BIOPTERIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C9H11N5O3
Molecular Weight	237.2153
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@H](O)[C@H](O)C1=NC2=C(N=C1)N=C(N)NC2=O

InChI

InChIKey=LHQIJBMDNUYRAM-DZSWIPIPSA-N

InChI=1S/C9H11N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h2-3,6,15-16H,1H3,(H3,10,11,13,14,17)/t3-,6-/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1600692 | https://www.ncbi.nlm.nih.gov/pubmed/6150460 | https://www.ncbi.nlm.nih.gov/pubmed/6150460

Biopterin (also known as L-erythro-biopterin or 6-Biopterin) is an oxidation product of tetrahydrobiopterin. Bioptrrin is an endogenous enzyme cofactor and its accumulation serves as markers of Parkinson's disease, Hyperphenylalaninemia and in addition, it can serve as a non-invasive biomarker for cancer.

Approval Year

Conditions

Condition	Modality	Highest Phase	Product
Hyperphenylalaninemia 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6150460	Diagnostic	Natural Metabolite	Unknown Approved Use Unknown
Parkinson's disease 226 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1880542	Diagnostic	Natural Metabolite	Unknown Approved Use Unknown
Haematological malignancies 4 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1600692	Diagnostic	Natural Metabolite	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Titration of low K(d) binding sites: binding of arginine analogs to nitric oxide synthases.	2001	11587559
Identification of three novel 6-pyruvoyl-tetrahydropterin synthase gene mutations (226C>T, IVS3+1G>A, 116-119delTGTT) in Chinese hyperphenylalaninemia caused by tetrahydrobiopterin synthesis deficiency.	2001	11438997
Parallel induction of nitric oxide and tetrahydrobiopterin synthesis in alveolar macrophages.	2001	11416252
A structural hypothesis for BH4 responsiveness in patients with mild forms of hyperphenylalaninaemia and phenylketonuria.	2001 Apr	11405341
[Studies on neonatal screening, clinical and gene analysis for tetrahydrobiopterin deficiency in Southern Chinese].	2001 Apr	11295124
Ligand binding to the inhibitory and stimulatory GTP cyclohydrolase I/GTP cyclohydrolase I feedback regulatory protein complexes.	2001 Apr	11274478
Hypochlorite-modified low density lipoprotein inhibits nitric oxide synthesis in endothelial cells via an intracellular dislocalization of endothelial nitric-oxide synthase.	2001 Apr 27	11278358
Oxidations of N(omega)-hydroxyarginine analogues and various N-hydroxyguanidines by NO synthase II: key role of tetrahydrobiopterin in the reaction mechanism and substrate selectivity.	2001 Feb	11258969
Kinetics of CO and NO ligation with the Cys(331)-->Ala mutant of neuronal nitric-oxide synthase.	2001 Feb 16	11067850
Expression of GTP cyclohydrolase I in murine locus ceruleus is enhanced by peripheral administration of lipopolysaccharide.	2001 Feb 2	11164786
Tetrahydrobiopterin increases myocardial blood flow in healthy volunteers: a double-blind, placebo-controlled study.	2001 Feb 24	11416883
L-ascorbic acid potentiates endothelial nitric oxide synthesis via a chemical stabilization of tetrahydrobiopterin.	2001 Jan 5	11022034
Rapid kinetic studies link tetrahydrobiopterin radical formation to heme-dioxy reduction and arginine hydroxylation in inducible nitric-oxide synthase.	2001 Jan 5	11020389
Folate improves endothelial function in coronary artery disease: an effect mediated by reduction of intracellular superoxide?	2001 Jul	11451751
Use of surface plasmon resonance for real-time measurements of the global conformational transition in human phenylalanine hydroxylase in response to substrate binding and catalytic activation.	2001 Jul 15	11444803
Tetrahydrobiopterin-responsive phenylalanine hydroxylase deficiency in Dutch neonates.	2001 Jun	11486900
Hypoxia impairs endothelium-dependent relaxation in organ cultured pulmonary artery.	2001 Jun 1	11408048
The effect of substrate, dihydrobiopterin, and dopamine on the EPR spectroscopic properties and the midpoint potential of the catalytic iron in recombinant human phenylalanine hydroxylase.	2001 Jun 22	11301319
Effect of vitamin C on the availability of tetrahydrobiopterin in human endothelial cells.	2001 Mar	11243424
Tetrahydrobiopterin enhances apoptotic PC12 cell death following withdrawal of trophic support.	2001 Mar 23	11124941
Characterization of GTP cyclohydrolase I gene expression in the human neuroblastoma SKN-BE(2)M17: enhanced transcription in response to cAMP is conferred by the proximal promoter.	2001 Nov	11701761
Tetrahydrobiopterin, a cofactor for NOS, improves endothelial dysfunction during chronic alcohol consumption.	2001 Nov	11668045
Catecholamines and serotonin are differently regulated by tetrahydrobiopterin. A study from 6-pyruvoyltetrahydropterin synthase knockout mice.	2001 Nov 2	11517215
Reaction of tetrahydrobiopterin with superoxide: EPR-kinetic analysis and characterization of the pteridine radical.	2001 Oct 15	11595382
Structures of tetrahydrobiopterin binding-site mutants of inducible nitric oxide synthase oxygenase dimer and implicated roles of Trp457.	2001 Oct 30	11669619
Survival and graft function in a large animal lung transplant model after 30 h preservation and substitution of the nitric oxide pathway.	2001 Sep	11509271
Evidence that bacterial cyanide oxygenase is a pterin-dependent hydroxylase.	2001 Sep 21	11554758
Tetrahydrobiopterin deficiencies without hyperphenylalaninemia: diagnosis and genetics of dopa-responsive dystonia and sepiapterin reductase deficiency.	2001 Sep-Oct	11592814

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Unknown

Name

Type

Language

BIOPTERIN

Common Name

English

4(1H)-PTERIDINONE, 2-AMINO-6-((1R,2S)-1,2-DIHYDROXYPROPYL)-

Systematic Name

English

BIOPTERIN [MI]

Common Name

English

2-AMINO-6-((1R,2S)-1,2-DIHYDROXYPROPYL)-4(1H)-PTERIDINONE

Systematic Name

English

(-)-BIOPTERIN

Common Name

English

L-ERYTHRO-BIOPTERIN

Common Name

English

NSC-339699

Code

English

Classification Tree Code System Code

LOINC

47582-2