Record Information
Version1.0
Creation date2010-04-08 22:05:25 UTC
Update date2019-11-26 02:57:37 UTC
Primary IDFDB002558
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCaffeic acid
DescriptionCaffeic acid, also known as trans-caffeate or sodium caffeate, belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated. Caffeic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Caffeic acid has been detected, but not quantified in, several different foods, such as cereals and cereal products, chickpea, grape wines, common pea, and coffee and coffee products. This could make caffeic acid a potential biomarker for the consumption of these foods.
CAS Number331-39-5
Structure
Thumb
Synonyms
SynonymSource
3,4-Dihydroxy-trans-cinnamateChEBI
3,4-Dihydroxycinnamic acidChEBI
trans-CaffeateChEBI
3,4-Dihydroxy-trans-cinnamic acidGenerator
3,4-DihydroxycinnamateGenerator
CaffeateGenerator
Caffeic acid, monosodium saltHMDB
Caffeic acid, (e)-isomerHMDB
Sodium caffeateHMDB
(2E)-(3,4-Dihydroxyphenyl)-2-propenoic acidHMDB
(2E)-3-(3,4-Dihydroxyphenyl)-2-propenoic acidHMDB
(e)-3,4-Dihydroxycinnamic acidHMDB
(e)-3-(3,4-Dihydroxyphenyl)-2-propenoic acidHMDB
(e)-3-(3,4-Dihydroxyphenyl)acrylic acidHMDB
(e)-Caffeic acidHMDB
3,4-Dihydroxybenzeneacrylic acidHMDB
3-(3,4-Dihydroxyphenyl)-2-propenoic acidHMDB
3-(3,4-Dihydroxyphenyl)propenoic acidHMDB
4-(2'-Carboxyvinyl)-1,2-dihydroxybenzeneHMDB
4-(2-Carboxyethenyl)-1,2-dihydroxybenzeneHMDB
4-(2’-carboxyvinyl)-1,2-dihydroxybenzeneHMDB
DHCAHMDB
trans-3,4-Dihydroxycinnamic acidHMDB
Caffeic acidHMDB
3',4'-Dihydroxycinnamic acidHMDB
(2E)-3-(3,4-Dihydroxyphenyl)prop-2-enoic acid;HMDB
3,4-DihydroxybenzeneacrylateHMDB
3,4-Dihydroxycinnamic acid, 8CIdb_source
Caffeic acid pureHMDB
CaffeicacidHMDB
cis-CaffeateGenerator
cis-Caffeic acidChEBI
Predicted Properties
PropertyValueSource
Water Solubility1.61 g/LALOGPS
logP1.67ALOGPS
logP1.53ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)3.64ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity47.02 m³·mol⁻¹ChemAxon
Polarizability17.34 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC9H8O4
IUPAC name(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid
InChI IdentifierInChI=1S/C9H8O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1-5,10-11H,(H,12,13)/b4-2+
InChI KeyQAIPRVGONGVQAS-DUXPYHPUSA-N
Isomeric SMILESOC(=O)\C=C\C1=CC(O)=C(O)C=C1
Average Molecular Weight180.1574
Monoisotopic Molecular Weight180.042258744
Classification
Description Belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentHydroxycinnamic acids
Alternative Parents
Substituents
  • Cinnamic acid
  • Coumaric acid or derivatives
  • Hydroxycinnamic acid
  • Catechol
  • Styrene
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological 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 60.00%; H 4.48%; O 35.52%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 Data320 () (MeOH) (Berdy)DFC
    DensityNot Available
    Refractive IndexNot Available
    Spectra
    Spectra
    EI-MS/GC-MS
    TypeDescriptionSplash KeyView
    GC-MSCaffeic acid, 3 TMS, GC-MS Spectrumsplash10-014i-1593000000-b24e97b50ed1f50252f3Spectrum
    GC-MSCaffeic acid, non-derivatized, GC-MS Spectrumsplash10-001i-9800000000-bae43e98e22babcbf5a7Spectrum
    GC-MSCaffeic acid, non-derivatized, GC-MS Spectrumsplash10-000i-9600000000-6140146b8e32bda5e3c9Spectrum
    GC-MSCaffeic acid, non-derivatized, GC-MS Spectrumsplash10-014i-0593000000-16610dfa8ac4ac67a4c2Spectrum
    GC-MSCaffeic acid, non-derivatized, GC-MS Spectrumsplash10-014i-1593000000-b24e97b50ed1f50252f3Spectrum
    GC-MSCaffeic acid, non-derivatized, GC-MS Spectrumsplash10-014i-0592000000-1bb03bc99be6718d247eSpectrum
    Predicted GC-MSCaffeic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001i-1900000000-6a963e50b910f05b6825Spectrum
    Predicted GC-MSCaffeic acid, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00e9-5039000000-d55c6a31e04536d33b58Spectrum
    Predicted GC-MSCaffeic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    MS/MS
    TypeDescriptionSplash KeyView
    MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-03di-0900000000-f31bbdf32d6b72a381e72017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-90ad608487db4c1124692021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-001i-0900000000-dcc07d9a43defb5683a02021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-762c7a39be8e2819bc512021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0019-4900000000-e716811ee5cf56acce9e2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-000i-9000000000-ad7b879926d9c809f9c82021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-037f59c6ff1daadca2a02021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0019-6900000000-a67fe3c28be25c2fa72b2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0019-1900000000-62d755ec157c381054b32021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