Record Information
Version1.0
Creation date2010-04-08 22:04:41 UTC
Update date2025-11-18 22:22:03 UTC
Primary IDFDB000742
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGossypol
DescriptionGossypol, also known as gossypol, (+)-isomer or (-)-gossypol, is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. Thus, gossypol is considered to be an isoprenoid lipid molecule. Gossypol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Gossypol can be found in cottonseed, okra, soy bean, and sunflower, which makes gossypol a potential biomarker for the consumption of these food products. Gossypol is a non-carcinogenic (not listed by IARC) potentially toxic compound. Among other things, 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. Other researchers are investigating the anticancer properties of gossypol . Gossypol may cause apoptosis via the regulation of Bax and Bcl-2 proteins. It is also an inhibitor of calcineurin and protein kinases C, and has been shown to bind calmodulin (L1239) (T3DB).
CAS Number303-45-7
Structure
Thumb
Synonyms
SynonymSource
(+)-GossypolHMDB
(+-)-GossypolHMDB
(+/-)-gossypolHMDB
(R)-(-)-GossypolHMDB
(R)-GossypolHMDB
Dipotassium salt, gossypolHMDB, MeSH
GossypolHMDB
Gossypol dipotassium saltHMDB, MeSH
Gossypol from cotton seedsHMDB
Gossypol sodium saltHMDB, MeSH
Gossypol, (+)-isomerHMDB, MeSH
Gossypol, (+-)-isomerHMDB, MeSH
Gossypol, (-)-isomerHMDB, MeSH
PogosinHMDB
Racemic-gossypolHMDB
Sodium salt, gossypolHMDB, MeSH
Tash 1HMDB
1,1',6,6',7,7'-Hexahydroxy-3,3'-dimethyl-5,5'-bis(1-methylethyl)-[2,2'-binaphthalene]-8,8'-dicarboxaldehyde, 9CIdb_source
Thespesindb_source
Predicted Properties
PropertyValueSource
Water Solubility0.0038 g/LALOGPS
logP4.49ALOGPS
logP8.02ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)7.8ChemAxon
pKa (Strongest Basic)-6.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area155.52 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity147.61 m³·mol⁻¹ChemAxon
Polarizability55.95 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC30H30O8
IUPAC name7-[8-formyl-1,6,7-trihydroxy-3-methyl-5-(propan-2-yl)naphthalen-2-yl]-2,3,8-trihydroxy-6-methyl-4-(propan-2-yl)naphthalene-1-carbaldehyde
InChI IdentifierInChI=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
InChI KeyQBKSWRVVCFFDOT-UHFFFAOYSA-N
Isomeric SMILESCC(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
Average Molecular Weight518.5544
Monoisotopic Molecular Weight518.194067936
Classification
Description Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentSesquiterpenoids
Alternative Parents
Substituents
  • Cadinane sesquiterpenoid
  • Sesquiterpenoid
  • 2-naphthol
  • 1-naphthol
  • Naphthalene
  • Aryl-aldehyde
  • 1-hydroxy-4-unsubstituted benzenoid
  • Benzenoid
  • Vinylogous acid
  • Polyol
  • Organic oxygen compound
  • Organooxygen compound
  • Aldehyde
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 69.49%; H 5.83%; O 24.68%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data375 (e 15850) (MeOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSGossypol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0udi-0000690000-9df7326dd4ce60b1088cSpectrum
Predicted GC-MSGossypol, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0002-0000019000-f115e0a1dfade9af2f9bSpectrum
Predicted GC-MSGossypol, TMS_4_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGossypol, TMS_5_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGossypol, TMS_5_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGossypol, "(-)-Gossypol,4TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000190000-afd3b7806ba77c385fc92016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-016r-1030970000-364f0989158c0f8675912016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pb9-5030940000-cb58d99e7632b192bd4d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000090000-55621847e31c93e5127f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-066r-0070390000-dda96ff17c65a2928ec92016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4u-1390300000-346fa91db1c09ffd5bec2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000090000-fb746155c08fc86203982021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014r-0000950000-e97a10851934b81a75052021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-0000900000-5335728bfd70100979352021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000090000-4887f71c2e78af6991412021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0000390000-01a16a8a515827651a3e2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-0002910000-b9dfdfbb4b3c355cb8f02021-09-24View Spectrum
NMRNot Available
ChemSpider ID3383
ChEMBL IDCHEMBL51483
KEGG Compound IDC07667
Pubchem Compound ID3503
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB0040723
CRC / DFC (Dictionary of Food Compounds) IDBGS60-C:BGS60-C
EAFUS IDNot Available
Dr. Duke IDGOSSYPOL
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDGossypol
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
