Record Information
Version1.0
Creation date2010-04-08 22:05:31 UTC
Update date2020-09-17 15:33:10 UTC
Primary IDFDB002798
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameApigenin
DescriptionApigenin, also known as chamomile or versulin, belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one). Apigenin is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. It exists as a yellow crystalline solid that has been used to dye wool. Apigenin is abundantly found in fruits and vegetables including parsley, celery and chamomile tea. It exhibits antiproliferative, anti-inflammatory, and antimetastatic activities through poorly defined mechanisms. Apigenin has shown significant promise as a skin cancer chemopreventive agent. In particular, apigenin inhibits the expression of involucrin (hINV), a marker of keratinocyte differentiation. Apigenin suppresses the 12-O-tetradeconylphorbol-13-acetate-dependent increase in AP1 factor expression and binding to the hINV promoter. Apigenin also inhibits the increase in promoter activity observed following overexpression of PKCdelta, constitutively active Ras, or MEKK1. The suppression of PKCdelta activity is associated with reduced phosphorylation of PKCdelta-Y311 (PMID: 16982614). Apigenin provides selective activity to promote caspase-dependent-apoptosis of leukemia cells (PMID: 16844095). Apigenin induces the expression of death receptor 5 (DR5) and synergistically acts with exogenous soluble recombinant human tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) to induce apoptosis in malignant tumor cells (PMID: 16648565). Apigenin is biosynthetically derived from the general phenylpropanoid pathway. The phenylpropanoid pathway starts from the aromatic amino acids L-phenylalanine or L-tyrosine, both products of the Shikimate pathway. L-phenylalanine is deaminated by phenylalanine ammonia lyase (PAL) to make cinnamate, followed by oxidation at the para position by cinnamate 4-hydroxylase (C4H) to produce p-coumarate. 4-coumarate CoA ligase (4CL) then substitutes coenzyme A (CoA) at the carboxy group of p-coumarate. Later chalcone synthase (CHS) uses consecutive condensations of three equivalents of malonyl CoA followed by aromatization to convert p-coumaroyl-CoA to chalcone. Chalcone isomerase (CHI) then isomerizes the product to close the pyrone ring to make naringenin. Finally, a flavanone synthase (FNS) enzyme oxidizes naringenin to apigenin (PMID: 12636085, 11524111)
CAS Number520-36-5
Structure
Thumb
Synonyms
SynonymSource
2-(p-Hydroxyphenyl)-5,7-dihydroxychromoneChEBI
4',5,7-TrihydroxyflavoneChEBI
5,7,4'-TrihydroxyflavoneChEBI
5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-benzopyroneChEBI
5,7-Dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-oneChEBI
C.I. natural yellow 1ChEBI
ChamomileChEBI
SpigeninChEBI
VersulinChEBI
4',5,7-Trihydroxy-flavoneHMDB
4,5, 7-TrihydroxyflavoneHMDB
5,7-Dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-oneHMDB
ApigenolHMDB
4’,5,7-TrihydroxyflavonePhytoBank
5,7,4’-TrihydroxyflavonePhytoBank
5,7-Dihydroxy-2-(4-Hydroxyphenyl)chromen-4-onePhytoBank
5,7-Dihydroxy-2-p-hydroxyphenyl-4-chromenonePhytoBank
ApegeninPhytoBank
ApigeninPhytoBank
ApigeninePhytoBank
2-(P-Hydroxyphenyl)-5,7-dihydroxychromoneChEBI
5,7-Dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one, 9CIdb_source
Pelargidenonedb_source
Predicted Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
logP3.07ALOGPS
logP2.71ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)6.57ChemAxon
pKa (Strongest Basic)-5.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity72.91 m³·mol⁻¹ChemAxon
Polarizability26.78 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC15H10O5
IUPAC name5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
InChI IdentifierInChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-7,16-18H
InChI KeyKZNIFHPLKGYRTM-UHFFFAOYSA-N
Isomeric SMILESOC1=CC=C(C=C1)C1=CC(=O)C2=C(O)C=C(O)C=C2O1
Average Molecular Weight270.2369
Monoisotopic Molecular Weight270.05282343
Classification
Description Belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one).
