(1R,5R,7R)-3-(3,4-dihydroxybenzoyl)-4-hydroxy-8,8-dimethyl-5-[(2S)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-1,7-bis(3-methylbut-2-en-1-yl)bicyclo[3.3.1]non-3-ene-2,9-dione

• ChemBase编号: 153216
• 分子式: C38H50O6
• 平均质量: 602.8
• 单一同位素质量: 602.36073932
• SMILES: CC(=CC[C@@H]1C[C@@]2(C(=C(C(=O)[C@@](C2=O)(C1(C)C)CC=C(C)C)C(=O)c1ccc(c(c1)O)O)O)C[C@H](CC=C(C)C)C(=C)C)C
• Canonical SMILES: CC(=CC[C@]12C(=O)C(=C([C@@](C1=O)(C[C@@H](C(=C)C)CC=C(C)C)C[C@H](C2(C)C)CC=C(C)C)O)C(=O)c1ccc(c(c1)O)O)C
• InChI: InChI=1S/C38H50O6/c1-22(2)11-13-27(25(7)8)20-37-21-28(15-12-23(3)4)36(9,10)38(35(37)44,18-17-24(5)6)34(43)31(33(37)42)32(41)26-14-16-29(39)30(40)19-26/h11-12,14,16-17,19,27-28,39-40,42H,7,13,15,18,20-21H2,1-6,8-10H3/t27-,28+,37+,38-/m0/s1
• InChIKey: QDKLRKZQSOQWJQ-SMDXAGPFSA-N

名称和登记号

名称

• IUPAC标准名: (1R,5R,7R)-3-(3,4-dihydroxybenzoyl)-4-hydroxy-8,8-dimethyl-5-[(2S)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-1,7-bis(3-methylbut-2-en-1-yl)bicyclo[3.3.1]non-3-ene-2,9-dione
• IUPAC传统名: garcinol
• 别名: (1R,5R,7R)-3-(3,4-Dihydroxybenzoyl)-4-hydroxy-8,8-dimethyl-1,7-bis(3-methyl-2-buten-1-yl)-5-[(2S)-5-methyl-2-(1-methylethenyl)-4-hexen-1-yl]-Bicyclo[3.3.1]non-3-ene-2,9-dione; Camboginol; Garcinol

登记号

• CAS号: 78824-30-3
• MDL号: MFCD03700761
• PubChem SID: 162247355
• PubChem CID: 174159

理论计算性质

• Acid pKa: 2.312387
• 质子受体: 6
• 质子供体: 3
• LogD (pH = 5.5): 6.11443
• LogD (pH = 7.4): 5.5304914
• Log P: 9.140703
• 摩尔折射率: 180.584 cm^3
• 极化性: 68.62504 Å^3
• 极化表面积: 111.9 Å^2
• 可自由旋转的化学键: 11
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: : >5 mg/mL
• 外观: powder, yellow

安全信息

• 保存温度: -20°C

产品相关信息

• 纯度: ≥95%
• Empirical Formula (Hill Notation): C38H50O6

详细说明

Sigma Aldrich - G5173

Biochem/physiol Actions
Garcinol is a HAT (histone acetyltransferase) inhibitor. Garcinol is anti-inflammatory and anti-carcinogenic. Histone acetyltransferases provide opposing enzymatic mechanisms for chromatin remodeling and epigenetic control of gene expression. HATs are involved in regulation of transformation, transcription, differentiation, apoptosis, embryonic development and oncogenesis. IC50 p300 = 7 mM; IC50 PCAF = 5 mM (similar to anacardic acid). Garcinol is highly toxic compared to LTK-14, and does not discriminate between p300 and PCAF.