Record Information
Created at2020-03-19 00:33:25 UTC
Updated at2022-12-13 19:31:28 UTC
CannabisDB IDCDB000370
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common 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. Apigenin is also one of 23 flavonoids that are found in cannabis plants (PMID: 6991645 ). 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 )
C.I. natural yellow 1ChEBI
4,5, 7-TrihydroxyflavoneHMDB
Chemical FormulaC15H10O5
Average Molecular Weight270.24
Monoisotopic Molecular Weight270.0528
IUPAC Name5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
Traditional Namechamomile
CAS Registry Number461015-54-3
InChI Identifier
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
Sub ClassFlavones
Direct ParentFlavones
Alternative Parents
  • 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

Route of exposure:


Biological location:


Industrial application:

Physical Properties
Experimental Properties
Melting Point347.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logP3.02PERRISSOUD,D & TESTA,B (1986)
Predicted Properties
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
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
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 - 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
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-014i-0090000000-7a9b77ceb393c92394122017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00vi-0290000000-c9cb9331a28763da83a82017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-014i-0940000000-eb8b08c7beca627dc7282017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 50V, Negativesplash10-014i-0900000000-072fb056044b71de29672021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-014i-0900000000-35e54babc71b9d557d7b2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-d0d7979a02697bd4d8fd2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-014i-0290000000-832bf870255aa3b016172021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0uea-0900000000-52147353f7af35162dab2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 75V, Negativesplash10-00am-0960000000-155c48a2761e351e02e32021-09-20View Spectrum
NMRNot Available
Protein Targets
Protein NameGene NameLocusUniprot IDDetails
UDP-glucuronosyltransferase 1-1UGT1A12q37P22309 details
TransportersNot Available
Metal BindingsNot Available
Protein NameGene NameLocusUniprot IDDetails
Taste receptor type 2 member 10TAS2R1012p13Q9NYW0 details
Taste receptor type 2 member 16TAS2R167q31.1-q31.3|7q31Q9NYV7 details
Taste receptor type 2 member 40TAS2R407q34P59535 details
Taste receptor type 2 member 3TAS2R37q31.3-q32Q9NYW6 details
Taste receptor type 2 member 4TAS2R47q31.3-q32Q9NYW5 details
Taste receptor type 2 member 7TAS2R712p13Q9NYW3 details
Taste receptor type 2 member 9TAS2R912p13Q9NYW1 details
Tumor necrosis factor receptor superfamily member 10BTNFRSF10B8p21.3O14763 details
Taste receptor type 2 member 50TAS2R5012p13.2P59544 details
Taste receptor type 2 member 38TAS2R387q34P59533 details
Taste receptor type 2 member 31TAS2R3112p13.2P59538 details
Taste receptor type 2 member 1TAS2R15p15.31Q9NYW7 details
Taste receptor type 2 member 20TAS2R2012p13.2P59543 details
Taste receptor type 2 member 39TAS2R397q34P59534 details
Taste receptor type 2 member 19TAS2R1912p13.2P59542 details
Taste receptor type 2 member 45TAS2R45P59539 details
Taste receptor type 2 member 30TAS2R3012p13.2P59541 details
Taste receptor type 2 member 42TAS2R42Q7RTR8 details
Taste receptor type 2 member 41TAS2R417q35P59536 details
Taste receptor type 2 member 43TAS2R4312p13.2P59537 details
Taste receptor type 2 member 5TAS2R57q34Q9NYW4 details
Taste receptor type 2 member 46TAS2R4612p13.2P59540 details
Taste receptor type 2 member 13TAS2R1312p13.2Q9NYV9 details
Taste receptor type 2 member 60TAS2R607q35P59551 details
Taste receptor type 2 member 8TAS2R812p13.2Q9NYW2 details
Taste receptor type 2 member 14TAS2R1412p13.2Q9NYV8 details
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
Alien DawgDetected and Quantified0.000677 mg/g dry wt
    • David S. Wishart,...
GabriolaDetected and Quantified0.000823 mg/g dry wt
    • David S. Wishart,...
Island HoneyDetected and Quantified0.000422 mg/g dry wt
    • David S. Wishart,...
QuadraDetected and Quantified0.00061 mg/g dry wt
    • David S. Wishart,...
Sensi StarDetected and Quantified0.0027 mg/g dry wt
    • David S. Wishart,...
Tangerine DreamDetected and Quantified0.000418 mg/g dry wt
    • David S. Wishart,...
DrugBank IDDB07352
Phenol Explorer Compound ID228
FoodDB IDFDB002798
KNApSAcK IDC00003817
Chemspider ID4444100
KEGG Compound IDC01477
BioCyc IDCPD-431
BiGG IDNot Available
Wikipedia LinkApigenin
PubChem Compound5280443
PDB IDNot Available
ChEBI ID18388
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
  2. 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. doi: 10.1074/jbc.M605368200. Epub 2006 Sep 18. [PubMed:16982614 ]
  3. 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. doi: 10.1016/j.bcp.2006.06.010. Epub 2006 Jul 17. [PubMed:16844095 ]
  4. 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. doi: 10.1158/1535-7163.MCT-05-0431. [PubMed:16648565 ]
  5. Austin MB, Noel JP: The chalcone synthase superfamily of type III polyketide synthases. Nat Prod Rep. 2003 Feb;20(1):79-110. doi: 10.1039/b100917f. [PubMed:12636085 ]
  6. Martens S, Forkmann G, Matern U, Lukacin R: Cloning of parsley flavone synthase I. Phytochemistry. 2001 Sep;58(1):43-6. doi: 10.1016/s0031-9422(01)00191-1. [PubMed:11524111 ]

Only showing the first 10 proteins. There are 27 proteins in total.


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:
Uniprot ID:
Molecular weight:

Only showing the first 10 proteins. There are 27 proteins in total.