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavones
Direct ParentFlavones
Alternative Parents
Substituents
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Pyranone
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Vinylogous acid
  • Heteroaromatic compound
  • Organoheterocyclic compound
  • Oxacycle
  • Organic oxygen compound
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Foods
  • Cocoa and cocoa products
  • Grains:

    Nuts and legumes:

    Fruits and vegetables:

    Fats and oils:

    Beverages:

    Physico-Chemical Properties
    Physico-Chemical Properties - Experimental
    PropertyValueReference
    Physical stateSolid
    Physical DescriptionNot Available
    Mass CompositionC 66.67%; H 3.73%; O 29.60%DFC
    Melting PointMp 352°DFC
    Boiling PointNot Available
    Experimental Water SolubilityNot Available
    Experimental logP3.02PERRISSOUD,D & TESTA,B (1986)
    Experimental pKaNot Available
    Isoelectric pointNot Available
    ChargeNot Available
    Optical RotationNot Available
    Spectroscopic UV Data340 (e 20900) (MeOH) (Berdy)DFC
    DensityNot Available
    Refractive IndexNot Available
    Spectra
    Spectra
    EI-MS/GC-MS
    TypeDescriptionSplash KeyView
    GC-MSApigenin, 3 TMS, GC-MS Spectrumsplash10-00di-0000900000-b6d7fc88c039e719d164Spectrum
    GC-MSApigenin, non-derivatized, GC-MS Spectrumsplash10-00di-0433900000-b411d851fccc9f228d84Spectrum
    GC-MSApigenin, non-derivatized, GC-MS Spectrumsplash10-03xv-1913500000-be46740b1210f9e106eeSpectrum
    GC-MSApigenin, non-derivatized, GC-MS Spectrumsplash10-00di-0000900000-b6d7fc88c039e719d164Spectrum
    Predicted GC-MSApigenin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00fu-0390000000-746c7fa7b11e53e27235Spectrum
    Predicted GC-MSApigenin, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0229-4222900000-fe657c625506c272a036Spectrum
    Predicted GC-MSApigenin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    MS/MS
    TypeDescriptionSplash KeyView
    MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-014i-0940000000-eb8b08c7beca627dc7282017-08-14View Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-014i-0090000000-3fea3046af52ea21ae282017-08-14View Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-014i-0940000000-eb8b08c7beca627dc7282017-09-12View Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-014i-0090000000-3fea3046af52ea21ae282017-09-12View Spectrum
    MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-014i-0890000000-c8366acac0c0d42ae2e82017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-0udi-0920000000-812a3ee12823ec0b20252017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-003r-0194000200-b2908d4b21e6769c5a082017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00di-3970000000-5a23944b045cfe1763b12017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0090000000-0f608530bf761944dbf32017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0090000000-0c659ac43b543480168b2017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0690000000-e19eed49b8311d9cd3392017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0910000000-57a56bfe2cce55357a112017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0900000000-b8799a618cff0ac84ddb2017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0490000000-f9a416c79166c84ca7732017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0900000000-1499c7f2bceeb3e13f522017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0490000000-413a7da79773bc92a1122017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0090000000-8f4d30104539ae85cd502017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0290000000-32e8793c17b364eee1272017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0uea-0900000000-52147353f7af35162dab2017-09-14View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0090000000-7c7c531f383cbaad5b232016-08-03View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0090000000-bb93867833cf83cbdb012016-08-03View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-7890000000-ef384ab54a966e53fb232016-08-03View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-31e5cabfee91b72de2962016-08-03View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0090000000-12d2a0ddf52acf6dc93a2016-08-03View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gdi-3960000000-847553cbcf5b653a90592016-08-03View Spectrum
    NMRNot Available
    ChemSpider ID4444100
    ChEMBL IDCHEMBL28
    KEGG Compound IDC01477
    Pubchem Compound ID5280443
    Pubchem Substance IDNot Available
    ChEBI IDNot Available
    Phenol-Explorer ID228
    DrugBank IDDB07352
    HMDB IDHMDB02124
    CRC / DFC (Dictionary of Food Compounds) IDCNR54-G:CNR54-G
    EAFUS IDNot Available
