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Record Information
Version1.0
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
Description
Structure
Thumb
Synonyms
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
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

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point347.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logP3.02PERRISSOUD,D & TESTA,B (1986)
Predicted Properties
PropertyValueSource
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
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
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
UDP-glucuronosyltransferase 1-1UGT1A12q37P22309 details
TransportersNot Available
Metal BindingsNot Available
Receptors
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
Alien DawgDetected and Quantified0.000677 mg/g dry wt
    • David S. Wishart,...
details
GabriolaDetected and Quantified0.000823 mg/g dry wt
    • David S. Wishart,...
details
Island HoneyDetected and Quantified0.000422 mg/g dry wt
    • David S. Wishart,...
details
QuadraDetected and Quantified0.00061 mg/g dry wt
    • David S. Wishart,...
details
Sensi StarDetected and Quantified0.0027 mg/g dry wt
    • David S. Wishart,...
details
Tangerine DreamDetected and Quantified0.000418 mg/g dry wt
    • David S. Wishart,...
details
HMDB IDHMDB0002124
DrugBank IDDB07352
Phenol Explorer Compound ID228
FoodDB 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
References
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.

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

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