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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:45:45 UTC
Update Date2019-07-23 06:14:51 UTC
HMDB IDHMDB0033987
Secondary Accession Numbers
  • HMDB33987
Metabolite Identification
Common NameOnonin
DescriptionOnonin, also known as ononoside, belongs to the class of organic compounds known as isoflavonoid o-glycosides. These are o-glycosylated derivatives of isoflavonoids, which are natural products derived from 3-phenylchromen-4-one. Ononin is an extremely weak basic (essentially neutral) compound (based on its pKa). An in vitro anti-inflammatory effect on lipopolysaccharide (LPS)-induced inflammation has been demonstrated in one study. Outside of the human body, Ononin has been detected, but not quantified in, several different foods, such as annual wild rices, wild rices, common buckwheats, rices, and amaranths. This could make ononin a potential biomarker for the consumption of these foods. Ononin is an isoflavone glycoside, the 7-O-β-D-glucopyranoside of formononetin, which in turn is the 4'-O-methoxy derivative of the parent isoflavone daidzein. Ononin is a major isoflavone found in a number of plants and herbs like soybean and Glycyrrhiza uralensis. Intestinal bacterial metabolic pathways may include demethylation and deglycosylation. It follows that formation of formononetin and/or daidzein is possible.
Structure
Data?1563862491
Synonyms
ValueSource
4'-Methoxyisoflavone-7-O-beta-D-glucopyranosideHMDB
Formononetin 7-O-beta-D-glucopyranosideHMDB
Formononetin 7-O-glucosideHMDB
Formononetin glucosideHMDB
Formononetin-7-glucosideHMDB
Formononetin-7-O-beta-D-glucopyranosideHMDB
Ononin?HMDB
OnonosideHMDB
Calycosin-7-O-beta-D-glucosideMeSH
OnoninMeSH
Chemical FormulaC22H22O9
Average Molecular Weight430.4047
Monoisotopic Molecular Weight430.126382302
IUPAC Name3-(4-methoxyphenyl)-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one
Traditional Nameononin
CAS Registry Number486-62-4
SMILES
COC1=CC=C(C=C1)C1=COC2=C(C=CC(OC3OC(CO)C(O)C(O)C3O)=C2)C1=O
InChI Identifier
InChI=1S/C22H22O9/c1-28-12-4-2-11(3-5-12)15-10-29-16-8-13(6-7-14(16)18(15)24)30-22-21(27)20(26)19(25)17(9-23)31-22/h2-8,10,17,19-23,25-27H,9H2,1H3
InChI KeyMGJLSBDCWOSMHL-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as isoflavonoid o-glycosides. These are o-glycosylated derivatives of isoflavonoids, which are natural products derived from 3-phenylchromen-4-one.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassIsoflavonoid O-glycosides
Direct ParentIsoflavonoid O-glycosides
Alternative Parents
Substituents
  • Isoflavonoid-7-o-glycoside
  • Isoflavonoid o-glycoside
  • 4p-o-methylisoflavone
  • Isoflavone
  • Phenolic glycoside
  • Hexose monosaccharide
  • O-glycosyl compound
  • Glycosyl compound
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Phenoxy compound
  • Methoxybenzene
  • Phenol ether
  • Anisole
  • Pyranone
  • Alkyl aryl ether
  • Pyran
  • Monocyclic benzene moiety
  • Oxane
  • Monosaccharide
  • Benzenoid
  • Heteroaromatic compound
  • Secondary alcohol
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Polyol
  • Organic oxygen compound
  • Alcohol
  • Primary alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
  • an isoflavone-7-O-β-D-glucoside (ONONIN )
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point218 - 219 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.42 g/LALOGPS
logP1.13ALOGPS
logP0.61ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)12.2ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area134.91 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity106.33 m³·mol⁻¹ChemAxon
Polarizability43.49 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-096r-9315300000-8a7d05d41f74bb989976Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-001i-2283139000-75069057828723a050abSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-016r-0090500000-abc3ab9be6f16dc9bb67Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-014i-0090000000-2b4aa9f7667e91c7c304Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-014i-0090000000-40e8330b6def47a6f880Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0udi-0090000000-c0392fd74b36839d6a6eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-014i-0090000000-754d1e4621f3b19aa9f0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0159-0191700000-9abf847b1eb16f6bdbceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0090000000-593966db5b30d21f8dfeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-2390000000-e6093874c26996bf0191Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0159-0191700000-9abf847b1eb16f6bdbceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0090000000-593966db5b30d21f8dfeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-2390000000-e6093874c26996bf0191Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00or-1151900000-1e96ad8c2b5c0946a28bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1191100000-b11f18f51a14196c87e4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-3290000000-e69eaf894af3fad1989aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00or-1151900000-1e96ad8c2b5c0946a28bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1191100000-b11f18f51a14196c87e4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-3290000000-e69eaf894af3fad1989aSpectrum
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 IDFDB012220
KNApSAcK IDC00002553
Chemspider ID2963362
KEGG Compound IDC10509
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkOnonin
METLIN IDNot Available
PubChem Compound3733033
PDB IDNot Available
ChEBI ID7775
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .