Gossypol
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This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.
Explore a selection of our essential drug information below, or:
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
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism AApoptosis regulator Bcl-2 regulatorHumans UBcl-2-like protein 1 Not Available Humans - 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbciximab The therapeutic efficacy of Abciximab can be decreased when used in combination with Gossypol. Acenocoumarol The therapeutic efficacy of Acenocoumarol can be decreased when used in combination with Gossypol. Acetaminophen The metabolism of Gossypol can be increased when combined with Acetaminophen. Acetazolamide The metabolism of Gossypol can be increased when combined with Acetazolamide. Acetohexamide The 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
- External Links
- 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
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data3 Unknown Status Treatment Non-Small Cell Lung Cancer (NSCLC) 1 somestatus stop reason just information to hide
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
Property Value Source Water Solubility 0.00385 mg/mL ALOGPS logP 4.49 ALOGPS logP 8.02 Chemaxon logS -5.1 ALOGPS pKa (Strongest Acidic) 7.8 Chemaxon pKa (Strongest Basic) -6.1 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 8 Chemaxon Hydrogen Donor Count 6 Chemaxon Polar Surface Area 155.52 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 147.61 m3·mol-1 Chemaxon Polarizability 55.98 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 247.8474986 predictedDarkChem Lite v0.1.0 [M-H]- 247.4038986 predictedDarkChem Lite v0.1.0 [M-H]- 247.6464986 predictedDarkChem Lite v0.1.0 [M-H]- 220.1797 predictedDeepCCS 1.0 (2019) [M+H]+ 248.1184986 predictedDarkChem Lite v0.1.0 [M+H]+ 247.5748986 predictedDarkChem Lite v0.1.0 [M+H]+ 247.5256986 predictedDarkChem Lite v0.1.0 [M+H]+ 222.07762 predictedDeepCCS 1.0 (2019) [M+Na]+ 248.1479986 predictedDarkChem Lite v0.1.0 [M+Na]+ 247.8428986 predictedDarkChem Lite v0.1.0 [M+Na]+ 247.5225986 predictedDarkChem Lite v0.1.0 [M+Na]+ 227.90001 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsApoptosis regulator Bcl-2
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Regulator
- General Function
- Suppresses apoptosis in a variety of cell systems including factor-dependent lymphohematopoietic and neural cells (PubMed:1508712, PubMed:8183370). Regulates cell death by controlling the mitochondrial membrane permeability (PubMed:11368354). Appears to function in a feedback loop system with caspases (PubMed:11368354). Inhibits caspase activity either by preventing the release of cytochrome c from the mitochondria and/or by binding to the apoptosis-activating factor (APAF-1) (PubMed:11368354). Also acts as an inhibitor of autophagy: interacts with BECN1 and AMBRA1 during non-starvation conditions and inhibits their autophagy function (PubMed:18570871, PubMed:20889974, PubMed:21358617). May attenuate inflammation by impairing NLRP1-inflammasome activation, hence CASP1 activation and IL1B release (PubMed:17418785)
- Specific Function
- Bh domain binding
- Gene Name
- BCL2
- Uniprot ID
- P10415
- Uniprot Name
- Apoptosis regulator Bcl-2
- Molecular Weight
- 26265.66 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
2. DetailsBcl-2-like protein 1
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General 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 the caspase activator, CYC1, from the mitochondrial membrane. Also acts as a regulator of G2 checkpoint and progression to cytokinesis during mitosis
- Specific Function
- Bh domain binding
- Gene Name
- BCL2L1
- Uniprot ID
- Q07817
- Uniprot Name
- Bcl-2-like protein 1
- Molecular Weight
- 26048.8 Da
References
- 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 August 26, 2024 19:23