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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:09:21 UTC
HMDB IDHMDB00802
Secondary Accession NumbersNone
Metabolite Identification
Common NamePterin
DescriptionPterin is a chemical compound composed of a pyrazine ring and a pyrimidine ring; the pyrimidine ring has a carbonyl oxygen and an amino group. Several tautomers of pterin exist and are shown below. Pterin belongs to the pteridine family of heterocycles. -- Wikipedia.
Structure
Thumb
Synonyms
  1. 2-Amino-1H-pteridin-4-one
  2. 2-Amino-3H-pteridin-4-one
  3. 2-Amino-4(1H)-pteridinone
  4. 2-Amino-4(3H)-pteridinone
  5. 2-Amino-4-hydroxypteridine
  6. 2-Amino-4-oxopteridine
  7. 2-Amino-4-pteridinol
  8. 2-Amino-4-pteridone
  9. 2-Amino-Quinonoid dihydropterin
  10. 2-Aminopteridin-4-one
  11. 4-Oxo-2-aminopteridine
  12. 4-Oxopterin
  13. Pteridoxamine
  14. Pterine
Chemical FormulaC6H5N5O
Average Molecular Weight163.1368
Monoisotopic Molecular Weight163.049409807
IUPAC Name2-amino-3,4-dihydropteridin-4-one
Traditional Name2-aminopteridin-4(3H)-one
CAS Registry Number2236-60-4
SMILES
NC1=NC2=NC=CN=C2C(=O)N1
InChI Identifier
InChI=1S/C6H5N5O/c7-6-10-4-3(5(12)11-6)8-1-2-9-4/h1-2H,(H3,7,9,10,11,12)
InChI KeyHNXQXTQTPAJEJL-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAromatic Heteropolycyclic Compounds
ClassPteridines and Derivatives
Sub ClassPterins and Derivatives
Other Descriptors
  • Pteridines and Derivatives
  • a pterin(Cyc)
  • pterin(ChEBI)
Substituents
  • Aminopyrimidine
  • Pyrazine
  • Pyrimidine
  • Pyrimidone
Direct ParentPterins and Derivatives
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
Biofunction
  • Component of Phenylalanine, tyrosine and tryptophan biosynthesis
  • Component of Tryptophan metabolism
  • Component of Tyrosine metabolism
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.175 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.49 g/LALOGPS
logP-0.86ALOGPS
logP-0.96ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)10ChemAxon
pKa (Strongest Basic)1.34ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area93.26ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity41.82ChemAxon
Polarizability14.46ChemAxon
Spectra
SpectraMS/MS1D NMR2D NMR
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid LocationsNot Available
Tissue Location
  • Epidermis
  • Fibroblasts
  • Liver
PathwaysNot 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 IDFDB005613
KNApSAcK IDNot Available
Chemspider ID65806
KEGG Compound IDC00715
BioCyc ID2-AMINO-4-HYDROXYPTERIDINE
BiGG IDNot Available
Wikipedia LinkPterin
NuGOwiki LinkHMDB00802
Metagene LinkHMDB00802
METLIN ID5766
PubChem Compound73000
PDB IDPE0
ChEBI ID18265
References
Synthesis ReferenceTaylor, Edward C.; Kobylecki, Ryszard. Pteridines. 43. A facile synthesis of 6-chloropterin and 2,4-diamino-6-chloropteridine. Journal of Organic Chemistry (1978), 43(4), 680-3.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Bonafe L, Thony B, Penzien JM, Czarnecki B, Blau N: Mutations in the sepiapterin reductase gene cause a novel tetrahydrobiopterin-dependent monoamine-neurotransmitter deficiency without hyperphenylalaninemia. Am J Hum Genet. 2001 Aug;69(2):269-77. Epub 2001 Jul 6. Pubmed: 11443547
  2. Dhondt JL, Cotton RG, Danks DM: Liver enzyme activities in hyperphenylalaninaemia due to a defective synthesis of tetrahydrobiopterin. J Inherit Metab Dis. 1985;8(2):47-8. Pubmed: 3939528
