Record Information
Version1.0
Creation date2010-04-08 22:05:31 UTC
Update date2015-07-20 21:48:28 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). Thus, apigenin is considered to be a flavonoid lipid molecule. Apigenin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Apigenin is a bitter tasting compound. Apigenin is found, on average, in the highest concentration within a few different foods, such as parsley, malabar spinachs, and celery leaves and in a lower concentration in wild carrots, peppermints, and prunus (cherry, plum). Apigenin has also been detected, but not quantified in, several different foods, such as gingers, cascade huckleberries, jew's ears, coffee, and kiwis. This could make apigenin a potential biomarker for the consumption of these foods. Apigenin is a potentially toxic compound.
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
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)6.63ChemAxon
pKa (Strongest Basic)-5.2ChemAxon
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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 - Experimental
    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
    Spectrum TypeDescriptionSplash KeyView
    GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-00di-0000900000-b6d7fc88c039e719d164JSpectraViewer | MoNA
    GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-0433900000-b411d851fccc9f228d84JSpectraViewer | MoNA
    GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-03xv-1913500000-be46740b1210f9e106eeJSpectraViewer | MoNA
    GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00di-0000900000-b6d7fc88c039e719d164JSpectraViewer | MoNA
    Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00fu-0390000000-746c7fa7b11e53e27235JSpectraViewer
    Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0229-4222900000-fe657c625506c272a036JSpectraViewer
    LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-014i-0940000000-eb8b08c7beca627dc728JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-014i-0090000000-3fea3046af52ea21ae28JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-014i-0940000000-eb8b08c7beca627dc728JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-014i-0090000000-3fea3046af52ea21ae28JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-014i-0890000000-c8366acac0c0d42ae2e8JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-0udi-0920000000-812a3ee12823ec0b2025JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-003r-0194000200-b2908d4b21e6769c5a08JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00di-3970000000-5a23944b045cfe1763b1JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0090000000-0f608530bf761944dbf3JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0090000000-0c659ac43b543480168bJSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0690000000-e19eed49b8311d9cd339JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0910000000-57a56bfe2cce55357a11JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0900000000-b8799a618cff0ac84ddbJSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0490000000-f9a416c79166c84ca773JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0900000000-1499c7f2bceeb3e13f52JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0490000000-413a7da79773bc92a112JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0090000000-8f4d30104539ae85cd50JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0290000000-32e8793c17b364eee127JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0uea-0900000000-52147353f7af35162dabJSpectraViewer | MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0090000000-7c7c531f383cbaad5b23JSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0090000000-bb93867833cf83cbdb01JSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-7890000000-ef384ab54a966e53fb23JSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-31e5cabfee91b72de296JSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0090000000-12d2a0ddf52acf6dc93aJSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gdi-3960000000-847553cbcf5b653a9059JSpectraViewer
    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
    11beta-hydroxysteroid-dehydrogenase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
    anti ADDDUKE
    anti aflatoxin35222 A substance that diminishes the rate of a chemical reaction.DUKE
    anti aggregantDUKE
    anti aging52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
    anti allergic50857 A drug used to treat allergic reactions.DUKE
    anti angiogenic48422 An agent and endogenous substances that antagonize or inhibit the development of new blood vessels.DUKE
    anti arrhythmic38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
    anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
    anti cancer35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
    anti complementaryDUKE
    anti dermatitic50177 A drug used to treat or prevent skin disorders or for the routine care of skin.DUKE
    anti estrogenic35222 A substance that diminishes the rate of a chemical reaction.DUKE
    anti herpetic22587 A substance that destroys or inhibits replication of viruses.DUKE
    anti histaminic37956 Histamine antagonists are the drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists.DUKE
    anti HIV22587 A substance that destroys or inhibits replication of viruses.DUKE
    anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
    anti leukemic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
    anti melanomic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
    anti metastatic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
    anti mutagenicDUKE
    antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
