PTERIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C6H5N5O
Molecular Weight	163.1368
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC1=NC2=C(N=CC=N2)C(=O)N1

InChI

InChIKey=HNXQXTQTPAJEJL-UHFFFAOYSA-N

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)

HIDE SMILES / InChI

Molecular Formula	C6H5N5O
Molecular Weight	163.1368
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

PubMed

Title	Date	PubMed
Age estimation of Mexican fruit fly (Diptera: Tephritidae) based on accumulation of pterins.	2002 Dec	12539849
Fluorescence of pterin, 6-formylpterin, 6-carboxypterin and folic acid in aqueous solution: pH effects.	2002 Jun	12856711
Further case of paroxysmal exercise-induced dystonia and some insights into pathogenesis.	2002 Nov	12465091
Molecular motions and conformational changes of HPPK.	2002 Nov 1	12211000
Conformational changes in nitric oxide synthases induced by chlorzoxazone and nitroindazoles: crystallographic and computational analyses of inhibitor potency.	2002 Nov 26	12437348
Structure of a nitric oxide synthase heme protein from Bacillus subtilis.	2002 Sep 17	12220171
Inhibition of THP-1 cell-mediated low-density lipoprotein oxidation by the macrophage-synthesised pterin, 7,8-dihydroneopterin.	2003	12804014
Multifrequency cw-EPR investigation of the catalytic molybdenum cofactor of polysulfide reductase from Wolinella succinogenes.	2003 Apr	12761663
Structural studies of molybdopterin synthase provide insights into its catalytic mechanism.	2003 Apr 18	12571227
Mechanistic and mutational studies of Escherichia coli molybdopterin synthase clarify the final step of molybdopterin biosynthesis.	2003 Apr 18	12571226
Posttranslational hydroxylation of human phenylalanine hydroxylase is a novel example of enzyme self-repair within the second coordination sphere of catalytic iron.	2003 Apr 23	12696880
Tetrahydrofolate and 5-methyltetrahydrofolate are folates with high antioxidant activity. Identification of the antioxidant pharmacophore.	2003 Dec 18	14675781
Uncoupled forms of tyrosine hydroxylase unmask kinetic isotope effects on chemical steps.	2003 Dec 31	14692751
Single-turnover of nitric-oxide synthase in the presence of 4-amino-tetrahydrobiopterin: proposed role for tetrahydrobiopterin as a proton donor.	2003 Dec 5	14514694
Wavelength-dependent induction of a mycosporine-like amino acid in a rice-field cyanobacterium, Nostoc commune: role of inhibitors and salt stress.	2003 Feb	12664980
Structure of tetrahydrobiopterin tunes its electron transfer to the heme-dioxy intermediate in nitric oxide synthase.	2003 Feb 25	12590583
Order of substrate binding in bacterial phenylalanine hydroxylase and its mechanistic implication for pterin-dependent oxygenases.	2003 Jan	12459906
An extremely potent inhibitor of xanthine oxidoreductase. Crystal structure of the enzyme-inhibitor complex and mechanism of inhibition.	2003 Jan 17	12421831
Electronic structure and reactivity of high-spin iron--alkyl- and--pterinperoxo complexes.	2003 Jan 27	12693229
Mechanism of dioxygen cleavage in tetrahydrobiopterin-dependent amino acid hydroxylases.	2003 Jan 3	12506369
Molecular and biochemical characterization of two tungsten- and selenium-containing formate dehydrogenases from Eubacterium acidaminophilum that are associated with components of an iron-only hydrogenase.	2003 Jan-Feb	12560990
Physarum polycephalum expresses a dihydropteridine reductase with selectivity for pterin substrates with a 6-(1', 2'-dihydroxypropyl) substitution.	2003 Jul	12956422
The autoxidation of tetrahydrobiopterin revisited. Proof of superoxide formation from reaction of tetrahydrobiopterin with molecular oxygen.	2003 Jul 4	12714605
Increased folate catabolism following total body gamma-irradiation in mice.	2003 Jun	13678343
Mutations in the molybdenum cofactor biosynthetic genes MOCS1, MOCS2, and GEPH.	2003 Jun	12754701
Singlet oxygen (1deltag) production by pterin derivatives in aqueous solutions.	2003 Mar	12713224
