Home Other Building Blocks Dammar-24-ene-3,6,12,20-tetrol, (3β,6α,12β,20R)-

Dammar-24-ene-3,6,12,20-tetrol, (3β,6α,12β,20R)-

CAS No.:
1453-93-6
Catalog Number:
AG001KRQ
Molecular Formula:
C30H52O4
Molecular Weight:
476.7315
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Product Description
Catalog Number:
AG001KRQ
Chemical Name:
Dammar-24-ene-3,6,12,20-tetrol, (3β,6α,12β,20R)-
CAS Number:
1453-93-6
Molecular Formula:
C30H52O4
Molecular Weight:
476.7315
MDL Number:
MFCD01861517
IUPAC Name:
(3S,5R,6S,8R,9R,10R,12R,13R,14R,17S)-17-[(2R)-2-hydroxy-6-methylhept-5-en-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,6,12-triol
InChI:
InChI=1S/C30H52O4/c1-18(2)10-9-13-30(8,34)19-11-15-28(6)24(19)20(31)16-22-27(5)14-12-23(33)26(3,4)25(27)21(32)17-29(22,28)7/h10,19-25,31-34H,9,11-17H2,1-8H3/t19-,20+,21-,22+,23-,24-,25-,27+,28+,29+,30+/m0/s1
InChI Key:
SHCBCKBYTHZQGZ-DLHMIPLTSA-N
SMILES:
CC(=CCC[C@]([C@H]1CC[C@@]2([C@@H]1[C@H](O)C[C@H]1[C@@]2(C)C[C@@H]([C@@H]2[C@]1(C)CC[C@@H](C2(C)C)O)O)C)(O)C)C
Properties
Complexity:
817  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
11  
Defined Bond Stereocenter Count:
0
Exact Mass:
476.387g/mol
Formal Charge:
0
Heavy Atom Count:
34  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
4  
Isotope Atom Count:
0
Molecular Weight:
476.742g/mol
Monoisotopic Mass:
476.387g/mol
Rotatable Bond Count:
4  
Topological Polar Surface Area:
80.9A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
5.9  
Literature
Title Journal
Cytochrome P450 CYP716A53v2 catalyzes the formation of protopanaxatriol from protopanaxadiol during ginsenoside biosynthesis in Panax ginseng. Plant & cell physiology 20120901
Fungal sensitivity to and enzymatic deglycosylation of ginsenosides. Phytochemistry 20120601
Co-transformation of Panax major ginsenosides Rb₁ and Rg₁ to minor ginsenosides C-K and F₁ by Cladosporium cladosporioides. Journal of industrial microbiology & biotechnology 20120401
Effects of protopanaxatriol-ginsenoside metabolites on rat N-methyl-d-aspartic Acid receptor-mediated ion currents. The Korean journal of physiology & pharmacology : official journal of the Korean Physiological Society and the Korean Society of Pharmacology 20120401
Microbial transformation of ginsenoside Rg3 to ginsenoside Rh2 by Esteya vermicola CNU 120806. World journal of microbiology & biotechnology 20120401
Panax ginseng extract rich in ginsenoside protopanaxatriol attenuates blood pressure elevation in spontaneously hypertensive rats by affecting the Akt-dependent phosphorylation of endothelial nitric oxide synthase. Journal of agricultural and food chemistry 20120328
Target separation of a new anti-tumor saponin and metabolic profiling of leaves of Panax notoginseng by liquid chromatography with eletrospray ionization quadrupole time-of-flight mass spectrometry. Journal of pharmaceutical and biomedical analysis 20120205
Ginsenoside-Rg1 Protects the Liver against Exhaustive Exercise-Induced Oxidative Stress in Rats. Evidence-based complementary and alternative medicine : eCAM 20120101
Ginsenoside Re: Its chemistry, metabolism and pharmacokinetics. Chinese medicine 20120101
Antioxidant and hepatoprotective effects of the red ginseng essential oil in H(2)O(2)-treated hepG2 cells and CCl(4)-treated mice. International journal of molecular sciences 20120101
Inhibitory Effect of Ginsenoside Rg1 on Vascular Smooth Muscle Cell Proliferation Induced by PDGF-BB Is Involved in Nitric Oxide Formation. Evidence-based complementary and alternative medicine : eCAM 20120101
Application of Monoclonal Antibodies against Bioactive Natural Products: Eastern Blotting and Preparation of Knockout Extract. International journal of analytical chemistry 20120101
Korean Red Ginseng Suppresses Metastasis of Human Hepatoma SK-Hep1 Cells by Inhibiting Matrix Metalloproteinase-2/-9 and Urokinase Plasminogen Activator. Evidence-based complementary and alternative medicine : eCAM 20120101
The in vitro structure-related anti-cancer activity of ginsenosides and their derivatives. Molecules (Basel, Switzerland) 20111219
Dual functions of ginsenosides in protecting human endothelial cells against influenza H9N2-induced inflammation and apoptosis. Journal of ethnopharmacology 20111011
Simultaneous determination of ginsenoside (G-Re, G-Rg1, G-Rg2, G-F1, G-Rh1) and protopanaxatriol in human plasma and urine by LC-MS/MS and its application in a pharmacokinetics study of G-Re in volunteers. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20110715
