Identification

Name
ginsenoside Rb1
Accession Number
DB06749
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. Rb1 appears to be most abundant in Panax quinquefolius (American Ginseng). Rb1 seems to affect the reproductive system in animal testicles. Recent research shows that Rb1 affects rat embryo development and has teratogenic effects, causing birth defects. Another study shows that Rb1 may increase testosterone production in male rats indirectly through the stimulation of the luteinizing hormone. Traditional Chinese medicine asserts that Panax quinquefolius promotes yin in the body. It also inhibits chemoinvasion and angiogenesis.

Structure
Thumb
Synonyms
  • Arasaponin E1
  • GRb 1
  • Gynosaponin c
  • Gypenoside III
  • Panax saponin e
  • Pseudoginsenoside d
  • Sanchinoside E1
Categories
UNII
7413S0WMH6
CAS number
41753-43-9
Weight
Average: 1109.2945
Monoisotopic: 1108.60293925
Chemical Formula
C54H92O23
InChI Key
JRZQHNRYHFRTFZ-MHMDWUMYSA-N
InChI
InChI=1S/C54H92O23/c1-22(2)10-9-13-54(8,77-49-45(69)41(65)38(62)31(74-49)21-70-47-43(67)39(63)35(59)28(18-55)71-47)25-12-15-53(7)34(25)27(58)17-26-33-23(3)16-32(51(4,5)24(33)11-14-52(26,53)6)75-50-46(42(66)37(61)30(20-57)73-50)76-48-44(68)40(64)36(60)29(19-56)72-48/h10,23-50,55-69H,9,11-21H2,1-8H3/t23-,24-,25+,26-,27-,28-,29-,30-,31-,32+,33?,34+,35-,36-,37-,38-,39+,40+,41+,42+,43-,44-,45-,46-,47-,48+,49+,50+,52-,53-,54+/m1/s1
IUPAC Name
(2S,3R,4S,5S,6R)-2-{[(2R,3R,4S,5S,6R)-4,5-dihydroxy-2-{[(1R,3R,5S,7R,10R,11R,14S,15R,16R)-16-hydroxy-3,6,6,10,11-pentamethyl-14-[(2S)-6-methyl-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}hept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl]oxy}-6-(hydroxymethyl)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
SMILES
C[C@@H]1C[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C(C)(C)[C@@H]2CC[C@]3(C)[C@H](C[C@@H](O)[C@@H]4[C@H](CC[C@@]34C)[C@](C)(CCC=C(C)C)O[C@@H]3O[C@H](CO[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)[C@@H](O)[C@H](O)[C@H]3O)C12

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
USolute carrier organic anion transporter family member 1B3
inhibitor
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
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
PubChem Compound
46937026
PubChem Substance
99443285
ChemSpider
26330343
ChEBI
67989

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 Solubility1.18 mg/mLALOGPS
logP-0.34ALOGPS
logP-1.6ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)11.75ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count23ChemAxon
Hydrogen Donor Count15ChemAxon
Polar Surface Area377.29 Å2ChemAxon
Rotatable Bond Count16ChemAxon
Refractivity266.96 m3·mol-1ChemAxon
Polarizability119.29 Å3ChemAxon
Number of Rings8ChemAxon
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

Taxonomy

Description
This compound belongs to the class of organic compounds known as steroidal glycosides. These are sterol lipids containing a carbohydrate moiety glycosidically linked to the steroid skeleton.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Steroidal glycosides
Direct Parent
Steroidal glycosides
Alternative Parents
Diterpene glycosides / 12-hydroxysteroids / 14-alpha-methylsteroids / Diterpenoids / Fatty acyl glycosides of mono- and disaccharides / Alkyl glycosides / Disaccharides / O-glycosyl compounds / Oxanes / Secondary alcohols
show 6 more
Substituents
Diterpene glycoside / Steroidal glycoside / Diterpenoid / 14-alpha-methylsteroid / Hydroxysteroid / 12-hydroxysteroid / Terpene glycoside / Fatty acyl glycoside / Fatty acyl glycoside of mono- or disaccharide / Alkyl glycoside
show 17 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
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 13:53 / Updated on May 01, 2018 23:23