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Home > Other Heterocycles > 11079-53-1
11079-53-1 | Bicyclo[3.3.1]non-3-ene-2,9-dione,4-hydroxy-6-methyl-1,3,7-tris(3-methyl-2-butenyl)-5-(2-methyl-1-oxopropyl)-6-(4-methyl-3-pentenyl)-, (1R,5S,6R,7S)-
CAS No: 11079-53-1 Catalog No: AG01DP91 MDL No:MFCD01861497
Product Description
Catalog Number:
AG01DP91
Chemical Name:
Bicyclo[3.3.1]non-3-ene-2,9-dione,4-hydroxy-6-methyl-1,3,7-tris(3-methyl-2-butenyl)-5-(2-methyl-1-oxopropyl)-6-(4-methyl-3-pentenyl)-, (1R,5S,6R,7S)-
CAS Number:
11079-53-1
Molecular Formula:
C47H75NO4
Molecular Weight:
718.1027
MDL Number:
MFCD01861497
IUPAC Name:
(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
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/h13-15,18,26-27,37H,12,16-17,19-21H2,1-11H3/t27-,33+,34+,35-/m0/s1
InChI Key:
KGSZHKRKHXOAMG-HQKKAZOISA-N
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(=O)C(=C2O)CC=C(C)C)CC=C(C)C)C
EC Number:
601-000-9
UNII:
RM741E34FP
Properties
Complexity:
1140
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
4
Defined Bond Stereocenter Count:
0
Exact Mass:
536.387g/mol
Formal Charge:
0
Heavy Atom Count:
39
Hydrogen Bond Acceptor Count:
4
Hydrogen Bond Donor Count:
1
Isotope Atom Count:
0
Molecular Weight:
536.797g/mol
Monoisotopic Mass:
536.387g/mol
Rotatable Bond Count:
11
Topological Polar Surface Area:
71.4A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
9.6
Literature
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| Functional induction and de-induction of P-glycoprotein by St. John's wort and its ingredients in a human colon adenocarcinoma cell line. | Drug metabolism and disposition: the biological fate of chemicals 20050401 |
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| Biosynthesis of the hyperforin skeleton in Hypericum calycinum cell cultures. | Phytochemistry 20050101 |
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| Modulation of chemoselectivity by protein additives. Remarkable effects in the oxidation of hyperforin. | The Journal of organic chemistry 20041112 |
| Modulation of P-glycoprotein function by St John's wort extract and its major constituents. | Pharmacopsychiatry 20041101 |
| Hyperforin, the active component of St. John's wort, induces IL-8 expression in human intestinal epithelial cells via a MAPK-dependent, NF-kappaB-independent pathway. | Journal of clinical immunology 20041101 |
| Hyperforin depletes synaptic vesicles content and induces compartmental redistribution of nerve ending monoamines. | Life sciences 20041022 |
| Safety of Hypericum extract in mildly to moderately depressed outpatients: a review based on data from three randomized, placebo-controlled trials. | Journal of affective disorders 20041015 |
| Instability of St. John's wort (Hypericum perforatum L.) and degradation of hyperforin in aqueous solutions and functional beverage. | Journal of agricultural and food chemistry 20041006 |
| Undeclared exposure to St. John's Wort in hospitalized patients. | British journal of clinical pharmacology 20041001 |
| Hyperforin content determines the magnitude of the St John's wort-cyclosporine drug interaction. | Clinical pharmacology and therapeutics 20041001 |
| Hyperforin modifies neuronal membrane properties in vivo. | Neuroscience letters 20040902 |
| Hyperforin inhibits cancer invasion and metastasis. | Cancer research 20040901 |
| The antidepressant mechanism of Hypericum perforatum. | Life sciences 20040716 |
| Stimulation of hippocampal acetylcholine release by hyperforin, a constituent of St. John's Wort. | Neuroscience letters 20040708 |
| Development of a high-performance liquid chromatographic method with electrochemical detection for the determination of hyperforin. | Journal of chromatography. A 20040702 |
| Inhibitory effect of the antidepressant St. John's wort (hypericum perforatum) on rat bladder contractility in vitro. | Urology 20040701 |
