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
Kinetic and structural characterization of a product complex of 6-hydroxymethyl-7,8-dihydropterin pyrophosphokinase from Escherichia coli.	2004-06-15	15018613
Evidence of two distinct oxygen complexes of reduced endothelial nitric oxide synthase.	2004-05-07	15004019
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.	2004-04-30	14981076
The tetrahydropyranopterin structure of the sulfur-free and metal-free molybdenum cofactor precursor.	2004-04-16	14761975
Role of the second coordination sphere residue tyrosine 179 in substrate affinity and catalytic activity of phenylalanine hydroxylase.	2004-04	14999516
Effects of intracellular reactive oxygen species generated by 6-formylpterin on T cell functions.	2004-03-15	15006553
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.	2004-03	14669076
Dynamic regulation of the inducible nitric-oxide synthase by NO: comparison with the endothelial isoform.	2004-02-06	14594819
Quenching of the fluorescence of pterin derivatives by anions.	2004-02	14872232
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.	2004-01-27	14730985
Effect of cofactor binding and loop conformation on side chain methyl dynamics in dihydrofolate reductase.	2004-01-20	14717591
Mobilization of xanthine oxidase from the gastrointestinal tract in acute pancreatitis.	2004-01-19	14728722
Tungsten-containing aldehyde oxidoreductase of Eubacterium acidaminophilum.	2004-01	14686934
Redox reactions of the pyranopterin system of the molybdenum cofactor.	2004-01	14628171
Uncoupled forms of tyrosine hydroxylase unmask kinetic isotope effects on chemical steps.	2003-12-31	14692751
Tetrahydrofolate and 5-methyltetrahydrofolate are folates with high antioxidant activity. Identification of the antioxidant pharmacophore.	2003-12-18	14675781
Single-turnover of nitric-oxide synthase in the presence of 4-amino-tetrahydrobiopterin: proposed role for tetrahydrobiopterin as a proton donor.	2003-12-05	14514694
Ability of tetrahydrobiopterin analogues to support catalysis by inducible nitric oxide synthase: formation of a pterin radical is required for enzyme activity.	2003-11-18	14609340
A ruthenium pterin complex showing proton-coupled electron transfer: synthesis and characterization.	2003-10-20	14579448
Diagnostic chemical shift markers for loop conformation and substrate and cofactor binding in dihydrofolate reductase complexes.	2003-10	14500880
Tetrahydrobiopterin prevents nitration of tyrosine hydroxylase by peroxynitrite and nitrogen dioxide.	2003-10	14500751
Mechanism of aromatic hydroxylation by an activated FeIV=O core in tetrahydrobiopterin-dependent hydroxylases.	2003-09-05	12953191
The autoxidation of tetrahydrobiopterin revisited. Proof of superoxide formation from reaction of tetrahydrobiopterin with molecular oxygen.	2003-07-04	12714605
Physarum polycephalum expresses a dihydropteridine reductase with selectivity for pterin substrates with a 6-(1', 2'-dihydroxypropyl) substitution.	2003-07	12956422
Increased folate catabolism following total body gamma-irradiation in mice.	2003-06	13678343
Mutations in the molybdenum cofactor biosynthetic genes MOCS1, MOCS2, and GEPH.	2003-06	12754701
Spectroscopic and kinetic studies of PKU-inducing mutants of phenylalanine hydroxylase: Arg158Gln and Glu280Lys.	2003-05-14	12733906
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.	2003-05	12826063
Posttranslational hydroxylation of human phenylalanine hydroxylase is a novel example of enzyme self-repair within the second coordination sphere of catalytic iron.	2003-04-23	12696880
Structural studies of molybdopterin synthase provide insights into its catalytic mechanism.	2003-04-18	12571227
Mechanistic and mutational studies of Escherichia coli molybdopterin synthase clarify the final step of molybdopterin biosynthesis.	2003-04-18	12571226
Multifrequency cw-EPR investigation of the catalytic molybdenum cofactor of polysulfide reductase from Wolinella succinogenes.	2003-04	12761663
Importance of substrate and cofactor polarization in the active site of dihydrofolate reductase.	2003-03-21	12628257
Phenylalanine hydroxylase gene in psychiatric patients: screening and functional assay of mutations.	2003-03-15	12644360
Singlet oxygen (1deltag) production by pterin derivatives in aqueous solutions.	2003-03	12713224
Studies on the regulatory properties of the pterin cofactor and dopamine bound at the active site of human phenylalanine hydroxylase.	2003-03	12603331
Structure of tetrahydrobiopterin tunes its electron transfer to the heme-dioxy intermediate in nitric oxide synthase.	2003-02-25	12590583
Wavelength-dependent induction of a mycosporine-like amino acid in a rice-field cyanobacterium, Nostoc commune: role of inhibitors and salt stress.	2003-02	12664980
Electronic structure and reactivity of high-spin iron--alkyl- and--pterinperoxo complexes.	2003-01-27	12693229
An extremely potent inhibitor of xanthine oxidoreductase. Crystal structure of the enzyme-inhibitor complex and mechanism of inhibition.	2003-01-17	12421831
Mechanism of dioxygen cleavage in tetrahydrobiopterin-dependent amino acid hydroxylases.	2003-01-03	12506369
Order of substrate binding in bacterial phenylalanine hydroxylase and its mechanistic implication for pterin-dependent oxygenases.	2003-01	12459906
Inhibition of THP-1 cell-mediated low-density lipoprotein oxidation by the macrophage-synthesised pterin, 7,8-dihydroneopterin.	2003	12804014
Age estimation of Mexican fruit fly (Diptera: Tephritidae) based on accumulation of pterins.	2002-12	12539849
Conformational changes in nitric oxide synthases induced by chlorzoxazone and nitroindazoles: crystallographic and computational analyses of inhibitor potency.	2002-11-26	12437348
Molecular motions and conformational changes of HPPK.	2002-11-01	12211000
Further case of paroxysmal exercise-induced dystonia and some insights into pathogenesis.	2002-11	12465091
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.	2002-10-08	12560990
Structure of a nitric oxide synthase heme protein from Bacillus subtilis.	2002-09-17	12220171
Fluorescence of pterin, 6-formylpterin, 6-carboxypterin and folic acid in aqueous solution: pH effects.	2002-06	12856711

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:58:01 GMT 2025` Edited by `admin` on `Mon Mar 31 19:58:01 GMT 2025`
Record UNII	85MA24E1NH
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

NSC-11540

Preferred Name

English

Pterin

Common Name

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