Record Information
Version1.0
Created at2020-03-19 00:31:33 UTC
Updated at2020-11-18 16:35:04 UTC
CannabisDB IDCDB000335
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameApigenin-7-o-glucoside
DescriptionApigenin-7-O-glucoside, also known as cosmosiin or apigetrin, belongs to the class of organic compounds known as flavonoid 7-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. Thus, apigenin 7-O-glucoside consists of the apigenin flavanoid ring linked to glucose at the 7-position. Because of the conjugation of glucose, Apigenin 7-O-glucoside is a moderately water-soluble compound. Apigenin-7-O-glucoside can be found in a number of food items, such as common thyme, white lupine, common oregano, and orange mint. Apigenin-7-O-glucoside can also be found in dandelion coffee and in plants such as wild celery and anise. Apigenin-7-O-glucoside has been shown to exhibit anti-platelet function (PMID: 21834233 ). Apigenin-7-O-glucoside 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
Synonyms
ValueSource
5-Hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl beta-D-glucopyranosideChEBI
7-(beta-D-Glucopyranosyloxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-oneChEBI
7-O-beta-D-Glucosyl-5,7,4'-trihydroxyflavoneChEBI
Apigenin 7-O-glucosideChEBI
ApigetrinChEBI
CosmetinChEBI
CosmosiosideChEBI
5-Hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl b-D-glucopyranosideGenerator
5-Hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl β-D-glucopyranosideGenerator
7-(b-D-Glucopyranosyloxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-oneGenerator
7-(Β-D-glucopyranosyloxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-oneGenerator
7-O-b-D-Glucosyl-5,7,4'-trihydroxyflavoneGenerator
7-O-Β-D-glucosyl-5,7,4'-trihydroxyflavoneGenerator
4',5,7-Trihydroxyflavone 7-beta-D-glucosideHMDB
4',5,7-Trihydroxyflavone 7-β-D-glucosideHMDB
7-O-beta-D-GlucopyranosylapigeninHMDB
7-O-beta-D-GlucosylapigeninHMDB
7-O-Β-D-glucopyranosylapigeninHMDB
7-O-Β-D-glucosylapigeninHMDB
Apigenin 7-beta-D-glucosideHMDB
Apigenin 7-beta-glucopyranosideHMDB
Apigenin 7-glucosideHMDB
Apigenin 7-O-beta-D-glucopyranosideHMDB
Apigenin 7-O-beta-D-glucosideHMDB
Apigenin 7-O-beta-glucopyranosideHMDB
Apigenin 7-O-beta-glucosideHMDB
Apigenin 7-O-β-D-glucopyranosideHMDB
Apigenin 7-O-β-D-glucosideHMDB
Apigenin 7-O-β-glucopyranosideHMDB
Apigenin 7-O-β-glucosideHMDB
Apigenin 7-β-D-glucosideHMDB
Apigenin 7-β-glucopyranosideHMDB
Apigenin-7-glucosideHMDB
CosmociinHMDB
CosmosideHMDB
CosmosiineHMDB
Apigenin-7-D-glucosideHMDB
Apigenin-7-O-beta-D-glucopyranosideHMDB
Apigenin 7-O-b-D-glucosideHMDB
CosmosiinChEBI
4’,5,7-Trihydroxyflavone 7-β-D-glucosidePhytoBank
Apigenin-7-O-4C1-beta-D-glucosidePhytoBank
Apigenin-7-O-4C1-β-D-glucosidePhytoBank
Chemical FormulaC21H20O10
Average Molecular Weight432.38
Monoisotopic Molecular Weight432.1056
IUPAC Name5-hydroxy-2-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one
Traditional Nameapigenin 7-o-β-glucoside
CAS Registry Number578-74-5
SMILES
OC[C@H]1O[C@@H](OC2=CC(O)=C3C(=O)C=C(OC3=C2)C2=CC=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C21H20O10/c22-8-16-18(26)19(27)20(28)21(31-16)29-11-5-12(24)17-13(25)7-14(30-15(17)6-11)9-1-3-10(23)4-2-9/h1-7,16,18-24,26-28H,8H2/t16-,18-,19+,20-,21-/m1/s1
InChI KeyKMOUJOKENFFTPU-QNDFHXLGSA-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
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Flavone
  • Phenolic glycoside
  • Coumaric acid ester
  • Cinnamic acid ester
  • Cinnamic acid or derivatives
  • Coumaric acid or derivatives
  • Hydroxycinnamic acid or derivatives
  • O-glycosyl compound
  • Chromone
  • Glycosyl compound
  • 1-benzopyran
  • Benzopyran
  • Styrene
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Pyranone
  • Fatty acid ester
  • Monocyclic benzene moiety
  • Fatty acyl
  • Benzenoid
  • Monosaccharide
  • Pyran
  • Oxane
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Vinylogous acid
