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89687-39-8

89687-39-8 | 1,2-Propanedione,1-(2-amino-3,4,5,6,7,8-hexahydro-4-oxo-6-pteridinyl)-

CAS No: 89687-39-8 Catalog No: AG0044B6 MDL No:

Product Description

Catalog Number:
AG0044B6
Chemical Name:
1,2-Propanedione,1-(2-amino-3,4,5,6,7,8-hexahydro-4-oxo-6-pteridinyl)-
CAS Number:
89687-39-8
Molecular Formula:
C9H11N5O3
Molecular Weight:
237.2153
IUPAC Name:
1-(2-amino-4-oxo-5,6,7,8-tetrahydro-3H-pteridin-6-yl)propane-1,2-dione
InChI:
InChI=1S/C9H11N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h4,12H,2H2,1H3,(H4,10,11,13,14,17)
InChI Key:
WBJZXBUVECZHCE-UHFFFAOYSA-N
SMILES:
Nc1nc(O)c2c(n1)NCC(N2)C(=O)C(=O)C

Properties

Complexity:
479  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
237.086g/mol
Formal Charge:
0
Heavy Atom Count:
17  
Hydrogen Bond Acceptor Count:
6  
Hydrogen Bond Donor Count:
4  
Isotope Atom Count:
0
Molecular Weight:
237.219g/mol
Monoisotopic Mass:
237.086g/mol
Rotatable Bond Count:
2  
Topological Polar Surface Area:
126A^2
Undefined Atom Stereocenter Count:
1  
Undefined Bond Stereocenter Count:
0
XLogP3:
-1.7  

