Showing Compound Card for Apigenin-7-o-p-coumarylglucoside (CDB000334)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesXML
Record Information
Version1.0
Created at2020-03-19 00:31:30 UTC
Updated at2020-12-07 19:07:22 UTC
CannabisDB IDCDB000334
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameApigenin-7-o-p-coumarylglucoside
DescriptionApigenin-7-O-p-coumarylglucoside belongs to the class of organic compounds known as flavonoid O-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2- or 7-position of the phenylchromen-4-one flavonoid backbone. Apigenin-7-O-p-coumarylglucoside is a derivative of Apigenin in which both a glucose has been attached to the 7-position of the phenylchormen-4-one backbone and a coumaryl alcohol group has been attached to the glucose. The base flavonoid, Apigenin, is found in many fruits and vegetables, but parsley, celery, celeriac, and chamomile tea are the most common sources. Apigenin is particularly abundant in the flowers of chamomile plants, constituting 68% of total flavonoids (PMID:26487830 ). Apigenin exhibits antiproliferative, anti-inflammatory, and antimetastatic activities through poorly defined mechanisms. Apigenin is one of several dozen flavonoid glycosides that are known in cannabis plants. It was first isolated and identified as a cannabis constituent in 1973 (PMID: 6991645 ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
[(2R,3S,4S,5S,6S)-3,4,5-Trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoic acidGenerator
Chemical FormulaC30H26O12
Average Molecular Weight578.53
Monoisotopic Molecular Weight578.1424
IUPAC Name[(2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate
Traditional Name[(2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate
CAS Registry NumberNot Available
SMILES
O[C@@H]1[C@@H](COC(=O)\C=C\C2=CC=C(O)C=C2)O[C@@H](OC2=CC(O)=C3C(=O)C=C(OC3=C2)C2=CC=C(O)C=C2)[C@@H](O)[C@H]1O
InChI Identifier
InChI=1S/C30H26O12/c31-17-6-1-15(2-7-17)3-10-25(35)39-14-24-27(36)28(37)29(38)30(42-24)40-19-11-20(33)26-21(34)13-22(41-23(26)12-19)16-4-8-18(32)9-5-16/h1-13,24,27-33,36-38H,14H2/b10-3+/t24-,27-,28+,29+,30-/m1/s1
InChI KeyWPQRDUGBKUNFJW-SLUROAMNSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid-7-O-glycosides
Alternative Parents
Substituents
  • Flavonoid-7-o-glycoside
  • Hydroxyflavonoid
  • Flavone
  • 5-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • Phenolic glycoside
  • Coumaric acid ester
  • Cinnamic acid ester
  • Hydroxycinnamic acid or derivatives
  • Coumaric acid or derivatives
  • Cinnamic acid or derivatives
  • O-glycosyl compound
  • Glycosyl compound
  • Chromone
  • 1-benzopyran
  • Benzopyran
  • Styrene
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Phenol
  • Fatty acid ester
  • Fatty acyl
  • Benzenoid
  • Pyran
  • Oxane
  • Monosaccharide
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Vinylogous acid
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Secondary alcohol
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Acetal
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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
logP2.91ALOGPS
logP3.17ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)7.29ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area192.44 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity146.61 m³·mol⁻¹ChemAxon
Polarizability56.52 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSApigenin-7-o-p-coumarylglucoside, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSApigenin-7-o-p-coumarylglucoside, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSApigenin-7-o-p-coumarylglucoside, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSApigenin-7-o-p-coumarylglucoside, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSApigenin-7-o-p-coumarylglucoside, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSApigenin-7-o-p-coumarylglucoside, 1 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
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
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 IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Venigalla M, Gyengesi E, Munch G: Curcumin and Apigenin - novel and promising therapeutics against chronic neuroinflammation in Alzheimer's disease. Neural Regen Res. 2015 Aug;10(8):1181-5. doi: 10.4103/1673-5374.162686. [PubMed:26487830 ]
  2. 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 ]