Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB110730
Identification
Name: 2-amino-4-oxo-6-(1',2',3'-trihydroxypropyl)-diquinoid-7,8-dihydroxypterin
Description:2-Amino-4-oxo-6-(1',2',3'-trihydroxypropyl)-diquinoid-7,8-dihydroxypterin is a pterin derivative. Pterin is a heterocyclic compound composed of a pyrazine ring and a pyrimidine ring with Several tautomers; the pyrimidine ring has a carbonyl oxygen and an amino group. As a group, pterins are compounds that are derivatives of 2-amino-4-oxopteridine, with additional functional groups attached to the pyrazine ring. Pterins were first discovered in the pigments of butterfly wings and perform many roles in coloration in the biological world. Pterins also function as cofactors in enzyme catalysis (Wikipedia). Some pterin derivatives (biopterin, 6-formylpterin, 6-carboxypterin) accumulate in the skin of patients affected by vitiligo, a depigmentation disorder, where the protection against UV radiation fails due to the lack of melanin. Pterins participate in biologically important photosensitization processes; for example, pterins act as sensitizers in photochemical reactions that induce DNA damage4,5 and are able to generate singlet molecular oxygen6 and other reactive oxygen species (PMID: 19199487 ).
Structure
Thumb
Synonyms:Not Available
Chemical FormulaC9H15N5O6
Average Molecular Weight289.2453
Monoisotopic Molecular Weight289.102233237
IUPAC Name2-amino-7,8-dihydroxy-6-(1,2,3-trihydroxypropyl)-3,4,5,6,7,8-hexahydropteridin-4-one
Traditional Name2-amino-7,8-dihydroxy-6-(1,2,3-trihydroxypropyl)-3,5,6,7-tetrahydropteridin-4-one
CAS Registry NumberNot Available
SMILES
NC1=NC2=C(NC(C(O)C(O)CO)C(O)N2O)C(=O)N1
InChI Identifier
InChI=1S/C9H15N5O6/c10-9-12-6-4(7(18)13-9)11-3(8(19)14(6)20)5(17)2(16)1-15/h2-3,5,8,11,15-17,19-20H,1H2,(H3,10,12,13,18)
InChI KeyKQZRTOGFDRQBSR-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as biopterins and derivatives. These are coenzymes containing a 2-amino-pteridine-4-one derivative. They are mainly synthesized in several parts of the body, including the pineal gland.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassPteridines and derivatives
Direct ParentBiopterins and derivatives
Alternative Parents
Substituents
  • Biopterin
  • Aminopyrimidine
  • Pyrimidone
  • Secondary aliphatic/aromatic amine
  • Primary aromatic amine
  • Pyrimidine
  • Vinylogous amide
  • Heteroaromatic compound
  • 1,3-aminoalcohol
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Azacycle
  • N-organohydroxylamine
  • Secondary amine
  • Alkanolamine
  • Polyol
  • Hydrocarbon derivative
  • Primary alcohol
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Amine
  • Organopnictogen compound
  • Alcohol
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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
Chemical Formula: C9H14N5O6
Average Molecular Weight: 288.24
Monoisotopic Molecular Weight: 289.1022332401
InChI Key: KZVMFQIWKNDMFF-UHFFFAOYSA-N
InChI: InChI=1S/C9H14N5O6/c10-9-12-6-4(7(18)13-9)11-3(8(19)14(6)20)5(17)2(16)1-15/h2-3,5,8,11,15-17,19-20H,1H2,(H2,10,13,18)/q-1
CAS number: Not Available
IUPAC Name:2-amino-7,8-dihydroxy-6-(1,2,3-trihydroxypropyl)-3,4,5,6,7,8-hexahydropteridin-4-one
Traditional IUPAC Name: 2-amino-7,8-dihydroxy-6-(1,2,3-trihydroxypropyl)-3,5,6,7-tetrahydropteridin-4-one
SMILES:C12(=NC(N)=NC(=O)[C-](NC(C(O)C(O)CO)C(O)N(O)1)2)
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities known as biopterins and derivatives. These are coenzymes containing a 2-amino-pteridine-4-one derivative. They are mainly synthesized in several parts of the body, including the pineal gland.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Organoheterocyclic compounds
Sub ClassPteridines and derivatives
Direct Parent Biopterins and derivatives
Alternative Parents
Substituents
  • Biopterin
  • Aminopyrimidine
  • Pyrimidone
  • Secondary aliphatic/aromatic amine
  • Primary aromatic amine
  • Pyrimidine
  • Vinylogous amide
  • Heteroaromatic compound
  • 1,3-aminoalcohol
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Azacycle
  • N-organohydroxylamine
  • Secondary amine
  • Alkanolamine
  • Polyol
  • Hydrocarbon derivative
  • Primary alcohol
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Amine
  • Organopnictogen compound
  • Alcohol
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors Not Available
Physical Properties
State: Solid
Charge:Not Available
Melting point: Not Available
Experimental Properties:
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility11.5 mg/mLALOGPS
logP-2.4ALOGPS
logP-4.1ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)11.06ChemAxon
pKa (Strongest Basic)3.68ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area183.9 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity72.97 m3·mol-1ChemAxon
Polarizability26.02 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
Pathways:
    Spectra
    Spectra: Not Available
    References
    References:
    • Petroselli G, Dantola ML, Cabrerizo FM, Lorente C, Braun AM, Oliveros E, Thomas AH: Quenching of the fluorescence of aromatic pterins by deoxynucleotides. J Phys Chem A. 2009 Mar 5;113(9):1794-9. doi: 10.1021/jp8101496. [19199487 ]
    Synthesis Reference: Not Available
    Material Safety Data Sheet (MSDS) Not Available
    External Links:
    ResourceLink
    HMDBHMDB12144
    KEGGC05253
    PubChem25202238