Literature

Title Journal
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Advanced glycation end products-mediated hypertrophy is negatively regulated by tetrahydrobiopterin in renal tubular cells. Molecular and cellular endocrinology 20120515
Catalytic residues and a predicted structure of tetrahydrobiopterin-dependent alkylglycerol mono-oxygenase. The Biochemical journal 20120401
Effect of advanced glycation end products on oxidative stress and senescence of trabecular meshwork cells. Korean journal of ophthalmology : KJO 20120401
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Dicarbonyl reduction by single enzyme for the preparation of chiral diols. Chemical Society reviews 20120307
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Analgesia by inhibiting tetrahydrobiopterin synthesis. Current opinion in pharmacology 20120201
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Mutagenesis by imprecise excision of the piggyBac transposon in Drosophila melanogaster. Biochemical and biophysical research communications 20120106
HemaMax™, a recombinant human interleukin-12, is a potent mitigator of acute radiation injury in mice and non-human primates. PloS one 20120101
Transcriptome analysis in tardigrade species reveals specific molecular pathways for stress adaptations. Bioinformatics and biology insights 20120101
Endothelial dysfunction and diabetes: effects on angiogenesis, vascular remodeling, and wound healing. International journal of vascular medicine 20120101
NAD(P)H oxidase and eNOS play differential roles in cytomegalovirus infection-induced microvascular dysfunction. Free radical biology & medicine 20111215
Whole-genome sequencing informs treatment: personalized medicine takes another step forward. Clinical chemistry 20111201
C-reactive protein induces release of both endothelial microparticles and circulating endothelial cells in vitro and in vivo: further evidence of endothelial dysfunction. Clinical chemistry 20111201
Asymmetric uptake of sepiapterin and 7,8-dihydrobiopterin as a gateway of the salvage pathway of tetrahydrobiopterin biosynthesis from the lumenal surface of rat endothelial cells. Molecular genetics and metabolism 20111101
Role of sepiapterin reductase gene at the PARK3 locus in Parkinson's disease. Neurobiology of aging 20111101
Autophagy induction by tetrahydrobiopterin deficiency. Autophagy 20111101
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Sepiapterin enhances angiogenesis and functional recovery in mice after myocardial infarction. American journal of physiology. Heart and circulatory physiology 20111101
Decreased tetrahydrobiopterin and disrupted association of Hsp90 with eNOS by hyperglycemia impair myocardial ischemic preconditioning. American journal of physiology. Heart and circulatory physiology 20111101
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Impairment of nitrergic system and delayed gastric emptying in low density lipoprotein receptor deficient female mice. Neurogastroenterology and motility : the official journal of the European Gastrointestinal Motility Society 20110801
Genotype-phenotype correlations in sepiapterin reductase deficiency. A splicing defect accounts for a new phenotypic variant. Neurogenetics 20110801
Synthesis and recycling of tetrahydrobiopterin in endothelial function and vascular disease. Nitric oxide : biology and chemistry 20110801
Inhibition of nitric oxide synthase uncoupling by sepiapterin improves left ventricular function in streptozotocin-induced diabetic mice. Clinical and experimental pharmacology & physiology 20110801
Effects of sepiapterin infusion on renal oxygenation and early acute renal injury after suprarenal aortic clamping in rats. Journal of cardiovascular pharmacology 20110801
Non-conventional hydrogen bonds: pterins-metal anions. Physical chemistry chemical physics : PCCP 20110728
Whole-genome sequencing for optimized patient management. Science translational medicine 20110615
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Emission properties of dihydropterins in aqueous solutions. Physical chemistry chemical physics : PCCP 20110428
Mthfr deficiency induces endothelial progenitor cell senescence via uncoupling of eNOS and downregulation of SIRT1. American journal of physiology. Heart and circulatory physiology 20110301
eNOS-uncoupling in age-related erectile dysfunction. International journal of impotence research 20110301
Partial biopterin deficiency disturbs postnatal development of the dopaminergic system in the brain. The Journal of biological chemistry 20110114
Mechanisms of diesel-induced endothelial nitric oxide synthase dysfunction in coronary arterioles. Environmental health perspectives 20110101
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Basal Ganglia disorders associated with imbalances in the striatal striosome and matrix compartments. Frontiers in neuroanatomy 20110101
The eukaryotic-type serine/threonine protein kinase Stk is required for biofilm formation and virulence in Staphylococcus epidermidis. PloS one 20110101
Dtorsin, the Drosophila ortholog of the early-onset dystonia TOR1A (DYT1), plays a novel role in dopamine metabolism. PloS one 20110101
The evolution of metabolic networks of E. coli. BMC systems biology 20110101
Sepiapterin reverses the changes in gastric nNOS dimerization and function in diabetic gastroparesis. Neurogastroenterology and motility : the official journal of the European Gastrointestinal Motility Society 20101201
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Fluorine-18-FDG PET findings of focal eosinophilic liver disease: correlation with CT and/or MRI, laboratory, and pathologic findings. Abdominal imaging 20100801
Endothelium-derived vasoactive factors and hypertension: possible roles in pathogenesis and as treatment targets. Current hypertension reports 20100801
Dystonia-plus syndromes. European journal of neurology 20100701
Identification of genes influencing skeletal phenotypes in congenic P/NP rats. Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research 20100601
The role of cyanopterin in UV/blue light signal transduction of cyanobacterium Synechocystis sp. PCC 6803 phototaxis. Plant & cell physiology 20100601
Sepiapterin reductase deficiency: two Indian siblings with unusual clinical features. Movement disorders : official journal of the Movement Disorder Society 20100515
