Gossypol

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Gossypol
DrugBank Accession Number
DB13044
Background

Gossypol has been used in trials studying the treatment of Non-small Cell Lung Cancer.

Type
Small Molecule
Groups
Investigational
Structure
Weight
Average: 518.5544
Monoisotopic: 518.194067936
Chemical Formula
C30H30O8
Synonyms
Not Available

Pharmacology

Indication

Not Available

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Contraindications & Blackbox Warnings
Prevent Adverse Drug Events Today
Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events with our Clinical API
Learn more
Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UBcl-2-like protein 1Not AvailableHumans
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 outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!
See the data
Improve decision support & research outcomes with our structured adverse effects data.
See a data sample
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.
DrugInteraction
AbciximabThe therapeutic efficacy of Abciximab can be decreased when used in combination with Gossypol.
AcenocoumarolThe therapeutic efficacy of Acenocoumarol can be decreased when used in combination with Gossypol.
AcetaminophenThe metabolism of Gossypol can be increased when combined with Acetaminophen.
AcetazolamideThe metabolism of Gossypol can be increased when combined with Acetazolamide.
AcetohexamideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Gossypol.
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Prenol lipids
Sub Class
Sesquiterpenoids
Direct Parent
Sesquiterpenoids
Alternative Parents
Naphthols and derivatives / Aryl-aldehydes / 1-hydroxy-4-unsubstituted benzenoids / Vinylogous acids / Polyols / Organic oxides / Hydrocarbon derivatives
Substituents
1-hydroxy-4-unsubstituted benzenoid / 1-naphthol / 2-naphthol / Aldehyde / Aromatic homopolycyclic compound / Aryl-aldehyde / Benzenoid / Cadinane sesquiterpenoid / Hydrocarbon derivative / Naphthalene
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
polyphenol (CHEBI:28584) / Cadinane sesquiterpenoids, Terpenoids, Cadinanes (C07667) / Cadinane sesquiterpenoids (LMPR0103330002)
Affected organisms
Not Available

Chemical Identifiers

UNII
KAV15B369O
CAS number
303-45-7
InChI Key
QBKSWRVVCFFDOT-UHFFFAOYSA-N
InChI
InChI=1S/C30H30O8/c1-11(2)19-15-7-13(5)21(27(35)23(15)17(9-31)25(33)29(19)37)22-14(6)8-16-20(12(3)4)30(38)26(34)18(10-32)24(16)28(22)36/h7-12,33-38H,1-6H3
IUPAC Name
1,1',6,6',7,7'-hexahydroxy-3,3'-dimethyl-5,5'-bis(propan-2-yl)-[2,2'-binaphthalene]-8,8'-dicarbaldehyde
SMILES
CC(C)C1=C2C=C(C)C(=C(O)C2=C(C=O)C(O)=C1O)C1=C(O)C2=C(C=O)C(O)=C(O)C(C(C)C)=C2C=C1C

References

General References
Not Available
Human Metabolome Database
HMDB0040723
KEGG Compound
C07667
PubChem Compound
3503
PubChem Substance
347829175
ChemSpider
3383
BindingDB
23223
ChEMBL
CHEMBL51483
ZINC
ZINC000003775575
PDBe Ligand
GO3
Wikipedia
Gossypol
PDB Entries
7yjj / 8gy6

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3Unknown StatusTreatmentNon-Small Cell Lung Cancer (NSCLC)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00385 mg/mLALOGPS
logP4.49ALOGPS
logP8.02Chemaxon
logS-5.1ALOGPS
pKa (Strongest Acidic)7.8Chemaxon
pKa (Strongest Basic)-6.1Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count8Chemaxon
Hydrogen Donor Count6Chemaxon
Polar Surface Area155.52 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity147.61 m3·mol-1Chemaxon
Polarizability55.98 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0udi-0000690000-9df7326dd4ce60b1088c
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0000090000-a3c078fc5668589d7a82
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0000090000-466d1a5e5ea678d79a6f
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0000490000-5075613211761bc90c49
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-014r-0000950000-bff403484652838c7e52
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ap3-0000910000-e37ed25b0a873a8c48f9
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4l-0000900000-6fde68ce0ca34310ce74
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-247.8474986
predicted
DarkChem Lite v0.1.0
[M-H]-247.4038986
predicted
DarkChem Lite v0.1.0
[M-H]-247.6464986
predicted
DarkChem Lite v0.1.0
[M-H]-220.1797
predicted
DeepCCS 1.0 (2019)
[M+H]+248.1184986
predicted
DarkChem Lite v0.1.0
[M+H]+247.5748986
predicted
DarkChem Lite v0.1.0
[M+H]+247.5256986
predicted
DarkChem Lite v0.1.0
[M+H]+222.07762
predicted
DeepCCS 1.0 (2019)
[M+Na]+248.1479986
predicted
DarkChem Lite v0.1.0
[M+Na]+247.8428986
predicted
DarkChem Lite v0.1.0
[M+Na]+247.5225986
predicted
DarkChem Lite v0.1.0
[M+Na]+227.90001
predicted
DeepCCS 1.0 (2019)

Targets

Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Learn more
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Protein kinase binding
Specific Function
Potent inhibitor of cell death. Inhibits activation of caspases. Appears to regulate cell death by blocking the voltage-dependent anion channel (VDAC) by binding to it and preventing the release of...
Gene Name
BCL2L1
Uniprot ID
Q07817
Uniprot Name
Bcl-2-like protein 1
Molecular Weight
26048.8 Da
References
  1. Bauer JA, Trask DK, Kumar B, Los G, Castro J, Lee JS, Chen J, Wang S, Bradford CR, Carey TE: Reversal of cisplatin resistance with a BH3 mimetic, (-)-gossypol, in head and neck cancer cells: role of wild-type p53 and Bcl-xL. Mol Cancer Ther. 2005 Jul;4(7):1096-104. [Article]

Drug created at October 21, 2016 02:22 / Updated at June 12, 2020 16:53