Development of a rapid and convenient method to separate eight ginsenosides from Panax ginseng by high-speed counter-current chromatography coupled with evaporative light scattering detection. Journal of separation science 20110501
Development of new staining technology 'eastern blotting' using monoclonal antibody. Current drug discovery technologies 20110301
Protopanaxatriol-type ginsenosides from the root of Panax ginseng. Journal of agricultural and food chemistry 20110112
Ginseng (Panax quinquefolius) and Licorice (Glycyrrhiza uralensis) Root Extract Combinations Increase Hepatocarcinoma Cell (Hep-G2) Viability. Evidence-based complementary and alternative medicine : eCAM 20110101
Cellular uptake of ginsenosides in Korean white ginseng and red ginseng and their apoptotic activities in human breast cancer cells. Planta medica 20110101
Effect of 20(S)-protopanaxatriol and its epimeric derivatives on myocardial injury induced by isoproterenol. Arzneimittel-Forschung 20110101
Neuroprotective effects of ginsenosides Rh1 and Rg2 on neuronal cells. Chinese medicine 20110101
Ginseng (Panax quinquefolius) Reduces Cell Growth, Lipid Acquisition and Increases Adiponectin Expression in 3T3-L1 Cells. Evidence-based complementary and alternative medicine : eCAM 20110101
Comparative study on saponin fractions from Panax notoginseng inhibiting inflammation-induced endothelial adhesion molecule expression and monocyte adhesion. Chinese medicine 20110101
Analysis of the transcriptome of Panax notoginseng root uncovers putative triterpene saponin-biosynthetic genes and genetic markers. BMC genomics 20110101
Ginseng for cognition. The Cochrane database of systematic reviews 20101208
Anti-Obesity effects of protopanaxdiol types of Ginsenosides isolated from the leaves of American ginseng (Panax quinquefolius L.) in mice fed with a high-fat diet. Fitoterapia 20101201
Microsomal cytochrome p450-mediated metabolism of protopanaxatriol ginsenosides: metabolite profile, reaction phenotyping, and structure-metabolism relationship. Drug metabolism and disposition: the biological fate of chemicals 20101001
Effects of American ginseng (Panax quinquefolius) on neurocognitive function: an acute, randomised, double-blind, placebo-controlled, crossover study. Psychopharmacology 20101001
Antihepatocarcinoma activity of lactic acid bacteria fermented Panax notoginseng. Journal of agricultural and food chemistry 20100811
Characterization of metabolism and in vitro permeability study of notoginsenoside R1 from Radix notoginseng. Journal of agricultural and food chemistry 20100512
[Pharmacokinetics of ginsenosides Rg1 and its metabolites in rats]. Yao xue xue bao = Acta pharmaceutica Sinica 20100501
Validated quantification for selective cellular uptake of ginsenosides on MCF-7 human breast cancer cells by liquid chromatography-mass spectrometry. Analytical and bioanalytical chemistry 20100401
Protopanaxatriol metabolites identified by LC-MS/MS after oral administration in mice. International journal of clinical pharmacology and therapeutics 20100401
The ginsenoside protopanaxatriol protects endothelial cells from hydrogen peroxide-induced cell injury and cell death by modulating intracellular redox status. Free radical biology & medicine 20100201
Isolation, synthesis and structures of ginsenoside derivatives and their anti-tumor bioactivity. Molecules (Basel, Switzerland) 20100119
Microbial conversion of rare ginsenoside Rf to 20(S)-protopanaxatriol by Aspergillus niger. Bioscience, biotechnology, and biochemistry 20100101
De novo sequencing and analysis of the American ginseng root transcriptome using a GS FLX Titanium platform to discover putative genes involved in ginsenoside biosynthesis. BMC genomics 20100101
Pharmacology of ginsenosides: a literature review. Chinese medicine 20100101
Ginseng on hyperglycemia: effects and mechanisms. Evidence-based complementary and alternative medicine : eCAM 20091201
New achievements in ginseng research and its future prospects. Chinese journal of integrative medicine 20091201
Induction of chemoprotective phase 2 enzymes by ginseng and its components. Planta medica 20090801
Antioxidant and apoptotic effects of korean white ginseng extracted with the same ratio of protopanaxadiol and protopanaxatriol saponins in human hepatoma HepG2 cells. Annals of the New York Academy of Sciences 20090801
Improvement of memory in mice and increase of hippocampal excitability in rats by ginsenoside Rg1's metabolites ginsenoside Rh1 and protopanaxatriol. Journal of pharmacological sciences 20090401
