H13N5O3
Average Molecular Weight239.2312
Monoisotopic Molecular Weight239.101839307
IUPAC Name2-amino-6-(1-hydroxy-2-oxopropyl)-3,4,5,6,7,8-hexahydropteridin-4-one
Traditional Name2-amino-6-(1-hydroxy-2-oxopropyl)-5,6,7,8-tetrahydro-3H-pteridin-4-one
CAS Registry NumberNot Available
SMILES
CC(=O)C(O)C1CNC2=C(N1)C(=O)NC(N)=N2
InChI Identifier
InChI=1S/C9H13N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h4,6,12,16H,2H2,1H3,(H4,10,11,13,14,17)
InChI KeyPSNIIJBQEZDDMR-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as pterins and derivatives. These are polycyclic aromatic compounds containing a pterin moiety, which consist of a pteridine ring bearing a ketone and an amine group to form 2-aminopteridin-4(3H)-one.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPteridines and derivatives
Sub ClassPterins and derivatives
Direct ParentPterins and derivatives
Alternative Parents
Substituents
  • Pterin
  • Aminopyrimidine
  • Pyrimidone
  • Secondary aliphatic/aromatic amine
  • Acyloin
  • Beta-aminoketone
  • Gamma-aminoketone
  • Pyrimidine
  • Heteroaromatic compound
  • Vinylogous amide
  • Alpha-hydroxy ketone
  • Secondary alcohol
  • Ketone
  • Secondary amine
  • Azacycle
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Primary amine
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Organic nitrogen compound
  • Amine
  • Organopnictogen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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 Solubility1.25 g/LALOGPS
logP-1.6ALOGPS
logP-2.1ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)11.11ChemAxon
pKa (Strongest Basic)4.63ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area128.84 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity67.63 m³·mol⁻¹ChemAxon
Polarizability22.72 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014l-4900000000-5cfc1bf3dcc901756820Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-014i-2910000000-e5658a7e84aee3202598Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006x-0090000000-3ec89e6be3fb3fdb3095Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0g4l-0980000000-6438d719c7fc7a1b7e7dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-1900000000-dc0850d3bfb4b08aa23dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0190000000-336218c15d6088c22892Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002n-0920000000-c2833e53328b585a2469Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9400000000-77b69e6dc7b7d2991742Spectrum
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 IDFDB029613
KNApSAcK IDNot Available
Chemspider ID26777299
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound13846017
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Longo N: Disorders of biopterin metabolism. J Inherit Metab Dis. 2009 Jun;32(3):333-42. doi: 10.1007/s10545-009-1067-2. Epub 2009 Feb 9. [PubMed:19234759 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the final one or two reductions in tetra-hydrobiopterin biosynthesis to form 5,6,7,8-tetrahydrobiopterin.
Gene Name:
SPR
Uniprot ID:
P35270
Molecular weight:
28048.13