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Ginsenoside Rg3

PubChem CID
9918693
Structure
Ginsenoside Rg3_small.png
Molecular Formula
Synonyms
  • Ginsenoside Rg3
  • 14197-60-5
  • 20(S)-Ginsenoside Rg3
  • (20S)-ginsenoside Rg3
  • (20S)-Propanaxadiol
Molecular Weight
785.0 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2006-10-25
  • Modify:
    2025-01-11
Description
(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 apoptosis inducer, an antineoplastic agent, a plant metabolite and an angiogenesis modulating agent. It is a ginsenoside, a tetracyclic triterpenoid and a glycoside. It is functionally related to a (20S)-protopanaxadiol. It derives from a hydride of a dammarane.
Ginsenoside Rg3 has been reported in Panax notoginseng, Panax ginseng, and other organisms with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Ginsenoside Rg3.png

1.2 3D Status

Conformer generation is disallowed since too many atoms

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(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
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

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
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

RWXIFXNRCLMQCD-JBVRGBGGSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 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@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)C)C)O)C)O)C
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C42H72O13
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

2.3.2 Deprecated CAS

11019-45-7, 12770-19-3, 47891-53-2

2.3.3 European Community (EC) Number

2.3.4 UNII

2.3.5 ChEBI ID

2.3.6 ChEMBL ID

2.3.7 DSSTox Substance ID

2.3.8 KEGG ID

2.3.9 Lipid Maps ID (LM_ID)

2.3.10 Metabolomics Workbench ID

2.3.11 Nikkaji Number

2.3.12 Pharos Ligand ID

2.3.13 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 20(R)-ginsenoside Rg(3)
  • 20(S)-ginsenoside Rg(3)
  • 20s-ginsenoside rg3
  • 3-O-beta-D-glucopyranosyl-(1->2)-beta-D-glucopyranosyldammar-24-ene-3beta,12beta,20s-triol
  • beta-D-glucopyranoside, (3beta,12beta)-12,20-dihydroxydammar-24-en-3-yl 2-O-beta-D-glucopyranosyl-
  • ginsenoside 20-rg3
  • ginsenoside Rg(3)
  • ginsenoside Rg3
  • ginsenoside rg3, (+)-
  • ginsenoside rg3, (s)-
  • s-ginsenoside rg3

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
785.0 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
4
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
9
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
13
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
10
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
784.49729235 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
784.49729235 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
219 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
55
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
1370
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
20
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Chemical Classes

3.2.1 Lipids

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

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 LC-MS

1 of 2
MoNA ID
MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor Type
[M+H]+
Precursor m/z
785.4946
Instrument
QTOF Premier
Instrument Type
Q-TOF
Ionization
ESI
Ionization Mode
positive
Collision Energy
6->10V
Top 5 Peaks

623.4408 100

425.3821 48

461.3887 39

Thumbnail
Thumbnail
2 of 2
MoNA ID
MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor m/z
785.03
Instrument
3DQ LC/Ion Trap system
Instrument Type
QIT
Ionization
SSI (Sonic spray ionization)
Ionization Mode
negative
Collision Energy
50%
Top 5 Peaks

784 100

621.5 100

459.5 35

Thumbnail
Thumbnail

6 Chemical Vendors

7 Drug and Medication Information

7.1 Clinical Trials

7.1.1 ClinicalTrials.gov

8 Pharmacology and Biochemistry

8.1 MeSH Pharmacological Classification

Antineoplastic Agents, Phytogenic
Agents obtained from higher plants that have demonstrable cytostatic or antineoplastic activity. (See all compounds classified as Antineoplastic Agents, Phytogenic.)

8.2 Biochemical Reactions

9 Safety and Hazards

9.1 Hazards Identification

9.1.1 GHS Classification

Pictogram(s)
Irritant
Signal
Warning
GHS Hazard Statements
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
Precautionary Statement Codes

P264, P270, P301+P317, P330, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 39 reports by companies from 1 notifications to the ECHA C&L Inventory.

