ginkgolide-B

Identification

Name
ginkgolide-B
Accession Number
DB06744
Type
Small Molecule
Groups
Nutraceutical
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 424.3986
Monoisotopic: 424.136946988
Chemical Formula
C20H24O10
InChI Key
SQOJOAFXDQDRGF-MMQTXUMRSA-N
InChI
InChI=1S/C20H24O10/c1-6-12(23)28-11-9(21)18-8-5-7(16(2,3)4)17(18)10(22)13(24)29-15(17)30-20(18,14(25)27-8)19(6,11)26/h6-11,15,21-22,26H,5H2,1-4H3/t6-,7+,8-,9+,10+,11+,15+,17+,18+,19-,20-/m1/s1
IUPAC Name
(1R,3R,6R,7S,8S,10R,11R,12R,13S,16S,17R)-8-tert-butyl-6,12,17-trihydroxy-16-methyl-2,4,14,19-tetraoxahexacyclo[8.7.2.0¹,¹¹.0³,⁷.0⁷,¹¹.0¹³,¹⁷]nonadecane-5,15,18-trione
SMILES
C[C@@H]1C(=O)O[C@H]2[C@H](O)[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

Pharmacology

Indication
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

General References
  1. Wang SJ, Chen HH: Ginkgolide B, a constituent of Ginkgo biloba, facilitates glutamate exocytosis from rat hippocampal nerve terminals. Eur J Pharmacol. 2005 May 9;514(2-3):141-9. [PubMed:15910800]
External Links
PubChem Compound
6324617
PubChem Substance
99443280
ChemSpider
21105603
BindingDB
50251276
ChEMBL
CHEMBL514432

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 Solubility5.21 mg/mLALOGPS
logP0.49ALOGPS
logP-0.58ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)11.71ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area148.82 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity91.38 m3·mol-1ChemAxon
Polarizability39.2 Å3ChemAxon
Number of Rings6ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.7952
Blood Brain Barrier+0.7395
Caco-2 permeable-0.6884
P-glycoprotein substrateSubstrate0.5693
P-glycoprotein inhibitor INon-inhibitor0.7251
P-glycoprotein inhibitor IINon-inhibitor0.9375
Renal organic cation transporterNon-inhibitor0.9384
CYP450 2C9 substrateNon-substrate0.7957
CYP450 2D6 substrateNon-substrate0.8535
CYP450 3A4 substrateSubstrate0.5679
CYP450 1A2 substrateNon-inhibitor0.9307
CYP450 2C9 inhibitorNon-inhibitor0.9341
CYP450 2D6 inhibitorNon-inhibitor0.9449
CYP450 2C19 inhibitorNon-inhibitor0.9528
CYP450 3A4 inhibitorNon-inhibitor0.9335
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9699
Ames testNon AMES toxic0.5883
CarcinogenicityNon-carcinogens0.9065
BiodegradationNot ready biodegradable0.9788
Rat acute toxicity2.4970 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9961
hERG inhibition (predictor II)Non-inhibitor0.9662
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 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 / Polyols
show 5 more
Substituents
Ginkgolide-skeleton / Diterpenoid / Tricarboxylic acid or derivatives / Furofuran / Gamma butyrolactone / Cyclic alcohol / Tetrahydrofuran / Tertiary alcohol / Carboxylic acid ester / Lactone
show 13 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
Not Available

Drug created on September 06, 2010 13:32 / Updated on November 02, 2018 06:19