Angiotensin converting enzyme inhibitor35457 An agent that blocks the conversion of angiotensin I to angiotensin II, reducing blood pressure and fluid retention. Therapeutically, it's used to treat hypertension, heart failure, and protect kidney function in diabetes, thereby reducing the risk of cardiovascular disease and stroke.DUKE
Aldose reductase inhibitor48550 An agent that blocks the activity of aldose reductase, an enzyme involved in glucose metabolism. It reduces oxidative stress and inflammation, commonly used in managing diabetic complications, such as neuropathy, nephropathy, and retinopathy.DUKE
Amebicide33281 An agent that kills or inhibits the growth of amoebas, used to treat amoebic infections such as amoebic dysentery and liver abscess, commonly targeting Entamoeba histolytica.DUKE
AnaphrodisiacAn agent that reduces or suppresses sexual desire, used therapeutically to manage hypersexuality, sex addiction, or paraphilias, and in treating conditions like priapism or excessive sexual arousal.DUKE
Anti bacterial33282 An agent that inhibits the growth of or destroys bacteria, playing a crucial role in preventing and treating infections. Therapeutically, it is used to combat bacterial infections, with key medical applications including treating pneumonia, tuberculosis, and skin infections, as well as preventing surgical site infections and sepsis.DUKE
Antibiotic22582 An agent that inhibits the growth of or destroys microorganisms, particularly bacteria. Therapeutically, antibiotics are used to treat bacterial infections, such as pneumonia, tuberculosis, and skin infections, by targeting specific biochemical processes essential for microbial survival.DUKE
Anti-cancer35610 An agent that inhibits the growth and proliferation of cancer cells, used to treat and manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, to reduce tumor size, prevent metastasis, and improve patient survival.DUKE
Anti corpus-luteumAn antibody detecting ovarian dysfunction by targeting corpus luteum hormone levels, aiding in diagnosing reproductive disorders, and monitoring fertility and menstrual health.DUKE
Anti-encephalitic52217 An agent that combats encephalitis, reducing inflammation and viral replication in the brain. Its therapeutic applications include treating viral encephalitis, such as herpes simplex and Japanese encephalitis, to alleviate symptoms and prevent neurological damage, ultimately improving patient outcomes.DUKE
Anti estrogenic35222 An agent that blocks or reduces estrogen's effects, used to treat hormone-sensitive cancers, such as breast cancer, and manage conditions like endometriosis and uterine fibroids, by inhibiting estrogen's biological role in promoting cell growth.DUKE
Anti feedantA substance that inhibits normal feeding behavior, found in certain plants, deterring insects and animals from consuming them. Its therapeutic applications include pest control, while key medical uses involve managing insect-borne diseases and reducing crop damage.DUKE
Anti-fertilityAn agent that inhibits reproduction, playing a biological role in population control. Therapeutically, it's used as a contraceptive, with key medical applications in family planning and birth control, preventing unwanted pregnancies and managing reproductive health.DUKE
Anti-flu22587 An agent that prevents or treats influenza virus infections, reducing symptoms and complications. Its biological role involves blocking viral replication, and its therapeutic applications include prophylaxis and treatment of flu outbreaks. Key medical uses include reducing the risk of flu-related hospitalizations and mortality, especially in high-risk populations such as the elderly and young children.DUKE
Anti-herpetic22587 An agent that inhibits the replication of herpes viruses, reducing symptoms and severity of infections. Therapeutically, it is used to treat herpes simplex (HSV-1 and HSV-2) and varicella-zoster virus (VZV) infections, commonly used in managing genital herpes, cold sores, and shingles.DUKE
Anti HIV22587 An agent that prevents the replication of the Human Immunodeficiency Virus (HIV), used to treat and manage HIV infection and Acquired Immunodeficiency Syndrome (AIDS), reducing viral load and slowing disease progression.DUKE
Anti implantationAn agent that prevents the adherence of the blastocyst to the uterine wall, playing a biological role in regulating fertility. Therapeutically, it is used to prevent pregnancy, with key medical applications in contraception and family planning.DUKE
Anti keratiticAn agent that prevents or treats corneal inflammation, promoting healing and reducing scarring. Its biological role is to inhibit keratitis, a condition characterized by corneal inflammation. Therapeutically, it is used to manage corneal ulcers, abrasions, and infections, key medical uses include treating eye injuries and infections.DUKE
