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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:37:59 UTC
Update Date2022-03-07 02:52:37 UTC
HMDB IDHMDB0030617
Secondary Accession Numbers
  • HMDB30617
Metabolite Identification
Common NamePratensein
DescriptionPratensein belongs to the class of organic compounds known as 3'-hydroxy,4'-methoxyisoflavonoids. These are isoflavonoids carrying a methoxy group attached to the C4' atom, as well as a hydroxyl group at the C3'-position of the isoflavonoid backbone. Pratensein has been detected, but not quantified in, a few different foods, such as chickpeas (Cicer arietinum), peanuts (Arachis hypogaea), and pulses. This could make pratensein a potential biomarker for the consumption of these foods. Pratensein 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 small amount of articles have been published on Pratensein.
Structure
Data?1563862013
Synonyms
ValueSource
3',5,7-Trihydroxy-4'-methoxyisoflavoneChEBI
3'-Hydroxy-biochanin aChEBI
3'-Hydroxybiochanin aChEBI
5,7,3'-Trihydroxy-4'-methoxyisoflavoneChEBI
5,7-Dihydroxy-3-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-oneChEBI
4776b CompoundMeSH, HMDB
4'-Methoxy-3',5,7-trihydroxyisoflavoneMeSH, HMDB
Chemical FormulaC16H12O6
Average Molecular Weight300.2629
Monoisotopic Molecular Weight300.063388116
IUPAC Name5,7-dihydroxy-3-(3-hydroxy-4-methoxyphenyl)-4H-chromen-4-one
Traditional Namepratensein
CAS Registry Number2284-31-3
SMILES
COC1=C(O)C=C(C=C1)C1=COC2=CC(O)=CC(O)=C2C1=O
InChI Identifier
InChI=1S/C16H12O6/c1-21-13-3-2-8(4-11(13)18)10-7-22-14-6-9(17)5-12(19)15(14)16(10)20/h2-7,17-19H,1H3
InChI KeyFPIOBTBNRZPWJW-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 3'-hydroxy,4'-methoxyisoflavonoids. These are isoflavonoids carrying a methoxy group attached to the C4' atom, as well as a hydroxyl group at the C3'-position of the isoflavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassO-methylated isoflavonoids
Direct Parent3'-hydroxy,4'-methoxyisoflavonoids
Alternative Parents
Substituents
  • 3'-hydroxy,4'-methoxyisoflavonoid
  • 4p-o-methylisoflavone
  • Isoflavone
  • Hydroxyisoflavonoid
  • Chromone
  • Methoxyphenol
  • 1-benzopyran
  • Benzopyran
  • Phenoxy compound
  • Phenol ether
  • Anisole
  • Methoxybenzene
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Pyranone
  • Benzenoid
  • Pyran
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Vinylogous acid
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point272 - 273 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.08 g/LALOGPS
logP3.05ALOGPS
logP2.92ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)6.61ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area96.22 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity78.15 m³·mol⁻¹ChemAxon
Polarizability29.54 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
DeepCCS[M+H]+169.730932474
DeepCCS[M-H]-167.34230932474
DeepCCS[M-2H]-200.61930932474
DeepCCS[M+Na]+175.84630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PratenseinCOC1=C(O)C=C(C=C1)C1=COC2=CC(O)=CC(O)=C2C1=O4616.8Standard polar33892256
PratenseinCOC1=C(O)C=C(C=C1)C1=COC2=CC(O)=CC(O)=C2C1=O2976.8Standard non polar33892256
PratenseinCOC1=C(O)C=C(C=C1)C1=COC2=CC(O)=CC(O)=C2C1=O3113.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Pratensein,1TMS,isomer #1COC1=CC=C(C2=COC3=CC(O)=CC(O)=C3C2=O)C=C1O[Si](C)(C)C3205.3Semi standard non polar33892256
Pratensein,1TMS,isomer #2COC1=CC=C(C2=COC3=CC(O[Si](C)(C)C)=CC(O)=C3C2=O)C=C1O3239.0Semi standard non polar33892256
Pratensein,1TMS,isomer #3COC1=CC=C(C2=COC3=CC(O)=CC(O[Si](C)(C)C)=C3C2=O)C=C1O3190.1Semi standard non polar33892256
Pratensein,2TMS,isomer #1COC1=CC=C(C2=COC3=CC(O[Si](C)(C)C)=CC(O)=C3C2=O)C=C1O[Si](C)(C)C3077.7Semi standard non polar33892256
Pratensein,2TMS,isomer #2COC1=CC=C(C2=COC3=CC(O)=CC(O[Si](C)(C)C)=C3C2=O)C=C1O[Si](C)(C)C3018.3Semi standard non polar33892256
