4-hydroxy-6-methyl-1,3,7-tris(3-methylbut-2-en-1-yl)-6-(4-methylpent-3-en-1-yl)-5-(2-methylpropanoyl)bicyclo[3.3.1]non-3-ene-2,9-dione

• ChemBase编号: 1660
• 分子式: C35H52O4
• 平均质量: 536.78498
• 单一同位素质量: 536.38656014
• SMILES: CC(C)C(=O)C12C(=C(CC=C(C)C)C(=O)C(CC=C(C)C)(CC(CC=C(C)C)C1(C)CCC=C(C)C)C2=O)O
• Canonical SMILES: CC(=CCCC1(C)C(CC=C(C)C)CC2(C(=O)C1(C(=O)C(C)C)C(=C(C2=O)CC=C(C)C)O)CC=C(C)C)C
• InChI: InChI=1S/C35H52O4/c1-22(2)13-12-19-33(11)27(16-14-23(3)4)21-34(20-18-25(7)8)30(37)28(17-15-24(5)6)31(38)35(33,32(34)39)29(36)26(9)10/h13-15,18,26-27,38H,12,16-17,19-21H2,1-11H3
• InChIKey: IWBJJCOKGLUQIZ-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 4-hydroxy-6-methyl-1,3,7-tris(3-methylbut-2-en-1-yl)-6-(4-methylpent-3-en-1-yl)-5-(2-methylpropanoyl)bicyclo[3.3.1]non-3-ene-2,9-dione
• IUPAC传统名: tetrahydrohyperforin
• 别名: Hiperforina; Hyperforine; Hyperforin

登记号

• CAS号: 11079-53-1
• PubChem SID: 46506104; 160965117
• PubChem CID: 3662

理论计算性质

JChem

• Acid pKa: 6.315648
• 质子受体: 4
• 质子供体: 1
• LogD (pH = 5.5): 9.604594
• LogD (pH = 7.4): 8.549195
• Log P: 9.666359
• 摩尔折射率: 166.6825 cm^3
• 极化性: 63.38986 Å^3
• 极化表面积: 71.44 Å^2
• 可自由旋转的化学键: 11
• 里宾斯基五规则: false

ALOGPS 2.1

• Log P: 6.32
• LOG S: -5.93
• 溶解度: 6.32e-04 g/l

详细说明

DrugBank - DB01892

• Drug Groups: nutraceutical
• Description: Hyperforin is a phytochemical produced by some of the members of the plant genus Hypericum, notably Hypericum perforatum (St John's wort).
• Pharmacology: Hyperforin is believed to be the primary active constituent responsible for the antidepressant and anxiolytic properties of the extracts of St. John's wort. It acts as a reuptake inhibitor of monoamines, including serotonin, norepinephrine, dopamine, and of GABA and glutamate, with IC50 values of 0.05-0.10 mcg/ml for all compounds, with the exception of glutamate, which is in the 0.5 mcg/ml range. It appears to exert these effects by activating the transient receptor potential ion channel TRPC6. Activation of TRPC6 induces the entry of sodium and calcium into the cell which causes inhibition of monoamine reuptake. Hyperforin is also thought to be responsible for the induction of the cytochrome P450 enzymes CYP3A4 and CYP2C9 by binding to and activating the pregnane X receptor (PXR).
• Toxicity: Oral LD50 (rat):5628 mg/kg; Skin LD50 (rabbit): 15800 mg/kg; Subcutaneous LD50 (mouse):9800 mg/kg; Intraperitoneal LD50 (rabbit):1826 mg/kg
• Half Life: 9 hours
• References: Chatterjee SS, Bhattacharya SK, Wonnemann M, Singer A, Muller WE: Hyperforin as a possible antidepressant component of hypericum extracts. Life Sci. 1998;63(6):499-510. [Pubmed] ; Leuner K, Kazanski V, Muller M, Essin K, Henke B, Gollasch M, Harteneck C, Muller WE: Hyperforin--a key constituent of St. John's wort specifically activates TRPC6 channels. FASEB J. 2007 Dec;21(14):4101-11. Epub 2007 Jul 31. [Pubmed] ; Moore LB, Goodwin B, Jones SA, Wisely GB, Serabjit-Singh CJ, Willson TM, Collins JL, Kliewer SA: St. John's wort induces hepatic drug metabolism through activation of the pregnane X receptor. Proc Natl Acad Sci U S A. 2000 Jun 20;97(13):7500-2. [Pubmed]
• External Links: Wikipedia

参考文献

• Chatterjee SS, Bhattacharya SK, Wonnemann M, Singer A, Muller WE: Hyperforin as a possible antidepressant component of hypericum extracts. Life Sci. 1998;63(6):499-510. Pubmed
• Leuner K, Kazanski V, Muller M, Essin K, Henke B, Gollasch M, Harteneck C, Muller WE: Hyperforin--a key constituent of St. John's wort specifically activates TRPC6 channels. FASEB J. 2007 Dec;21(14):4101-11. Epub 2007 Jul 31. Pubmed
• Moore LB, Goodwin B, Jones SA, Wisely GB, Serabjit-Singh CJ, Willson TM, Collins JL, Kliewer SA: St. John's wort induces hepatic drug metabolism through activation of the pregnane X receptor. Proc Natl Acad Sci U S A. 2000 Jun 20;97(13):7500-2. Pubmed