-6c93facd0d3caabc67f12021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-001r-0900000000-7b2d4553b6a25b853d4b2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-3ed879b5217c5d703cd52021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-014s-1900000000-d3c79213f8f23833fadc2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-3adb4dbfdaeb614b61e62021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-000i-9000000000-8f7413c3605b295159312021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-03di-2900000000-467621cde3e4486ad6bf2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-014i-0900000000-7fdae010c3ffe7ab11562021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-000i-9000000000-a67e2178525a89f45da92021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-8407d64b83bf427de33f2021-09-20View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0900000000-3f202efcd71f15f33da92016-08-03View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q0-1900000000-c772ffdf277b1e52c37a2016-08-03View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kdr-9700000000-5a4b1d97b748046bf13a2016-08-03View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-f196cd5c6ab6f34ffec72016-08-04View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0900000000-359be86d681a339215152016-08-04View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0913-2900000000-8a1b926d906ffae34e162016-08-04View Spectrum
    NMRNot Available
    ChemSpider ID1266077
    ChEMBL IDCHEMBL1320034
    KEGG Compound IDC01481
    Pubchem Compound ID1549111
    Pubchem Substance IDNot Available
    ChEBI IDNot Available
    Phenol-Explorer ID457
    DrugBank IDNot Available
    HMDB IDHMDB01964
    CRC / DFC (Dictionary of Food Compounds) IDCMK09-G:CMK09-G
    EAFUS IDNot Available
    Dr. Duke IDCIS-CAFFEIC-ACID|CAFFEIC-ACID|3,4-DIHYDROXYCINNAMIC-ACID
    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 IDCaffeic_acid
    Phenol-Explorer Metabolite ID457
    Duplicate IDSNot Available
    Old DFC IDSNot Available
    Associated Foods
    FoodContent Range AverageReference
    FoodReference
    Biological Effects and Interactions
    Health Effects / Bioactivities
    DescriptorIDDefinitionReference
    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
    Allergenic50904 A substance that triggers an immune response, causing allergic reactions. Its biological role is to stimulate the immune system, but it has no therapeutic applications. Key medical uses include diagnosing allergies and developing immunotherapies to desensitize patients to specific allergens, reducing the risk of severe reactions.DUKE
    Analgesic35480 An agent that relieves pain by reducing or blocking pain signals in the brain, commonly used to manage acute or chronic pain, inflammation, and fever, with therapeutic applications in surgery, injury, and disease treatment.DUKE
    Anti adenoviral22587 An agent that inhibits adenovirus replication, reducing infection severity. Therapeutically, it's used to treat adenovirus-related illnesses, such as conjunctivitis, gastroenteritis, and respiratory infections, particularly in immunocompromised patients.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-atherogenic38070 An agent that prevents or reduces the formation of atheromas (plaques) in arteries, thereby lowering the risk of cardiovascular disease. It inhibits the biological processes leading to atherosclerosis, and has therapeutic applications in managing hyperlipidemia, hypertension, and cardiovascular disease, with key medical uses including reducing inflammation and improving lipid profiles.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 carcinogenic35610 An agent that prevents or inhibits the formation of cancer, reducing tumor growth and proliferation. It plays a biological role in protecting cells from DNA damage and mutation. Therapeutically, it is used to prevent cancer development, with key medical applications in chemotherapy, radiation protection, and cancer prevention programs.DUKE
    Anti depressant52217 An agent that regulates mood, reducing symptoms of depression and anxiety by altering neurotransmitter levels in the brain, commonly used in managing depression, anxiety disorders, and other mood disorders.DUKE
    Anti-edemicAn agent that relieves or prevents edema, reducing abnormal fluid accumulation in tissues or the circulatory system, commonly used to treat conditions such as swelling, inflammation, and water retention.DUKE
    Anti elastase23924 An agent that inhibits elastase activity, reducing tissue damage and inflammation. It plays a biological role in protecting tissues from enzymatic degradation. Therapeutically, it is used to manage conditions such as chronic obstructive pulmonary disease (COPD), cystic fibrosis, and acute respiratory distress syndrome (ARDS), where excessive elastase activity contributes to disease progression.DUKE
