2-amino-6-[(2S)-2-hydroxypropanoyl]-1,4,7,8-tetrahydropteridin-4-one

• ChemBase编号: 105333
• 分子式: C9H11N5O3
• 平均质量: 237.21534
• 单一同位素质量: 237.08618924
• SMILES: C[C@H](O)C(=O)C1=Nc2c(NC1)[nH]c(N)nc2=O
• Canonical SMILES: C[C@@H](C(=O)C1=Nc2c(NC1)[nH]c(nc2=O)N)O
• InChI: InChI=1S/C9H11N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h3,15H,2H2,1H3,(H4,10,11,13,14,17)/t3-/m0/s1
• InChIKey: VPVOXUSPXFPWBN-VKHMYHEASA-N

名称和登记号

名称

• IUPAC标准名: 2-amino-6-[(2S)-2-hydroxypropanoyl]-1,4,7,8-tetrahydropteridin-4-one
• IUPAC传统名: sepiapterin
• 别名: S-(-)-2-氨基-7,8-二氢-6-(2-羟基-1-氧代丙基)-4(1H)-蝶啶酮; 墨蝶呤; Sepiapterin; L-Sepiapterin; S-(-)-2-Amino-7,8-dihydro-6-(2-hydroxy-1-oxopropyl)-4(1H)-pteridinone; Sepiapterin; L-SEPIAPTERIN DIHYDRATE

登记号

• CAS号: 17094-01-8
• MDL号: MFCD00210214
• PubChem SID: 24278058; 162093831
• PubChem CID: 65253
• CHEMBL: 1255653
• Chemspider ID: 58746
• KEGG ID: C00835
• 维基百科标题: Sepiapterin

理论计算性质

• Acid pKa: 7.9298806
• 质子受体: 8
• 质子供体: 4
• LogD (pH = 5.5): -1.3707932
• LogD (pH = 7.4): -1.4704309
• Log P: -1.3689492
• 摩尔折射率: 67.4968 cm^3
• 极化性: 21.422352 Å^3
• 极化表面积: 129.17 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: 0.1 M NaOH: soluble9.8 mg/mL; DMSO: soluble27 mg/mL
• 外观: yellow solid

安全信息

• 保存条件: -20°C, Desiccate, Store Under Nitrogen, Protect from light
• 德国WGK号: 3
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: -20°C

药理学性质

• 相关基因信息: human ... NOS1(4842), NOS2(4843), NOS2B(201288), NOS2C(645740), NOS3(4846)

产品相关信息

• 纯度: ≥99%
• abs.: εmax/409 nm, 0.1 M HCl 6170; εmax1%/271 nm, 0.1 M HCl 7410
• Empirical Formula (Hill Notation): C9H11N5O3

详细说明

MP Biomedicals - 02195063

Purity: >99%
Dihydrate
Important intermediate in the pterin salvage pathway, tetrahydropterin biosynthesis.

MP Biomedicals - 02159813

Sepiapterin is converted intracellularly into tetrahydrobiopterin, which causes stimulation of NO production.

Sigma Aldrich - S154

Biochem/physiol Actions
一氧化氮合成酶辅因子；细胞内转化为四氢-生物蝶呤，刺激一氧化氮的生成。
包装
25 mg in poly bottle
5 mg in glass bottle

参考文献

• Nichol, C., et al., Annu. Rev. Biochem. , 54 : 729, (1985).
• Gross, S.S. and Levi, R.J., J. Biol. Chem. , 267 : 25722, (1992).