U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C42H72O13
Molecular Weight 785.0149
Optical Activity UNSPECIFIED
Defined Stereocenters 20 / 20
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GINSENOSIDE RG3

SMILES

CC(=CCC[C@@](C)([C@@]1([H])CC[C@]2(C)[C@]1([H])[C@@]([H])(C[C@]3([H])[C@@]4(C)CC[C@@]([H])(C(C)(C)[C@]4([H])CC[C@]32C)O[C@@]5([H])[C@@]([H])([C@]([H])([C@@]([H])([C@@]([H])(CO)O5)O)O)O[C@@]6([H])[C@@]([H])([C@]([H])([C@@]([H])([C@@]([H])(CO)O6)O)O)O)O)O)C

InChI

InChIKey=RWXIFXNRCLMQCD-JBVRGBGGSA-N
InChI=1S/C42H72O13/c1-21(2)10-9-14-42(8,51)22-11-16-41(7)29(22)23(45)18-27-39(5)15-13-28(38(3,4)26(39)12-17-40(27,41)6)54-37-35(33(49)31(47)25(20-44)53-37)55-36-34(50)32(48)30(46)24(19-43)52-36/h10,22-37,43-51H,9,11-20H2,1-8H3/t22-,23+,24+,25+,26-,27+,28-,29-,30+,31+,32-,33-,34+,35+,36-,37-,39-,40+,41+,42-/m0/s1

HIDE SMILES / InChI

Description
Curator's Comment:: https://www.ncbi.nlm.nih.gov/pubmed/27800005 | https://www.ncbi.nlm.nih.gov/pubmed/22403544 | https://www.ncbi.nlm.nih.gov/pubmed/24678300

Ginsenoside Rg3 (Rg3) is one of the most effective steroidal saponins extracted from Ginseng, a common Traditional Chinese medicine (TCM) herb which tonifies Qi in TCM theory and inhibits tumors. Rg3 suppresses tumor growth and tumor angiogenesis. For its significant antitumor effects, Rg3 has been used in clinical trials in combination with chemotherapy regimens. 20(S) and 20(R) forms of ginsenosides are stereoisomers of each other that depend on the orientation of the C-20 hydroxyl in ginsenosides. In general, the 20(S) compounds have been shown to possess better anti-proliferative effects than their 20(R) counterparts whereas 20(R) compounds such as 20(R)-Rg3 have been shown to inhibit cancer cell invasion and metastasis. Ginsenoside Rg3 regulates voltage-gated ion channels such as Ca(2+), K(+), and Na(+) channels, and ligand-gated ion channels such as GABAA, 5-HT3, nicotinic acetylcholine, and N-methyl-D-aspartate (NMDA) receptors through interactions with various sites including channel blocker binding sites, toxin-binding sites, channel gating regions, and allosteric channel regulator binding sites when the respective ion channels or receptors are stimulated with depolarization or ligand treatment. Shenyi capsule which contains ginsenoside Rg3 as the main ingredient has been approved by China Food and Drug Administration (CFDA) to be used clinically for cancer treatment.

CNS Activity

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Shenyi capsule

Approved Use

Shenyi capsule which contains ginsenoside Rg3 as the main ingredient has been approved by China Food and Drug Administration (CFDA) to be used clinically for cancer treatment

Launch Date

946598400000
Primary
Shenyi capsule

Approved Use

Shenyi capsule which contains ginsenoside Rg3 as the main ingredient has been approved by China Food and Drug Administration (CFDA) to be used clinically for cancer treatment

Launch Date

946598400000
Primary
Shenyi capsule

Approved Use

Shenyi capsule which contains ginsenoside Rg3 as the main ingredient has been approved by China Food and Drug Administration (CFDA) to be used clinically for cancer treatment

Launch Date

946598400000
Primary
Shenyi capsule

Approved Use

Shenyi capsule which contains ginsenoside Rg3 as the main ingredient has been approved by China Food and Drug Administration (CFDA) to be used clinically for cancer treatment

