(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 ID: 154772
• Molecular Formular: C47H75NO4
• Molecular Mass: 718.1027
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (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 Traditional name: dicha; hyperforine
• Synonyms: Hyp-DCHA; Hyperforin-DCHA; Hyperforin (dicyclohexylammonium) salt

Database IDs

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

CALCULATED PROPERTIES

• Acid pKa: 6.315648
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 9.604594
• LogD (pH = 7.4): 8.549195
• Log P: 9.666359
• Molar Refractivity: 166.6825 cm^3
• Polarizability: 63.38986 Å^3
• Polar Surface Area: 71.44 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: ≥10 mg/mL
• Apperance: white to off-white powder

Safety Information

• Storage Condition: protect from light
• European Hazard Symbols: Corrosive (C); Nature polluting (N)
• German water hazard class: 3
• Risk Statements: 22-34-50/53
• Safety Statements: 26-36/37/39-45-60-61
• GHS Pictograms: GHS05; GHS07; GHS09
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H314-H400
• GHS Precautionary statements: P273-P280-P305 + P351 + P338-P310
• Storage Temperature: -20°C

Product Information

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

DETAILS

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.