2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-1,4-dihydropteridin-4-one

• ChemBase编号: 126161
• 分子式: C9H11N5O3
• 平均质量: 237.21534
• 单一同位素质量: 237.08618924
• SMILES: O=c1nc([nH]c2ncc(nc12)[C@@H](O)[C@@H](O)C)N
• Canonical SMILES: C[C@@H]([C@@H](c1cnc2c(n1)c(=O)nc([nH]2)N)O)O
• InChI: 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
• InChIKey: LHQIJBMDNUYRAM-DZSWIPIPSA-N

名称和登记号

名称

• IUPAC标准名: 2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-1,4-dihydropteridin-4-one
• IUPAC传统名: 2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-1H-pteridin-4-one
• 别名: (1’R,2’S)-Biopterin; 2-Amino-4-hydroxy-6-(1,2-dihydroxypropyl)pteridine; L-erythro-6-(1,2-Dihydroxypropyl)pterin; 6-Biopterin; Biopterin

登记号

• CAS号: 22150-76-1
• EC号: 244-807-8
• MDL号: MFCD00036787
• Beilstein号: 87860
• PubChem SID: 162220502; 24891654
• PubChem CID: 445040
• Chemspider ID: 392795
• KEGG ID: C06313
• 医学主题词(MeSH): Biopterin
• 维基百科标题: Biopterin

理论计算性质

• Acid pKa: 7.598084
• 质子受体: 8
• 质子供体: 4
• LogD (pH = 5.5): -1.1910951
• LogD (pH = 7.4): -1.3875011
• Log P: -1.1878132
• 摩尔折射率: 58.1331 cm^3
• 极化性: 21.483948 Å^3
• 极化表面积: 133.72 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

• 比旋光度: [α]20/D -65±8°, c = 0.2% in 0.1 M HCl

安全信息

• RTECS编号: UO3506000
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 3
• 危险公开号: 36/37/38
• 安全公开号: 26-36
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H315-H319-H335
• GHS警示性声明: P261-P305 + P351 + P338
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥97%; ≥98.0% (sum of enantiomers, HPLC)
• Empirical Formula (Hill Notation): C9H11N5O3

详细说明

Sigma Aldrich - B2517

Application
6-Biopterin is an oxidation product from the melanogenesis regulating cofactor (6R)5,6,7,8 tetrahydrobiopterin (6-BH4). In vitro, 6-Biopterin is cytotoxic to melanocytes. However, in vivo, 6-Biopterin is rapidly and sequentially reduced back to 6-GH4 via q-BH2. Recent studies suggest that 6-Biopterin among other pteridines may be a useful non-invasive biomarker for cancer.

Sigma Aldrich - 14390

Other Notes
Review: Chemical mechanisms in the action of pteridine coenzymes1