    Dr. Duke IDAPIGENIN
    BIGG IDNot Available
    KNApSAcK IDC00003817
    HET IDAGI
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    Flavornet IDNot Available
    GoodScent IDNot Available
    SuperScent IDNot Available
    Wikipedia IDApigenin
    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
    11-beta-hydroxysteroid-dehydrogenase inhibitor23924 An agent that blocks the conversion of cortisone to cortisol, reducing glucocorticoid activity. Therapeutically, it's used to treat conditions like Cushing's syndrome, obesity, and metabolic disorders, by regulating cortisol levels and improving insulin sensitivity.DUKE
    Anti ADHDA medication that treats attention deficit hyperactivity disorder (ADHD), typically a stimulant that enhances focus, attention, and impulse control, promoting cognitive function and behavioral management.DUKE
    Anti aflatoxin35222 An agent that neutralizes or removes aflatoxins, toxic compounds produced by mold, reducing the risk of liver damage and cancer. Therapeutically, it is used to prevent aflatoxin poisoning, commonly in food safety and liver protection applications, and may have potential in cancer prevention and treatment.DUKE
    Anti-aggregantAn agent that prevents platelet aggregation, reducing blood clot formation. Its biological role is to inhibit platelet activation, and its therapeutic applications include preventing thrombosis and stroke. Key medical uses include treating cardiovascular diseases, such as myocardial infarction and atrial fibrillation, and managing conditions that increase the risk of blood clots.DUKE
    Anti-aging52217 An agent that slows or reverses cellular aging, promoting youthful function. Its biological role involves protecting against oxidative stress and DNA damage. Therapeutically, it has applications in dermatology, gerontology, and regenerative medicine, with key medical uses including skin rejuvenation, reducing age-related diseases, and improving overall healthspan.DUKE
    Anti-allergic50857 An agent that reduces or blocks allergic reactions, commonly used to manage symptoms of allergies, such as itching, sneezing, and inflammation, by inhibiting the release of histamine and other chemical mediators, providing relief in conditions like hay fever, asthma, and skin allergies.DUKE
    Anti-angiogenic48422 An agent that inhibits the formation of new blood vessels, playing a crucial role in cancer treatment by starving tumors of oxygen and nutrients. Therapeutically, it is used to manage cancer, age-related macular degeneration, and other diseases characterized by excessive angiogenesis, reducing tumor growth and slowing disease progression.DUKE
    Anti-arrhythmic38070 An agent that regulates heart rhythm, correcting irregular heartbeat patterns. Therapeutically, it restores normal cardiac function, commonly used to manage arrhythmias, prevent sudden cardiac death, and treat conditions like atrial fibrillation and ventricular tachycardia.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
    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 complementaryA substance that diminishes or abolishes the action of a complement, playing a role in regulating the immune system. Therapeutically, it's used to prevent excessive inflammation and tissue damage. Key medical uses include treating autoimmune disorders, transplant rejection, and inflammatory diseases.DUKE
    Anti dermatitic50177 An agent that reduces skin inflammation and irritation, commonly used to treat dermatitis, eczema, and other skin disorders, providing relief from itching, redness, and swelling.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-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 histaminic37956 An agent that blocks histamine receptors, reducing allergic symptoms. Therapeutically, it alleviates itching, sneezing, and runny nose, commonly used in managing allergies, itching, and hives, as well as treating conditions like anaphylaxis and allergic rhinitis.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-inflammatory35472 An agent that reduces inflammation, playing a biological role in suppressing immune responses and therapeutic applications in managing pain, swelling, and redness. Key medical uses include treating arthritis, allergies, and autoimmune disorders, as well as relieving symptoms of conditions such as asthma and dermatitis.DUKE
    Anti leukemic35610 An agent that targets and inhibits the growth of leukemia cells, playing a crucial role in cancer treatment. Therapeutically, it is used to induce remission, manage symptoms, and improve survival rates in patients with leukemia. Key medical uses include treating acute and chronic leukemia, lymphoma, and other hematological malignancies.DUKE
