Ginkgolide A
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Identification
- Generic Name
- Ginkgolide A
- DrugBank Accession Number
- DB06743
- Background
Ginkgolide A is 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.
- Type
- Small Molecule
- Groups
- Nutraceutical
- Structure
- Weight
- Average: 408.3992
Monoisotopic: 408.142032366 - Chemical Formula
- C20H24O9
- Synonyms
- Ginkgolide-A
- External IDs
- BN 52020
- BN-52020
Pharmacology
- Indication
Not Available
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- 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
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- 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
- Acetal / Alcohol / Aliphatic heteropolycyclic compound / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Cyclic alcohol / Diterpenoid / Furofuran / Gamma butyrolactone show 12 more
- Molecular Framework
- Aliphatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- TAZ2DPR77B
- CAS number
- 15291-75-5
- 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[8.7.2.0^{1,11}.0^{3,7}.0^{7,11}.0^{13,17}]nonadecane-5,15,18-trione
- SMILES
- C[C@@H]1C(=O)O[C@H]2C[C@@]34[C@H]5C[C@@H](C(C)(C)C)[C@@]33[C@@H](O)C(=O)O[C@H]3O[C@@]4(C(=O)O5)[C@@]12O
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
- ChEBI
- 5355
- ChEMBL
- CHEMBL465161
- ZINC
- ZINC000004245650
Clinical Trials
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
Property Value Source Water Solubility 3.05 mg/mL ALOGPS logP 1.21 ALOGPS logP 0.34 Chemaxon logS -2.1 ALOGPS pKa (Strongest Acidic) 11.77 Chemaxon pKa (Strongest Basic) -4.1 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 128.59 Å2 Chemaxon Rotatable Bond Count 1 Chemaxon Refractivity 90.17 m3·mol-1 Chemaxon Polarizability 38.24 Å3 Chemaxon Number of Rings 6 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9252 Blood Brain Barrier + 0.8384 Caco-2 permeable - 0.6669 P-glycoprotein substrate Substrate 0.6133 P-glycoprotein inhibitor I Non-inhibitor 0.649 P-glycoprotein inhibitor II Non-inhibitor 0.7998 Renal organic cation transporter Non-inhibitor 0.922 CYP450 2C9 substrate Non-substrate 0.8544 CYP450 2D6 substrate Non-substrate 0.8587 CYP450 3A4 substrate Substrate 0.6069 CYP450 1A2 substrate Non-inhibitor 0.9046 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.9665 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.9056 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9863 Ames test Non AMES toxic 0.5071 Carcinogenicity Non-carcinogens 0.9182 Biodegradation Not ready biodegradable 0.9898 Rat acute toxicity 2.8802 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9936 hERG inhibition (predictor II) Non-inhibitor 0.9252
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 195.1978156 predictedDarkChem Lite v0.1.0 [M-H]- 194.8582156 predictedDarkChem Lite v0.1.0 [M-H]- 186.31558 predictedDeepCCS 1.0 (2019) [M+H]+ 196.4412156 predictedDarkChem Lite v0.1.0 [M+H]+ 196.1376156 predictedDarkChem Lite v0.1.0 [M+H]+ 188.37784 predictedDeepCCS 1.0 (2019) [M+Na]+ 194.8432156 predictedDarkChem Lite v0.1.0 [M+Na]+ 195.1897156 predictedDarkChem Lite v0.1.0 [M+Na]+ 194.75975 predictedDeepCCS 1.0 (2019)
Drug created at September 06, 2010 19:28 / Updated at June 12, 2020 16:52