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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:34:39 UTC
Update Date2019-07-23 06:23:34 UTC
HMDB IDHMDB0037340
Secondary Accession Numbers
  • HMDB37340
Metabolite Identification
Common NameCosmosiin
DescriptionCosmosiin, also known as apigenin 7-O-glucoside or apigetrin, is a member of the class of compounds known as flavonoid-7-O-glycosides. Flavonoid-7-O-glycosides are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. Cosmosiin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Cosmosiin can be found in a number of food items, such as common thyme, white lupine, common oregano, and orange mint. Cosmosiin can also be found in dandelion coffee and in Teucrium gnaphalodes (Wikipedia). Cosmosiin can also be found plants such as wild celery and anise. Cosmosiin has been shown to exhibit anti-platelet function (PMID: 21834233 ).
Structure
Data?1563863014
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
CosmosiinChEBI
Apigenin 7-O-b-D-glucosideGenerator
Chemical FormulaC21H20O10
Average Molecular Weight432.381
Monoisotopic Molecular Weight432.105646844
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
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • Phenolic glycoside
  • Hexose monosaccharide
  • O-glycosyl compound
  • Chromone
  • Glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Pyranone
  • Pyran
  • Monosaccharide
  • Benzenoid
  • Oxane
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Vinylogous acid
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Acetal
  • Polyol
  • Primary alcohol
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot 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
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
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
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
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB016362
KNApSAcK IDC00001017
Chemspider ID4532607
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
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
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. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .