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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:37 UTC
Update Date2021-10-13 04:37:39 UTC
HMDB IDHMDB0002124
Secondary Accession Numbers
  • HMDB02124
Metabolite Identification
Common NameApigenin
DescriptionApigenin is a plant-derived flavonoid that has significant promise as a skin cancer chemopreventive agent. Apigenin inhibits the expression of involucrin (hINV), a marker of keratinocyte differentiation, is increased by differentiating agents via a protein kinase Cdelta (PKCdelta), Ras, MEKK1, and MEK3 cascade that increases AP1 factor level and AP1 factor binding to DNA elements in the hINV promoter. 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. Activation of hINV promoter activity by the green tea polyphenol, (-)-epigellocathecin-3-gallate, is also inhibited by apigenin, suggesting that the two chemopreventive agents can produce opposing actions in keratinocytes (PMID: 16982614 ). Apigenin, a flavone abundantly found in fruits and vegetables, exhibits antiproliferative, anti-inflammatory, and antimetastatic activities through poorly defined mechanisms. This flavonoid provides selective activity to promote caspase-dependent-apoptosis of leukemia cells and uncover an essential role of PKCdelta during the induction of apoptosis by apigenin (PMID: 16844095 ). Apigenin markedly 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. On the other hand, apigenin-mediated induction of DR5 expression is not observed in normal human peripheral blood mononuclear cells. Moreover, apigenin does not sensitize normal human peripheral blood mononuclear cells to TRAIL-induced apoptosis (PMID: 16648565 ).
Structure
Data?1582752230
Synonyms
ValueSource
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
Chemical FormulaC15H10O5
Average Molecular Weight270.2369
Monoisotopic Molecular Weight270.05282343
IUPAC Name5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
Traditional Namechamomile
CAS Registry Number520-36-5
SMILES
OC1=CC=C(C=C1)C1=CC(=O)C2=C(O)C=C(O)C=C2O1
InChI Identifier
InChI=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
Chemical Taxonomy
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

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point347.5 °CNot Available
Boiling Point555.50 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility182.5 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP3.02PERRISSOUD,D & TESTA,B (1986)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
logP10(3.07) g/LALOGPS
logP10(2.71) g/LChemAxon
logS10(-3.4) g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ApigeninOC1=CC=C(C=C1)C1=CC(=O)C2=C(O)C=C(O)C=C2O14774.2Standard polar33892256
ApigeninOC1=CC=C(C=C1)C1=CC(=O)C2=C(O)C=C(O)C=C2O13018.9Standard non polar33892256
ApigeninOC1=CC=C(C=C1)C1=CC(=O)C2=C(O)C=C(O)C=C2O13172.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Apigenin,1TMS,isomer #1C[Si](C)(C)OC1=CC=C(C2=CC(=O)C3=C(O)C=C(O)C=C3O2)C=C13149.0Semi standard non polar33892256
Apigenin,1TMS,isomer #2C[Si](C)(C)OC1=CC(O)=CC2=C1C(=O)C=C(C1=CC=C(O)C=C1)O23039.7Semi standard non polar33892256
Apigenin,1TMS,isomer #3C[Si](C)(C)OC1=CC(O)=C2C(=O)C=C(C3=CC=C(O)C=C3)OC2=C13089.7Semi standard non polar33892256
Apigenin,2TMS,isomer #1C[Si](C)(C)OC1=CC=C(C2=CC(=O)C3=C(O[Si](C)(C)C)C=C(O)C=C3O2)C=C13065.7Semi standard non polar33892256
Apigenin,2TMS,isomer #2C[Si](C)(C)OC1=CC=C(C2=CC(=O)C3=C(O)C=C(O[Si](C)(C)C)C=C3O2)C=C13151.8Semi standard non polar33892256
Apigenin,2TMS,isomer #3C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C2C(=O)C=C(C3=CC=C(O)C=C3)OC2=C13066.8Semi standard non polar33892256
Apigenin,3TMS,isomer #1C[Si](C)(C)OC1=CC=C(C2=CC(=O)C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3O2)C=C13116.3Semi standard non polar33892256
Apigenin,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(C2=CC(=O)C3=C(O)C=C(O)C=C3O2)C=C13393.3Semi standard non polar33892256
Apigenin,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC(O)=CC2=C1C(=O)C=C(C1=CC=C(O)C=C1)O23295.2Semi standard non polar33892256
Apigenin,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)C=C(C3=CC=C(O)C=C3)OC2=C13346.7Semi standard non polar33892256
Apigenin,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(C2=CC(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C3O2)C=C13614.1Semi standard non polar33892256
Apigenin,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C(C2=CC(=O)C3=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)C=C13669.4Semi standard non polar33892256
Apigenin,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C=C(C3=CC=C(O)C=C3)OC2=C13609.0Semi standard non polar33892256
Apigenin,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(C2=CC(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)C=C13852.