    anti peristalticDUKE
    anti proliferantDUKE
    anti spasmodic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
    anti stress52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
    anti thyroidDUKE
    antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
    anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
    anxiolytic35474 Anxiolytic drugs are agents that alleviate anxiety, tension, and anxiety disorders, promote sedation, and have a calming effect without affecting clarity of consciousness or neurologic conditions.DUKE
    apoptoticDUKE
    aromatase inhibitor50790 An EC 1.14.14.* (oxidoreductase acting on paired donors, incorporating of 1 atom of oxygen, with reduced flavin or flavoprotein as one donor) inhibitor which interferes with the action of aromatase (EC 1.14.14.14) and so reduces production of estrogenic steroid hormones.DUKE
    beta-glucuronidase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
    calcium antagonist48706 Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances.DUKE
    cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
    cholereticDUKE
    central nervous system depressant35470 A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.DUKE
    cyclooxygenase-1 inhibitor50630 A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 1.DUKE
    cyclooxygenase-2 inhibitor50629 A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.DUKE
    cyclooxygenase inhibitor35544 A compound or agent that combines with cyclooxygenases (EC 1.14.99.1) and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of icosanoids, prostaglandins, and thromboxanes.DUKE
    cytochrome-P450-1A1 inhibitor50183 An enzyme inhibitor that interferes with the activity of cytochrome P450 involved in catalysis of organic substances.DUKE
    cytotoxic52209 A role played by the molecular entity or part thereof which causes the development of a pathological process.DUKE
    deiodinase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
    differentiatorDUKE
    diuretic35498 An agent that promotes the excretion of urine through its effects on kidney function.DUKE
    DNA-protectiveDUKE
    estrogenicDUKE
    HIF-1alpha inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
    hyaluronidase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
    hypotensiveDUKE
    ICAM-1 inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
    IKK inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
    iNOS inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
    inotropicDUKE
    interleukin-6 inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
    monoamine-oxidase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
    mitogen-activated-protein-kinase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
    musculotropicDUKE
    mutagenicDUKE
    myorelaxantDUKE
    NADPH-oxidase inhibitor50423 An EC 1.6.3.* (oxidoreductase acting on NADH or NADPH with oxygen as acceptor) inhibitor that interferes with the action of NAD(P)H oxidase (H2O2-forming), EC 1.6.3.1.DUKE
    NF-kappa-B inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
    nitric-oxide-synthase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
    nodulation signalDUKE
    ornithine-decarboxylase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
    cytochrome-P21 inducerDUKE
    pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
    protein kinase C inhibitor37700 An EC 2.7.11.* (protein-serine/threonine kinase) inhibitor that interferes with the action of protein kinase C (EC 2.7.11.13).DUKE
    polyamine synthesis inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
    progestationalDUKE
    protein-tyrosine-kinase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
    quinone-reductase inducerDUKE
    radioprotective35232 Any pharmaceutical compound containing a radioisotope.DUKE
    sedative35717 A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.DUKE
    sunscreen52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
    TNF-alpha inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
    topoisomerase-II inhibitor50750 A topoisomerase inhibitor that inhibits DNA topoisomerase (ATP-hydrolysing), EC 5.99.1.3 (topoisomerase II), which catalyses ATP-dependent breakage of both strands of DNA, passage of the unbroken strands through the breaks, and rejoining of the broken strands.DUKE
    topoisomerase-I inhibitor50276 A topoisomerase inhibitor that inhibits the bacterial enzymes of the DNA topoisomerases, Type I class (EC 5.99.1.2) that catalyze ATP-independent breakage of one of the two strands of DNA, passage of the unbroken strand through the break, and rejoining of the broken strand. These bacterial enzymes reduce the topological stress in the DNA structure by relaxing negatively, but not positively, supercoiled DNA.DUKE
    utero trophic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
    vasodilator35620 A drug used to cause dilation of the blood vessels.DUKE
    VEGF inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
    xanthine oxidase inhibitor35634 An EC 1.17.3.* (oxidoreductase acting on CH or CH2 with oxygen as acceptor) inhibitor that interferes with the action of xanthine oxidase (EC 1.17.3.2).DUKE
    EnzymesNot Available
    PathwaysNot Available
    MetabolismNot Available
    BiosynthesisNot Available
    Organoleptic Properties
    Flavours
    FlavorCitations
    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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    MSDSshow
    References
    Synthesis ReferenceNot Available
    General ReferenceNot Available
    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).