NAV

ginkgolide-B

Identification

Generic Name
ginkgolide-B
DrugBank Accession Number
DB06744
Background

Not Available

Type
Small Molecule
Groups
Nutraceutical
Structure
3D
Similar Structures
Weight
Average: 424.3986
Monoisotopic: 424.136946988
Chemical Formula
C20H24O10
Synonyms
Not Available
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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
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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
Not Available
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 / Polyols
show 5 more
Substituents
Acetal / Alcohol / Aliphatic heteropolycyclic compound / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Cyclic alcohol / Diterpenoid / Furofuran / Gamma butyrolactone
show 13 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
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[8.7.2.0^{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]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

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. [Article]
PubChem Compound
6324617
PubChem Substance
99443280
ChemSpider
21105603
BindingDB
50251276
ChEMBL
CHEMBL514432
ZINC
ZINC000008552017

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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
Polarizability39.09 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/MSsplash10-004i-0000900000-a8e7b6a67994278d3299
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-01b9-0009300000-4cb740ebb681275c8bbf
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-0006900000-84e497373a644c403bb1
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-006y-0509300000-533f3c702f485dffaf5b
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-003r-0079300000-27861988193a1aa56f72
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-02tc-1900000000-dd61692ec581a33bf347
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-198.502126
predicted
DarkChem Lite v0.1.0
[M-H]-196.687526
predicted
DarkChem Lite v0.1.0
[M-H]-185.46439
predicted
DeepCCS 1.0 (2019)
[M+H]+198.312126
predicted
DarkChem Lite v0.1.0
[M+H]+197.106226
predicted
DarkChem Lite v0.1.0
[M+H]+187.52583
predicted
DeepCCS 1.0 (2019)
[M+Na]+198.046126
predicted
DarkChem Lite v0.1.0
[M+Na]+196.259126
predicted
DarkChem Lite v0.1.0
[M+Na]+193.91261
predicted
DeepCCS 1.0 (2019)

Drug created at September 06, 2010 19:32 / Updated at June 12, 2020 16:52