Protopanaxadiol and protopanaxatriol bind to glucocorticoid and oestrogen receptors in endothelial cells. British journal of pharmacology 20090201
Comparison of the antiobesity effects of the protopanaxadiol- and protopanaxatriol-type saponins of red ginseng. Phytotherapy research : PTR 20090101
Determination of 20(S)-ginsenoside Rh1 and its aglycone 20(S)-protopanaxatriol in rat plasma by sensitive LC-APCI-MS method and its application to pharmacokinetic study. European journal of mass spectrometry (Chichester, England) 20090101
[Clinical value of protoparaxotril saporlirs combined with aspirin in the secondary prevention of cerebral infarction]. Zhongguo Zhong xi yi jie he za zhi Zhongguo Zhongxiyi jiehe zazhi = Chinese journal of integrated traditional and Western medicine 20080901
Protopanaxadiol 6-hydroxylase and its role in regulating the ginsenoside heterogeneity in Panax notoginseng cells. Biotechnology and bioengineering 20080801
Antitumor agents. 261. 20(S)-protopanaxadiol and 20(s)-protopanaxatriol as antiangiogenic agents and total assignment of (1)H NMR spectra. Journal of natural products 20080301
Manipulation of ginsenoside heterogeneity of Panax notoginseng cells in flask and bioreactor cultivations with addition of phenobarbital. Bioprocess and biosystems engineering 20080201
Effects of ginsenosides Re and Rg3 on intracellular redox state and cell proliferation in C6 glioma cells. Chinese medicine 20080101
Structure-activity relationship and substrate-dependent phenomena in effects of ginsenosides on activities of drug-metabolizing P450 enzymes. PloS one 20080101
Two new dammarane triterpene glycosides from the rhizomes of Panax notoginseng. Journal of Asian natural products research 20080101
Potential role of ginseng in the treatment of colorectal cancer. The American journal of Chinese medicine 20080101
Biotransformation of 20(S)-protopanaxatriol by Mucor spinosus and the cytotoxic structure activity relationships of the transformed products. Phytochemistry 20071001
Microbial transformation of 20(S)-protopanaxatriol-type saponins by Absidia coerulea. Journal of natural products 20070701
Eastern blotting and immunoaffinity concentration using monoclonal antibody for ginseng saponins in the field of traditional chinese medicines. Journal of agricultural and food chemistry 20070516
Purification and characterization of new special ginsenosidase hydrolyzing multi-glycisides of protopanaxadiol ginsenosides, ginsenosidase type I. Chemical & pharmaceutical bulletin 20070201
Adjuvant effects of protopanaxadiol and protopanaxatriol saponins from ginseng roots on the immune responses to ovalbumin in mice. Vaccine 20070122
Effect of Salvia leriifolia Benth. root extracts on ischemia-reperfusion in rat skeletal muscle. BMC complementary and alternative medicine 20070101
Dammarenediol-II synthase, the first dedicated enzyme for ginsenoside biosynthesis, in Panax ginseng. FEBS letters 20061002
Chemical characteristics for different parts of Panax notoginseng using pressurized liquid extraction and HPLC-ELSD. Journal of pharmaceutical and biomedical analysis 20060828
Ginsenoside content and variation among and within American ginseng (Panax quinquefolius L.) populations. Phytochemistry 20060701
[Analysis of ginsenosides in Sheng-Mai-Yin decoction by high performance liquid chromatography-diode array detection-electrospray mass spectrometry]. Se pu = Chinese journal of chromatography 20060701
Ginsenoside Re and notoginsenoside R1: Immunologic adjuvants with low haemolytic effect. Chemistry & biodiversity 20060701
Ginsenoside metabolites, rather than naturally occurring ginsenosides, lead to inhibition of human cytochrome P450 enzymes. Toxicological sciences : an official journal of the Society of Toxicology 20060601
Natural products from ginseng inhibit [3H]batrachotoxinin A 20-alpha-benzoate binding to Na+ channels in mammalian brain. European journal of pharmacology 20060113
Structure and biological activity of protopanaxatriol-type saponins from the roots of Panax notoginseng. International immunopharmacology 20060101
Effect of ginseng saponins on a rat visceral hypersensitivity model. Biological & pharmaceutical bulletin 20051101
Induction and characterization of adventitious roots directly from the explants of Panax notoginseng. Biotechnology letters 20051101
Metabolism of ginsenoside Re by human intestinal microflora and its estrogenic effect. Biological & pharmaceutical bulletin 20051001
[Alkaline-degradation products of ginsenosides from leaves and stems of Panax quinquefolium]. Yao xue xue bao = Acta pharmaceutica Sinica 20051001
