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

• ChemBase编号: 69911
• 分子式: C20H30O5
• 平均质量: 350.4492
• 单一同位素质量: 350.20932406
• SMILES: O1C(=O)/C(=C/C[C@@H]2C(=C)CC[C@@H]3[C@]([C@@H](CC[C@@]23C)O)(C)CO)/[C@@H](C1)O
• Canonical SMILES: OC[C@]1(C)[C@H](O)CC[C@@]2([C@@H]1CCC(=C)[C@H]2C/C=C/1\[C@H](O)COC1=O)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/h5,14-17,21-23H,1,4,6-11H2,2-3H3/b13-5+/t14-,15-,16+,17-,19+,20+/m1/s1
• InChIKey: BOJKULTULYSRAS-OTESTREVSA-N

名称和登记号

名称

• IUPAC标准名: (4S)-3-{2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-decahydronaphthalen-1-yl]ethylidene}-4-hydroxyoxolan-2-one; (3E,4S)-3-{2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-decahydronaphthalen-1-yl]ethylidene}-4-hydroxyoxolan-2-one
• IUPAC传统名: (4S)-3-{2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-hexahydro-1H-naphthalen-1-yl]ethylidene}-4-hydroxyoxolan-2-one; (3E,4S)-3-{2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-hexahydro-1H-naphthalen-1-yl]ethylidene}-4-hydroxyoxolan-2-one
• 别名: 穿心莲内酯; Andrographolide; Andrographolide

登记号

• CAS号: 5508-58-7
• EC号: 226-852-5
• MDL号: MFCD07778082
• Beilstein号: 42762
• PubChem SID: 24862550; 162035636
• PubChem CID: 5318517

理论计算性质

• Acid pKa: 13.477876
• 质子受体: 4
• 质子供体: 3
• LogD (pH = 5.5): 1.6623217
• LogD (pH = 7.4): 1.6623213
• Log P: 1.6623217
• 摩尔折射率: 94.9305 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

• 外观: Powder
• 熔点: 229-232 °C(lit.)
• 比旋光度: [α]20/D -126°, c = 1.5 in acetic acid

安全信息

• 保存注意事项: IRRITANT
• RTECS编号: LU3490750
• 德国WGK号: 3
• TSCA收录: false
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

产品相关信息

• 纯度: 95+%; 98%; 98.0
• Empirical Formula (Hill Notation): C20H30O5

详细说明

Sigma Aldrich - 365645

Biochem/physiol Actions
具有抗炎特性的双萜内酯。它可阻断外源刺激下的 T 细胞增殖和补体诱导的巨噬细胞趋化迁移。可阻断几种癌细胞系的体外增殖。
包装
100, 500 mg in glass bottle