Studies on the regulatory properties of the pterin cofactor and dopamine bound at the active site of human phenylalanine hydroxylase.	2003 Mar	12603331
Phenylalanine hydroxylase gene in psychiatric patients: screening and functional assay of mutations.	2003 Mar 15	12644360
Importance of substrate and cofactor polarization in the active site of dihydrofolate reductase.	2003 Mar 21	12628257
Competition and binding of arginine, imidazole, and aminoguanidine to endothelial nitric oxide synthase: aminoguanidine is a poor model for substrate, intermediate, and arginine analog inhibitor binding.	2003 May	12826063
Spectroscopic and kinetic studies of PKU-inducing mutants of phenylalanine hydroxylase: Arg158Gln and Glu280Lys.	2003 May 14	12733906
Ability of tetrahydrobiopterin analogues to support catalysis by inducible nitric oxide synthase: formation of a pterin radical is required for enzyme activity.	2003 Nov 18	14609340
Diagnostic chemical shift markers for loop conformation and substrate and cofactor binding in dihydrofolate reductase complexes.	2003 Oct	14500880
Tetrahydrobiopterin prevents nitration of tyrosine hydroxylase by peroxynitrite and nitrogen dioxide.	2003 Oct	14500751
A ruthenium pterin complex showing proton-coupled electron transfer: synthesis and characterization.	2003 Oct 20	14579448
Mechanism of aromatic hydroxylation by an activated FeIV=O core in tetrahydrobiopterin-dependent hydroxylases.	2003 Sep 5	12953191
Role of the second coordination sphere residue tyrosine 179 in substrate affinity and catalytic activity of phenylalanine hydroxylase.	2004 Apr	14999516
The tetrahydropyranopterin structure of the sulfur-free and metal-free molybdenum cofactor precursor.	2004 Apr 16	14761975
Inactivation of the Leishmania tarentolae pterin transporter (BT1) and reductase (PTR1) genes leads to viable parasites with changes in folate metabolism and hypersensitivity to the antifolate methotrexate.	2004 Apr 30	14981076
Quenching of the fluorescence of pterin derivatives by anions.	2004 Feb	14872232
Dynamic regulation of the inducible nitric-oxide synthase by NO: comparison with the endothelial isoform.	2004 Feb 6	14594819
Tungsten-containing aldehyde oxidoreductase of Eubacterium acidaminophilum.	2004 Jan	14686934
Redox reactions of the pyranopterin system of the molybdenum cofactor.	2004 Jan	14628171
Mobilization of xanthine oxidase from the gastrointestinal tract in acute pancreatitis.	2004 Jan 19	14728722
Effect of cofactor binding and loop conformation on side chain methyl dynamics in dihydrofolate reductase.	2004 Jan 20	14717591
Voltammetric studies of the catalytic mechanism of the respiratory nitrate reductase from Escherichia coli: how nitrate reduction and inhibition depend on the oxidation state of the active site.	2004 Jan 27	14730985
Kinetic and structural characterization of a product complex of 6-hydroxymethyl-7,8-dihydropterin pyrophosphokinase from Escherichia coli.	2004 Jun 15	15018613
Incorporation of either molybdenum or tungsten into formate dehydrogenase from Desulfovibrio alaskensis NCIMB 13491; EPR assignment of the proximal iron-sulfur cluster to the pterin cofactor in formate dehydrogenases from sulfate-reducing bacteria.	2004 Mar	14669076
Effects of intracellular reactive oxygen species generated by 6-formylpterin on T cell functions.	2004 Mar 15	15006553
Evidence of two distinct oxygen complexes of reduced endothelial nitric oxide synthase.	2004 May 7	15004019

Patents

Substance Class	Chemical Created by `admin` on `Fri Dec 15 19:49:42 GMT 2023` Edited by `admin` on `Fri Dec 15 19:49:42 GMT 2023`
Record UNII	85MA24E1NH
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PTERIN

Common Name

English

NSC-11540

Code

English

PTERIDOXAMINE

Common Name

English

NSC-18696

Code

English

2-AMINO-4-HYDROXYPTERIDINE

Systematic Name

English

2-AMINO-4-PTERIDONE

Systematic Name

English

NSC-170929

Code

English

Classification Tree Code System Code

LOINC

80166-2