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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
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ChemBase ID:
1660
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Molecular Formular:
C35H52O4
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Molecular Mass:
536.78498
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Monoisotopic Mass:
536.38656014
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SMILES and InChIs
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
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Cite this record
CBID:1660 http://www.chembase.cn/molecule-1660.html
NAMES AND DATABASE IDS
NAMES AND DATABASE IDS
Names Database IDs
IUPAC name
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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
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IUPAC Traditional name
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Synonyms
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Hiperforina
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Hyperforine
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Hyperforin
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CAS Number
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PubChem SID
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PubChem CID
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DATA SOURCES
DATA SOURCES
All Sources Commercial Sources Non-commercial Sources
Data Source
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Data ID
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Price
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CALCULATED PROPERTIES
CALCULATED PROPERTIES
JChem
ALOGPS 2.1
Acid pKa
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6.315648
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H Acceptors
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4
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H Donor
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1
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LogD (pH = 5.5)
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9.604594
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LogD (pH = 7.4)
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8.549195
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Log P
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9.666359
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Molar Refractivity
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166.6825 cm3
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Polarizability
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63.38986 Å3
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Polar Surface Area
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71.44 Å2
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Rotatable Bonds
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11
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Lipinski's Rule of Five
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false
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Log P
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6.32
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LOG S
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-5.93
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Solubility (Water)
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6.32e-04 g/l
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PROPERTIES
PROPERTIES
Bioassay(PubChem)
DETAILS
DETAILS
DrugBank
DrugBank -
DB01892
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Item |
Information |
Drug Groups
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nutraceutical |
Description
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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 |
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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]
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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]
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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]
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External Links |
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REFERENCES
REFERENCES
From Suppliers
Google Scholar
PubMed
Google Books
- • 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
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PATENTS
PATENTS
PubChem Patent
Google Patent