Showing Compound Card for Cannflavin A (CDB000742)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (2) Show 3 proteinsXML
Record Information
Version1.0
Created at2020-03-19 00:54:20 UTC
Updated at2020-12-07 19:07:44 UTC
CannabisDB IDCDB000742
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameCannflavin A
DescriptionCannflavin A belongs to the class of organic compounds known as 6-prenylated flavones. These are flavones that features 2 units of C5-isoprenoid substituent at the 6-position. There are three known cannflavins including Cannflavin A, B and C. Cannflavins are unique to Cannabis sativa (PMID: 3754224 ). Cannflavin A was first identified as a cannabis constituent in 1980s (PMID: 18774146 ). Chemically, cannflavins are prenylflavonoids and are unrelated to THC and other cannabinoids. Cannflavin A is biosynthesized via the prenylation of chrysoeriol (PMID: 31151063 ). Specifically, an aromatic prenyltransferase (CsPT3) catalyzes the regiospecific addition of geranyl diphosphate (GPP) to the methylated flavone, chrysoeriol to produce Cannflavin A. Chrysoeriol is produced through the conversion of luteolin via the O-methyltransferase (CsOMT21) (PMID: 31151063 ). Cannflavin A is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Cannflavins exhibit anti-inflammatory activity that is thirty times that of aspirin (PMID: 31151063 ). It has been found that cannflavin A is an inhibitor of prostaglandin E2 production which appears to help explain its strong anti-inflammatory properties (PMID: 3859295 ; PMID: 3754224 ). Cannflavins were the first flavonoids identified to have direct inhibitory activity of two important pro-inflammatory mediators: arachidonate 5-lipoxygenase (5-LOX) and prostaglandin E synthase (mPGES-1).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
CannflavinMeSH
Cannflavin bMeSH
Canniflavone 2PhytoBank
Chemical FormulaC21H20O6
Average Molecular Weight368.39
Monoisotopic Molecular Weight368.126
IUPAC Name6-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-chromen-4-one
Traditional Namecannflavin A
CAS Registry NumberNot Available
SMILES
COC1=C(O)C=CC(=C1)C1=CC(=O)C2=C(O1)C=C(O)C(CC=C(C)C)=C2O
InChI Identifier
InChI=1S/C21H20O6/c1-11(2)4-6-13-15(23)9-19-20(21(13)25)16(24)10-17(27-19)12-5-7-14(22)18(8-12)26-3/h4-5,7-10,22-23,25H,6H2,1-3H3
InChI KeyIXCUTZUASDSIJO-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 6-prenylated flavones. These are flavones that features a C5-isoprenoid substituent at the 6-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavones
Direct Parent6-prenylated flavones
Alternative Parents
Substituents
  • 6-prenylated flavone
  • 3p-methoxyflavonoid-skeleton
  • Hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Chromone
  • Methoxyphenol
  • Monoterpenoid
  • Bicyclic monoterpenoid
  • 1-benzopyran
  • Benzopyran
  • Aromatic monoterpenoid
  • Phenoxy compound
  • Phenol ether
  • Anisole
  • Methoxybenzene
  • 1-hydroxy-4-unsubstituted benzenoid
  • Pyranone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Vinylogous acid
  • Heteroaromatic compound
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP5.26ALOGPS
logP5.94ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)6.39ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area96.22 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity127.42 m³·mol⁻¹ChemAxon
Polarizability48.2 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS, 2 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS, 2 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS, 2 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS, 3 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available2020-06-30View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Prostaglandin E synthasePTGES9q34.3O14684 details
Arachidonate 5-lipoxygenaseALOX510q11.2P09917 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Arachidonate 5-lipoxygenaseALOX510q11.2P09917 details
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID8247235
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10071695
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Barrett ML, Scutt AM, Evans FJ: Cannflavin A and B, prenylated flavones from Cannabis sativa L. Experientia. 1986 Apr 15;42(4):452-3. doi: 10.1007/bf02118655. [PubMed:3754224 ]
  2. Radwan MM, Elsohly MA, Slade D, Ahmed SA, Wilson L, El-Alfy AT, Khan IA, Ross SA: Non-cannabinoid constituents from a high potency Cannabis sativa variety. Phytochemistry. 2008 Oct;69(14):2627-33. doi: 10.1016/j.phytochem.2008.07.010. Epub 2008 Sep 4. [PubMed:18774146 ]
  3. Rea KA, Casaretto JA, Al-Abdul-Wahid MS, Sukumaran A, Geddes-McAlister J, Rothstein SJ, Akhtar TA: Biosynthesis of cannflavins A and B from Cannabis sativa L. Phytochemistry. 2019 Aug;164:162-171. doi: 10.1016/j.phytochem.2019.05.009. Epub 2019 May 28. [PubMed:31151063 ]
  4. Barrett ML, Gordon D, Evans FJ: Isolation from Cannabis sativa L. of cannflavin--a novel inhibitor of prostaglandin production. Biochem Pharmacol. 1985 Jun 1;34(11):2019-24. doi: 10.1016/0006-2952(85)90325-9. [PubMed:3859295 ]

Enzymes

Enzyme Details
1. Prostaglandin E synthase
General function:
Involved in prostaglandin-E synthase activity
Specific function:
Catalyzes the oxidoreduction of prostaglandin endoperoxide H2 (PGH2) to prostaglandin E2 (PGE2).
Gene Name:
PTGES
Uniprot ID:
O14684
Molecular weight:
17102.135
Enzyme Details
2. Arachidonate 5-lipoxygenase
General function:
Involved in metal ion binding
Specific function:
Catalyzes the first step in leukotriene biosynthesis, and thereby plays a role in inflammatory processes.
Gene Name:
ALOX5
Uniprot ID:
P09917
Molecular weight:
77982.595