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Ginsenoside CK

CAS No.:
39262-14-1
Catalog Number:
AG00BYG7
Molecular Formula:
C36H62O8
Molecular Weight:
622.8727
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
5mg
98%
1 week
United States
$207
- +
10mg
98%
1 week
United States
$307
- +
Product Description
Catalog Number:
AG00BYG7
Chemical Name:
Ginsenoside CK
CAS Number:
39262-14-1
Molecular Formula:
C36H62O8
Molecular Weight:
622.8727
MDL Number:
MFCD07772261
IUPAC Name:
(2S,3R,4S,5S,6R)-2-[(2S)-2-[(3S,5R,8R,9R,10R,12R,13R,14R,17S)-3,12-dihydroxy-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methylhept-5-en-2-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
InChI:
InChI=1S/C36H62O8/c1-20(2)10-9-14-36(8,44-31-30(42)29(41)28(40)23(19-37)43-31)21-11-16-35(7)27(21)22(38)18-25-33(5)15-13-26(39)32(3,4)24(33)12-17-34(25,35)6/h10,21-31,37-42H,9,11-19H2,1-8H3/t21-,22+,23+,24-,25+,26-,27-,28+,29-,30+,31-,33-,34+,35+,36-/m0/s1
InChI Key:
FVIZARNDLVOMSU-IRFFNABBSA-N
SMILES:
OC[C@H]1O[C@@H](O[C@]([C@H]2CC[C@@]3([C@@H]2[C@H](O)C[C@H]2[C@@]3(C)CC[C@@H]3[C@]2(C)CC[C@@H](C3(C)C)O)C)(CCC=C(C)C)C)[C@@H]([C@H]([C@@H]1O)O)O
Properties
Complexity:
1070  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
15  
Defined Bond Stereocenter Count:
0
Exact Mass:
622.444g/mol
Formal Charge:
0
Heavy Atom Count:
44  
Hydrogen Bond Acceptor Count:
8  
Hydrogen Bond Donor Count:
6  
Isotope Atom Count:
0
Molecular Weight:
622.884g/mol
Monoisotopic Mass:
622.444g/mol
Rotatable Bond Count:
7  
Topological Polar Surface Area:
140A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
5.6  
Literature
Title Journal
Ginsenoside F1 suppresses astrocytic senescence-associated secretory phenotype. Chemico-biological interactions 20180301
Production of bioactive ginsenoside compound K in metabolically engineered yeast. Cell research 20140601
Absorption mechanism of ginsenoside compound K and its butyl and octyl ester prodrugs in Caco-2 cells. Journal of agricultural and food chemistry 20121017
Inhibition of P-glycoprotein leads to improved oral bioavailability of compound K, an anticancer metabolite of red ginseng extract produced by gut microflora. Drug metabolism and disposition: the biological fate of chemicals 20120801
Ginsenoside compound K, not Rb1, possesses potential chemopreventive activities in human colorectal cancer. International journal of oncology 20120601
Compound K, a novel ginsenoside metabolite, inhibits adipocyte differentiation in 3T3-L1 cells: involvement of angiogenesis and MMPs. Biochemical and biophysical research communications 20120601
Enzymatic biotransformation of ginsenoside Rb1 to compound K by recombinant β-glucosidase from Microbacterium esteraromaticum. Journal of agricultural and food chemistry 20120411
Anti-inflammatory mechanism of compound K in activated microglia and its neuroprotective effect on experimental stroke in mice. The Journal of pharmacology and experimental therapeutics 20120401
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
Intestinal metabolite compound K of panaxoside inhibits the growth of gastric carcinoma by augmenting apoptosis via Bid-mediated mitochondrial pathway. Journal of cellular and molecular medicine 20120101
Hypoglycemic effect of protopanaxadiol-type ginsenosides and compound K on Type 2 diabetes mice induced by high-fat diet combining with streptozotocin via suppression of hepatic gluconeogenesis. Fitoterapia 20120101
Snailase preparation of ginsenoside M1 from protopanaxadiol-type ginsenoside and their protective effects against CCl4-induced chronic hepatotoxicity in mice. Molecules (Basel, Switzerland) 20111206
Ginsenoside metabolite compound K differentially antagonizing tumor necrosis factor-α-induced monocyte-endothelial trafficking. Chemico-biological interactions 20111015
Subchronic toxicity studies with ginsenoside compound K delivered to dogs via intravenous administration. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20110801