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Apigenin GC-MS (3 TMS)splash10-00di-0000900000-b6d7fc88c039e719d1642014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Apigenin GC-EI-TOF (Non-derivatized)splash10-00di-0433900000-b411d851fccc9f228d842017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Apigenin GC-EI-TOF (Non-derivatized)splash10-03xv-1913500000-be46740b1210f9e106ee2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Apigenin GC-MS (Non-derivatized)splash10-00di-0000900000-b6d7fc88c039e719d1642017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Apigenin GC-MS (Non-derivatized) - 70eV, Positivesplash10-00fu-0390000000-746c7fa7b11e53e272352017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Apigenin GC-MS (3 TMS) - 70eV, Positivesplash10-0229-4222900000-fe657c625506c272a0362017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Apigenin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Apigenin ESI-TOF 30V, Negative-QTOFsplash10-014i-0940000000-eb8b08c7beca627dc7282017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Apigenin ESI-TOF , Negative-QTOFsplash10-014i-0090000000-3fea3046af52ea21ae282017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Apigenin ESI-TOF 30V, Negative-QTOFsplash10-014i-0940000000-eb8b08c7beca627dc7282017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Apigenin ESI-TOF , Negative-QTOFsplash10-014i-0090000000-3fea3046af52ea21ae282017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Apigenin DI-ESI-qTof , Negative-QTOFsplash10-014i-0890000000-c8366acac0c0d42ae2e82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Apigenin DI-ESI-qTof , Positive-QTOFsplash10-0udi-0920000000-812a3ee12823ec0b20252017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Apigenin LC-ESI-qTof , Positive-QTOFsplash10-003r-0194000200-b2908d4b21e6769c5a082017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Apigenin LC-ESI-qTof , Positive-QTOFsplash10-00di-3970000000-5a23944b045cfe1763b12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Apigenin LC-ESI-QTOF , negative-QTOFsplash10-014i-0090000000-0f608530bf761944dbf32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Apigenin LC-ESI-QTOF , negative-QTOFsplash10-014i-0090000000-0c659ac43b543480168b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Apigenin LC-ESI-QTOF , negative-QTOFsplash10-014i-0690000000-e19eed49b8311d9cd3392017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Apigenin LC-ESI-QTOF , negative-QTOFsplash10-014i-0910000000-57a56bfe2cce55357a112017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Apigenin LC-ESI-QTOF , negative-QTOFsplash10-014i-0900000000-b8799a618cff0ac84ddb2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Apigenin LC-ESI-QTOF , negative-QTOFsplash10-014i-0490000000-f9a416c79166c84ca7732017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Apigenin LC-ESI-QTOF , negative-QTOFsplash10-014i-0900000000-1499c7f2bceeb3e13f522017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Apigenin LC-ESI-QTOF , negative-QTOFsplash10-014i-0490000000-413a7da79773bc92a1122017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Apigenin LC-ESI-QTOF , negative-QTOFsplash10-014i-0090000000-8f4d30104539ae85cd502017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Apigenin LC-ESI-QTOF , negative-QTOFsplash10-014i-0290000000-32e8793c17b364eee1272017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Apigenin LC-ESI-QTOF , negative-QTOFsplash10-0uea-0900000000-52147353f7af35162dab2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Apigenin 10V, Positive-QTOFsplash10-00di-0090000000-7c7c531f383cbaad5b232016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Apigenin 20V, Positive-QTOFsplash10-00di-0090000000-bb93867833cf83cbdb012016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Apigenin 40V, Positive-QTOFsplash10-0udi-7890000000-ef384ab54a966e53fb232016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Apigenin 10V, Negative-QTOFsplash10-014i-0090000000-31e5cabfee91b72de2962016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Apigenin 20V, Negative-QTOFsplash10-014i-0090000000-12d2a0ddf52acf6dc93a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Apigenin 40V, Negative-QTOFsplash10-0gdi-3960000000-847553cbcf5b653a90592016-08-03Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.0106 +/- 0.0123 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.0119 +/- 0.0126 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.127 +/- 0.081 uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.000222 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.00533 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.0110 +/- 0.0210 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDDB07352
Phenol Explorer Compound ID228
FooDB IDFDB002798
KNApSAcK IDC00003817
Chemspider ID4444100
KEGG Compound IDC01477
BioCyc IDCPD-431
BiGG IDNot Available
Wikipedia LinkApigenin
METLIN ID3397
PubChem Compound5280443
PDB IDNot Available
ChEBI ID18388
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000379
Good Scents IDrw1108801
References
Synthesis ReferenceChen, Xin; Li, Ping. Processes for the preparation of apigenin from naringin via rhoifolin or naringenin intermediate. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 9 pp
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Balasubramanian S, Zhu L, Eckert RL: Apigenin inhibition of involucrin gene expression is associated with a specific reduction in phosphorylation of protein kinase Cdelta Tyr311. J Biol Chem. 2006 Nov 24;281(47):36162-72. Epub 2006 Sep 18. [PubMed:16982614 ]
  2. Vargo MA, Voss OH, Poustka F, Cardounel AJ, Grotewold E, Doseff AI: Apigenin-induced-apoptosis is mediated by the activation of PKCdelta and caspases in leukemia cells. Biochem Pharmacol. 2006 Sep 14;72(6):681-92. Epub 2006 Jul 17. [PubMed:16844095 ]
  3. Horinaka M, Yoshida T, Shiraishi T, Nakata S, Wakada M, Sakai T: The dietary flavonoid apigenin sensitizes malignant tumor cells to tumor necrosis factor-related apoptosis-inducing ligand. Mol Cancer Ther. 2006 Apr;5(4):945-51. [PubMed:16648565 ]

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Apigenin → 3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxane-2-carboxylic aciddetails
Apigenin → 3,4,5-trihydroxy-6-{[7-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-5-yl]oxy}oxane-2-carboxylic aciddetails
Apigenin → 6-[4-(5,7-dihydroxy-4-oxo-4H-chromen-2-yl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails