Ginsenoside Rg1

Identification

Name
Ginsenoside Rg1
Accession Number
DB06750
Type
Small Molecule
Groups
Nutraceutical
Description

Ginsenosides are a class of steroid glycosides, and triterpene saponins, found exclusively in the plant genus Panax (ginseng). Ginsenosides have been the target of research, as they are viewed as the active compounds behind the claims of ginseng's efficacy. Because ginsenosides appear to affect multiple pathways, their effects are complex and difficult to isolate. Rg1 Appears to be most abundant in Panax ginseng (Chinese/Korean Ginseng). It improves spatial learning and increase hippocampal synaptophysin level in mice, plus demonstrates estrogen-like activity.

Structure
Thumb
Synonyms
  • Ginsenoside A2
  • Panaxoside A
  • Sanchinoside C1
Categories
UNII
PJ788634QY
CAS number
22427-39-0
Weight
Average: 801.024
Monoisotopic: 800.492206998
Chemical Formula
C42H72O14
InChI Key
YURJSTAIMNSZAE-HHNZYBFYSA-N
InChI
InChI=1S/C42H72O14/c1-20(2)10-9-13-42(8,56-37-34(52)32(50)30(48)25(19-44)55-37)21-11-15-40(6)28(21)22(45)16-26-39(5)14-12-27(46)38(3,4)35(39)23(17-41(26,40)7)53-36-33(51)31(49)29(47)24(18-43)54-36/h10,21-37,43-52H,9,11-19H2,1-8H3/t21-,22+,23-,24+,25+,26+,27-,28-,29+,30+,31-,32-,33+,34+,35-,36+,37-,39+,40+,41+,42-/m0/s1
IUPAC Name
(2S,3R,4S,5S,6R)-2-{[(2S)-2-[(1R,2R,5S,7R,8S,10R,11R,14S,15R,16R)-5,16-dihydroxy-2,6,6,10,11-pentamethyl-8-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-6-methylhept-5-en-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
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]3[C@H](C[C@@]21C)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
USolute carrier organic anion transporter family member 1B3Not AvailableHumans
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

M1 (20- O -β- D -glucopyranosyl-20( S )- protopanaxadiol ) is a ppd-type monoglucoside ginsenoside metabolized by intestinal bacteria in humans

Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
KEGG Compound
C08946
PubChem Compound
441923
PubChem Substance
99443286
ChemSpider
390498
ChEBI
67987
ChEMBL
CHEMBL501637
Wikipedia
Ginsenoside_Rg1

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.304 mg/mLALOGPS
logP1ALOGPS
logP0.68ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)11.91ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area239.22 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity203.66 m3·mol-1ChemAxon
Polarizability88.31 Å3ChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.6159
Blood Brain Barrier+0.5773
Caco-2 permeable-0.9066
P-glycoprotein substrateSubstrate0.8843
P-glycoprotein inhibitor IInhibitor0.7261
P-glycoprotein inhibitor IINon-inhibitor0.8102
Renal organic cation transporterNon-inhibitor0.8362
CYP450 2C9 substrateNon-substrate0.8625
CYP450 2D6 substrateNon-substrate0.8748
CYP450 3A4 substrateSubstrate0.7082
CYP450 1A2 substrateNon-inhibitor0.9057
CYP450 2C9 inhibitorNon-inhibitor0.8671
CYP450 2D6 inhibitorNon-inhibitor0.938
CYP450 2C19 inhibitorNon-inhibitor0.9036
CYP450 3A4 inhibitorNon-inhibitor0.9502
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9413
Ames testNon AMES toxic0.9373
CarcinogenicityNon-carcinogens0.9607
BiodegradationNot ready biodegradable0.9697
Rat acute toxicity4.0254 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9348
hERG inhibition (predictor II)Inhibitor0.6172
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-ITTOF , negativeLC-MS/MSsplash10-0f9b-0002605980-2883c3d8483f8a68a52b

Taxonomy

Description
This compound belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Prenol lipids
Sub Class
Terpene glycosides
Direct Parent
Triterpene saponins
Alternative Parents
Triterpenoids / 12-hydroxysteroids / 14-alpha-methylsteroids / 3-beta-hydroxysteroids / Fatty acyl glycosides of mono- and disaccharides / Alkyl glycosides / O-glycosyl compounds / Oxanes / Monosaccharides / Cyclic alcohols and derivatives
show 6 more
Substituents
Triterpene saponin / Triterpenoid / 3-hydroxysteroid / 14-alpha-methylsteroid / 12-hydroxysteroid / Hydroxysteroid / 3-beta-hydroxysteroid / Steroid / Fatty acyl glycoside / Fatty acyl glycoside of mono- or disaccharide
show 18 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
beta-D-glucoside, tetracyclic triterpenoid, 12beta-hydroxy steroid, ginsenoside (CHEBI:67987) / Dammarenes (C08946)

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Curator comments
Ginsenoside Rg1 is a substrate and weak inhibitor of transporter.
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent uptake of organic anions such as 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotre...
Gene Name
SLCO1B3
Uniprot ID
Q9NPD5
Uniprot Name
Solute carrier organic anion transporter family member 1B3
Molecular Weight
77402.175 Da
References
  1. Jiang R, Dong J, Li X, Du F, Jia W, Xu F, Wang F, Yang J, Niu W, Li C: Molecular mechanisms governing different pharmacokinetics of ginsenosides and potential for ginsenoside-perpetrated herb-drug interactions on OATP1B3. Br J Pharmacol. 2015 Feb;172(4):1059-73. doi: 10.1111/bph.12971. Epub 2015 Jan 20. [PubMed:25297453]

Drug created on September 06, 2010 13:55 / Updated on November 02, 2018 06:19