Pratensein,2TMS,isomer #3COC1=CC=C(C2=COC3=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3C2=O)C=C1O3127.3Semi standard non polar33892256
Pratensein,3TMS,isomer #1COC1=CC=C(C2=COC3=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3C2=O)C=C1O[Si](C)(C)C2984.5Semi standard non polar33892256
Pratensein,1TBDMS,isomer #1COC1=CC=C(C2=COC3=CC(O)=CC(O)=C3C2=O)C=C1O[Si](C)(C)C(C)(C)C3446.3Semi standard non polar33892256
Pratensein,1TBDMS,isomer #2COC1=CC=C(C2=COC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C3C2=O)C=C1O3510.1Semi standard non polar33892256
Pratensein,1TBDMS,isomer #3COC1=CC=C(C2=COC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C=C1O3455.5Semi standard non polar33892256
Pratensein,2TBDMS,isomer #1COC1=CC=C(C2=COC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C3C2=O)C=C1O[Si](C)(C)C(C)(C)C3620.7Semi standard non polar33892256
Pratensein,2TBDMS,isomer #2COC1=CC=C(C2=COC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C=C1O[Si](C)(C)C(C)(C)C3572.5Semi standard non polar33892256
Pratensein,2TBDMS,isomer #3COC1=CC=C(C2=COC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C=C1O3644.5Semi standard non polar33892256
Pratensein,3TBDMS,isomer #1COC1=CC=C(C2=COC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C=C1O[Si](C)(C)C(C)(C)C3728.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Pratensein GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fl0-0392000000-b33a9f600255a76453312017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pratensein GC-MS (3 TMS) - 70eV, Positivesplash10-0udi-2180970000-37a9800477d82a62a0a22017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pratensein GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pratensein 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 - Pratensein LC-ESI-QFT 21V, positive-QTOFsplash10-0udr-0096000000-f8f401a8a48dd8fb870d2020-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pratensein LC-ESI-IT 21V, positive-QTOFsplash10-00kr-0090000000-9331cc69724483ba671c2020-07-24HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pratensein 10V, Positive-QTOFsplash10-0udi-0109000000-99b3ff2ff09032c773922016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pratensein 20V, Positive-QTOFsplash10-0udi-0329000000-07e3785d7c0ec0e324272016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pratensein 40V, Positive-QTOFsplash10-0fk9-6940000000-d65be68235fd05108d602016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pratensein 10V, Negative-QTOFsplash10-0002-0090000000-9bdb9b13d7148406dc382016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pratensein 20V, Negative-QTOFsplash10-0002-0390000000-6f6b16a3d9e7b25e542d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pratensein 40V, Negative-QTOFsplash10-0ugi-2790000000-d080df272f8cc794ba142016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pratensein 10V, Positive-QTOFsplash10-0udi-0009000000-545fc7c692e0abcd79662021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pratensein 20V, Positive-QTOFsplash10-0udi-0009000000-545fc7c692e0abcd79662021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pratensein 40V, Positive-QTOFsplash10-004i-0290000000-700da632aef4c754c8f22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pratensein 10V, Negative-QTOFsplash10-0002-0090000000-fb4a565723d52a1e46242021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pratensein 20V, Negative-QTOFsplash10-0002-0090000000-185770323f5773ae368c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pratensein 40V, Negative-QTOFsplash10-0ufr-0090000000-d5386a1b1f88b835a2982021-09-23Wishart 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 IDNot Available
FooDB IDFDB002514
KNApSAcK IDC00002563
Chemspider ID4445115
KEGG Compound IDC10520
BioCyc IDCPD-3622
BiGG IDNot Available
Wikipedia LinkPratensein
METLIN IDNot Available
PubChem Compound5281803
PDB IDNot Available
ChEBI ID8359
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.. .