| Identification | Back Directory | [Name]
Hyperforin . DCHA | [CAS]
238074-03-8 | [Synonyms]
Hyp-DCHA
C47H75NO4
Hyperforin . DCHA
Hyperforin (dicylcohexylammonium) salt
Hyperforin (stable Dicyclohexylammonium salt)
Hyperforin / AdhyperforinDicyclohexylammonium salt (4:1)
Hyperforin (dicyclohexylammonium) salt analytical standard
N-cyclohexylcyclohexanamine,(1R,5R,6R,7S)-2-hydroxy-6-methyl-1,3,7-tris(3-methylbut-2-enyl)-6-(4-methylpent-3-enyl)-5-(2-methylpropanoyl)bicyclo[3.3.1]non-2-ene-4,9-dione | [Molecular Formula]
C47H75NO4 | [MDL Number]
MFCD04000098 | [MOL File]
238074-03-8.mol | [Molecular Weight]
718.103 |
| Chemical Properties | Back Directory | [storage temp. ]
-20°C | [solubility ]
DMSO: ≥10mg/mL | [form ]
powder | [color ]
white to off-white | [InChIKey]
ZUYCAROZOLUHJY-DNSWOBEMSA-N | [SMILES]
C1CCC(CC1)NC2CCCCC2.CC(C)C(=O)[C@@]34C(O)=C(C\C=C(\C)C)C(=O)[C@@](C\C=C(\C)C)(C[C@H](C\C=C(/C)C)[C@@]3(C)CC\C=C(\C)C)C4=O |
| Hazard Information | Back Directory | [Description]
Hyperforin is a natural activator of the steroid X receptor (active at 0.1 to 0.5 μg/ml) and inhibitor of several cytochrome P450 (CYP) isoforms (IC50 = 10 μg/ml for CYP2D6). It can also inhibit microsomal prostaglandin E2 synthase-1 (mPGES-1; IC50 = 1 μM), 5-lipoxygenase activating protein, and sirtuins. | [Uses]
Hyperforin Dicyclohexylammonium Salt is an inhibitor of monoamine uptake and TRPC6 agonist. | [General Description]
This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG | [Biochem/physiol Actions]
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. | [storage]
+4°C | [References]
[1] J M WENTWORTH. St John’s wort, a herbal antidepressant, activates the steroid X receptor.[J]. Journal of Endocrinology, 2000, 166 3: R11-6. DOI: 10.1677/joe.0.166r011
[2] OBACH R S. Inhibition of human cytochrome P450 enzymes by constituents of St. John’s Wort, an herbal preparation used in the treatment of depression.[J]. Journal of Pharmacology and Experimental Therapeutics, 2000, 294 1: 88-95.
[3] HUI-HUA CHANG E J M. Identification and development of mPGES-1 inhibitors: where we are at?[J]. Future medicinal chemistry, 2011, 3 15: 1909-1934. DOI: 10.4155/fmc.11.136
[4] C GREINER. 2-(4-(Biphenyl-4-ylamino)-6-chloropyrimidin-2-ylthio)octanoic acid (HZ52) – a novel type of 5-lipoxygenase inhibitor with favourable molecular pharmacology and efficacy in vivo[J]. British Journal of Pharmacology, 2011, 164 2b: 781-793. DOI: 10.1111/j.1476-5381.2011.01451.x
[5] JILL C MILNE John M D. The Sirtuin family: therapeutic targets to treat diseases of aging[J]. Current Opinion in Chemical Biology, 2008, 12 1: Pages 11-17. DOI: 10.1016/j.cbpa.2008.01.019 |
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