Anti-malarial33281 An agent that prevents or treats malaria, a disease caused by Plasmodium parasites. It works by targeting the parasite's life cycle, reducing symptoms and preventing transmission. Therapeutically, anti-malarials are used to treat and prevent malaria, as well as to manage related conditions such as babesiosis and toxoplasmosis.DUKE
Anti-oxidant22586 An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects.DUKE
Anti plasmodial33281 An agent that inhibits the growth of Plasmodium parasites, reducing malaria symptoms. Therapeutically, it's used to treat and prevent malaria, with key medical applications including prophylaxis and treatment of malaria infections.DUKE
Anti progesterone49020 An agent that blocks the activity of progesterone, a hormone involved in pregnancy and menstrual cycle regulation. Therapeutically, it is used to terminate early pregnancies, manage endometriosis, and treat conditions like uterine fibroids, with key medical applications in gynecology and reproductive health.DUKE
Anti proliferantAn agent that prevents or inhibits cell growth and division, used therapeutically to treat cancer, manage tumor growth, and prevent restenosis after angioplasty, reducing abnormal cell proliferation.DUKE
Anti rabies22587 An agent that prevents rabies virus infection, used therapeutically to treat bites or exposure, and medically to provide post-exposure prophylaxis, preventing the development of rabies disease.DUKE
Anti-spermatogenicAn agent that blocks spermatogenesis, inhibiting male fertility. Its biological role is to suppress sperm production. Therapeutically, it has applications in male contraception and treating conditions like benign prostatic hyperplasia and prostate cancer. Key medical uses include regulating hormonal imbalances and managing fertility-related issues.DUKE
Anti-stomatiticAn agent that relieves inflammation of the mucous membrane of the mouth, reducing oral discomfort and pain. Its biological role is to soothe and protect the mucosa, with therapeutic applications in managing mouth ulcers, oral thrush, and other stomatitis-related conditions. Key medical uses include treating oral inflammation, irritation, and infections.DUKE
Anti-testosterone35222 An agent that blocks the activity of testosterone, reducing its effects on the body. Therapeutically, it's used to treat conditions like prostate cancer, acne, and excessive hair growth. Key medical uses include hormone-sensitive cancer treatment, managing polycystic ovary syndrome (PCOS), and gender affirmation therapy for transgender individuals.DUKE
Anti trypanosomic33281 An agent that targets and eliminates trypanosomes, parasites causing diseases like sleeping sickness and Chagas disease. It plays a crucial role in treating and preventing these diseases, with therapeutic applications in tropical medicine and key medical uses in treating parasitic infections.DUKE
Antitumor35610 An agent that inhibits tumor growth and proliferation, playing a crucial role in cancer treatment. Therapeutically, antitumors are used to manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, helping to reduce tumor size, prevent metastasis, and improve patient outcomes.DUKE
Anti-viral22587 An agent that inhibits the replication of viruses, playing a crucial role in preventing and treating viral infections. Therapeutically, anti-virals are used to manage diseases such as HIV, herpes, and influenza, reducing symptoms and slowing disease progression. Key medical uses include treating viral hepatitis, respiratory syncytial virus, and COVID-19.DUKE
Avicide33289 A bird toxin inhibitor, avicide plays a biological role in controlling bird populations. Therapeutically, it has applications in managing bird-related diseases and pests. Key medical uses include preventing avian-borne illnesses and protecting crops from bird damage, while also being used in research to study bird behavior and ecology.DUKE
Calcium antagonist48706 A medication that blocks calcium ion entry into cells, reducing muscle contraction and vascular resistance. It treats hypertension, angina, and arrhythmias by dilating blood vessels and decreasing cardiac workload, commonly used in managing cardiovascular diseases.DUKE
Contraceptive52217 An agent that prevents pregnancy by inhibiting ovulation, fertilization, or implantation, used to control birth rates, manage menstrual disorders, and reduce the risk of sexually transmitted infections, commonly applied in various forms such as pills, injections, and barrier methods.DUKE
Cytotoxic52209 An agent that kills or damages cells, playing a biological role in immune responses and therapeutic applications in cancer treatment. Key medical uses include chemotherapy, targeting and destroying cancer cells, and treating certain autoimmune diseases by eliminating harmful cells.DUKE
Fungicide24127 An agent that kills or inhibits the growth of fungi, playing a biological role in preventing fungal infections. Therapeutically, it is used to treat fungal diseases, with key medical applications including athlete's foot, ringworm, and candidiasis, as well as agricultural uses to protect crops from fungal damage.DUKE
