Ginsenoside K

HCID 9852086

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Grundinformationen

CAS: 39262-14-1
Standard-SMILES: CC(C)=CCC[C@](C)(O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)[C@H]1CC[C@]2(C)[C@@H]1[C@H](O)C[C@@H]1[C@@]3(C)CC[C@H](O)C(C)(C)[C@@H]3CC[C@]12C
InChIKey: FVIZARNDLVOMSU-IRFFNABBSA-N
Summenformel: C36H62O8
Durchschnittliche Molmasse: 622,9 g/mol
Monoisotopische Masse: 622,44446894

Überblick

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 an antineoplastic agent, an anti-allergic agent, a hepatoprotective agent, an anti-inflammatory agent and a plant metabolite. It is a 3beta-hydroxy-4,4-dimethylsteroid, a beta-D-glucoside, a tetracyclic triterpenoid, a 3beta-hydroxy steroid, a 12beta-hydroxy steroid and a ginsenoside. It derives from a hydride of a dammarane.

Namen und Bezeichner

Bevorzugter Name: Ginsenoside K
IUPAC: (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
Englischer Name: Ginsenoside CK
Summenformel: C36H62O8
Molmasse: 622.88

Namen und Synonyme

Ginsenoside KRefChem:639972ginsenoside C-K39262-14-1ginsenoside CKginsenoside compound Kginsenoside M120(S)-GINSENOSIDE CKginsenosideCKginsenoside-C-KMFCD0777226120(S)-Ginsenoside C-K

Weitere Namen anzeigen

IH-901CoMpoundCKGinsenosinde CK20S-Ginsenoside CS-Ginsenoside C-KGinsenoside C-K-RMGINSENOSIDE COMPOUND K(P)Compound K-Ginsenoside CKGinsenoside C-K (Standard)

(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-triol20-O-beta-D-glucopyranosyl-20(S)-protopanaxadiol3-O-Deglucosylginsenoside F2Protopanaxadiol 20-O-glucosideCHEMBL3355096CHEBI:77146G8D4792Q7KIH 901

Datenbank-Bezeichner

CAS: 39262-14-1

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 5,6
Polarare Oberfläche (TPSA): 140 Å²
H-Brücken-Donoren: 6
H-Brücken-Akzeptoren: 8
Frei drehbare Bindungen: 7
Schwere Atome: 44
Formalladung: 0
Komplexität: 1.070

Experimentelle und physikochemische Eigenschaften

LipidsLipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C30 isoprenoids (triterpenes) [PR0106]

Physikochemische Eigenschaften

Schmelzpunkt: 181 · 181~183℃
Siedepunkt: 723.1 · 723.1±60.0 °C(Predicted)
Dichte: 1.19 · 1.19
storage temp.: -20 °C · -20°C
Löslichkeit: 10 mg/ml; · DMF: 10 mg/ml; DMSO: 10 mg/ml; DMSO:PBS (pH 7.2) (1:1): 0.5 mg/ml
pka: 12.94 · 12.94±0.70(Predicted)
Aggregatzustand: powder
Farbe: White
Stabilität: Hygroscopic
Major Application: metabolomicsvitamins, nutraceuticals, and natural products
InChIKey: FVIZARNDLVOMSU-SFEJUJENNA-N
SMILES: CC(C)=CCC[C@](C1C2[C@H](O)CC3[C@@]([C@]2(C)CC1)(C)CCC4C(C)(C)[C@@H](O)CC[C@@]43C)(C)O[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O

Sicherheit und Regulatorisches

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GHS-Klassifizierung

GHS Classification · 4 Einträge

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 2 reports by companies from 1 notifications to the ECHA C&L Inventory.

Gefahrenhinweise

Hazard Classes and CategoriesAcute Tox. 4 (100%)

Sicherheitsdaten

wgk: WGK 3
Speicherklasse: 11 - Combustible Solids
Hazard Classifications: Acute Tox. 4 Oral

Chemie und Industrie

Anwendungen · 2 Einträge

BeschreibungGinsenoside compound K (C-K) is a metabolite of the protopanaxadiol-type saponins of Panax ginseng C.A. Meyer, has long been used to treat against the development of cancer, inflammation, allergies, and diabetes; C-K acts as a unique HUVEC migration inhibitor by regulating MMP expression, as well as the activity of SPHK1 and its related sphingolipid metabolites. C-K exhibits anti-inflammatory effects by reducing iNOS and COX-2, C-K exhibits an inhibition against the activity of CYP2C9 and CYP2A6 in human liver microsomes with IC50s of 32.0±3.6 μM and 63.6±4.2 μM, respectively. C-K promotes Aβ clearance by enhancing autophagy via the mTOR signaling pathway in primary astrocytes.

VerwendenGinsenoside C-K is reported to exhibit anti-wrinkle effects. Also, it potentiates tumor necrosis factor (TNF)-related apotosis-inducing ligand (TRAIL)-induced apotosis in HCT116 colon cancer.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

Folienetriol

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