trisodium (3R,4S,5R)-4,5-dihydroxy-3-(phosphonatooxy)cyclohex-1-ene-1-carboxylate

• ChemBase编号: 177759
• 分子式: C7H8Na3O8P
• 平均质量: 320.076691
• 单一同位素质量: 319.96498669
• SMILES: [C@@H]1([C@H]([C@@H](CC(=C1)C(=O)[O-])O)O)OP(=O)([O-])[O-].[Na+].[Na+].[Na+]
• Canonical SMILES: O[C@H]1[C@H](O)CC(=C[C@H]1OP(=O)([O-])[O-])C(=O)[O-].[Na+].[Na+].[Na+]
• InChI: InChI=1S/C7H11O8P.3Na/c8-4-1-3(7(10)11)2-5(6(4)9)15-16(12,13)14;;;/h2,4-6,8-9H,1H2,(H,10,11)(H2,12,13,14);;;/q;3*+1/p-3/t4-,5-,6+;;;/m1.../s1
• InChIKey: SQZCNOWSDNBSGQ-PFYBVYJXSA-K

名称和登记号

名称

• IUPAC标准名: trisodium (3R,4S,5R)-4,5-dihydroxy-3-(phosphonatooxy)cyclohex-1-ene-1-carboxylate
• IUPAC传统名: trisodium 3-phosphoshikimate
• 别名: (3R,4S,5R)-4,5-Dihydroxy-3-(phosphonooxy)-1-cyclohexene-1-carboxylic Acid Sodium Salt; [3R-(3α,4α,5β)]-4,5-Dihydroxy-3-(phosphonooxy)-1-cyclohexene-1-carboxylic Acid Trisodium Salt; S-3-P Trisodium; Shikimate-3-phosphate Trisodium Salt 90%

登记号

• CAS号: 143393-03-7
• PubChem SID: 164233669
• PubChem CID: 11771565

理论计算性质

• Acid pKa: 1.3157644
• 质子受体: 7
• 质子供体: 2
• LogD (pH = 5.5): -5.590323
• LogD (pH = 7.4): -8.215488
• Log P: -1.7636402
• 摩尔折射率: 58.4269 cm^3
• 极化性: 19.479197 Å^3
• 极化表面积: 153.01 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: Water
• 外观: White to Off-White Solid
• 熔点: >135°C (dec.)

安全信息

• 保存条件: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

详细说明

Toronto Research Chemicals - S357026

S-3-p is the substrate for 5-Enolpyruvoyl-shikimate 3-phosphate synthase (EPSPS) which is the target for the broad-spectrum herbicide N-(phosphonomethyl)glycine(glyphosate).

参考文献

• Chahoua, L., et al.: J. Org. Chem., 57, 5798 (1992)