    Anti-escherichicAn antibody binding to Escherichia-specific targets, playing a role in immune defense. Therapeutically, it is used to combat E. coli infections, with key medical applications in treating urinary tract infections, sepsis, and gastrointestinal diseases.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 gonadotropicAn agent that suppresses gonadotropin activity, specifically follicle-stimulating hormone (FSH) and luteinizing hormone (LH). Used to treat hormonally-sensitive cancers, delay puberty, and manage conditions like endometriosis and hypersexuality.DUKE
    Anti-hemolytic50248 An agent that prevents or reduces the breakdown of red blood cells, used to treat conditions such as hemolytic anemia, and other disorders where red blood cell destruction occurs, promoting healthy red blood cell count and preventing related complications.DUKE
    Anti hepatoadenomic35610 An agent that inhibits the growth of hepatoadenoma cells, reducing tumor size and preventing liver damage. It plays a biological role in regulating cell proliferation and apoptosis. Therapeutically, it is used to manage hepatocellular adenoma, a rare liver tumor, and has potential applications in treating liver cancer and other hepatic disorders.DUKE
    Anti hepatotoxic62868 An agent that protects the liver from damage, reducing toxicity and promoting liver health. It plays a biological role in preventing liver injury and supporting liver function. Therapeutically, it is used to treat liver diseases, such as hepatitis and cirrhosis, and to counteract liver-damaging effects of certain medications and toxins.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 hypercholesterolemicAn agent that prevents or controls an increase of cholesterol in the blood, playing a crucial role in reducing cardiovascular risk. Therapeutically, it helps manage hypercholesterolemia, preventing plaque buildup and lowering the risk of heart disease, making it a key treatment for conditions like atherosclerosis and coronary artery disease.DUKE
    Anti hyperthyroid52217 An agent that reduces thyroid hormone production, used to manage hyperthyroidism by decreasing thyroid-stimulating hormone (TSH) and thyroid hormone levels, commonly used to treat conditions such as Graves' disease and thyroid storm.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-legionella33282 An agent that targets and eliminates Legionella bacteria, reducing the risk of Legionnaires' disease and Pontiac fever. It plays a crucial role in water treatment and disinfection, with therapeutic applications in preventing outbreaks and managing related infections in healthcare settings and public water systems.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 leukotriene35222 An agent that blocks the action of leukotrienes, reducing inflammation and bronchoconstriction. Therapeutically, it is used to treat asthma, allergic rhinitis, and other respiratory disorders by inhibiting the biological role of leukotrienes in mediating inflammatory responses.DUKE
    Anti-melanogenic35610 An agent that inhibits melanin production, reducing skin pigmentation. It plays a biological role in regulating melanogenesis, and has therapeutic applications in treating hyperpigmentation disorders, such as melasma and freckles, and key medical uses in skin whitening and depigmentation treatments.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-nitrosaminicAn agent that inhibits the formation of nitrosamines, carcinogenic compounds. It plays a biological role in cancer prevention, with therapeutic applications in reducing the risk of tobacco-related and other cancers. Key medical uses include chemoprevention and protection against carcinogenic exposures.DUKE
    Anti ophidicAn antivenom agent used to treat venomous bites or stings, created by milking and diluting venom from relevant species, and injected to neutralize toxins, reducing inflammation and preventing systemic complications.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 peroxidantAn agent that prevents oxygen atom and peroxide formation, reducing oxidative stress and cell damage. It plays a biological role in protecting cells from free radicals. Therapeutically, it's used to manage conditions like cancer, Alzheimer's, and atherosclerosis, with key medical applications in neuroprotection, cardiovascular health, and anti-aging.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 prostaglandin49020 An agent that inhibits prostaglandin production, reducing inflammation and pain. Therapeutically, it's used to treat conditions like arthritis, menstrual cramps, and post-surgical pain, by blocking prostaglandin-mediated responses, providing relief from inflammation and discomfort.DUKE
