Apigenin 7-glucoside (CHEM030842)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 02:12:32 UTC
Update Date2016-11-09 01:19:09 UTC
Accession NumberCHEM030842
Identification
Common NameApigenin 7-glucoside
ClassSmall Molecule
DescriptionA glycosyloxyflavone that is apigenin substituted by a beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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 Mass432.378 g/mol
Monoisotopic Mass432.106 g/mol
CAS Registry Number578-74-5
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
SMILESOCC1OC(OC2=CC(O)=C3C(=O)C=C(OC3=C2)C2=CC=C(O)C=C2)C(O)C(O)C1O
InChI IdentifierInChI=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
InChI KeyKMOUJOKENFFTPU-UHFFFAOYSA-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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.97 g/LALOGPS
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
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-014r-0101900000-f6718e10f3de7520652fSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-014r-0101900000-f6718e10f3de7520652fSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-014r-0101900000-f6718e10f3de7520652fSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-014r-0101900000-f6718e10f3de7520652fSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-014i-0090000000-eedd23913ab9497a0eacSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-001i-0000900000-e2260ea719dbee112e94Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 30V, positivesplash10-00di-0090000000-931de09c88fa2bf10835Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 32V, positivesplash10-00di-0190100000-328716d021915ac0b1caSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 32V, positivesplash10-00di-0090000000-ef5fba33036a2fc3eefeSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF , positivesplash10-00di-0090000000-42a8500af8e4003c64d8Spectrum
LC-MS/MSLC-MS/MS Spectrum - NA , positivesplash10-00di-0090000000-bc14fdabab276d59d19eSpectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 18V, positivesplash10-00di-0090000000-17b09902cbc2dacc4f53Spectrum
LC-MS/MSLC-MS/MS Spectrum - NA , positivesplash10-00di-0290000000-de36e4361d200d1581cdSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 10V, positivesplash10-00di-0090100000-1ddbdf7336facbeee0e6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 30V, positivesplash10-00di-0090000000-d5568c51391bbc9cf958Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 50V, positivesplash10-00di-0690000000-66369226057bbb9d461eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 6V, positivesplash10-00di-0090100000-248119996a69ff1ac28bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 10V, positivesplash10-00di-0090200000-82152bf26be497666fbbSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 20V, positivesplash10-00di-0090000000-97145fc5c68f12c58362Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00e9-0190800000-d6fb1bf837b7e2f19b9bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0090000000-be62ac4071bbf231aebbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dl-2290000000-45b3c356a68218e5c2dbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00lr-1151900000-829923d6de81818f47a3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1090200000-a27b90fa5b842325e59dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-3290000000-4e0d09fb8af7034a03ebSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0037340
FooDB IDFDB003911
Phenol Explorer IDNot Available
KNApSAcK IDC00001017
BiGG IDNot Available
BioCyc IDAPIGENIN-7-O-BETA-D-GLUCOSIDE
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkApigetrin
Chemspider ID4444290
ChEBI ID16778
PubChem Compound ID5280704
Kegg Compound IDC04608
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=17186490
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=19112896
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21656359
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=21756194
5. 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.
6. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.