| In vitro effects of the dicyclohexylammonium salt of hyperforin on interleukin-6 release in different experimental models. | Planta medica 20040701 |
| Induction and inhibition of cytochromes P450 by the St. John's wort constituent hyperforin in human hepatocyte cultures. | Drug metabolism and disposition: the biological fate of chemicals 20040501 |
| Suppression of receptor-mediated Ca2+ mobilization and functional leukocyte responses by hyperforin. | Biochemical pharmacology 20040415 |
| Proteome analysis reveals a distinct molecular profile of cellular stress following incubation of DDT1-MF2 smooth muscle cells in the presence of a high concentration of hyperforin. | Planta medica 20040401 |
| Enrichment of hyperforin from St. John's wort (Hypericum perforatum) by pilot-scale supercritical carbon dioxide extraction. | European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences 20040301 |
| The production of hypericins and hyperforin by in vitro cultures of St. John's wort (Hypericum perforatum). | Biotechnology and applied biochemistry 20040201 |
| Induction of human CYP2C9 by rifampicin, hyperforin, and phenobarbital is mediated by the pregnane X receptor. | The Journal of pharmacology and experimental therapeutics 20040201 |
| Extracts of St. John's wort and various constituents affect beta-adrenergic binding in rat frontal cortex. | Life sciences 20040109 |
| In vitro metabolism of hyperforin in rat liver microsomal systems. | Drug metabolism and disposition: the biological fate of chemicals 20040101 |
| Quantitative characterization of direct P-glycoprotein inhibition by St John's wort constituents hypericin and hyperforin. | The Journal of pharmacy and pharmacology 20040101 |
| In vitro interaction of the HIV protease inhibitor ritonavir with herbal constituents: changes in P-gp and CYP3A4 activity. | American journal of therapeutics 20040101 |
| Role of hyperforin in the pharmacological activities of St. John's Wort. | CNS drug reviews 20040101 |
| Liquid chromatographic determination of St. John's wort components in functional foods. | Journal of AOAC International 20040101 |
| Hyperforin-containing extracts of St John's wort fail to alter gene transcription in brain areas involved in HPA axis control in a long-term treatment regimen in rats. | Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology 20031201 |
| Enhancement of proteolytic processing of the beta-amyloid precursor protein by hyperforin. | Biochemical pharmacology 20031201 |
| Correlation of hyperforin content of Hypericum perforatum (St John's Wort) extracts with their effects on alcohol drinking in C57BL/6J mice: a preliminary study. | Journal of psychopharmacology (Oxford, England) 20031201 |
| Induction of hypericins and hyperforins in Hypericum perforatum in response to damage by herbivores. | Journal of chemical ecology 20031201 |
| A new synthetic approach to the polycyclic polyprenylated acylphloroglucinols. | Organic letters 20031127 |
| Determination of hyperforin in mouse brain by high-performance liquid chromatography/tandem mass spectrometry. | Analytical chemistry 20031115 |
| St. John's wort extracts and some of their constituents potently inhibit ultimate carcinogen formation from benzo[a]pyrene-7,8-dihydrodiol by human CYP1A1. | Cancer research 20031115 |
| Vitamin K2 regulation of bone homeostasis is mediated by the steroid and xenobiotic receptor SXR. | The Journal of biological chemistry 20031107 |
| Hypericum perforatum subspecies angustifolium shows a protective activity on the consequences of unavoidable stress exposure at lower doses than Hypericum perforatum perforatum. | Pharmacopsychiatry 20031101 |
| Hyperforin contributes to the hepatic CYP3A-inducing effect of Hypericum perforatum extract in the mouse. | Toxicological sciences : an official journal of the Society of Toxicology 20030901 |
