(2S,3S,4S,5R,6S)-6-({5-[(2E)-5-carboxy-3-methylpent-2-en-1-yl]-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-4-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase编号: 174874
• 分子式: C23H28O12
• 平均质量: 496.46122
• 单一同位素质量: 496.15807634
• SMILES: c1(c(c(c2c(c1O[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C(=O)O)O)O)O)C(=O)OC2)C)OC)C/C=C(/CCC(=O)O)\C
• Canonical SMILES: COc1c(C/C=C(/CCC(=O)O)\C)c(O[C@@H]2O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]2O)O)O)c2c(c1C)COC2=O
• InChI: InChI=1S/C23H28O12/c1-9(5-7-13(24)25)4-6-11-18(32-3)10(2)12-8-33-22(31)14(12)19(11)34-23-17(28)15(26)16(27)20(35-23)21(29)30/h4,15-17,20,23,26-28H,5-8H2,1-3H3,(H,24,25)(H,29,30)/b9-4+/t15-,16-,17+,20-,23+/m0/s1
• InChIKey: BYFGTSAYQQIUCN-HGIHDBQLSA-N

名称和登记号

名称

• IUPAC标准名: (2S,3S,4S,5R,6S)-6-({5-[(2E)-5-carboxy-3-methylpent-2-en-1-yl]-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-4-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC传统名: (2S,3S,4S,5R,6S)-6-({5-[(2E)-5-carboxy-3-methylpent-2-en-1-yl]-6-methoxy-7-methyl-3-oxo-1H-2-benzofuran-4-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• 别名: 5-[(2E)-5-Carboxy-3-methyl-2-penten-1-yl]-1,3-dihydro-6-methoxy-7-methyl-3-oxo-4-isobenzofuranyl β-D-Glucopyranosiduronic Acid; Mycophenolic Acid Glucosiduronate; Mycophenolic Acid Glucuronide; MPAG; Mycophenolic Acid β-D-Glucuronide

登记号

• CAS号: 31528-44-6
• PubChem SID: 164230784
• PubChem CID: 6442661

理论计算性质

• Acid pKa: 2.739151
• 质子受体: 11
• 质子供体: 5
• LogD (pH = 5.5): -3.6937711
• LogD (pH = 7.4): -5.941499
• Log P: 0.9298039
• 摩尔折射率: 117.2452 cm^3
• 极化性: 45.854965 Å^3
• 极化表面积: 189.28 Å^2
• 可自由旋转的化学键: 9
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: Methanol; Water
• 外观: Off-White Solid
• 熔点: 98-100°C

安全信息

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

详细说明

Toronto Research Chemicals - M831520

A metabolite of Mycophenolic Acid, an antibiotic produced by Penicillium brevi-compactum, P. Stoloniferum and related spp. A selective inhibitor of lymphocyte proliferation by blocking inosine monophosphate dehydrogenase, an enzyme involved in the de nov

参考文献

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• Gummert, J.F., et al.: J. Pharmacol. Exp. Ther., 291, 1100 (1995)