Ginsenoside Rb1 and its metabolite compound K inhibit IRAK-1 activation--the key step of inflammation. Biochemical pharmacology 20110801
Inhibition of JAK1/STAT3 signaling mediates compound K-induced apoptosis in human multiple myeloma U266 cells. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20110601
Compound K, a metabolite of ginsenosides, induces cardiac protection mediated nitric oxide via Akt/PI3K pathway. Life sciences 20110411
Ginsenoside compound K attenuates metastatic growth of hepatocellular carcinoma, which is associated with the translocation of nuclear factor-κB p65 and reduction of matrix metalloproteinase-2/9. Planta medica 20110301
Compound K increases type I procollagen level and decreases matrix metalloproteinase-1 activity and level in ultraviolet-A-irradiated fibroblasts. Journal of the Formosan Medical Association = Taiwan yi zhi 20110301
Production of aglycon protopanaxadiol via compound K by a thermostable β-glycosidase from Pyrococcus furiosus. Applied microbiology and biotechnology 20110201
Post-exposure treatment with ginsenoside compound K ameliorates auditory functional injury associated with noise-induced hearing loss in mice. Neuroscience letters 20110107
Compound K, a metabolite of ginsenosides, facilitates spontaneous GABA release onto CA3 pyramidal neurons. Journal of neurochemistry 20100801
Effect and mechanism of ginsenosides CK and Rg1 on stimulation of glucose uptake in 3T3-L1 adipocytes. Journal of agricultural and food chemistry 20100526
Isatis tinctoria L. combined with co-stimulatory molecules blockade prolongs survival of cardiac allografts in alloantigen-primed mice. Transplant immunology 20100501
Compound K inhibits basic fibroblast growth factor-induced angiogenesis via regulation of p38 mitogen activated protein kinase and AKT in human umbilical vein endothelial cells. Biological & pharmaceutical bulletin 20100101
Compound K, a metabolite of ginseng saponin, induces mitochondria-dependent and caspase-dependent apoptosis via the generation of reactive oxygen species in human colon cancer cells. International journal of molecular sciences 20100101
Compound K induces apoptosis via CAMK-IV/AMPK pathways in HT-29 colon cancer cells. Journal of agricultural and food chemistry 20091125
Glucocorticoid receptor agonist compound K regulates Dectin-1-dependent inflammatory signaling through inhibition of reactive oxygen species. Life sciences 20091021
Effect of compound K, a metabolite of ginseng saponin, combined with gamma-ray radiation in human lung cancer cells in vitro and in vivo. Journal of agricultural and food chemistry 20090708
Compound K, intestinal metabolite of ginsenoside, attenuates hepatic lipid accumulation via AMPK activation in human hepatoma cells. Journal of agricultural and food chemistry 20090225
Compound K, a metabolite of ginseng saponin, induces apoptosis via caspase-8-dependent pathway in HL-60 human leukemia cells. BMC cancer 20090101
Compound K suppresses ultraviolet radiation-induced apoptosis by inducing DNA repair in human keratinocytes. Archives of pharmacal research 20081101
The ginsenoside metabolite compound K, a novel agonist of glucocorticoid receptor, induces tolerance to endotoxin-induced lethal shock. Journal of cellular and molecular medicine 20080901
Development and validation of a reversed-phase HPLC method for quantitative determination of ginsenosides Rb1, Rd, F2, and compound K during the process of biotransformation of ginsenoside Rb1. Journal of separation science 20080401
Biotransformation of Panax notoginseng saponins into ginsenoside compound K production by Paecilomyces bainier sp. 229. Journal of applied microbiology 20080301
A ginseng saponin metabolite suppresses tumor necrosis factor-alpha-promoted metastasis by suppressing nuclear factor-kappaB signaling in murine colon cancer cells. Oncology reports 20080301
Compound K enhances insulin secretion with beneficial metabolic effects in db/db mice. Journal of agricultural and food chemistry 20071226