    Anti-melanomic35610 An agent that inhibits melanin production, reducing melanoma cell growth. It has therapeutic applications in treating skin cancers, particularly melanoma, and key medical uses include preventing tumor progression and metastasis, as well as managing pigmentation disorders.DUKE
    Anti metastatic35610 An agent that inhibits cancer cell spread, reducing tumor metastasis. It plays a biological role in blocking cell migration and invasion, and has therapeutic applications in cancer treatment. Key medical uses include preventing cancer recurrence and improving survival rates in patients with various types of cancer.DUKE
    Anti-mutagenicAn agent that interferes with the mutagenicity of a substance, preventing DNA damage and mutations. Its biological role is to protect cells from genetic alterations, and it has therapeutic applications in cancer prevention and treatment, as well as key medical uses in reducing the risk of genetic disorders and birth defects.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 peristalticAn agent that opposes the force of peristalsis, reducing muscle contractions in the digestive tract. Its biological role is to slow down gut movement, and it has therapeutic applications in managing diarrhea, irritable bowel syndrome, and gastrointestinal spasms. Key medical uses include treating bowel disorders and preventing opioid-induced constipation.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-spasmodic52217 An agent that relaxes smooth muscle, reducing muscle spasms and cramps. It plays a biological role in regulating muscle tone and is therapeutically applied to treat conditions such as irritable bowel syndrome, menstrual cramps, and muscle spasms, providing relief from abdominal pain and discomfort.DUKE
    Anti-stress52217 An agent that reduces stress symptoms, commonly used in managing anxiety disorders, promoting relaxation, and mitigating the biological effects of stress on the body, such as hypertension and immune suppression, with therapeutic applications in mental health and key medical uses in cardiology and neurology.DUKE
    Anti-thyroidAn agent that inhibits thyroid hormone production, used to treat hyperthyroidism by reducing thyroid hormone levels, commonly applied in managing conditions like Graves' disease.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
    Anxiolytic35474 An agent that reduces anxiety symptoms, commonly used in managing anxiety disorders, such as generalized anxiety disorder and panic disorder, by modulating neurotransmitters like GABA, promoting relaxation and calming effects.DUKE
    ApoptoticAn agent that stimulates programmed cell death, playing a crucial biological role in eliminating damaged or unwanted cells. It has therapeutic applications in cancer treatment, and key medical uses include inducing cell death in malignant cells, reducing tumor growth, and enhancing chemotherapy efficacy.DUKE
    Aromatase inhibitor50790 An agent that blocks the activity of aromatase, an enzyme converting androgens to estrogens, reducing estrogen levels. Therapeutically, it's used to treat hormone-sensitive breast cancer, endometriosis, and infertility, by decreasing estrogen-dependent growth and symptoms.DUKE
    Beta-glucuronidase inhibitor23924 An agent that blocks the activity of beta-glucuronidase, an enzyme that breaks down glucuronides. It reduces the toxicity of certain drugs and is used to manage conditions like cancer, inflammatory bowel disease, and irinotecan-induced diarrhea, improving treatment outcomes and reducing side effects.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
    Cancer preventive35610 An agent that inhibits the development and progression of cancer, reducing tumor formation and growth. It plays a biological role in blocking carcinogenic pathways, and has therapeutic applications in chemoprevention. Key medical uses include reducing the risk of cancer in high-risk individuals and preventing cancer recurrence.DUKE
    CholereticAn agent that increases bile production and secretion from the liver, enhancing digestion and fat absorption. Therapeutically, it's used to treat gallstones, liver disease, and indigestion, promoting healthy bile flow and liver function.DUKE
    Central nervous system depressant35470 An agent that slows brain activity, reducing anxiety, stress, and excitability. Therapeutically, it's used to manage insomnia, seizures, and anxiety disorders, promoting relaxation and sedation. Key medical uses include treating insomnia, epilepsy, and panic disorders, as well as inducing anesthesia.DUKE