Simultaneous rapid quantification of ginsenoside Rg1 and its secondary glycoside Rh1 and aglycone protopanaxatriol in rat plasma by liquid chromatography-mass spectrometry after solid-phase extraction. Journal of pharmaceutical and biomedical analysis 20050601
Microbial transformation of 20(S)-protopanaxatriol by Mucor spinosus. Journal of natural products 20050501
Immunological-adjuvant saponins from the roots of Panax notoginseng. Chemistry & biodiversity 20050401
Protopanaxatriol-type ginsenosides differentially modulate type 1 and type 2 cytokines production from murine splenocytes. Planta medica 20050301
Immunoenhancing activity of protopanaxatriol-type ginsenoside-F3 in murine spleen cells. Acta pharmacologica Sinica 20041201
The inhibitory effect of intestinal bacterial metabolite of ginsenosides on CYP3A activity. Biological & pharmaceutical bulletin 20041001
Selection of high ginsenoside producing ginseng hairy root lines using targeted metabolic analysis. Phytochemistry 20041001
Simultaneous determination of triterpene saponins in ginseng drugs by high-performance liquid chromatography. Chemical & pharmaceutical bulletin 20040801
20(S)-Protopanaxatriol, one of ginsenoside metabolites, inhibits inducible nitric oxide synthase and cyclooxygenase-2 expressions through inactivation of nuclear factor-kappaB in RAW 264.7 macrophages stimulated with lipopolysaccharide. Cancer letters 20040308
Ginsenosides 20(S)-protopanaxadiol and Rh2 reduce cell proliferation and increase sub-G1 cells in two cultured intestinal cell lines, Int-407 and Caco-2. Canadian journal of physiology and pharmacology 20040301
Differential effect of ginsenoside metabolites on the 5-HT3A receptor-mediated ion current in Xenopus oocytes. Molecules and cells 20040227
In vitro inhibition of adrenal catecholamine secretion by steroidal metabolites of ginseng saponins. Biochemical pharmacology 20031201
Modulating effects of Korean ginseng saponins on ovarian function in immature rats. Biological & pharmaceutical bulletin 20031101
Differential effect of bovine serum albumin on ginsenoside metabolite-induced inhibition of alpha3beta4 nicotinic acetylcholine receptor expressed in Xenopus oocytes. Archives of pharmacal research 20031001
In vitro study of the relationship between the structure of ginsenoside and its antioxidative or prooxidative activity in free radical induced hemolysis of human erythrocytes. Journal of agricultural and food chemistry 20030423
Reversal of P-glycoprotein-mediated multidrug resistance by protopanaxatriol ginsenosides from Korean red ginseng. Planta medica 20030301
Ginsenosides inhibit EGF-induced proliferation of renal proximal tubule cells via decrease of c-fos and c-jun gene expression in vitro. Planta medica 20021101
Axonal and dendritic extension by protopanaxadiol-type saponins from ginseng drugs in SK-N-SH cells. Japanese journal of pharmacology 20021101
Structure-function relationship exists for ginsenosides in reducing cell proliferation and inducing apoptosis in the human leukemia (THP-1) cell line. Archives of biochemistry and biophysics 20021001
Can ginsenosides protect human erythrocytes against free-radical-induced hemolysis? Biochimica et biophysica acta 20020815
Prevention of growth and metastasis of murine melanoma through enhanced natural-killer cytotoxicity by fatty acid-conjugate of protopanaxatriol. Biological & pharmaceutical bulletin 20020701
[Comparative study of cytotoxic and hemolytic effects of triterpenoids isolated from Ginseng and Sea cucumber]. Izvestiia Akademii nauk. Seriia biologicheskaia 20020101
Ginsenosides protect apical transporters of cultured proximal tubule cells from dysfunctions induced by h(2)o(2). Kidney & blood pressure research 20020101
Double staining of ginsenosides by Western blotting using anti-ginsenoside Rb1 and Rg1 monoclonal antibodies. Biological & pharmaceutical bulletin 20011001
In vitro anti-Helicobacter pylori activity of panaxytriol isolated from ginseng. Archives of pharmacal research 20010801
Effects of ginsenosides from Panax ginseng on cell-to-cell communication function mediated by gap junctions. Planta medica 20010701
Regioselective enzymatic glycosylation of natural polyhydroxylated compounds: galactosylation and glucosylation of protopanaxatriol ginsenosides. The Journal of organic chemistry 20010112
Korean red ginseng saponins with low ratios of protopanaxadiol and protopanaxatriol saponin improve scopolamine-induced learning disability and spatial working memory in mice. Journal of ethnopharmacology 19990801
Properties