| A simple and reliable semipreparative high-performance liquid chromatography technique for the isolation of marker-grade hyperforin from Hypericum perforatum L extract. | Journal of chromatographic science 20030901 |
| Further degradation product of hyperforin from Hypericum perforatum (St John's Wort). | Fitoterapia 20030701 |
| Hyperforin a constituent of St John's wort (Hypericum perforatum L.) extract induces apoptosis by triggering activation of caspases and with hypericin synergistically exerts cytotoxicity towards human malignant cell lines. | European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V 20030701 |
| Comparison of the growth-inhibitory effect of Hypericum perforatum L. extracts, differing in the concentration of phloroglucinols and flavonoids, on leukaemia cells. | The Journal of pharmacy and pharmacology 20030701 |
| Step by step removal of hyperforin and hypericin: activity profile of different Hypericum preparations in behavioral models. | Life sciences 20030620 |
| Hyperforin inhibits vesicular uptake of monoamines by dissipating pH gradient across synaptic vesicle membrane. | Life sciences 20030613 |
| Phosphorylation- and stimulus-dependent inhibition of cellular 5-lipoxygenase activity by nonredox-type inhibitors. | FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20030501 |
| [Topical treatment of atopic dermatitis with Hypericum cream. A randomised, placebo-controlled, double-blind half-side comparison study]. | Der Hautarzt; Zeitschrift fur Dermatologie, Venerologie, und verwandte Gebiete 20030301 |
| Treatment with Hypericum perforatum L. does not trigger decreased resistance in Staphylococcus aureus against antibiotics and hyperforin. | Phytomedicine : international journal of phytotherapy and phytopharmacology 20030301 |
| 2.1 A crystal structure of human PXR in complex with the St. John's wort compound hyperforin. | Biochemistry 20030218 |
| Current St John's wort research from mode of action to clinical efficacy. | Pharmacological research 20030201 |
| Antagonist effect of pseudohypericin at CRF1 receptors. | European journal of pharmacology 20030105 |
| Human organic anion transporting polypeptide-C (SLC21A6) is a major determinant of rifampin-mediated pregnane X receptor activation. | The Journal of pharmacology and experimental therapeutics 20030101 |
| Hypericum perforatum, a source of neuroactive lead structures. | Current topics in medicinal chemistry 20030101 |
| [Dangerous interaction of St. John's wort with chemotherapy?]. | Pharmazie in unserer Zeit 20030101 |
| [Formulation of St. John's wort extract. A medicinal obstacle course]. | Pharmazie in unserer Zeit 20030101 |
| [Charge conformity and biopharmaceutic characterization. St. John's Wort extract preparations in comparison]. | Pharmazie in unserer Zeit 20030101 |
| Structural investigations of isomeric oxidised forms of hyperforin by HPLC-NMR and HPLC-MSn. | Phytochemical analysis : PCA 20030101 |
| Fast high-performance liquid chromatographic analysis of naphthodianthrones and phloroglucinols from Hypericum perforatum extracts. | Phytochemical analysis : PCA 20030101 |
| Hyperforin is a dual inhibitor of cyclooxygenase-1 and 5-lipoxygenase. | Biochemical pharmacology 20021215 |
| Role of hyperforin in the antidepressant-like activity of Hypericum perforatum extracts. | Psychopharmacology 20021201 |
| Pharmacological activity of hyperforin acetate in rats. | Behavioural pharmacology 20021201 |
| An in vitro and hydroponic growing system for hypericin, pseudohypericin, and hyperforin production of St. John's wort (Hypericum perforatum CV new stem). | Planta medica 20021201 |
| Biorelevant dissolution testing of St John's wort products. | The Journal of pharmacy and pharmacology 20021201 |
| Determination of hyperforin in human plasma using solid-phase extraction and high-performance liquid chromatography with ultraviolet detection. | Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20021115 |