  3. Kaufman S, Kapatos G, Rizzo WB, Schulman JD, Tamarkin L, Van Loon GR: Tetrahydropterin therapy for hyperphenylalaninemia caused by defective synthesis of tetrahydrobiopterin. Ann Neurol. 1983 Sep;14(3):308-15. Pubmed: 6139056
  4. Katoh S, Sueoka T, Matsuura S, Sugimoto T: Biopterin and neopterin in human saliva. Life Sci. 1989;45(26):2561-8. Pubmed: 2615555
  5. Dhondt JL, Tilmont P, Ringel J, Farriaux JP: Pterins analysis in amniotic fluid for the prenatal diagnosis of GTP cyclohydrolase deficiency. J Inherit Metab Dis. 1990;13(6):879-82. Pubmed: 2079836
  6. Bonafe L, Thony B, Leimbacher W, Kierat L, Blau N: Diagnosis of dopa-responsive dystonia and other tetrahydrobiopterin disorders by the study of biopterin metabolism in fibroblasts. Clin Chem. 2001 Mar;47(3):477-85. Pubmed: 11238300
  7. Krumdieck CL, Fukushima K, Fukushima T, Shiota T, Butterworth CE Jr: A long-term study of the excretion of folate and pterins in a human subject after ingestion of 14C folic acid, with observations on the effect of diphenylhydantoin administration. Am J Clin Nutr. 1978 Jan;31(1):88-93. Pubmed: 413430
  8. Han F, Huynh BH, Shi H, Lin B, Ma Y: Pteridine analysis in urine by capillary electrophoresis using laser-induced fluorescence detection. Anal Chem. 1999 Apr 1;71(7):1265-9. Pubmed: 10204031
  9. Yamamoto T, Moriwaki Y, Takahashi S, Tsutsumi Z, Yamakita J, Nasako Y, Hiroishi K, Higashino K: Determination of human plasma xanthine oxidase activity by high-performance liquid chromatography. J Chromatogr B Biomed Appl. 1996 Jun 7;681(2):395-400. Pubmed: 8811453
  10. Beckman JS, Parks DA, Pearson JD, Marshall PA, Freeman BA: A sensitive fluorometric assay for measuring xanthine dehydrogenase and oxidase in tissues. Free Radic Biol Med. 1989;6(6):607-15. Pubmed: 2753392
  11. Gordon JH, Perry KO: Pre- and postsynaptic neurochemical alterations following estrogen-induced striatal dopamine hypo- and hypersensitivity. Brain Res Bull. 1983 Apr;10(4):425-8. Pubmed: 6134572
  12. Stupperich E: Recent advances in elucidation of biological corrinoid functions. FEMS Microbiol Rev. 1993 Nov;12(4):349-65. Pubmed: 8268006
  13. Niederwieser A, Blau N, Wang M, Joller P, Atares M, Cardesa-Garcia J: GTP cyclohydrolase I deficiency, a new enzyme defect causing hyperphenylalaninemia with neopterin, biopterin, dopamine, and serotonin deficiencies and muscular hypotonia. Eur J Pediatr. 1984 Feb;141(4):208-14. Pubmed: 6734669
  14. Blau N, Kierat L, Matasovic A, Leimbacher W, Heizmann CW, Guardamagna O, Ponzone A: Antenatal diagnosis of tetrahydrobiopterin deficiency by quantification of pterins in amniotic fluid and enzyme activity in fetal and extrafetal tissue. Clin Chim Acta. 1994 May;226(2):159-69. Pubmed: 7923811
  15. Rokos H, Beazley WD, Schallreuter KU: Oxidative stress in vitiligo: photo-oxidation of pterins produces H(2)O(2) and pterin-6-carboxylic acid. Biochem Biophys Res Commun. 2002 Apr 12;292(4):805-11. Pubmed: 11944885

Enzymes

General function:
Involved in cobalamin binding
Specific function:
Catalyzes the transfer of a methyl group from methyl-cobalamin to homocysteine, yielding enzyme-bound cob(I)alamin and methionine. Subsequently, remethylates the cofactor using methyltetrahydrofolate (By similarity).
Gene Name:
MTR
Uniprot ID:
Q99707
Molecular weight:
140525.91