Structure via PubChem · Public domain (PubChem)
gossypol
Sign in to saveGossypol () is a natural phenol derived from the cotton plant (genus Gossypium). Gossypol is a phenolic aldehyde that permeates cells and acts as an inhibitor for several dehydrogenase enzymes. It is a yellow pigment. The structure exhibits atropisomerism, with the two enantiomers having different biochemical properties.
Chemical data
- Formula
- C30H30O8
- Molecular weight
- 518.6 g/mol
- IUPAC name
- 7-(8-formyl-1,6,7-trihydroxy-3-methyl-5-propan-2-ylnaphthalen-2-yl)-2,3,8-trihydroxy-6-methyl-4-propan-2-ylnaphthalene-1-carbaldehyde
- SMILES
- CC1=CC2=C(C(=C(C(=C2C(C)C)O)O)C=O)C(=C1C3=C(C4=C(C=C3C)C(=C(C(=C4C=O)O)O)C(C)C)O)O
- InChIKey
- QBKSWRVVCFFDOT-UHFFFAOYSA-N
- XLogP
- 6.9
- Polar surface area
- 156 Ų
- H-bond donors
- 6
- H-bond acceptors
- 8
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 3
- Molecule type
- Small molecule
- Indications
- non-small cell lung carcinoma
via ChEMBL · EBI
Research
2,424 papers- Gossypol: phytoalexin of cotton.Science China. Life sciences · 2016
- Gossypol and Semisynthetic Derivatives: Chemistry, Bioactivities, and Mechanism of Actions.Chemistry & biodiversity · 2025
- Gossypol-hypokalaemia interrelationships.International journal of andrology · 1985
- Natural Product Gossypol and its Derivatives in Precision Cancer Medicine.Current medicinal chemistry · 2019
- Gossypol--a polyphenolic compound from cotton plant.Advances in food and nutrition research · 2009
via PubMed
Wikidata facts
- Has part
- carbon
- Mass
- 518.194068
Show 4 more facts
- found in taxon
- Anoda cristata
- Commons category
- Gossypol
- chemical formula
- C₃₀H₃₀O₈
- canonical SMILES
- CC1=C(C(=C2C(=C1)C(=C(C(=C2C=O)O)O)C(C)C)O)C3=C(C=C4C(=C3O)C(=C(C(=C4C(C)C)O)O)C=O)C
Sources (3)
via Wikidata · CC0
~6 min read
Encyclopedic overview
7 sectionsContents
- History
- Biosynthesis
- Research
- Contraception
- Toxicity
- References
- External links
Gossypol () is a natural phenol derived from the cotton plant (genus Gossypium). Gossypol is a phenolic aldehyde that permeates cells and acts as an inhibitor for several dehydrogenase enzymes. It is a yellow pigment. The structure exhibits atropisomerism, with the two enantiomers having different biochemical properties.
Among other applications, it has been tested as a male oral contraceptive in China. In addition to its putative contraceptive properties, gossypol has also long been known to possess antimalarial properties.
Excerpted from Wikipedia’s “gossypol” article, available under the CC BY-SA 4.0 licence.