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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:45:01 UTC
Update Date2022-03-07 02:53:05 UTC
HMDB IDHMDB0031720
Secondary Accession Numbers
  • HMDB31720
Metabolite Identification
Common NameXenognosin B
DescriptionXenognosin B belongs to the class of organic compounds known as 4'-o-methylisoflavones. These are isoflavones with methoxy groups attached to the C4' atom of the isoflavone backbone. Thus, xenognosin b is considered to be a flavonoid. Xenognosin B exists in all living organisms, ranging from bacteria to humans. Xenognosin B has been detected, but not quantified in, several different foods, such as limes (Citrus aurantiifolia), cereals and cereal products, italian sweet red peppers (Capsicum annuum), shiitakes (Lentinus edodes), and radishes (Raphanus sativus). This could make xenognosin b a potential biomarker for the consumption of these foods. Xenognosin B is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Xenognosin B.
Structure
Data?1563862161
Synonyms
ValueSource
2'-HydroformononetinChEBI
Xenognosin bChEBI
2',7-Dihydroxy-4'-methoxyisoflavoneHMDB
2-HYDROXYFORMONONETINHMDB
7,2'-Dihydroxy-4'-methoxyisoflavoneHMDB
7-Hydroxy-3-(2-hydroxy-4-methoxyphenyl)-4H-chromen-4-oneHMDB
Chemical FormulaC16H12O5
Average Molecular Weight284.2635
Monoisotopic Molecular Weight284.068473494
IUPAC Name7-hydroxy-3-(2-hydroxy-4-methoxyphenyl)-4H-chromen-4-one
Traditional Name2'-hydroxyformononetin
CAS Registry Number1890-99-9
SMILES
COC1=CC(O)=C(C=C1)C1=COC2=C(C=CC(O)=C2)C1=O
InChI Identifier
InChI=1S/C16H12O5/c1-20-10-3-5-11(14(18)7-10)13-8-21-15-6-9(17)2-4-12(15)16(13)19/h2-8,17-18H,1H3
InChI KeyXKHHKXCBFHUOHM-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 4'-o-methylisoflavones. These are isoflavones with methoxy groups attached to the C4' atom of the isoflavone backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassO-methylated isoflavonoids
Direct Parent4'-O-methylisoflavones
Alternative Parents
Substituents
  • 4p-o-methylisoflavone
  • Isoflavone
  • Hydroxyisoflavonoid
  • Chromone
  • Methoxyphenol
  • 1-benzopyran
  • Benzopyran
  • Phenoxy compound
  • Anisole
  • Phenol ether
  • Methoxybenzene
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Pyranone
  • Pyran
  • Monocyclic benzene moiety
  • Benzenoid
  • Heteroaromatic compound
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point215 - 217 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.054 g/LALOGPS
logP3.35ALOGPS
logP2.57ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)6.47ChemAxon
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.99 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity76.17 m³·mol⁻¹ChemAxon
Polarizability28.73 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+165.22331661259
DarkChem[M-H]-168.60331661259
DeepCCS[M+H]+170.48230932474
DeepCCS[M-H]-168.12430932474
DeepCCS[M-2H]-201.01130932474
DeepCCS[M+Na]+176.57530932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Xenognosin BCOC1=CC(O)=C(C=C1)C1=COC2=C(C=CC(O)=C2)C1=O4035.3Standard polar33892256
Xenognosin BCOC1=CC(O)=C(C=C1)C1=COC2=C(C=CC(O)=C2)C1=O2734.0Standard non polar33892256
Xenognosin BCOC1=CC(O)=C(C=C1)C1=COC2=C(C=CC(O)=C2)C1=O2984.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Xenognosin B,1TMS,isomer #1COC1=CC=C(C2=COC3=CC(O)=CC=C3C2=O)C(O[Si](C)(C)C)=C12937.4Semi standard non polar33892256
Xenognosin B,1TMS,isomer #2COC1=CC=C(C2=COC3=CC(O[Si](C)(C)C)=CC=C3C2=O)C(O)=C12966.3Semi standard non polar33892256
Xenognosin B,2TMS,isomer #1COC1=CC=C(C2=COC3=CC(O[Si](C)(C)C)=CC=C3C2=O)C(O[Si](C)(C)C)=C12844.7Semi standard non polar33892256
Xenognosin B,1TBDMS,isomer #1COC1=CC=C(C2=COC3=CC(O)=CC=C3C2=O)C(O[Si](C)(C)C(C)(C)C)=C13158.7Semi standard non polar33892256
Xenognosin B,1TBDMS,isomer #2COC1=CC=C(C2=COC3=CC(O[Si](C)(C)C(C)(C)C)=CC=C3C2=O)C(O)=C13188.7Semi standard non polar33892256
Xenognosin B,2TBDMS,isomer #1COC1=CC=C(C2=COC3=CC(O[Si](C)(C)C(C)(C)C)=CC=C3C2=O)C(O[Si](C)(C)C(C)(C)C)=C13310.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Xenognosin B GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-0390000000-5c4de61ba5b89c667b7c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Xenognosin B GC-MS (2 TMS) - 70eV, Positivesplash10-08mi-3329700000-00460e1ae90ab67568c12017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Xenognosin B GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Xenognosin B GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Xenognosin B LC-ESI-QFT 19V, positive-QTOFsplash10-002r-0090000000-a76c5843eab6e63461e12020-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Xenognosin B LC-ESI-IT 19V, positive-QTOFsplash10-004r-0390000000-ffb6cbbf2ee84308691b2020-07-24HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xenognosin B 10V, Positive-QTOFsplash10-000i-0090000000-8db47da9a8da9759ebce2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xenognosin B 20V, Positive-QTOFsplash10-000i-0090000000-d05ab2af43c03031f34d2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xenognosin B 40V, Positive-QTOFsplash10-0f79-3790000000-f358200cb91e59b4f1612015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xenognosin B 10V, Negative-QTOFsplash10-001i-0090000000-008f0b278059bd09a52a2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xenognosin B 20V, Negative-QTOFsplash10-001i-0090000000-178fe8c37dc1fce0ae422015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xenognosin B 40V, Negative-QTOFsplash10-0ap4-6970000000-357a3524fe9adb9d4fa32015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xenognosin B 10V, Negative-QTOFsplash10-001i-0090000000-549f6b30f75977e8ff352021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xenognosin B 20V, Negative-QTOFsplash10-001i-0090000000-2a227ddde8ecc774ca9d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xenognosin B 40V, Negative-QTOFsplash10-01pa-0970000000-d8f1141b9cc45bbd574f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xenognosin B 10V, Positive-QTOFsplash10-000i-0090000000-edc9ea273e98ea6aa00a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xenognosin B 20V, Positive-QTOFsplash10-000i-0090000000-6bc22e96020665f64ad02021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xenognosin B 40V, Positive-QTOFsplash10-052r-0950000000-f2882df3fc9efa6c0b9b2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
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 ID827
FooDB IDFDB008383
KNApSAcK IDC00000257
Chemspider ID4444180
KEGG Compound IDC02920
BioCyc ID2-HYDROXYFORMONONETIN
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5280551
PDB IDNot Available
ChEBI ID17678
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents 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.. .