Record Information
Version2.0
Creation Date2012-08-03 14:57:54 -0600
Update Date2015-09-13 15:15:32 -0600
Secondary Accession Numbers
  • ECMDB21400
Identification
Name:Pterin
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:
  • 2-amino-1H-pteridin-4-one
  • 2-amino-3H-pteridin-4-one
  • 2-Amino-4(1H)-pteridinone
  • 2-Amino-4(3H)-pteridinone
  • 2-Amino-4-hydroxypteridine
  • 2-Amino-4-oxopteridine
  • 2-amino-4-pteridinol
  • 2-Amino-4-pteridone
  • 2-amino-Quinonoid dihydropterin
  • 2-Aminopteridin-4-one
  • 4-Oxo-2-aminopteridine
  • 4-Oxopterin
  • Pteridoxamine
  • Pterin
  • Pterine
Chemical Formula:C6H5N5O
Weight:Average: 163.1368
Monoisotopic: 163.049409807
InChI Key:HNXQXTQTPAJEJL-UHFFFAOYSA-N
InChI: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)
CAS number:2236-60-4
IUPAC Name:2-amino-3,4-dihydropteridin-4-one
Traditional IUPAC Name:2-amino-4-oxopteridine
SMILES:NC1=NC2=NC=CN=C2C(=O)N1
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
  • Pyrazine
  • Pyrimidine
  • Heteroaromatic compound
  • Vinylogous amide
  • Azacycle
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Water Solubility:0.175 mg/mL [BEILSTEIN]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility1.49 g/LALOGPS
logP-0.86ALOGPS
logP-0.96ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)10ChemAxon
pKa (Strongest Basic)-1.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area93.26 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity41.82 m³·mol⁻¹ChemAxon
Polarizability14.46 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
ConcentrationStrainMediaGrowth StatusGrowth SystemTemperatureDetails
24± 0 uMBW2511348 mM Na2HPO4, 22 mM KH2PO4, 10 mM NaCl, 45 mM (NH4)2SO4, supplemented with 1 mM MgSO4, 1 mg/l thiamine·HCl, 5.6 mg/l CaCl2, 8 mg/l FeCl3, 1 mg/l MnCl2·4H2O, 1.7 mg/l ZnCl2, 0.43 mg/l CuCl2·2H2O, 0.6 mg/l CoCl2·2H2O and 0.6 mg/l Na2MoO4·2H2O. 4 g/L GlucoStationary Phase, glucose limitedBioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h37 oCPMID: 17379776
Find out more about how we convert literature concentrations.
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-3900000000-e0c5aa11edc5408b2afdView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-0900000000-815f9d4247cb9067f9fbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-014l-5900000000-6bd37ba7d9f26d33ffd5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014l-9100000000-b809a46cbde852be02deView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-03di-0900000000-71eab96d7f1dfed51963View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-03di-1900000000-36d14ee4f35692f07beeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-03di-0900000000-7d6238777a46df27af01View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-066u-9000000000-289c0930b78dd1447e10View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-066r-4900000000-8c47f8f3ca753ec1cf6fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0aor-9300000000-938f26c8bed8f1edc185View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-014i-3900000000-ca751d8c09c98e0c9d3dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-03di-0900000000-a67b522aa27e6f75f46eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-ad3fade684bdebfb41e3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-f1eb4d0b367f209bc766View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0900000000-a250d1c9d32e286b29f6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-9300000000-190579d7d5ba6d0c14c5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-4005b83e558e2b0c5772View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-a4698cb941c94fd08799View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9000000000-8ed28777d0de229aa6a3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-99937f8026369fb0e183View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03xr-2900000000-41450f7664125a38cc97View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9000000000-5a06c4c35a067e936a16View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-0dba7b98ddf974fcc10cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0900000000-ba39f053d7d33e17ee00View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9100000000-7334fbd934d9e46491f7View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597. Pubmed: 17379776
  • Katoh S, Sueoka T, Matsuura S, Sugimoto T: Biopterin and neopterin in human saliva. Life Sci. 1989;45(26):2561-8. Pubmed: 2615555
  • 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
  • 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
  • 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
  • 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
  • Stupperich E: Recent advances in elucidation of biological corrinoid functions. FEMS Microbiol Rev. 1993 Nov;12(4):349-65. Pubmed: 8268006
  • 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
Synthesis Reference:Taylor, 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)
External Links:
ResourceLink
CHEBI ID18265
HMDB IDHMDB00802
Pubchem Compound ID73000
Kegg IDC00715
ChemSpider ID65806
WikipediaPterin
BioCyc IDNot Available
Ligand ExpoPE0