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

Molecular Formula	C9H11N5O3
Molecular Weight	237.2153
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

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 232 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
Nitric oxide (NO) traffic in endothelial NO synthase. Evidence for a new NO binding site dependent on tetrahydrobiopterin?	2002-03-01	11719512
Nitrocatechols versus nitrocatecholamines as novel competitive inhibitors of neuronal nitric oxide synthase: lack of the aminoethyl side chain determines loss of tetrahydrobiopterin-antagonizing properties.	2002-01-07	11738563
Citrulline is not the major product using the standard "NOS activity" assay on renal cortical homogenates.	2002-01	11742852
Structural basis for pterin antagonism in nitric-oxide synthase. Development of novel 4-oxo-pteridine antagonists of (6R)-5,6,7,8-tetrahydrobiopterin.	2001-12-28	11590164
Impaired endothelial regulation of ventricular relaxation in cardiac hypertrophy: role of reactive oxygen species and NADPH oxidase.	2001-12-11	11739314
Coronary endothelial dysfunction in the insulin-resistant state is linked to abnormal pteridine metabolism and vascular oxidative stress.	2001-12	11738280
Mechanisms of synergistic cytokine-induced nitric oxide production in human alveolar epithelial cells.	2001-12	11730360
Tetrahydrobiopterin attenuates cholesterol induced coronary hyperreactivity to endothelin.	2001-12	11711478
Involvement of tetrahydrobiopterin in trophic effect of erythropoietin on PC12 cells.	2001-11-30	11716480
High resolution crystal structures of the catalytic domain of human phenylalanine hydroxylase in its catalytically active Fe(II) form and binary complex with tetrahydrobiopterin.	2001-11-23	11718561
Intraplatelet tetrahydrobiopterin plays an important role in regulating canine coronary arterial thrombosis by modulating intraplatelet nitric oxide and superoxide generation.	2001-11-13	11705828
Crystal structure of nitric oxide synthase bound to nitro indazole reveals a novel inactivation mechanism.	2001-11-13	11695891
Catecholamines and serotonin are differently regulated by tetrahydrobiopterin. A study from 6-pyruvoyltetrahydropterin synthase knockout mice.	2001-11-02	11517215
Supplemention with tetrahydrobiopterin suppresses the development of hypertension in spontaneously hypertensive rats.	2001-11	11711495
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.	2001-11	11701761
Tetrahydrobiopterin-deficient hyperphenylalaninemia in the Chinese.	2001-11	11694255
Tetrahydrobiopterin, a cofactor for NOS, improves endothelial dysfunction during chronic alcohol consumption.	2001-11	11668045
Structures of tetrahydrobiopterin binding-site mutants of inducible nitric oxide synthase oxygenase dimer and implicated roles of Trp457.	2001-10-30	11669619
A conserved tryptophan in nitric oxide synthase regulates heme-dioxy reduction by tetrahydrobiopterin.	2001-10-30	11669618
Reaction of tetrahydrobiopterin with superoxide: EPR-kinetic analysis and characterization of the pteridine radical.	2001-10-15	11595382
Tetrahydrobiopterin deficiencies without hyperphenylalaninemia: diagnosis and genetics of dopa-responsive dystonia and sepiapterin reductase deficiency.	2001-10-11	11592814
[Orphan drugs and metabolic disorders].	2001-10-06	11588713
Evidence that bacterial cyanide oxygenase is a pterin-dependent hydroxylase.	2001-09-21	11554758
Effect of electroconvulsive therapy on biopterin and large neutral amino acids in severe, medication-resistant depression.	2001-09-20	11549400
Tetrahydrobiopterin scavenges superoxide in dopaminergic neurons.	2001-09-14	11447224
Treatable neurotransmitter deficiency in mild phenylketonuria.	2001-09-11	11552030
Carboxy-PTIO increases the tetrahydrobiopterin level in mouse brain microvascular endothelial cells.	2001-09	11676198
Vascular endothelial dysfunction: does tetrahydrobiopterin play a role?	2001-09	11514262
Survival and graft function in a large animal lung transplant model after 30 h preservation and substitution of the nitric oxide pathway.	2001-09	11509271
Molecular cloning and disruption of a novel gene encoding UDP-glucose: tetrahydrobiopterin alpha-glucosyltransferase in the cyanobacterium Synechococcus sp. PCC 7942.	2001-08-03	11583114
Constitutive expression of ectopic c-Myc delays glucocorticoid-evoked apoptosis of human leukemic CEM-C7 cells.	2001-08-02	11498786
Nitric oxide synthases: structure, function and inhibition.	2001-08-01	11463332
Determination of tetrahydrobiopterin in murine locus coeruleus by HPLC with fluorescence detection.	2001-08	11522525
Tetrahydrobiopterin improves endothelial dysfunction in coronary microcirculation in patients without epicardial coronary artery disease.	2001-08	11499743
Catecholamines decrease nitric oxide production by cytokine-stimulated hepatocytes.	2001-08	11490358
X-ray absorption spectroscopic analysis of the high-spin ferriheme site in substrate-bound neuronal nitric-oxide synthase.	2001-08	11481035
Preparation and crystallization of the stimulatory and inhibitory complexes of GTP cyclohydrolase I and its feedback regulatory protein GFRP.	2001-08	11468403
Effects of tetrahydrobiopterin on ataxia in Machado-Joseph disease may be based upon the theory of 'cerebellar long-term depression'.	2001-08	11461169
Tetrahydrobiopterin levels regulate endothelial cell proliferation.	2001-08	11454549
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.	2001-07-15	11444803
Homomeric and heteromeric interactions between wild-type and mutant phenylalanine hydroxylase subunits: evaluation of two-hybrid approaches for functional analysis of mutations causing hyperphenylalaninemia.	2001-07	11461190
Role of nitric oxide synthase in the light-induced development of sporangiophores in Phycomyces blakesleeanus.	2001-07	11457983
Folate improves endothelial function in coronary artery disease: an effect mediated by reduction of intracellular superoxide?	2001-07	11451751
The 4-amino analogue of tetrahydrobiopterin efficiently prolongs murine cardiac-allograft survival.	2001-07	11448802
Tetrahydrobiopterin-responsive phenylalanine hydroxylase deficiency in Dutch neonates.	2001-06	11486900
A splice mutation in the GTP cyclohydrolase I gene causes dopa-responsive dystonia by exon skipping.	2001-06	11486899
Circulating tetrahydrobiopterin concentrations in patients with septic shock.	2001-04	11573638
Differential nitric oxide synthase activity, cofactor availability and cGMP accumulation in the central nervous system during anaesthesia.	2001-03	11573530
Titration of low K(d) binding sites: binding of arginine analogs to nitric oxide synthases.	2001	11587559
[Biopterin synthesis deficiency (involv. DHPR deficiency)].	2001	11462433

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:52:20 GMT 2025` Edited by `admin` on `Mon Mar 31 17:52:20 GMT 2025`
Record UNII	E54CTM794Y
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

Biopterin

Common Name

English

NSC-339699

Preferred 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

Classification Tree Code System Code

LOINC

47582-2