(2R,4R,6S,7S,12S)-6,7,16-trihydroxy-18-methoxy-12-methyl-3,13-dioxatricyclo[13.4.0.02,4]nonadeca-1(19),9,15,17-tetraene-8,14-dione

• ChemBase编号: 5536
• 分子式: C19H22O8
• 平均质量: 378.37318
• 单一同位素质量: 378.13146766
• SMILES: O=C1O[C@@H](C)C/C=C\C(=O)[C@H]([C@H](C[C@@H]2[C@@H](c3c1c(O)cc(OC)c3)O2)O)O
• Canonical SMILES: COc1cc2[C@H]3O[C@@H]3C[C@H](O)[C@H](O)C(=O)/C=C\C[C@@H](OC(=O)c2c(c1)O)C
• InChI: InChI=1S/C19H22O8/c1-9-4-3-5-12(20)17(23)14(22)8-15-18(27-15)11-6-10(25-2)7-13(21)16(11)19(24)26-9/h3,5-7,9,14-15,17-18,21-23H,4,8H2,1-2H3/b5-3-/t9-,14-,15+,17+,18+/m0/s1
• InChIKey: SSNQAUBBJYCSMY-KNTMUCJRSA-N

名称和登记号

名称

• IUPAC标准名: (2R,4R,6S,7S,12S)-6,7,16-trihydroxy-18-methoxy-12-methyl-3,13-dioxatricyclo[13.4.0.0^2,^4]nonadeca-1(19),9,15,17-tetraene-8,14-dione; (2R,4R,6S,7S,9Z,12S)-6,7,16-trihydroxy-18-methoxy-12-methyl-3,13-dioxatricyclo[13.4.0.0^{2,4}]nonadeca-1(19),9,15,17-tetraene-8,14-dione
• IUPAC传统名: (2R,4R,6S,7S,12S)-6,7,16-trihydroxy-18-methoxy-12-methyl-3,13-dioxatricyclo[13.4.0.0^2,^4]nonadeca-1(19),9,15,17-tetraene-8,14-dione; (2R,4R,6S,7S,9Z,12S)-6,7,16-trihydroxy-18-methoxy-12-methyl-3,13-dioxatricyclo[13.4.0.0^{2,4}]nonadeca-1(19),9,15,17-tetraene-8,14-dione
• 别名: 3H-Oxireno[k][2]benzoxacyclotetradecin-5,11(2H,4H)-dione,1a,8,9,15b-tetrahydro-3,4,12-trihydroxy-14-methoxy-9-methyl-,(1aR,3S,4S,6Z,9S,15bR)-; NSC354462; Hypothemycin; (1aR,8S,13S,14S,15aR)-5,13,14-trihydroxy-3-methoxy-8-methyl-8,9,13,14,15,15a-hexahydro-6H-oxireno[k][2]benzoxacyclotetradecine-6,12(1aH)-dione

登记号

• CAS号: 76958-67-3
• MDL号: MFCD08457932
• PubChem SID: 160968964; 99444376
• PubChem CID: 9929643

理论计算性质

JChem

• Acid pKa: 9.474741
• 质子受体: 7
• 质子供体: 3
• LogD (pH = 5.5): 1.6342845
• LogD (pH = 7.4): 1.6307199
• Log P: 1.6343302
• 摩尔折射率: 94.9755 cm^3
• 极化性: 36.720337 Å^3
• 极化表面积: 125.82 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 0.95
• LOG S: -2.31
• 溶解度: 1.86e+00 g/l

分子性质

理化性质

• 溶解度: acetone: soluble; deionized water: insoluble; DMSO: soluble

安全信息

• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 22
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302
• 保存温度: -20°C

产品相关信息

• 纯度: ≥98% (HPLC)
• 生物来源: from Hypomyces trichothecoides
• Empirical Formula (Hill Notation): C19H22O8

详细说明

DrugBank - DB07905

Drug information: experimental

Sigma Aldrich - H1667

Biochem/physiol Actions
Hypothemycin, one of the highly oxygenated analogues in the group of 14-membered resorcylic acid lactones (RAL),1,2,3 has minor antifungal and cytotoxic activity and exhibits an in vitro anti-malarial activity with an IC50 of 2.2 μg/mL.4 Hypothemycin is also reported to selectively and irreversibly inhibit protein kinases that contain a conserved cysteine residue (Cys166) that is located within the ATP-binding domain.1,2,3,5 Though this group accounts for less then 10% of all identified kinases, there are several targets implicated in aberrant cellular proliferation such as ERKs, MEK, FMS-like tyrosine kinase protein (FLT), and platelet-derived growth factor receptors (PDGFR).1 In cell culture, hypothemycin displays potent cytotoxicity against cancer cell lines that are dependent on certain activating kinase mutations. Additionally, hypothemycin demonstrates significant tumor growth inhibition in at least three separate murine xenograft models.1,5 Hypothemycin also inhibits the production of several cytokines such as IL2, IL6, IFNγ, and TNFα.5