Effects of sepiapterin supplementation and NOS inhibition on glucocorticoid-induced hypertension. American journal of hypertension 20100501
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Sleep and rhythm consequences of a genetically induced loss of serotonin. Sleep 20100301
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Is tetrahydrobiopterin a therapeutic option in diabetic hypertensive patients? Integrated blood pressure control 20100101
Sepiapterin reductase deficiency in a 2-year-old girl with incomplete response to treatment during short-term follow-up. Journal of inherited metabolic disease 20091201
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Role of tetrahydrobiopterin in resistance to myocardial ischemia in Brown Norway and Dahl S rats. American journal of physiology. Heart and circulatory physiology 20091101
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eNOS uncoupling and endothelial dysfunction in aged vessels. American journal of physiology. Heart and circulatory physiology 20091101
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Sepiapterin reductase regulation of endothelial tetrahydrobiopterin and nitric oxide bioavailability. American journal of physiology. Heart and circulatory physiology 20090701
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Disorders of biopterin metabolism. Journal of inherited metabolic disease 20090601
Sepiapterin decreases acute rejection and apoptosis in cardiac transplants independently of changes in nitric oxide and inducible nitric-oxide synthase dimerization. The Journal of pharmacology and experimental therapeutics 20090601
Neuroimaging findings in children with paediatric neurotransmitter diseases. Journal of inherited metabolic disease 20090601
Polymorphisms of sepiapterin reductase gene alter promoter activity and may influence risk of bipolar disorder. Pharmacogenetics and genomics 20090501
The silkworm mutant lemon (lemon lethal) is a potential insect model for human sepiapterin reductase deficiency. The Journal of biological chemistry 20090424
Certain progestins prevent the enhancing effect of 17beta-estradiol on NO-mediated inhibition of platelet aggregation by endothelial cells. Arteriosclerosis, thrombosis, and vascular biology 20090401
[Mutational analysis of patients with 6-pyruvoyltetrahydrobiopterin synthesis deficiency]. Zhonghua yi xue yi chuan xue za zhi = Zhonghua yixue yichuanxue zazhi = Chinese journal of medical genetics 20090401
Escherichia coli QueD is a 6-carboxy-5,6,7,8-tetrahydropterin synthase. Biochemistry 20090324
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Two Greek siblings with sepiapterin reductase deficiency. Molecular genetics and metabolism 20080801
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Sepiapterin reductase expression is increased in Parkinson's disease brain tissue. Brain research 20070330
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Endothelin mediates superoxide production and vasoconstriction through activation of NADPH oxidase and uncoupled nitric-oxide synthase in the rat aorta. The Journal of pharmacology and experimental therapeutics 20051201
Hyperhomocystinemia impairs endothelial function and eNOS activity via PKC activation. Arteriosclerosis, thrombosis, and vascular biology 20051201
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Enhanced oxidative stress impairs cAMP-mediated dilation by reducing Kv channel function in small coronary arteries of diabetic rats. American journal of physiology. Heart and circulatory physiology 20051101
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Functional comparison of the endothelial nitric oxide synthase Glu298Asp polymorphic variants in human endothelial cells. Pharmacogenetics 20041201
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Heterozygous mutation in 5'-untranslated region of sepiapterin reductase gene (SPR) in a patient with dopa-responsive dystonia. Neurogenetics 20040901
Moderate hyperhomocysteinemia decreases endothelial-dependent vasorelaxation in pregnant but not nonpregnant mice. Hypertension (Dallas, Tex. : 1979) 20040901
Microvascular dysfunction after transient high glucose is caused by superoxide-dependent reduction in the bioavailability of NO and BH(4). American journal of physiology. Heart and circulatory physiology 20040801
Tetrahydropteridines suppress gene expression and induce apoptosis of activated RAW264.7 cells via formation of hydrogen peroxide. Free radical biology & medicine 20040801
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Functional tetrahydrobiopterin synthesis in human platelets. Circulation 20040713
Homocysteine induces oxidative stress by uncoupling of NO synthase activity through reduction of tetrahydrobiopterin. Free radical biology & medicine 20040615
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Suppression of cytokine-inducible nitric oxide synthesis during intraperitoneal Meth A tumor growth. The Journal of veterinary medical science 20040501
1-Methyl-4-phenylpyridinium-induced apoptosis in cerebellar granule neurons is mediated by transferrin receptor iron-dependent depletion of tetrahydrobiopterin and neuronal nitric-oxide synthase-derived superoxide. The Journal of biological chemistry 20040430
Nuclear localization of tetrahydrobiopterin biosynthetic enzymes. Biochimica et biophysica acta 20040105
Activity of synthetic enzymes of tetrahydrobiopterin in the human placenta. International journal of molecular medicine 20040101
Glucocorticoids decrease GTP cyclohydrolase and tetrahydrobiopterin-dependent vasorelaxation through glucocorticoid receptors. Journal of cardiovascular pharmacology 20040101
Sepiapterin decreases vasorelaxation in nitric oxide synthase inhibition-induced hypertension. Journal of cardiovascular pharmacology 20040101
Tetrahydrobiopterin, a critical factor in the production and role of nitric oxide in mast cells. The Journal of biological chemistry 20031212
A haplotype at the PARK3 locus influences onset age for Parkinson's disease: the GenePD study. Neurology 20031209
Peroxisome proliferator-activated receptor agonists inhibit interleukin-1beta-mediated nitric oxide production in cultured lacrimal gland acinar cells. Journal of ocular pharmacology and therapeutics : the official journal of the Association for Ocular Pharmacology and Therapeutics 20031201
