4-[(1S,2S,8R,17S,19R)-12-hydroxy-8,21,21-trimethyl-5-(3-methylbut-2-en-1-yl)-8-(4-methylpent-3-en-1-yl)-14,18-dioxo-3,7,20-trioxahexacyclo[15.4.1.02,15.02,19.04,13.06,11]docosa-4(13),5,9,11,15-pentaen-19-yl]-2-methylbut-2-enoic acid

• ChemBase编号: 153841
• 分子式: C38H44O8
• 平均质量: 628.75116
• 单一同位素质量: 628.30361837
• SMILES: CC(=CCC[C@@]1(C=Cc2c(c3c(c(c2O1)CC=C(C)C)O[C@@]12[C@H]4C[C@@H](C=C1C3=O)C(=O)[C@@]2(OC4(C)C)C/C=C(\C)/C(=O)O)O)C)C
• Canonical SMILES: CC(=CCc1c2O[C@]34[C@@]5(C/C=C(/C(=O)O)\C)OC([C@@H]4C[C@H](C5=O)C=C3C(=O)c2c(c2c1O[C@](C)(CCC=C(C)C)C=C2)O)(C)C)C
• InChI: InChI=1S/C38H44O8/c1-20(2)10-9-15-36(8)16-14-24-29(39)28-30(40)26-18-23-19-27-35(6,7)46-37(33(23)41,17-13-22(5)34(42)43)38(26,27)45-32(28)25(31(24)44-36)12-11-21(3)4/h10-11,13-14,16,18,23,27,39H,9,12,15,17,19H2,1-8H3,(H,42,43)/t23-,27+,36-,37+,38-/m1/s1
• InChIKey: GEZHEQNLKAOMCA-VDMQVCGESA-N

名称和登记号

名称

• IUPAC标准名: 4-[(1S,2S,8R,17S,19R)-12-hydroxy-8,21,21-trimethyl-5-(3-methylbut-2-en-1-yl)-8-(4-methylpent-3-en-1-yl)-14,18-dioxo-3,7,20-trioxahexacyclo[15.4.1.0^2,^1^5.0^2,^1^9.0^4,^1^3.0^6,^1^1]docosa-4(13),5,9,11,15-pentaen-19-yl]-2-methylbut-2-enoic acid
• IUPAC传统名: 4-[(1S,2S,8R,17S,19R)-12-hydroxy-8,21,21-trimethyl-5-(3-methylbut-2-en-1-yl)-8-(4-methylpent-3-en-1-yl)-14,18-dioxo-3,7,20-trioxahexacyclo[15.4.1.0^2,^1^5.0^2,^1^9.0^4,^1^3.0^6,^1^1]docosa-4(13),5,9,11,15-pentaen-19-yl]-2-methylbut-2-enoic acid
• 别名: 1,51,5-Methano-1H,3H,11H-furo(3,4-G)pyrano(3,2-B)xanthene-1-crotonic acid; B"-Guttiferrin; Beta-Guttiferrin; Beta-Guttilactone; Cambogic acid; Guttatic acid; Guttic acid; Gambogic acid

登记号

• CAS号: 2752-65-0
• PubChem SID: 162247980
• PubChem CID: 70697925

理论计算性质

• Acid pKa: 3.7568264
• 质子受体: 8
• 质子供体: 2
• LogD (pH = 5.5): 6.039832
• LogD (pH = 7.4): 4.5002728
• Log P: 7.783757
• 摩尔折射率: 179.1616 cm^3
• 极化性: 67.7759 Å^3
• 极化表面积: 119.36 Å^2
• 可自由旋转的化学键: 8
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: DMSO: ≥10 mg/mL; H2O: insoluble
• 外观: yellow to orange powder

安全信息

• RTECS编号: PB9268200
• 欧盟危险性物质标志: 有毒(Toxic) (T)
• 联合国危险货物编号: 2811
• 德国WGK号: 1
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): 3
• 危险公开号: 25-36/37/38
• 安全公开号: 26-45
• GHS危险品标识: GHS06
• GHS警示词: Danger
• GHS危险声明: H301-H315-H319-H335
• GHS警示性声明: P261-P301 + P310-P305 + P351 + P338
• 个人保护装置: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3
• 保存温度: -20°C

产品相关信息

• 纯度: ≥95% (HPLC)
• Empirical Formula (Hill Notation): C38H44O8

详细说明

Sigma Aldrich - G8171

Biochem/physiol Actions
Gambogic acid acts as a caspase activator and apoptosis inducer, which causes an irreversible arrest in the G2/M phase of the cell cycle.