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17528-72-2 分子结构
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2-amino-6-(1,2-dihydroxypropyl)-1,4,5,6,7,8-hexahydropteridin-4-one

ChemBase编号:244
分子式:C9H15N5O3
平均质量:241.2471
单一同位素质量:241.11748937
SMILES和InChIs

SMILES:
OC(C1Nc2c(NC1)[nH]c(nc2=O)N)C(O)C
Canonical SMILES:
CC(C(C1CNc2c(N1)c(=O)nc([nH]2)N)O)O
InChI:
InChI=1S/C9H15N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h3-4,6,12,15-16H,2H2,1H3,(H4,10,11,13,14,17)
InChIKey:
FNKQXYHWGSIFBK-UHFFFAOYSA-N

引用这个纪录

CBID:244 http://www.chembase.cn/molecule-244.html

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名称和登记号

名称和登记号

名称 登记号
IUPAC标准名
2-amino-6-(1,2-dihydroxypropyl)-1,4,5,6,7,8-hexahydropteridin-4-one
IUPAC传统名
tetrahydrobiopterin
商标名
Dapropterin
Sapropterin
Kuvan
Phenoptin
别名
5,6,7,8 Tetrahydrobiopterin
BH4
sapropterin
Tetrahydrobiopterin
CAS号
17528-72-2
PubChem SID
160963707
46508597
PubChem CID
1125

数据来源

数据来源

所有数据来源 商品来源 非商品来源
数据来源 数据ID
DrugBank DB00360 external link
PubChem 1125 external link
数据来源 数据ID 价格

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 10.021745  质子受体
质子供体 LogD (pH = 5.5) -3.0598261 
LogD (pH = 7.4) -2.6819317  Log P -2.6621299 
摩尔折射率 68.4334 cm3 极化性 22.361328 Å3
极化表面积 132.0 Å2 可自由旋转的化学键
里宾斯基五规则 false 
Log P -1.66  LOG S -2.04 
溶解度 2.21e+00 g/l 

分子性质

分子性质

理化性质 生物活性(PubChem)
溶解度
>20 mg/mL (dichloride salt) expand 查看数据来源
疏水性(logP)
-1.7 expand 查看数据来源

详细说明

详细说明

DrugBank DrugBank
DrugBank -  DB00360 external link
Item Information
Drug Groups approved; investigational
Description Tetrahydrobiopterin or BH4 is a cofactor in the synthesis of nitric oxide. It is also essential in the conversion of phenylalanine to tyrosine by the enzyme phenylalanine-4-hydroxylase; the conversion of tyrosine to L-dopa by the enzyme tyrosine hydroxylase; and conversion of tryptophan to 5-hydroxytryptophan via tryptophan hydroxylase. [Wikipedia]
Indication For the treatment of tetrahydrobiopterin (BH4) deficiency.
Pharmacology Tetrahydrobiopterin (BH4) is used to convert several amino acids, including phenylalanine, to other essential molecules in the body including neurotransmitters. Tetrahydrobiopterin deficiency can be caused by mutations in GTP cyclohydrolase 1 (GCH1), 6-pyruvoyl-tetrahydropterin synthase/dimerization cofactor of hepatocyte nuclear factor 1 alpha (PCBD1), 6-pyruvoyltetrahydropterin synthase (PTS), and quinoid dihydropteridine reductase (QDPR) genes. These genes make the enzymes that are critical for producing and recycling tetrahydrobiopterin. If one of the enzymes fails to function correctly because of a gene mutation, little or no tetrahydrobiopterin is produced. As a result, phenylalanine from the diet builds up in the bloodstream and other tissues and can damage nerve cells in the brain. High levels of phenylalanine can result in signs and symptoms ranging from temporary low muscle tone to mental retardation, movement disorders, difficulty swallowing, seizures, behavioral problems, progressive problems with development, and an inability to control body temperature.
Affected Organisms
Humans and other mammals
References
Thony B, Auerbach G, Blau N: Tetrahydrobiopterin biosynthesis, regeneration and functions. Biochem J. 2000 Apr 1;347 Pt 1:1-16. [Pubmed]
External Links
Wikipedia

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • Thony B, Auerbach G, Blau N: Tetrahydrobiopterin biosynthesis, regeneration and functions. Biochem J. 2000 Apr 1;347 Pt 1:1-16. Pubmed
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专利

专利

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互联网资源

互联网资源

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