    Cyclooxygenase-1 inhibitor50630 An agent that blocks the activity of cyclooxygenase-1 (COX-1), reducing inflammation and pain. Therapeutically, it is used to manage conditions like arthritis, and as a nonsteroidal anti-inflammatory drug (NSAID) to relieve pain, fever, and inflammation, while minimizing gastrointestinal side effects.DUKE
    Cyclooxygenase-2 inhibitor50629 An agent that blocks the activity of cyclooxygenase-2 (COX-2), reducing inflammation and pain. Therapeutically, it is used to manage conditions such as arthritis, menstrual cramps, and other inflammatory disorders, providing relief from symptoms with reduced gastrointestinal side effects compared to non-selective NSAIDs.DUKE
    Cyclooxygenase inhibitor35544 An agent that blocks the activity of cyclooxygenase enzymes, reducing inflammation and pain. Therapeutically, it is used to treat conditions such as arthritis, headaches, and menstrual cramps, by decreasing prostaglandin production, a key mediator of inflammation.DUKE
    Cytochrome-P450-1A1 inhibitor50183 An agent that blocks the activity of cytochrome-P450-1A1, an enzyme involved in metabolizing toxins and drugs. Therapeutically, it reduces toxicity and carcinogenesis, with applications in cancer prevention and treatment, as well as managing drug interactions and environmental toxin exposure.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
    Deiodinase inhibitor23924 An agent that blocks the activity of deiodinases, enzymes involved in thyroid hormone regulation. It reduces thyroid hormone conversion, commonly used in managing thyroid disorders, such as hyperthyroidism, and certain types of cancer, including thyroid cancer.DUKE
    DifferentiatorAn agent that induces cell differentiation, promoting mature cell formation. Its biological role involves regulating cell growth and development. Therapeutically, it has applications in cancer treatment, helping to mature cancer cells, making them more susceptible to chemotherapy. Key medical uses include leukemia and other malignancies, where differentiation therapy can improve treatment outcomes.DUKE
    Diuretic35498 An agent that increases urine production, helping remove excess fluids and salts from the body. It plays a key biological role in regulating fluid balance and blood pressure. Therapeutically, diuretics are used to treat conditions such as hypertension, edema, and heart failure, helping reduce swelling and lower blood pressure.DUKE
    DNA-protectiveAn agent that prevents or repairs DNA damage, playing a crucial role in maintaining genomic stability. Therapeutically, it has applications in cancer prevention, neuroprotection, and anti-aging. Key medical uses include reducing chemotherapy-induced DNA damage and mitigating radiation exposure effects.DUKE
    EstrogenicAn agent that mimics the effects of estrogen, regulating female reproductive processes and development. Therapeutically, estrogenic agents are used in hormone replacement therapy, contraception, and treating menopausal symptoms, as well as certain cases of osteoporosis and infertility.DUKE
    HIF-1alpha inhibitor35222 An agent that blocks the activity of hypoxia-inducible factor-1 alpha, reducing angiogenesis and tumor growth. Therapeutically, it has applications in cancer treatment, particularly for solid tumors, and may also be used to manage conditions involving excessive angiogenesis, such as retinal diseases.DUKE
    Hyaluronidase inhibitor23924 An agent that blocks the activity of hyaluronidase, an enzyme that breaks down hyaluronic acid. This inhibition helps maintain hyaluronic acid levels, reducing inflammation and improving tissue hydration, with therapeutic applications in ophthalmology, dermatology, and oncology, and key medical uses in treating dry eye, wrinkles, and certain cancers.DUKE
    HypotensiveAn agent that lowers blood pressure, playing a biological role in regulating cardiovascular function. Therapeutically, it's used to manage hypertension, heart failure, and angina, with key medical applications in preventing stroke, kidney disease, and cardiac complications.DUKE
    ICAM-1 inhibitor35222 An agent that blocks the activity of Intercellular Adhesion Molecule-1 (ICAM-1), reducing inflammation and immune cell adhesion. Therapeutically, it's used to treat conditions like multiple sclerosis, psoriasis, and ischemia/reperfusion injury, by minimizing immune cell infiltration and tissue damage.DUKE
    IKK inhibitor23924 An agent that blocks the activity of I_B kinase (IKK), reducing inflammation and immune responses. Therapeutically, it's used to treat autoimmune diseases, such as rheumatoid arthritis, and certain cancers, by inhibiting NF-_B signaling pathways.DUKE