Transformation of bioactive compounds by Fusarium sacchari fungus isolated from the soil-cultivated ginseng. Journal of agricultural and food chemistry 20071114
Anti-diabetic effects of compound K versus metformin versus compound K-metformin combination therapy in diabetic db/db mice. Biological & pharmaceutical bulletin 20071101
Marked production of ginsenosides Rd, F2, Rg3, and compound K by enzymatic method. Chemical & pharmaceutical bulletin 20071001
[Advances in the study of ginsenoside compound K]. Yao xue xue bao = Acta pharmaceutica Sinica 20070901
Ginsenosides compound K and Rh(2) inhibit tumor necrosis factor-alpha-induced activation of the NF-kappaB and JNK pathways in human astroglial cells. Neuroscience letters 20070621
Deletion of the sphingosine kinase-1 gene influences cell fate during hypoxia and glucose deprivation in adult mouse cardiomyocytes. Cardiovascular research 20070401
Effect of ginsenosides on glucose uptake in human Caco-2 cells is mediated through altered Na+/glucose cotransporter 1 expression. Journal of agricultural and food chemistry 20070307
Purification and characterization of new special ginsenosidase hydrolyzing multi-glycisides of protopanaxadiol ginsenosides, ginsenosidase type I. Chemical & pharmaceutical bulletin 20070201
A ginsenoside metabolite, 20-O-beta-D-glucopyranosyl-20(S)-protopanaxadiol, triggers apoptosis in activated rat hepatic stellate cells via caspase-3 activation. Planta medica 20061001
Ginseng saponin metabolite suppresses phorbol ester-induced matrix metalloproteinase-9 expression through inhibition of activator protein-1 and mitogen-activated protein kinase signaling pathways in human astroglioma cells. International journal of cancer 20060115
Pharmacokinetics of a ginseng saponin metabolite compound K in rats. Biopharmaceutics & drug disposition 20060101
Hepatoprotective effect of ginsenoside Rb1 and compound K on tert-butyl hydroperoxide-induced liver injury. Liver international : official journal of the International Association for the Study of the Liver 20051001
Antipruritic effect of ginsenoside rb1 and compound k in scratching behavior mouse models. Journal of pharmacological sciences 20050901
Effect of ginsenoside Rb1 and compound K in chronic oxazolone-induced mouse dermatitis. International immunopharmacology 20050701
[Determination of ginsenoside compound-K by reversed-phase high performance liquid chromatography]. Se pu = Chinese journal of chromatography 20050501
Inhibitory effect of ginsenoside Rb1 and compound K on NO and prostaglandin E2 biosyntheses of RAW264.7 cells induced by lipopolysaccharide. Biological & pharmaceutical bulletin 20050401
Metabolic activities of ginsenoside Rb1, baicalin, glycyrrhizin and geniposide to their bioactive compounds by human intestinal microflora. Biological & pharmaceutical bulletin 20041001
Compound K induces expression of hyaluronan synthase 2 gene in transformed human keratinocytes and increases hyaluronan in hairless mouse skin. Biochemical and biophysical research communications 20040402
Differential effect of ginsenoside metabolites on the 5-HT3A receptor-mediated ion current in Xenopus oocytes. Molecules and cells 20040227
A novel ginseng saponin metabolite induces apoptosis and down-regulates fibroblast growth factor receptor 3 in myeloma cells. International journal of oncology 20031001
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
Degradation of ginsenosides in humans after oral administration. Drug metabolism and disposition: the biological fate of chemicals 20030801
Inhibition of intracerebroventricular injection stress-induced plasma corticosterone levels by intracerebroventricularly administered compound K, a ginseng saponin metabolite, in mice. Biological & pharmaceutical bulletin 20030701
Ginseng intestinal metabolite-I (GIM-I) reduces doxorubicin toxicity in the mouse testis. Reproductive toxicology (Elmsford, N.Y.) 20020101
The antimetastatic and immunomodulating activities of ginseng minor glycosides. Doklady. Biochemistry and biophysics 20010101
Properties