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Details

Stereochemistry ABSOLUTE
Molecular Formula C53H90O22
Molecular Weight 1079.2685
Optical Activity UNSPECIFIED
Defined Stereocenters 29 / 29
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GINSENOSIDE RB3

SMILES

[H][C@@]1(CC[C@]2(C)[C@]1([H])[C@H](O)C[C@]3([H])[C@@]4(C)CC[C@H](O[C@]5([H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O[C@]6([H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O)C(C)(C)[C@]4([H])CC[C@@]23C)[C@](C)(CCC=C(C)C)O[C@@H]7O[C@H](CO[C@@H]8OC[C@@H](O)[C@H](O)[C@H]8O)[C@@H](O)[C@H](O)[C@H]7O

InChI

InChIKey=NODILNFGTFIURN-USYOXQFSSA-N
InChI=1S/C53H90O22/c1-23(2)10-9-14-53(8,75-47-43(67)39(63)37(61)29(72-47)22-69-45-41(65)34(58)26(57)21-68-45)24-11-16-52(7)33(24)25(56)18-31-50(5)15-13-32(49(3,4)30(50)12-17-51(31,52)6)73-48-44(40(64)36(60)28(20-55)71-48)74-46-42(66)38(62)35(59)27(19-54)70-46/h10,24-48,54-67H,9,11-22H2,1-8H3/t24-,25+,26+,27+,28+,29+,30-,31+,32-,33-,34-,35+,36+,37+,38-,39-,40-,41+,42+,43+,44+,45-,46-,47-,48-,50-,51+,52+,53-/m0/s1

HIDE SMILES / InChI
Molecular Formula C53H90O22
Molecular Weight 1079.2685
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 29 / 29
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/22741793 | https://www.ncbi.nlm.nih.gov/pubmed/21158074 | https://www.ncbi.nlm.nih.gov/pubmed/21591990 | https://www.ncbi.nlm.nih.gov/pubmed/19655413 | https://www.ncbi.nlm.nih.gov/pubmed/20969942 | https://www.ncbi.nlm.nih.gov/pubmed/20662827 | https://www.ncbi.nlm.nih.gov/pubmed/25371727 | https://www.ncbi.nlm.nih.gov/pubmed/25084093 | https://www.ncbi.nlm.nih.gov/pubmed/26287932 | https://www.ncbi.nlm.nih.gov/pubmed/25577870 | https://www.ncbi.nlm.nih.gov/pubmed/24571453

Ginsenoside Rb3 is a protopanaxadiol ginsenoside that can be isolated from several different Panax species. Ginsenoside Rb3 exerts antidepressant and antidiabetic activities as well as cardio- and neroprotective action in ischemic tissue injury in animal models. Ginsenoside Rb3 inhibits apoptosis and cell proliferation, in addition it demonstrates antiaxidant properties. Ginsenoside Rb3 may modulate activity of GABA-A and NMDA receptors.

CNS Activity

CNS Active
3913
Curator's Comment: Ginsenosides Rb3 is CNS active in animals. No human data available.

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
Inhibitor
8297
Inhibitor
8297
 8.2 µM [IC50]
Inhibitor
8297
Inhibitor
8297
Activator
1430
Inhibitor
8297
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Preclinical
Unknown

Approved Use

Unknown
Primary
Preclinical
Unknown

Approved Use

Unknown
Primary
Preclinical
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Ginsenoside Rb3 protects cardiomyocytes against ischemia-reperfusion injury via the inhibition of JNK-mediated NF-κB pathway: a mouse cardiomyocyte model.
2014
Antitumor effects of dammarane-type saponins from steamed Notoginseng.
2014 Jul
Ginsenoside Rb3 attenuates oxidative stress and preserves endothelial function in renal arteries from hypertensive rats.
2014 Jul
Protective properties of ginsenoside Rb3 against UV-B radiation-induced oxidative stress in HaCaT keratinocytes.
2016
Antidepressant-like effects of ginsenosides: A comparison of ginsenoside Rb3 and its four deglycosylated derivatives, Rg3, Rh2, compound K, and 20(S)-protopanaxadiol in mice models of despair.
2016 Jan

Sample Use Guides

In Vivo Use Guide
myocardial ischemia-reperfusion injury in rats: 5-20 mg/kg. antidepressant-like effects in rodent models: 30-150 mg/kg.
Route of Administration: Oral
In Vitro Use Guide
Ginsenosides Rb3 (0.1-10 uM) inhibits with IC50 8.2 uM tumor necrosis factor-α (TNF)-induced nuclear factor kappa-light-chain-enhancer of activated B cells (NF-κB) luciferase reporter activity using a human kidney 293T cell-based assay. In vitro, at concentrations of 100 and 200 µM, ginsenoside Rb3 increased glucose consumption in C2C12 myotubes by 76.83% and 97.20%, respectively, as compared to the control group.
Substance Class Chemical
Created
by admin
on Sat Dec 16 11:43:38 GMT 2023
Edited
by admin
on Sat Dec 16 11:43:38 GMT 2023
Record UNII
W6V49A8FJQ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
GINSENOSIDE RB3
Common Name English
.BETA.-D-GLUCOPYRANOSIDE, (3.BETA.,12.BETA.)-3-((2-O-.BETA.-D-GLUCOPYRANOSYL-.BETA.-D-GLUCOPYRANOSYL)OXY)-12-HYDROXYDAMMAR-24-EN-20-YL 6-O-.BETA.-D-XYLOPYRANOSYL-
Systematic Name English
GYPENOSIDE IV
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID601317092
Created by admin on Sat Dec 16 11:43:38 GMT 2023 , Edited by admin on Sat Dec 16 11:43:38 GMT 2023
PRIMARY
CHEBI
77153
Created by admin on Sat Dec 16 11:43:38 GMT 2023 , Edited by admin on Sat Dec 16 11:43:38 GMT 2023
PRIMARY
PUBCHEM
12912363
Created by admin on Sat Dec 16 11:43:38 GMT 2023 , Edited by admin on Sat Dec 16 11:43:38 GMT 2023
PRIMARY
FDA UNII
W6V49A8FJQ
Created by admin on Sat Dec 16 11:43:38 GMT 2023 , Edited by admin on Sat Dec 16 11:43:38 GMT 2023
PRIMARY
CAS
68406-26-8
Created by admin on Sat Dec 16 11:43:38 GMT 2023 , Edited by admin on Sat Dec 16 11:43:38 GMT 2023
PRIMARY
NIH
NCATS
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