ginkgolide-A

Identification

Name
ginkgolide-A
Accession Number
DB06743
Type
Small Molecule
Groups
Nutraceutical
Description

A highly active PAF antagonist cage molecule that is isolated from the leaves of the Ginkgo biloba tree. Shows potential in a wide variety of inflammatory and immunological disorders.

Structure
Thumb
Synonyms
  • Ginkgolide a
Categories
UNII
TAZ2DPR77B
CAS number
15291-75-5
Weight
Average: 408.3992
Monoisotopic: 408.142032366
Chemical Formula
C20H24O9
InChI Key
FPUXKXIZEIDQKW-VKMVSBOZSA-N
InChI
InChI=1S/C20H24O9/c1-7-12(22)26-10-6-17-9-5-8(16(2,3)4)18(17)11(21)13(23)28-15(18)29-20(17,14(24)27-9)19(7,10)25/h7-11,15,21,25H,5-6H2,1-4H3/t7-,8+,9-,10+,11+,15+,17-,18+,19-,20-/m1/s1
IUPAC Name
(1R,3R,6R,7S,8S,10R,11S,13S,16S,17R)-8-tert-butyl-6,17-dihydroxy-16-methyl-2,4,14,19-tetraoxahexacyclo[8.7.2.0¹,¹¹.0³,⁷.0⁷,¹¹.0¹³,¹⁷]nonadecane-5,15,18-trione
SMILES

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
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

Synthesis Reference

Koji Nakanishi, Nina Berova, Katsunori Tanaka, "Preparation Of Ginkgolide And F-Seco-Ginkgolide Lactols." U.S. Patent US20080306145, issued December 11, 2008.

US20080306145
General References
Not Available
External Links
PubChem Compound
9909368
PubChem Substance
99443279
ChemSpider
21468875
BindingDB
50292287
ChEMBL
CHEMBL465161

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 Solubility3.05 mg/mLALOGPS
logP1.21ALOGPS
logP0.34ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)11.77ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area128.59 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity90.17 m3·mol-1ChemAxon
Polarizability38.35 Å3ChemAxon
Number of Rings6ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9252
Blood Brain Barrier+0.8384
Caco-2 permeable-0.6669
P-glycoprotein substrateSubstrate0.6133
P-glycoprotein inhibitor INon-inhibitor0.649
P-glycoprotein inhibitor IINon-inhibitor0.7998
Renal organic cation transporterNon-inhibitor0.922
CYP450 2C9 substrateNon-substrate0.8544
CYP450 2D6 substrateNon-substrate0.8587
CYP450 3A4 substrateSubstrate0.6069
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9665
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.9056
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9863
Ames testNon AMES toxic0.5071
CarcinogenicityNon-carcinogens0.9182
BiodegradationNot ready biodegradable0.9898
Rat acute toxicity2.8802 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9936
hERG inhibition (predictor II)Non-inhibitor0.9252
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
MS/MS Spectrum - DI-ESI-qTof , NegativeLC-MS/MSNot Available
MS/MS Spectrum - DI-ESI-qTof , PositiveLC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as ginkgolides and bilobalides. These are diterpene lactones with a structure based either on the gingkolide or the bilobalide skeleton. The ginkgolide skeleton is a very rigid structure consisting of hexacyclic C20 trilactone. The cis-fused F/A/D/C ring junction forms an empty semi-ball hole, the D ring contains a cage form tetrahydrofuran ring which occupies the center of the empty hole, and the oxygen atoms of the D,C and F ring and 10-hydroxyl group consist of an analogous crown ether structure.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Prenol lipids
Sub Class
Terpene lactones
Direct Parent
Ginkgolides and bilobalides
Alternative Parents
Diterpenoids / Tricarboxylic acids and derivatives / Furofurans / Gamma butyrolactones / Tetrahydrofurans / Tertiary alcohols / Secondary alcohols / Cyclic alcohols and derivatives / Carboxylic acid esters / Oxacyclic compounds
show 4 more
Substituents
Ginkgolide-skeleton / Diterpenoid / Tricarboxylic acid or derivatives / Furofuran / Gamma butyrolactone / Cyclic alcohol / Tetrahydrofuran / Tertiary alcohol / Carboxylic acid ester / Lactone
show 12 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
Not Available

Drug created on September 06, 2010 13:28 / Updated on November 09, 2017 03:55