  • Heteroaromatic compound
  • Secondary alcohol
  • Carboxylic acid ester
  • Polyol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Acetal
  • Organoheterocyclic compound
  • Oxacycle
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Alcohol
  • Organic oxygen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.68ALOGPS
logP0.44ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)7.3ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area166.14 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity105.06 m³·mol⁻¹ChemAxon
Polarizability42.1 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSApigenin-7-o-glucoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSApigenin-7-o-glucoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-014r-0101900000-f6718e10f3de7520652f2017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-014r-0101900000-f6718e10f3de7520652f2017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-014r-0101900000-f6718e10f3de7520652f2017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-014r-0101900000-f6718e10f3de7520652f2017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-014i-0090000000-eedd23913ab9497a0eac2017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-001i-0000900000-e2260ea719dbee112e942017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 30V, positivesplash10-00di-0090000000-931de09c88fa2bf108352020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 32V, positivesplash10-00di-0190100000-328716d021915ac0b1ca2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 32V, positivesplash10-00di-0090000000-ef5fba33036a2fc3eefe2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF , positivesplash10-00di-0090000000-42a8500af8e4003c64d82020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - NA , positivesplash10-00di-0090000000-bc14fdabab276d59d19e2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 18V, positivesplash10-00di-0090000000-17b09902cbc2dacc4f532020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - NA , positivesplash10-00di-0290000000-de36e4361d200d1581cd2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 10V, positivesplash10-00di-0090100000-1ddbdf7336facbeee0e62020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 30V, positivesplash10-00di-0090000000-d5568c51391bbc9cf9582020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 50V, positivesplash10-00di-0690000000-66369226057bbb9d461e2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 6V, positivesplash10-00di-0090100000-248119996a69ff1ac28b2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 10V, positivesplash10-00di-0090200000-82152bf26be497666fbb2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 20V, positivesplash10-00di-0090000000-97145fc5c68f12c583622020-07-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00e9-0190800000-d6fb1bf837b7e2f19b9b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0090000000-be62ac4071bbf231aebb2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dl-2290000000-45b3c356a68218e5c2db2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00lr-1151900000-829923d6de81818f47a32016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1090200000-a27b90fa5b842325e59d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-3290000000-4e0d09fb8af7034a03eb2016-08-03View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0037340
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003911
KNApSAcK IDC00001017
Chemspider ID4444290
KEGG Compound IDC04608
BioCyc IDAPIGENIN-7-O-BETA-D-GLUCOSIDE
BiGG IDNot Available
Wikipedia LinkApigetrin
METLIN IDNot Available
PubChem Compound5280704
PDB IDNot Available
ChEBI ID16778
References
General References
  1. Chaves DS, Frattani FS, Assafim M, de Almeida AP, de Zingali RB, Costa SS: Phenolic chemical composition of Petroselinum crispum extract and its effect on haemostasis. Nat Prod Commun. 2011 Jul;6(7):961-4. [PubMed:21834233 ]
  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 ]