Hyperforin dicyclohexylammonium salt - ≥97% , CAS No.238074-03-8

CAS: 238074-03-8 Cat. No.: H329540 Molecular Weight: 536.7818132 EC Number: 663-645-2 PubChem CID: 46926346

GRADE & PURITY ≥97%

Synonyms

HY-116330A | DTXSID30677360 | Hyperforin (dicyclohexylammonium) salt | (1R,5R,7S,8R)-4-Hydroxy-8-methyl-3,5,7-tris(3-methylbut-2-en-1-yl)-8-(4-methylpent-3-en-1-yl)-1-(2-methylpropanoyl)bicyclo[3.3.1]non-3-ene-2,9-dione--N-cyclohexylcyclohexanamine (1/1)

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Hyperforin dicyclohexylammonium salt is the dicyclohexylammonium salt preparation of the natural product Hyperforin isolated from|Hypericum perforatum|. Hyperforin inhibits the uptake of the monoamine neurotransmitters serotonin, dopamine, noradrenaline, and GABA. The specific mechanism of serotonin uptake inhibition is correlated with Hyperforin-induced elevation of intracellular Na|+|levels. AMPA induced currents were shown to be competitively and incompletely inhibited by Hyperforin, while NMDA receptor-activated ionic conductance was completely and uncompetitively inhibited. Hyperforin is described to present neuroprotective effects, demonstrating the induction of amyloid-beta aggregate disassembly, improvement of spatial memory, and decrease of astrogliosis and microglia activation. The action of inducible nitric oxide synthase (iNOS) was modulated by Hyperforin, demonstrating reduced NO production through suppression of iNOS on the mRNA and protein levels, further correlating to the neuroprotection generated by this compound. Hyperforin demonstrates selective activation of the transient receptor potential channel 6. Activation of the PXR (pregnane X receptor) by Hyperforin produces induction of cytochrome p450 3A4 monooxygenase expression, promoting oxidation metabolism activity of this enzyme. Hyperforin dicyclohexylammonium salt is an activator of TRPC6.

Specifications

Synonyms

HY-116330A | DTXSID30677360 | Hyperforin (dicyclohexylammonium) salt | (1R, 5R, 7S, 8R)-4-Hydroxy-8-methyl-3, 5, 7-tris(3-methylbut-2-en-1-yl)-8-(4-methylpent-3-en-1-yl)-1-(2-methylpropanoyl)bicyclo[3.3.1]non-3-ene-2, 9-dione--N-cyclohexylcyclohexanamine (1/1)

Specifications & Purity

≥97%

Source

Hypericum perforatum

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥97%

Product Properties

• pKa: pKa: 4.5 (Predicted)

Names and Identifiers

• Canonical Smiles: CC(C)C(=O)C12C(=O)C(=C(C(C1=O)(CC(C2(C)CCC=C(C)C)CC=C(C)C)CC=C(C)C)O)CC=C(C)C.C1CCC(CC1)NC2CCCCC2
• IUPAC Name: N-cyclohexylcyclohexanamine;(1R,5R,7S,8R)-4-hydroxy-8-methyl-3,5,7-tris(3-methylbut-2-enyl)-8-(4-methylpent-3-enyl)-1-(2-methylpropanoyl)bicyclo[3.3.1]non-3-ene-2,9-dione
• InChIKey: KJVNMVCMFQAPDM-DNSWOBEMSA-N
• 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/h13-15,18,26-27,37H,12,16-17,19-21H2,1-11H3;11-13H,1-10H2/t27-,33+,34+,35-;/m0./s1
• Isomeric SMILES: CC(C)C(=O)[C@]12C(=O)C(=C([C@](C1=O)(C[C@@H]([C@@]2(C)CCC=C(C)C)CC=C(C)C)CC=C(C)C)O)CC=C(C)C.C1CCC(CC1)NC2CCCCC2
• WGK Germany: 3
• PubChem CID: 46926346
• Molecular Weight: 536.7818132

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Prenol lipids
      • Subclass Monoterpenoids

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Prenol lipids
• Subclass: Monoterpenoids
• Intermediate Tree Nodes: Not available
• Direct Parent: Bicyclic monoterpenoids
• Alternative Parents: Cyclohexylamines Cyclohexenones Vinylogous acids Enols Dialkylamines Organic oxides Hydrocarbon derivatives
• Molecular Framework: Not available
• Substituents: Bicyclic monoterpenoid - Cyclohexylamine - Cyclohexenone - Vinylogous acid - Ketone - Secondary aliphatic amine - Enol - Secondary amine - Amine - Organonitrogen compound - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Carbonyl group - Organic nitrogen compound - Aliphatic homopolycyclic compound
• Description: This compound belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(non-human)

Staphylococcus aureus (210822 Activities)

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Escherichia coli (133304 Activities)

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Enterococcus faecalis (29875 Activities)

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Plasmodium falciparum (966862 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in DMSO (≥10 mg/ml), methanol, and 100% ethanol.
• Molecular Weight: 718.100 g/mol
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 13
• Exact Mass: 717.57 Da
• Monoisotopic Mass: 717.57 Da
• Topological Polar Surface Area: 83.500 Ų
• Heavy Atom Count: 52
• Formal Charge: 0
• Complexity: 1260.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 4
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 2

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