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Ginsenoside Rg3

HCID 9918693
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Grundinformationen

CAS
14197-60-5
Standard-SMILES
CC(C)=CCC[C@](C)(O)[C@H]1CC[C@]2(C)[C@@H]1[C@H](O)C[C@@H]1[C@@]3(C)CC[C@H](O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)C(C)(C)[C@@H]3CC[C@]12C
InChIKey
RWXIFXNRCLMQCD-JBVRGBGGSA-N
Summenformel
C42H72O13
Durchschnittliche Molmasse
785 g/mol
Monoisotopische Masse
784,49729235

Überblick

(20S)-ginsenoside Rg3 is a ginsenoside found in Panax ginseng and Panax japonicus var. major 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 3 has been converted to the corresponding beta-D-glucopyranosyl-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 angiogenesis modulating agent, an apoptosis inducer and a plant metabolite. It is a glycoside, a tetracyclic triterpenoid and a ginsenoside. It is functionally related to a (20S)-protopanaxadiol. It derives from a hydride of a dammarane.

Namen und Bezeichner

Bevorzugter Name
Ginsenoside Rg3
IUPAC
(2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-2-[[(3S,5R,8R,9R,10R,12R,13R,14R,17S)-12-hydroxy-17-[(2S)-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]phenanthren-3-yl]oxy]-6-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
Englischer Name
Ginsenoside Rg3
Summenformel
C42H72O13
Molmasse
785.01

Namen und Synonyme

Ginsenoside Rg314197-60-5(20S)-ginsenoside Rg3(20S)-Propanaxadiol20S-propanaxadiol20s-ginsenoside rg3S-Ginsenoside Rg3ginsenoside 20-rg3ginsenoside rg3, (s)-ginsenoside rg3, (+)-227D367Y57CHEBI:67991
Weitere Namen anzeigen
Rg3CS-1328gensenoside RG3opyransoyl)oxy)-20S-Ginseniside Rg3GINSENOSIDE Rg3(SH)Ginsenosides rg3(s)Ginsenoside Rg3 (S-)
DTXSID101316982(2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-2-[[(3S,5R,8R,9R,10R,12R,13R,14R,17S)-12-hydroxy-17-[(2S)-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]phenanthren-3-yl]oxy]-6-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triolginsenoside Rg(3)RefChem:14322420(S)-ginsenoside Rg(3)DTXCID901746804(2S,3R,4S,5S,6R)-2-((2R,3R,4S,5S,6R)-4,5-Dihydroxy-2-(((3S,5R,8R,9R,10R,12R,13R,14R,17S)-12-Hydroxy-17-((2S)-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)Phenanthren-3-Yl)Oxy)-6-(Hydroxymethyl)Oxan-3-Yl)Oxy-6-(Hydroxymethyl)Oxane-3,4,5-Triolbeta-D-glucopyranoside, (3beta,12beta)-12,20-dihydroxydammar-24-en-3-yl 2-O-beta-D-glucopyranosyl-

Datenbank-Bezeichner

CAS
14197-60-5
PubChem CID
9918693
DTXSID
DTXSID101316982
ChEMBL
CHEMBL398412
ChEBI
CHEBI:67991
UNII
227D367Y57
EC Number
683-189-8
Nikkaji
J38.864E

Eigenschaften

Berechnete Struktureigenschaften

XLogP
4
Polarare Oberfläche (TPSA)
219 Ų
H-Brücken-Donoren
9
H-Brücken-Akzeptoren
13
Frei drehbare Bindungen
10
Schwere Atome
55
Formalladung
0
Komplexität
1.370

Experimentelle und physikochemische Eigenschaften

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

Physikochemische Eigenschaften

Schmelzpunkt
315 · 315-318°C
Siedepunkt
885 · 885.0±65.0 °C(Predicted)
Dichte
1.3 · 1.30
storage temp.
2 · 2-8°C
Löslichkeit
5 mg/mL · DMSO: ≥5mg/mL
pka
12.85 · 12.85±0.70(Predicted)
Aggregatzustand
powder
Farbe
white to beige
Major Application
food and beverages
InChIKey
RWXIFXNRCLMQCD-JBVRGBGGSA-N
CAS Datenbank
14197 · 14197-60-5(CAS DataBase Reference)

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

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 40 reports by companies from 1 notifications to the ECHA C&L Inventory.

Gefahrenhinweise

Hazard Classes and CategoriesAcute Tox. 4 (100%)

Sicherheitsdaten

wgk
3
hs_code
29389090
RTECS-Nr.
LY9537300
risk_code
22
Toxizität
mouse,LD50,intraperitoneal,1250mg/kg (1250mg/kg),Arzneimittel-Forschung. Drug Research. Vol. 25, Pg. 343, 1975.
hazard_code
Xn
Speicherklasse
11 - Combustible Solids
Hazard Classifications
Acute Tox. 4 Oral

Chemie und Industrie

Pharmakologische Informationen

MeSH Pharmacological ClassificationAgents obtained from higher plants that have demonstrable cytostatic or antineoplastic activity.
Anwendungen · 2 Einträge

BeschreibungGinsenosides are pharmacologically active natural constituents of ginseng and other plants of the genus Panax. Structurally, they are steroid glycosides derived from the triterpene squalene. Ginsenoside Rg3 is a panaxadiol found in white and red P. ginseng. This ginsenoside has diverse in vitro and in vivo effects, including anti-cancer, neuroprotective, anti-hypertensive, and anti-inflammatory actions. Ginsenoside Rg3 induces apoptosis and inhibits angiogenesis in a variety of cancer models. Notably, this ginsenoside can be produced by heating other ginsenosides, leading to elevated levels in steamed or dried ginseng preparations.

VerwendenGinsenoside Rg3 shows a synergistic antitumor effect with cisplatin in cisplatin-resistant bladder tumor cell lines and is considered to be an anti-tumor agent.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

2-O-β-D-Glucopyranosyl-(3β,12β)-20-(β-D-glucopyranosyloxy)-12-hydroxydammar-24-en-3-yl-β-D-glucopyranosidGinsenoside rb1Ginseng extractASIAN GINSENG

Nachgelagerte Produkte

Ginsenoside Rh2(20S)-ProtopanaxadiolGinsenoside-Rg5Ginsenoside RK2

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