(1R,5S,6R,7S)-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; N-cyclohexylcyclohexanamine

• ChemBase编号: 154772
• 分子式: C47H75NO4
• 平均质量: 718.1027
• 单一同位素质量: 717.56960989
• SMILES: CC(C)C(=O)[C@]12C(=C(C(=O)[C@](C1=O)(C[C@@H]([C@@]2(C)CCC=C(C)C)CC=C(C)C)CC=C(C)C)CC=C(C)C)O.C1CCC(CC1)NC1CCCCC1
• Canonical SMILES: C1CCC(CC1)NC1CCCCC1.CC(=CCC[C@]1(C)[C@@H](CC=C(C)C)C[C@]2(C(=O)[C@]1(C(=O)C(C)C)C(=C(C2=O)CC=C(C)C)O)CC=C(C)C)C
• InChI: InChI=1S/C35H52O4.C12H23N/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;1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h13-15,18,26-27,38H,12,16-17,19-21H2,1-11H3;11-13H,1-10H2/t27-,33+,34+,35-;/m0./s1
• InChIKey: ZUYCAROZOLUHJY-DNSWOBEMSA-N

名称和登记号

名称

• IUPAC标准名: (1R,5S,6R,7S)-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; N-cyclohexylcyclohexanamine
• IUPAC传统名: dicha; hyperforine
• 别名: Hyp-DCHA; Hyperforin-DCHA; Hyperforin (dicyclohexylammonium) salt

登记号

• CAS号: 238074-03-8
• MDL号: MFCD04000098
• PubChem SID: 162248910
• PubChem CID: 46926346

理论计算性质

• 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: 13
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: DMSO: ≥10 mg/mL
• 外观: white to off-white powder

安全信息

• 保存条件: protect from light
• 欧盟危险性物质标志: 腐蚀性(Corrosive) (C); 环境危害性(Nature polluting) (N)
• 德国WGK号: 3
• 危险公开号: 22-34-50/53
• 安全公开号: 26-36/37/39-45-60-61
• GHS危险品标识: GHS05; GHS07; GHS09
• GHS警示词: Danger
• GHS危险声明: H302-H314-H400
• GHS警示性声明: P273-P280-P305 + P351 + P338-P310
• 保存温度: -20°C

产品相关信息

• 纯度: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C35H52O4·C12H23N

详细说明

Sigma Aldrich - H1792

Biochem/physiol Actions
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 by activating the transient receptor potential ion channel TRPC6. It also is an activator of the pregnane X receptor (PXR), which serves as a key regulator of CYP3A4 transcription, a member of the cytochrome (CYP) P450 enzyme system. Recent studies have found it to have neuroprotective effects against Alzheimer′s disease (AD) neuropathology, including the ability to disassemble amyloid-β aggregates in vitro and improve spatial memory in vivo.1
Stable salt of hyperforin. 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 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. It also is an activator of the pregnane X receptor (PXR), which serves as a key regulator of CYP3A4 transcription, a member of the cytochrome (CYP) P450 enzyme system. Recent studies have found other neurological effects, effects on inflammation, as well as antibacterial, antitumoral and antiangiogenic effects.