(4E,5R)-4-{2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-decahydronaphthalen-1-yl]ethylidene}-5-hydroxyoxolan-3-one

• ChemBase编号: 160619
• 分子式: C20H30O5
• 平均质量: 350.4492
• 单一同位素质量: 350.20932406
• SMILES: C1(=C)CC[C@H]2[C@]([C@@H]1C/C=C\1/C(=O)CO[C@H]1O)(CC[C@H]([C@]2(CO)C)O)C
• Canonical SMILES: OC[C@]1(C)[C@H](O)CC[C@@]2([C@@H]1CCC(=C)[C@H]2C/C=C\1/C(=O)CO[C@H]1O)C
• InChI: InChI=1S/C20H30O5/c1-12-4-7-16-19(2,9-8-17(23)20(16,3)11-21)14(12)6-5-13-15(22)10-25-18(13)24/h5,14,16-18,21,23-24H,1,4,6-11H2,2-3H3/b13-5-/t14-,16+,17-,18-,19+,20+/m1/s1
• InChIKey: ASLUCFFROXVMFL-QGICXFDVSA-N

名称和登记号

名称

• IUPAC标准名: (4E,5R)-4-{2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-decahydronaphthalen-1-yl]ethylidene}-5-hydroxyoxolan-3-one
• IUPAC传统名: (4E,5R)-4-{2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-hexahydro-1H-naphthalen-1-yl]ethylidene}-5-hydroxyoxolan-3-one
• 别名: (3E,4S)-3-[2-[(1R,4aS,5R,6R,8aS)-Decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl]ethylidene]dihydro-4-hydroxy-2(3H)-furanone; [1R-[1α[E(S*)],4aβ,5α,6α,8aα]]-3-[2-[Decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl]ethylidene]dihydro-4-hydroxy-2(3H)-furanone; 3α,14,15,18-Tetrahydroxy-5β,9βH,10α-labda-8(20),12-dien-16-oic Acid γ-Lactone; Andrographis; Andrographolid; Andrographolide

登记号

• CAS号: 5508-58-7
• PubChem SID: 162254754
• PubChem CID: 71313401

理论计算性质

• Acid pKa: 11.638457
• 质子受体: 5
• 质子供体: 3
• LogD (pH = 5.5): 1.7047089
• LogD (pH = 7.4): 1.7046843
• Log P: 1.7047093
• 摩尔折射率: 95.2333 cm^3
• 极化性: 37.537582 Å^3
• 极化表面积: 86.99 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: DMSO
• 外观: White Solid
• 熔点: 232-235°C

安全信息

• 保存条件: Refrigerator

详细说明

Toronto Research Chemicals - A637475

Andrographolide is a labdane diterpenoid. Andrographolide is the main bioactive component isolated from the medicinal plant Andrographis paniculata. Andrographolide showed significant antihepatotoxic action in P. berghei K173- induced hepatic damage in M.

参考文献

• Chander, R. et al.: Int. J. Pharmacog., 33, 135 (1995)
• Chen, H.-W. et al.: J. Nat. Prod., 74, 2408 (1995)
• J. Agric. Food Chem., 59, 5263 (1995)