GTP cyclohydrolase 1 inhibition attenuates vasodilation and increases blood pressure in rats. American journal of physiology. Heart and circulatory physiology 20031101
Ascorbate enhances iNOS activity by increasing tetrahydrobiopterin in RAW 264.7 cells. Free radical biology & medicine 20031015
Sepiapterin reduces postischemic injury in the rat heart. Pflugers Archiv : European journal of physiology 20031001
Localization of sepiapterin reductase in pigment cells of Oryzias latipes. Pigment cell research 20031001
Tetrahydrobiopterin prevents nitration of tyrosine hydroxylase by peroxynitrite and nitrogen dioxide. Molecular pharmacology 20031001
Chronic oral supplementation with sepiapterin prevents endothelial dysfunction and oxidative stress in small mesenteric arteries from diabetic (db/db) mice. British journal of pharmacology 20031001
Genetic engineering of Escherichia coli for production of tetrahydrobiopterin. Metabolic engineering 20031001
Tetrahydrobiopterin is synthesized from 6-pyruvoyl-tetrahydropterin by the human aldo-keto reductase AKR1 family members. Archives of biochemistry and biophysics 20030815
Effect of hyperhomocystinemia and hypertension on endothelial function in methylenetetrahydrofolate reductase-deficient mice. Arteriosclerosis, thrombosis, and vascular biology 20030801
Exogenous biopterins requirement for iNOS function in vascular smooth muscle cells. Journal of cardiovascular pharmacology 20030801
Overexpression of V-1 prevents nitric oxide-induced cell death: involvement of enhanced tetrahydrobiopterin biosynthesis. Journal of neuroscience research 20030615
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Mycophenolic acid inhibits activation of inducible nitric oxide synthase in rodent fibroblasts. Clinical and experimental immunology 20030501
Co-ordinate transcriptional regulation of dopamine synthesis genes by alpha-synuclein in human neuroblastoma cell lines. Journal of neurochemistry 20030501
Possible impact of tetrahydrobiopterin and sepiapterin on endothelial dysfunction. Arteriosclerosis, thrombosis, and vascular biology 20030501
Tetrahydrobiopterin precursor sepiapterin provides protection against neurotoxicity of 1-methyl-4-phenylpyridinium in nigral slice cultures. Journal of neurochemistry 20030401
GTP cyclohydrolase 1 downregulation contributes to glucocorticoid hypertension in rats. Hypertension (Dallas, Tex. : 1979) 20030301
Effect of antisense oligodeoxynucleotide for sepiapterin reductase on the viability of PC12 cells in the presence of exogenous carbonyl compounds. Chemico-biological interactions 20030201
Specific potentiation of endothelium-dependent contractions in SHR by tetrahydrobiopterin. Hypertension (Dallas, Tex. : 1979) 20030101
Peripheral administration of lipopolysaccharide enhances the expression of guanosine triphosphate cyclohydrolase I mRNA in murine locus coeruleus. Neuroscience 20030101
Lack of nitric oxide mediation of flow-dependent arteriolar dilation in type I diabetes is restored by sepiapterin. Journal of vascular research 20030101
Nitric oxide production by decidual endothelial cells is not reduced in preeclampsia. Hypertension in pregnancy 20030101
Recent segmental and gene duplications in the mouse genome. Genome biology 20030101
Age estimation of Mexican fruit fly (Diptera: Tephritidae) based on accumulation of pterins. Journal of economic entomology 20021201
Localization of sepiapterin reductase in the human brain. Brain research 20021108
Developmental regulation of neurotransmitter phenotype through tetrahydrobiopterin. The Journal of neuroscience : the official journal of the Society for Neuroscience 20021101
Altered tetrahydrobiopterin metabolism in atherosclerosis: implications for use of oxidized tetrahydrobiopterin analogues and thiol antioxidants. Arteriosclerosis, thrombosis, and vascular biology 20021001
Mycophenolic acid downregulates inducible nitric oxide synthase induction in astrocytes. Glia 20020901
Escherichia coli 6-pyruvoyltetrahydropterin synthase ortholog encoded by ygcM has a new catalytic activity for conversion of sepiapterin to 7,8-dihydropterin. FEBS letters 20020717
Anti-inflammatory effects of tetrahydrobiopterin on early rejection in renal allografts: modulation of inducible nitric oxide synthase. FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20020701
Interaction of 5-methyltetrahydrofolate and tetrahydrobiopterin on endothelial function. American journal of physiology. Heart and circulatory physiology 20020601
Enhanced expression of GTP cyclohydrolase I in V-1-overexpressing PC12D cells. Biochemical and biophysical research communications 20020510
Glutathione depletion in nigrostriatal slice cultures: GABA loss, dopamine resistance and protection by the tetrahydrobiopterin precursor sepiapterin. Brain research 20020510
Cellular basis of endothelial dysfunction in small mesenteric arteries from spontaneously diabetic (db/db -/-) mice: role of decreased tetrahydrobiopterin bioavailability. British journal of pharmacology 20020501
Interleukin-1beta-induced nitric oxide production and inhibition of insulin secretion in rat islets of langerhans is dependent upon the nitric oxide synthase cofactor tetrahidrobiopterin. Cytokine 20020421
Oxidative stress in vitiligo: photo-oxidation of pterins produces H(2)O(2) and pterin-6-carboxylic acid. Biochemical and biophysical research communications 20020412
Disorders of tetrahydrobiopterin metabolism and their treatment. Current drug metabolism 20020401
The enzymes with benzil reductase activity conserved from bacteria to mammals. Journal of biotechnology 20020328
Bacterial lipopolysaccharide down-regulates expression of GTP cyclohydrolase I feedback regulatory protein. The Journal of biological chemistry 20020322
The ratio between tetrahydrobiopterin and oxidized tetrahydrobiopterin analogues controls superoxide release from endothelial nitric oxide synthase: an EPR spin trapping study. The Biochemical journal 20020315
Analysis of xanthophore and pterinosome biogenesis in zebrafish using methylene blue and pteridine autofluorescence. Pigment cell research 20020201
Detection of sepiapterin in CSF of patients with sepiapterin reductase deficiency. Molecular genetics and metabolism 20020201
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