    iNOS inhibitor23924 An agent that blocks the activity of inducible nitric oxide synthase (iNOS), reducing excessive nitric oxide production. It has therapeutic applications in managing inflammatory and neurodegenerative disorders, with key medical uses in treating conditions such as sepsis, arthritis, and stroke.DUKE
    InotropicAn agent that alters the force or energy of muscular contractions, particularly in the heart. It has therapeutic applications in treating heart failure and cardiogenic shock. Positively inotropic agents, such as digoxin, increase contraction strength, while negatively inotropic agents, like beta blockers, weaken it, commonly used to manage arrhythmias and hypertension.DUKE
    Interleukin-6 inhibitor35222 An agent that blocks the activity of interleukin-6, a cytokine involved in inflammation and immune response. Therapeutically, it reduces inflammation and is used to treat autoimmune diseases, such as rheumatoid arthritis, and certain types of cancer.DUKE
    Monoamine-oxidase inhibitor23924 An agent that blocks monoamine oxidase enzymes, increasing neurotransmitter levels. Therapeutically, it reduces depression symptoms and is commonly used in managing depression, anxiety disorders, and Parkinson's disease.DUKE
    Mitogen-activated-protein-kinase inhibitor23924 An agent that blocks the activity of mitogen-activated protein kinases, reducing inflammation and cell proliferation. Therapeutically, it's used to treat cancer, autoimmune diseases, and neurodegenerative disorders, by inhibiting signaling pathways involved in disease progression.DUKE
    MusculotropicAn agent that acts on muscle tissue, stimulating muscle activity and contraction. It plays a biological role in regulating muscle tone and movement. Therapeutically, musculotropic agents are used to treat muscle weakness, paralysis, and atrophy, with key medical applications in neurology and physical medicine.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
    MyorelaxantAn agent that reduces muscle contractility by blocking nerve impulses or decreasing motor end plate excitability, used therapeutically to relieve muscle spasms, tension, and pain, commonly in managing musculoskeletal disorders, anxiety, and insomnia.DUKE
    NADPH-oxidase inhibitor50423 An agent that blocks the activity of NADPH-oxidase, reducing oxidative stress and inflammation. Therapeutically, it's used to manage conditions like atherosclerosis, hypertension, and neurodegenerative diseases, by mitigating oxidative damage and improving cardiovascular health.DUKE
    NF-kappa-B inhibitor35222 An agent that blocks the activity of NF-kappa-B, a protein complex involved in inflammation and immune responses, reducing inflammation and cell proliferation. Therapeutically, it is used to treat conditions such as cancer, autoimmune disorders, and inflammatory diseases, including rheumatoid arthritis and asthma.DUKE
    Nitric-oxide-synthase inhibitor23924 An agent that blocks the activity of nitric oxide synthase, reducing nitric oxide production. It has therapeutic applications in managing hypertension, septic shock, and cerebral vasospasm, and is used to treat conditions such as erectile dysfunction and angina.DUKE
    Nodulation signalA signaling molecule produced by rhizobia bacteria, initiating nodule formation on legume roots, facilitating symbiotic nitrogen fixation. Its biological role is in plant-bacteria symbiosis. Therapeutic applications and key medical uses are being explored for potential agricultural and environmental benefits, such as improving soil fertility and reducing fertilizer dependence.DUKE
    Ornithine-decarboxylase inhibitor23924 An agent that blocks the activity of ornithine decarboxylase, an enzyme involved in cell growth and proliferation. It reduces polyamine synthesis, inhibiting tumor growth and proliferation. Therapeutically, it is used to treat cancer, particularly in combination with other therapies, and has potential applications in managing parasitic infections and skin disorders.DUKE
    Cytochrome-P21 inducerAn agent that increases the production of cytochrome P450 enzymes, enhancing drug metabolism. Therapeutically, it aids in detoxification and is used to manage conditions like cancer, where it boosts the efficacy of certain chemotherapies, and in treating drug overdoses by accelerating toxin clearance.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
    Protein kinase C inhibitor37700 An agent that blocks protein kinase C activity, reducing cell signaling and inflammation. Therapeutically, it's used to treat cancer, cardiovascular diseases, and neurological disorders, with key medical applications in managing Alzheimer's disease, diabetes, and stroke.DUKE
