Structure Database (LMSD)

Common Name
Gossypol
Systematic Name
Synonyms
LM ID
LMPR0103330002
Formula
Exact Mass
Calculate m/z
518.19407
Status
Curated


Classification

Biological Context

Gossypol is a racemic mixture of natural polyphenols isolated from parts of the cotton plant (genus Gossypium). It causes infertility in a variety of cotton pests and spermatogenesis arrest in humans.1 Gossypol also has antimalarial properties, preventing the growth of P. falciparum at low micromolar concentrations.2 It inhibits aldose reductase (Ki = 0.5 µM).3 Gossypol also acts as an anticancer agent, inhibiting cell growth in various cancer cell lines, in part by blocking the anti-apoptotic functions of Bcl-2 and Bcl-xL, again at low micromolar concentrations.4

This information has been provided by Cayman Chemical

References

1. Coutinho, E.M. Gossypol: A contraceptive for men. Contraception 65(4), 259-263 (2002).
2. Deck, L.M., Vander Jagt, D.L., and Royer, R.E. Gossypol and derivatives: A new class of aldose reductase inhibitors. J. Med. Chem. 34(11), 3301-3305 (1991).
4. Yan, F., Cao, X.X., Jiang, H.X., et al. A novel water-soluble gossypol derivative increases chemotherapeutic sensitivity and promotes growth inhibition in colon cancer. J. Med. Chem. 53(15), 5502-5510 (2010).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Gossypium hirsutum (#3635)
Magnoliopsida (#3398)
Hemigossypol, a constituent in developing glanded cottonseed (Gossypium hirsutum).,
J Agric Food Chem, 2012
Pubmed ID: 22369216

String Representations

InChiKey (Click to copy)
QBKSWRVVCFFDOT-UHFFFAOYSA-N
InChi (Click to copy)
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
SMILES (Click to copy)
C12C=C(C(C3C(C)=CC4C(C(C)C)=C(C(O)=C(C=O)C=4C=3O)O)=C(O)C=1C(C=O)=C(C(O)=C2C(C)C)O)C

Other Databases

Wikipedia
KEGG ID
HMDB ID
PubChem CID
Cayman ID
PDB ID
GuidePharm ID

Calculated Physicochemical Properties

Heavy Atoms 38
Rings 4
Aromatic Rings 4
Rotatable Bonds 5
Van der Waals Molecular Volume 473.16
Topological Polar Surface Area 155.52
Hydrogen Bond Donors 6
Hydrogen Bond Acceptors 8
logP 6.38
Molar Refractivity 145.31

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Created at
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Updated at
22nd Mar 2024