    Anti radicularAn agent that relieves inflammation or irritation of the nerve root of a tooth, reducing pain and discomfort. Its biological role is to target and alleviate radicular pain, with therapeutic applications in endodontics and key medical uses in root canal treatments and tooth sensitivity management.DUKE
    Anti septic33281 An agent that prevents or reduces the growth of microorganisms, such as bacteria, fungi, or viruses, to promote wound healing and prevent infection. Therapeutically, anti septics are used to treat minor cuts, scrapes, and burns, and are commonly applied topically to reduce the risk of infection and promote tissue repair. Key medical uses include wound care, surgical site preparation, and skin infection management.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-staphylococcic33282 An agent that combats Staphylococcus infections, playing a crucial role in preventing bacterial growth. Therapeutically, it is used to treat skin and soft tissue infections, respiratory tract infections, and bloodstream infections. Key medical uses include treating methicillin-resistant Staphylococcus aureus (MRSA) and other staphylococcal infections, reducing the risk of infection and promoting wound healing.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 sunburn52217 An agent that protects the skin from sun damage, reducing inflammation and preventing burns. Its biological role is to absorb or reflect UV radiation, therapeutic applications include preventing skin cancer and photoaging, and key medical uses include treating sunburn, premature aging, and skin discoloration.DUKE
    Anti-thiaminA compound that destroys thiamine, used to study thiamine deficiency, with potential applications in managing thiamine-dependent conditions, and researching beriberi and Wernicke-Korsakoff syndrome.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
    Antitumor promoter35610 An agent that inhibits tumor growth and progression, reducing cancer cell proliferation. Therapeutically, it prevents tumor development and spread, with key medical uses in cancer prevention and treatment, particularly in combating carcinogenesis and metastasis.DUKE
    Anti-ulcerogenic49201 An agent that prevents or reduces the formation of ulcers, particularly in the stomach and intestines. It plays a biological role in protecting the mucosal lining, and has therapeutic applications in managing gastroesophageal reflux disease (GERD), peptic ulcers, and other gastrointestinal disorders.DUKE
    Anti-vaccinia22587 An antibody that neutralizes the vaccinia virus, used to treat complications from smallpox vaccination, such as eczema vaccinatum and progressive vaccinia, by reducing viral replication and promoting healing.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
    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
    Carcinogenic50903 An agent that causes cancer, damaging cellular DNA and disrupting normal cell growth. It has no therapeutic applications, but understanding its biological role informs cancer prevention and treatment strategies, with key medical uses in oncology research and risk assessment.DUKE
    Chemopreventive35610 An agent that prevents or delays the development of cancer, reducing the risk of tumor formation and progression. It plays a biological role in inhibiting carcinogenesis, and has therapeutic applications in cancer prevention, with key medical uses including reducing the risk of colorectal, breast, and prostate cancers.DUKE
    CholagogueAn agent that stimulates the release of bile from the gallbladder, promoting digestion and relieving bile duct issues. Therapeutically, it aids in treating gallstones, jaundice, and liver disorders, while also supporting digestive health.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
    ClastogenicAn agent inducing chromosomal breakages, leading to genetic mutations and rearrangements, with potential therapeutic applications in cancer treatment and research, and medical uses in genetic toxicology and mutagenesis studies.DUKE
    Central nervous system active35470 An agent that affects brain and spinal cord function, influencing mood, cognition, and physical responses. Therapeutically, it's used to manage neurological and psychiatric disorders, such as depression, anxiety, and insomnia, by modulating neurotransmitter activity and neural pathways.DUKE
    Collagen-sparingAn agent that preserves collagen, reducing its degradation and promoting tissue repair. It plays a biological role in maintaining skin and joint health. Therapeutically, it has applications in wound healing, osteoarthritis, and skin rejuvenation, with key medical uses in dermatology and orthopedics to prevent tissue damage and promote regeneration.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