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

9.1.2 Hazard Classes and Categories

Acute Tox. 4 (100%)

10 Toxicity

10.1 Toxicological Information

10.1.1 Acute Effects

11 Associated Disorders and Diseases

12 Literature

12.1 Consolidated References

12.2 NLM Curated PubMed Citations

12.3 Chemical Co-Occurrences in Literature

12.4 Chemical-Gene Co-Occurrences in Literature

12.5 Chemical-Disease Co-Occurrences in Literature

13 Patents

13.1 Depositor-Supplied Patent Identifiers

13.2 Chemical Co-Occurrences in Patents

13.3 Chemical-Disease Co-Occurrences in Patents

13.4 Chemical-Gene Co-Occurrences in Patents

14 Interactions and Pathways

14.1 Chemical-Target Interactions

14.2 Pathways

15 Biological Test Results

15.1 BioAssay Results

16 Taxonomy

The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106

17 Classification

17.1 MeSH Tree

17.2 ChEBI Ontology

17.3 LIPID MAPS Classification

17.4 KEGG: Lipid

17.5 ChemIDplus

17.6 IUPHAR / BPS Guide to PHARMACOLOGY Target Classification

17.7 ChEMBL Target Tree

17.8 UN GHS Classification

17.9 EPA DSSTox Classification

17.10 LOTUS Tree

17.11 MolGenie Organic Chemistry Ontology

18 Information Sources

  1. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  4. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
  5. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  6. ChEBI
  7. LOTUS - the natural products occurrence database
    LICENSE
    The code for LOTUS is released under the GNU General Public License v3.0.
    https://lotus.nprod.net/
  8. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  9. ClinicalTrials.gov
    LICENSE
    The ClinicalTrials.gov data carry an international copyright outside the United States and its Territories or Possessions. Some ClinicalTrials.gov data may be subject to the copyright of third parties; you should consult these entities for any additional terms of use.
    https://clinicaltrials.gov/ct2/about-site/terms-conditions#Use
  10. Comparative Toxicogenomics Database (CTD)
    LICENSE
    It is to be used only for research and educational purposes. Any reproduction or use for commercial purpose is prohibited without the prior express written permission of NC State University.
    http://ctdbase.org/about/legal.jsp
  11. IUPHAR/BPS Guide to PHARMACOLOGY
    LICENSE
    The Guide to PHARMACOLOGY database is licensed under the Open Data Commons Open Database License (ODbL) https://opendatacommons.org/licenses/odbl/. Its contents are licensed under a Creative Commons Attribution-ShareAlike 4.0 International License (http://creativecommons.org/licenses/by-sa/4.0/)
    https://www.guidetopharmacology.org/about.jsp#license
    Guide to Pharmacology Target Classification
    https://www.guidetopharmacology.org/targets.jsp
  12. Therapeutic Target Database (TTD)
  13. Japan Chemical Substance Dictionary (Nikkaji)
  14. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
  15. LIPID MAPS
    Lipid Classification
    https://www.lipidmaps.org/
  16. Natural Product Activity and Species Source (NPASS)
    (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
    https://bidd.group/NPASS/compound.php?compoundID=NPC120123
  17. MassBank of North America (MoNA)
    LICENSE
    The content of the MoNA database is licensed under CC BY 4.0.
    https://mona.fiehnlab.ucdavis.edu/documentation/license
  18. Metabolomics Workbench
    (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
    https://www.metabolomicsworkbench.org/data/StructureData.php?RegNo=133493
  19. Pharos
    LICENSE
    Data accessed from Pharos and TCRD is publicly available from the primary sources listed above. Please respect their individual licenses regarding proper use and redistribution.
    https://pharos.nih.gov/about
  20. Rhea - Annotated Reactions Database
    LICENSE
    Rhea has chosen to apply the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0/). This means that you are free to copy, distribute, display and make commercial use of the database in all legislations, provided you credit (cite) Rhea.
    https://www.rhea-db.org/help/license-disclaimer
  21. Wikidata
  22. PubChem
  23. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
    Antineoplastic Agents, Phytogenic
    https://www.ncbi.nlm.nih.gov/mesh/68000972
  24. GHS Classification (UNECE)
  25. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
CONTENTS