Hepatotoxic50908 An agent that causes liver damage or toxicity, disrupting normal liver function. It has no therapeutic applications, but is often a side effect of certain medications, such as acetaminophen overdose, and is a key consideration in medical uses, including monitoring liver function during drug therapy.DUKE
HypokalemicA condition characterized by abnormally low potassium levels in the blood, playing a crucial role in muscle and nerve function. Therapeutically, it is managed with potassium supplements. Key medical uses include treating muscle weakness, fatigue, and heart arrhythmias, while also preventing complications in conditions like kidney disease and hormonal imbalances.DUKE
Immunostimulant50847 An agent that stimulates the immune system, enhancing its response to infections and diseases. Therapeutically, it boosts the body's natural defenses, commonly used to treat immunodeficiency disorders, prevent infections, and support cancer treatment, as well as manage chronic conditions like hepatitis and HIV.DUKE
Insectifuge24852 A substance that repels insects, playing a biological role in plant defense. Therapeutically, it has applications in preventing insect-borne diseases. Key medical uses include topical repellents for malaria, dengue fever, and other vector-borne illnesses, reducing the risk of transmission.DUKE
InterferonogenicAn agent that stimulates interferon production, enhancing immune response to pathogens, with therapeutic applications in treating viral infections and cancers, and key medical uses in immunotherapy and antiviral treatments.DUKE
LarvicideAn insecticide that targets the larval life stage of insects, preventing their development into adults. Its biological role is to control insect populations, and its therapeutic applications include managing mosquito-borne diseases such as malaria and dengue fever, as well as controlling pest infestations in agriculture and public health.DUKE
LibidolyticAn agent that reduces or suppresses libido, commonly used in managing hypersexuality, sex addiction, or paraphilic disorders, and sometimes in treating hormonal imbalances or certain psychiatric conditions.DUKE
MutagenicAn agent that induces genetic mutations, altering DNA sequences. It plays a biological role in evolution and adaptation. Therapeutically, mutagenic agents are used in cancer treatment, such as chemotherapy, and in gene therapy to introduce beneficial traits. Key medical uses include oncology and genetic research.DUKE
NematistatAn agent that disorients, paralyzes, or confuses nematodes, preventing root infestation, with potential therapeutic applications in agriculture and key medical uses in managing parasitic nematode infections.DUKE
ParalyticAn agent that induces temporary paralysis or muscle relaxation, used therapeutically to facilitate surgical procedures, manage muscle spasms, and treat conditions like tetanus and seizures, by blocking nerve transmission to muscles.DUKE
Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.DUKE
ProstaglandigenicAn agent that promotes the production of prostaglandins, which are hormonelike compounds that stimulate uterine contractions, among other effects. Therapeutically, prostaglandigenic agents are used to induce labor, manage postpartum hemorrhage, and treat certain gynecological conditions, showcasing their key role in obstetrics and women's health.DUKE
Prostaglandin synthesis inhibitor35222 An agent that blocks the production of prostaglandins, reducing inflammation and pain. Therapeutically, it's used to treat conditions like arthritis, menstrual cramps, and fever, commonly found in nonsteroidal anti-inflammatory drugs (NSAIDs).DUKE
SpermicideA contraceptive substance that destroys sperm, inserted vaginally prior to intercourse to prevent pregnancy, serving as a non-hormonal birth control method.DUKE
Topoisomerase-II inhibitor50750 An agent that blocks the activity of topoisomerase-II, an enzyme involved in DNA replication. It prevents cancer cell growth by disrupting DNA structure, commonly used in chemotherapy to treat various types of cancer, including leukemia and lymphoma.DUKE
Toxic52209 A substance that can harm or poison living organisms. Biologically, it can disrupt cellular functions and cause damage. Therapeutically, toxins are used in small, controlled doses for applications such as cancer treatment and immunosuppression. Key medical uses include chemotherapy and immunotherapy, where toxins are used to target and destroy diseased cells.DUKE
Tumorigenic50903 An agent or factor that promotes tumor formation and growth, playing a key role in cancer development. Therapeutically, understanding tumorigenic mechanisms informs cancer treatment strategies, with applications in oncology for developing targeted therapies to inhibit tumor growth and progression.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).