    CytoprotectiveAn agent that protects cells from damage caused by noxious chemicals, oxidative stress, or other harmful stimuli, playing a key role in preventing cell injury and death. Therapeutically, cytoprotectives are used to treat conditions such as gastroesophageal reflux disease, mucositis, and neurodegenerative disorders, with applications in oncology, gastroenterology, and neurology.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
    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-activeAn agent that interacts with DNA, modifying its structure or function. It plays a biological role in gene regulation and repair. Therapeutically, DNA-active agents have applications in cancer treatment, genetic disorders, and infectious diseases, with key medical uses including chemotherapy, gene therapy, and antimicrobial therapy.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
    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
    Hepatocarcinogenic50903 An agent that promotes the development of liver cancer, having a harmful biological role. It has no therapeutic applications, but understanding its effects is crucial in liver cancer research and prevention. Key medical uses include studying liver carcinogenesis and developing strategies to mitigate its harmful effects.DUKE
    Hepatoprotective62868 An agent that protects the liver from damage, promoting liver health and function. It plays a biological role in reducing oxidative stress and inflammation, and has therapeutic applications in managing liver diseases, such as hepatitis and cirrhosis, and key medical uses in treating drug-induced liver injury and toxicities.DUKE
    HepatotropicAn agent with a special affinity for the liver, influencing its function and regeneration. It plays a biological role in liver repair and detoxification. Therapeutically, hepatotropics are used to treat liver diseases, such as hepatitis and cirrhosis, and have applications in managing liver cancer and promoting liver health.DUKE
    Histamine inhibitor37956 An agent that blocks histamine activity, reducing allergic responses and inflammation. Therapeutically, it's used to treat conditions like allergic rhinitis, urticaria, and itching. Key medical uses include relieving symptoms of allergies, itching, and hives, making it a common treatment for allergic reactions and skin disorders.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
    Leukotriene inhibitor35222 An agent that blocks the action of leukotrienes, reducing inflammation and bronchoconstriction. Therapeutically, it's used to manage asthma, allergic rhinitis, and other respiratory disorders by preventing leukotriene-mediated responses, thereby alleviating symptoms such as wheezing, coughing, and shortness of breath.DUKE
    Lipoxygenase inhibitor35856 An agent that blocks the activity of lipoxygenase enzymes, reducing inflammation and oxidative stress. Therapeutically, it's used to manage conditions like asthma, atherosclerosis, and cancer, by inhibiting the production of pro-inflammatory leukotrienes. Key medical uses include treating respiratory and cardiovascular diseases.DUKE
    Lyase inhibitor23924 An agent that blocks the activity of lyase enzymes, which break down biomolecules. It has therapeutic applications in reducing inflammation and oxidative stress, with key medical uses in managing cancer, cardiovascular disease, and neurodegenerative disorders.DUKE
    Metal chelator38161 An agent that binds to metal ions, reducing their toxicity and availability. It plays a biological role in regulating metal ion homeostasis and has therapeutic applications in treating metal poisoning, iron overload, and neurodegenerative diseases, with key medical uses including Wilson's disease and hemochromatosis management.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
    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
    ProoxidantAn agent that induces oxidative stress by generating reactive oxygen species (ROS) or inhibiting antioxidant systems, playing a role in cell damage and disease progression. Therapeutically, prooxidants have applications in cancer treatment, as they can selectively kill cancer cells. Key medical uses include cancer therapy and antimicrobial treatments.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
    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
    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
    Vulnerary73336 An agent that promotes wound healing, tissue repair, and skin regeneration. It facilitates the biological process of recovery, reducing inflammation and infection. Therapeutically, vulneraries are used to treat cuts, burns, ulcers, and other skin injuries, supporting the body's natural healing mechanisms and minimizing scarring.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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    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.
    — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).