    Polyamine synthesis inhibitor35222 An agent that blocks the production of polyamines, essential for cell growth and proliferation, reducing cancer cell growth and tumor formation, with therapeutic applications in oncology, particularly in treating various types of cancer.DUKE
    ProgestationalAn agent that induces or supports the modifications of the female mammalian system, especially related to ovulation and corpus luteum formation, playing a key role in preparing the uterus for pregnancy. Therapeutically, progestational agents are used in hormone replacement therapy, contraception, and managing menstrual disorders.DUKE
    Protein-tyrosine-kinase inhibitor23924 An agent that blocks the activity of protein-tyrosine kinases, enzymes involved in cell signaling and growth. Therapeutically, it reduces abnormal cell proliferation, commonly used in managing cancer, particularly leukemia and solid tumors, by inhibiting tumor growth and angiogenesis.DUKE
    Quinone-reductase inducerAn agent that stimulates quinone reductase enzymatic activity, enhancing cellular antioxidant defenses and protecting against carcinogens, with therapeutic applications in cancer chemoprevention and potential uses in managing oxidative stress-related diseases.DUKE
    Radioprotective35232 An agent that shields cells from radiation damage, reducing oxidative stress and DNA harm. Its biological role is to mitigate radiation-induced injury, and it has therapeutic applications in cancer treatment, space exploration, and nuclear medicine, with key medical uses including protection of healthy tissues during radiation therapy.DUKE
    Sedative35717 An agent that calms nervous activity, reducing anxiety and inducing relaxation. Its biological role is to slow down brain function, promoting sleep and relieving stress. Therapeutically, sedatives are used to manage insomnia, anxiety disorders, and seizures, as well as to prepare patients for medical procedures.DUKE
    Sunscreen52217 A topical agent that blocks UV radiation, preventing skin damage and reducing the risk of skin cancer. Its therapeutic applications include protection against sunburn, photoaging, and photodermatoses. Key medical uses include prevention of melanoma, basal cell carcinoma, and squamous cell carcinoma, as well as management of photosensitive disorders.DUKE
    TNF-alpha inhibitor35222 An agent that blocks the activity of tumor necrosis factor-alpha, a pro-inflammatory cytokine, reducing inflammation and immune responses. Therapeutically used to treat autoimmune diseases, such as rheumatoid arthritis, psoriasis, and Crohn's disease, by decreasing inflammation and slowing disease progression.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
    Topoisomerase-I inhibitor50276 An agent that blocks the activity of topoisomerase I, an enzyme involved in DNA replication. It is used therapeutically in cancer treatment, particularly for solid tumors, by inducing DNA damage and inhibiting cancer cell growth, with key medical uses in colorectal, lung, and breast cancers.DUKE
    Utero trophic52217 A hormone that stimulates uterine growth and development, playing a crucial role in pregnancy. Therapeutically, it's used to support embryonic implantation and fetal development, with key medical applications in infertility treatments, such as in vitro fertilization (IVF) and recurrent miscarriage prevention.DUKE
    Vasodilator35620 An agent that widens blood vessels, reducing blood pressure and increasing blood flow. It plays a biological role in regulating cardiovascular function. Therapeutically, vasodilators are used to treat conditions such as hypertension, angina, and heart failure, improving oxygen delivery and reducing cardiac workload.DUKE
    VEGF inhibitor35222 An agent that blocks the activity of Vascular Endothelial Growth Factor (VEGF), reducing angiogenesis. Therapeutically, it's used to treat cancer, age-related macular degeneration, and diabetic retinopathy by inhibiting tumor growth and abnormal blood vessel formation.DUKE
    Xanthine oxidase inhibitor35634 An agent that blocks xanthine oxidase, an enzyme involved in uric acid production, reducing inflammation and oxidative stress. Therapeutically, it's used to treat gout, hyperuricemia, and prevent kidney stones, with key applications in managing cardiovascular disease and improving kidney function.DUKE
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    bitter
    1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
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    Synthesis ReferenceNot Available
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    Content Reference— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
    — U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
    — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).