Ginsenoside CK is a bacterial metabolite of Ginsenoside Rb1. Ginsenoside CK exerts anti~inflammatory effects by inhibiting inducible nitric oxide synthase (iNOS) and COX-2. In human liver microsomes, Ginsenoside CK inhibits CYP2C9 and CYP2A6 activities with IC50 of 32.0±3.6 μM and 63.6±4.2 μM, respectively.

Physicochemical Properties

Molecular Formula	C36H62O8
Molecular Weight	622.8727
Exact Mass	622.444
CAS #	39262-14-1
PubChem CID	9852086
Appearance	White to off-white solid powder
Density	1.2±0.1 g/cm3
Boiling Point	723.1±60.0 °C at 760 mmHg
Melting Point	178 °C
Flash Point	391.1±32.9 °C
Vapour Pressure	0.0±5.3 mmHg at 25°C
Index of Refraction	1.572
LogP	5.5
Hydrogen Bond Donor Count	6
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	7
Heavy Atom Count	44
Complexity	1070
Defined Atom Stereocenter Count	15
SMILES	CC(=CCC[C@@](C)([C@H]1CC[C@@]2([C@@H]1[C@@H](C[C@H]3[C@]2(CC[C@@H]4[C@@]3(CC[C@@H](C4(C)C)O)C)C)O)C)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)C
InChi Key	FVIZARNDLVOMSU-IRFFNABBSA-N
InChi Code	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
Chemical 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
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

ln Vitro	Ginsenoside CK, a bacterial metabolite of G-Rb1, has anti-inflammatory properties primarily by inhibiting inducible nitric oxide synthase (iNOS), cyclooxygenase (COX)-2, and pro-inflammatory cytokines. Ginsenoside CK reduces pro-inflammatory cytokine expression by inhibiting IAK-1, MAPK, IKK-α, and NF-κB activity in LPS-treated mouse peritoneal macrophages. Ginsenoside CK reduced iNOS and COX-2 expression by decreasing NF-κB activation in LPS-stimulated RAW264.7 cells. Ginsenoside CK decreased the inflammatory response in zymosan-treated bone marrow-derived macrophages (BMDM) and RAW264.7 cells by reducing pro-inflammatory cytokine release, MAPK activation, and ROS generation. Ginsenoside CK also shown anti-inflammatory action in LPS-stimulated microglial cells. Ginsenoside CK reduces inflammation by regulating ROS levels, MAPK, NF-κB, and AP-1 activity [1]. Ginsenoside CK, the major metabolite of ginsenoside in the gastrointestinal tract, suppresses NF-κB activation via PXR. Ginsenoside CK inhibits NF-κB activation, leading to improved recovery from DSS-induced colitis. Ginsenoside CK decreased TNF-α-induced elevation of IL-1β and iNOS mRNA levels while restoring PXR and CYP3A4 mRNA levels in LS174T cells [2]. Ginsenoside CK is an intestine metabolite of 20(S)-protopanaxadiol derivatives. It inhibits the activity of CYP2C9 in human liver microsomes. The IC50 value is 32.0 ± 3.6 μM. It reduces the activity of CYP2A6 in human liver microsomes. The activity weakly inhibits human liver microsome CYP2D6 activity, with an IC50 value of 63.6±4.2 μM and an IC50 value exceeding 100 μM [4].
ln Vivo	The body weight of mice with collagen-induced arthritis (CIA) grew gradually and was notably lower than that of normal DBA/1 mice beginning on the third day following emulsion injection. Mice given lotion injection on day 32 began to restore body weight when given ginsenoside CK at doses of 28, 56, and 112 mg/kg. On day 50, the body weight of the mice treated with ginsenoside CK (56 and 112 mg/kg) and methotrexate (MTX) (2 mg/kg) was considerably higher than that of the CIA mice. On day 24 following immunization, edema in the hind paws began. Treatment was given to CIA mice from day 28 to day 50. Every four days starting on day 24, arthritic scores were recorded. On day 51, ginsenoside CK (56 and 112 mg/kg) dramatically decreased the arthritis scores in mice [3].
References	[1]. Role of ginsenosides, the main active components of Panax ginseng, in inflammatory responsesand diseases. J Ginseng Res. 2017 Oct;41(4):435-443. [2]. Ginsenoside metabolites, rather than naturally occurring ginsenosides, lead to inhibition of human cytochrome P450 enzymes. Toxicol Sci. 2006 Jun;91(2):356-64. [3]. Ginsenosides Regulate PXR/NF-κB Signaling and Attenuate Dextran Sulfate Sodium-Induced Colitis. Drug Metab Dispos. 2015 Aug;43(8):1181-9. [4]. Ginsenoside compound K suppresses the abnormal activation of T lymphocytes in mice with collagen-induced arthritis. Acta Pharmacol Sin. 2014 May;35(5):599-612.
Additional Infomation	Ginsenoside C-K is a ginsenoside found in Panax species that is dammarane which is substituted by hydroxy groups at the 3beta, 12beta and 20 pro-S positions, in which the hydroxy group at position 20 has been converted to the corresponding beta-D-glucopyranoside, and in which a double bond has been introduced at the 24-25 position. It has a role as a plant metabolite, an antineoplastic agent, a hepatoprotective agent, an anti-allergic agent and an anti-inflammatory agent. It is a beta-D-glucoside, a 12beta-hydroxy steroid, a ginsenoside, a tetracyclic triterpenoid, a 3beta-hydroxy steroid and a 3beta-hydroxy-4,4-dimethylsteroid. It derives from a hydride of a dammarane. ginsenoside C-K has been reported in Panax ginseng and Fusarium sacchari with data available.

Solubility Data

Solubility (In Vitro)

DMSO : ≥ 100 mg/mL (~160.55 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.75 mg/mL (4.42 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 27.5 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.75 mg/mL (4.42 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 27.5 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.75 mg/mL (4.42 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 27.5 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	1.6055 mL	8.0274 mL	16.0547 mL
	5 mM	0.3211 mL	1.6055 mL	3.2109 mL
	10 mM	0.1605 mL	0.8027 mL	1.6055 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.