| The involvement of sodium and calcium ions in the release of amino acid neurotransmitters from mouse cortical slices elicited by hyperforin. | Life sciences 20021018 |
| Biosynthesis of hyperforin in Hypericum perforatum. | Journal of medicinal chemistry 20021010 |
| Inhibition of vesicular uptake of monoamines by hyperforin. | Life sciences 20020927 |
| Simultaneous determination of hypericin and hyperforin in human plasma and serum using liquid-liquid extraction, high-performance liquid chromatography and liquid chromatography-tandem mass spectrometry. | Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20020925 |
| Rapid quantification of constituents in St. John's wort extracts by NIR spectroscopy. | Journal of pharmaceutical and biomedical analysis 20020515 |
| A preliminary approach to nonenolizable beta,beta-tricarbonyls: assembly of a hyperevolutin prototype. | The Journal of organic chemistry 20020503 |
| Dual modulation of striatal acetylcholine release by hyperforin, a constituent of St. John's wort. | The Journal of pharmacology and experimental therapeutics 20020501 |
| Regulating natural health products. | Science (New York, N.Y.) 20020405 |
| Synthesis and biological evaluation of hyperforin analogues. Part I. Modification of the enolized cyclohexanedione moiety. | Journal of natural products 20020401 |
| Determining hyperforin and hypericin content in eight brands of St. John's wort. | American journal of health-system pharmacy : AJHP : official journal of the American Society of Health-System Pharmacists 20020315 |
| Inhibition of tumour cell growth by hyperforin, a novel anticancer drug from St. John's wort that acts by induction of apoptosis. | Oncogene 20020214 |
| Short term treatment with St. John's wort, hypericin or hyperforin fails to induce CYP450 isoforms in the Swiss Webster mouse. | Life sciences 20020201 |
| Regulation of multidrug resistance-associated protein 2 (ABCC2) by the nuclear receptors pregnane X receptor, farnesoid X-activated receptor, and constitutive androstane receptor. | The Journal of biological chemistry 20020125 |
| Separation of hypericins and hyperforins in extracts of Hypericum perforatum L. using non-aqueous capillary electrophoresis with reversed electro-osmotic flow. | Journal of pharmaceutical and biomedical analysis 20020101 |
| Quantitative analysis of the active components and the by-products of eight dry extracts of Hypericum perforatum L. (St John's Wort). | Phytochemical analysis : PCA 20020101 |
| [Hyperforin in St. John's wort--drug, extraction and preparations]. | Pharmazie in unserer Zeit 20020101 |
| Determination of hyperforin, hypericin, and pseudohypericin in human plasma using high-performance liquid chromatography analysis with fluorescence and ultraviolet detection. | Journal of chromatography. B, Biomedical sciences and applications 20011205 |
| Development of a simple, rapid and reproducible HPLC assay for the simultaneous determination of hypericins and stabilized hyperforin in commercial St. John's wort preparations. | Journal of pharmaceutical and biomedical analysis 20011201 |
| Antidepressant activity of hyperforin conjugates of the St. John's wort, Hypericum perforatum Linn.: an experimental study. | Indian journal of experimental biology 20011201 |
| Is St John's wort a 'Prozac-like' herbal antidepressant? | Trends in pharmacological sciences 20011101 |
| High-performance liquid chromatography-electrospray ionization mass spectrometry and multiple mass spectrometry studies of hyperforin degradation products. | Journal of chromatography. A 20010810 |
| Effects of two different extracts of St. John's wort and some of their constituents on cytochrome P450 activities in rat liver microsomes. | Pharmacopsychiatry 20010701 |
| Stimulation of glutamate, aspartate and gamma-aminobutyric acid release from synaptosomes by hyperforin. | Pharmacopsychiatry 20010701 |