Launch Date

946598400000
PubMed

PubMed

TitleDatePubMed
Ginsenoside Rg3 inhibits phenylephrine-induced vascular contraction through induction of nitric oxide synthase.
2003 Oct
[Experimental study on anti-angiogenesis in mice with Lewis lung carcinoma by low-dose of cyclophosphamide combined with ginsenoside Rg3].
2005 Aug
Memory enhancing and neuroprotective effects of selected ginsenosides.
2005 Mar
[Ginsenoside Rg3 induces apoptosis of human lung squamous cell carcinoma SK-MES-1 cell line].
2009 Sep
Ginsenoside Rg(3) decelerates hERG K(+) channel deactivation through Ser631 residue interaction.
2011 Aug 1
Red ginseng and 20(S)-Rg3 control testosterone-induced prostate hyperplasia by deregulating androgen receptor signaling.
2012 Jul
Ginsenoside Re and Rd enhance the expression of cholinergic markers and neuronal differentiation in Neuro-2a cells.
2014
Stereospecific effects of ginsenoside 20-Rg3 inhibits TGF-β1-induced epithelial-mesenchymal transition and suppresses lung cancer migration, invasion and anoikis resistance.
2014 Aug 1
YY162 prevents ADHD-like behavioral side effects and cytotoxicity induced by Aroclor1254 via interactive signaling between antioxidant potential, BDNF/TrkB, DAT and NET.
2014 Mar
Novel roles of ginsenoside Rg3 in apoptosis through downregulation of epidermal growth factor receptor.
2015 May 25
Patents

Sample Use Guides

Effect of 400-mg Ginsenoside Rg3-enriched Korean red ginseng extract on two separate visits with a 7-day washout period was studied on measures of arterial stiffness and peripheral and central blood pressure (BP) parameters in healthy volunteers.
Route of Administration: Oral
10-180 μg/ml Ginsenoside Rg3 significantly reduced both HUVEC and rat C6 glioma cell proliferation. The combination of Rg3 (50 uM) with cisplatin (10 uM) and doxorubicin (2 uM) was also more effective in the inhibition of prostate cancer cell growth and NF-kappaB activity than those by the treatment of Rg3 or chemotherapeutics alone.
Name Type Language
GINSENOSIDE RG3
Common Name English
S-GINSENOSIDE RG3
Common Name English
GINSENOSIDE 20-RG3
Common Name English
20(S)-GINSENOSIDE-RG3
Common Name English
.BETA.-D-GLUCOPYRANOSIDE, (3.BETA.,12.BETA.)-12,20-DIHYDROXYDAMMAR-24-EN-3-YL 2-O-.BETA.-D-GLUCOPYRANOSYL-
Common Name English
3-O-.BETA.-D-GLUCOPYRANOSYL-(1->2)-.BETA.-D-GLUCOPYRANOSYLDAMMAR-24-ENE-3.BETA.,12.BETA.,20S-TRIOL
Common Name English
GINSENOSIDE RG3 [WHO-DD]
Common Name English
GINSENOSIDE RG3, (+)-
Common Name English
20S-GINSENOSIDE RG3
Common Name English
GINSENOSIDE RG3, (S)-
Common Name English
Code System Code Type Description
CAS
14197-60-5
Created by admin on Sat Jun 26 03:45:10 UTC 2021 , Edited by admin on Sat Jun 26 03:45:10 UTC 2021
PRIMARY
FDA UNII
227D367Y57
Created by admin on Sat Jun 26 03:45:10 UTC 2021 , Edited by admin on Sat Jun 26 03:45:10 UTC 2021
PRIMARY
PUBCHEM
9918693
Created by admin on Sat Jun 26 03:45:10 UTC 2021 , Edited by admin on Sat Jun 26 03:45:10 UTC 2021
PRIMARY
EVMPD
SUB127965
Created by admin on Sat Jun 26 03:45:10 UTC 2021 , Edited by admin on Sat Jun 26 03:45:10 UTC 2021
PRIMARY