Identification
Nameginkgolide-A
Accession NumberDB06743
TypeSmall Molecule
GroupsNutraceutical
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
External IDs Not Available
Product Ingredients Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
Categories
UNIITAZ2DPR77B
CAS number15291-75-5
WeightAverage: 408.3992
Monoisotopic: 408.142032366
Chemical FormulaC20H24O9
InChI KeyFPUXKXIZEIDQKW-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
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot 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 ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials Not Available
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot 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
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , NegativeNot Available
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassPrenol lipids
Direct ParentGinkgolides and bilobalides
Alternative ParentsDiterpenoids / Tricarboxylic acids and derivatives / Furofurans / Gamma butyrolactones / Tetrahydrofurans / Tertiary alcohols / Secondary alcohols / Cyclic alcohols and derivatives / Carboxylic acid esters / Oxacyclic compounds
SubstituentsGinkgolide-skeleton / Diterpenoid / Tricarboxylic acid or derivatives / Furofuran / Gamma butyrolactone / Cyclic alcohol / Tetrahydrofuran / Tertiary alcohol / Carboxylic acid ester / Lactone
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Drug created on September 06, 2010 13:28 / Updated on September 01, 2017 11:30