| In vivo neurotransmitter release in the locus coeruleus--effects of hyperforin, inescapable shock and fear. | Pharmacopsychiatry 20010701 |
| A current review of the antimicrobial activity of Hypericum perforatum L. | Pharmacopsychiatry 20010701 |
| Acute and chronic actions of a dry methanolic extract of Hypericum perforatum and a hyperforin-rich extract on dopaminergic and serotonergic neurones in rat nucleus accumbens. | Pharmacopsychiatry 20010701 |
| Neuroendocrine effects of Hypericum extract WS 5570 in 12 healthy male volunteers. | Pharmacopsychiatry 20010701 |
| In vitro effects of St. John's wort extract and hyperforin on 5 HT uptake and efflux in human blood platelets. | Pharmacopsychiatry 20010701 |
| Evaluation of synaptosomal uptake inhibition of most relevant constituents of St. John's wort. | Pharmacopsychiatry 20010701 |
| Batch-to-batch reproducibility of St. John's wort preparations. | Pharmacopsychiatry 20010701 |
| Effects of hyperforin on the fluidity of brain membranes. | Pharmacopsychiatry 20010701 |
| Researching the antidepressant actions of Hypericum perforatum (St. John's wort) in animals and man. | Pharmacopsychiatry 20010701 |
| A study of the antidepressant activity of Hypericum perforatum on animal models. | Pharmacopsychiatry 20010701 |
| In vitro binding studies with two hypericum perforatum extracts--hyperforin, hypericin and biapigenin--on 5-HT6, 5-HT7, GABA(A)/benzodiazepine, sigma, NPY-Y1/Y2 receptors and dopamine transporters. | Pharmacopsychiatry 20010701 |
| Hypericum extract and hyperforin: memory-enhancing properties in rodents. | Pharmacopsychiatry 20010701 |
| Hyperforin stimulates intracellular calcium mobilisation and enhances extracellular acidification in DDT1-MF2 smooth muscle cells. | Pharmacopsychiatry 20010701 |
| Interleukin-6 involvement in antidepressant action of Hypericum perforatum. | Pharmacopsychiatry 20010701 |
| Effects of Hypericum perforatum L. on evoked potentials in guinea pig hippocampal slices. | Pharmacopsychiatry 20010701 |
| Hyperforin--antidepressant activity by a novel mechanism of action. | Pharmacopsychiatry 20010701 |
| St John's wort: Prozac from the plant kingdom. | Trends in pharmacological sciences 20010601 |
| Effect of St. John's wort on free radical production. | Life sciences 20010601 |
| St John's Wort and literature quotations. | Archives of internal medicine 20010409 |
| Adhyperforin as a contributor to the effect of Hypericum perforatum L. in biochemical models of antidepressant activity. | Life sciences 20010223 |
| Pharmacology. How the body's 'garbage disposal' may inactivate drugs. | Science (New York, N.Y.) 20010105 |
| Three new hyperforin analogues from Hypericum perforatum. | Journal of natural products 20010101 |
| Effects of a methanolic extract and a hyperforin-enriched CO2 extract of Hypericum perforatum on alcohol intake in rats. | Alcohol and alcoholism (Oxford, Oxfordshire) 20010101 |
| Comparative evaluation of St. John's wort from different Italian regions. | Farmaco (Societa chimica italiana : 1989) 20010101 |
| Comparison of German St. John's wort products according to hyperforin and total hypericin content. | Journal of the American Pharmaceutical Association (Washington,D.C. : 1996) 20010101 |
| Variability in St. John's wort formulations is an important consideration. | Alternative therapies in health and medicine 20010101 |
| Improved procedure for the quality control of Hypericum perforatum L. | Phytochemical analysis : PCA 20010101 |
| St John's wort, a herbal antidepressant, activates the steroid X receptor. | The Journal of endocrinology 20000901 |
| St. John's wort induces hepatic drug metabolism through activation of the pregnane X receptor. | Proceedings of the National Academy of Sciences of the United States of America 20000620 |
| Hyperforin as a possible antidepressant component of hypericum extracts. | Life sciences 19980101 |
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