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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:50:37 UTC
Update Date2022-03-07 02:53:23 UTC
HMDB IDHMDB0032584
Secondary Accession Numbers
  • HMDB32584
Metabolite Identification
Common Name4-Hydroxychalcone
Description4-Hydroxychalcone belongs to the class of organic compounds known as retrochalcones. These are a form of normal chalcones that are structurally distinguished by the lack of oxygen functionalities at the C2'- and C6'-positions. Based on a literature review very few articles have been published on 4-Hydroxychalcone.
Structure
Data?1563862278
Synonyms
ValueSource
(2E)-3-(4-Hydroxyphenyl)-1-phenylprop-2-en-1-oneHMDB
(e)-3-(4-Hydroxy-phenyl)-1-phenyl-propenoneHMDB
3-(4-Hydroxyphenyl)-1-phenyl-2-propen-1-oneHMDB
4-Hydroxy chalconeHMDB
4-Hydroxychalcone, 8ciHMDB
4-Hydroxystyryl phenyl ketoneHMDB
W-p-HydroxybenzylideneacetophenoneHMDB
Chemical FormulaC15H12O2
Average Molecular Weight224.2546
Monoisotopic Molecular Weight224.083729628
IUPAC Name(2Z)-3-(4-hydroxyphenyl)-1-phenylprop-2-en-1-one
Traditional Name(2Z)-3-(4-hydroxyphenyl)-1-phenylprop-2-en-1-one
CAS Registry Number20426-12-4
SMILES
OC1=CC=C(\C=C/C(=O)C2=CC=CC=C2)C=C1
InChI Identifier
InChI=1S/C15H12O2/c16-14-9-6-12(7-10-14)8-11-15(17)13-4-2-1-3-5-13/h1-11,16H/b11-8-
InChI KeyPWWCDTYUYPOAIU-FLIBITNWSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as retrochalcones. These are a form of normal chalcones that are structurally distinguished by the lack of oxygen functionalities at the C2'- and C6'-positions.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassLinear 1,3-diarylpropanoids
Sub ClassChalcones and dihydrochalcones
Direct ParentRetrochalcones
Alternative Parents
Substituents
  • Retrochalcone
  • Cinnamylphenol
  • Hydroxycinnamic acid or derivatives
  • Benzoyl
  • Styrene
  • Aryl ketone
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Monocyclic benzene moiety
  • Enone
  • Acryloyl-group
  • Alpha,beta-unsaturated ketone
  • Ketone
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point182 - 183 °CNot Available
Boiling Point394.00 to 395.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility240.3 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.911 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.016 g/LALOGPS
logP3.79ALOGPS
logP3.59ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)9.04ChemAxon
pKa (Strongest Basic)-6.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity68.86 m³·mol⁻¹ChemAxon
Polarizability24.3 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+155.79830932474
DeepCCS[M-H]-153.40230932474
DeepCCS[M-2H]-186.47530932474
DeepCCS[M+Na]+161.8230932474
AllCCS[M+H]+151.132859911
AllCCS[M+H-H2O]+146.832859911
AllCCS[M+NH4]+155.132859911
AllCCS[M+Na]+156.232859911
AllCCS[M-H]-152.032859911
AllCCS[M+Na-2H]-151.632859911
AllCCS[M+HCOO]-151.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-HydroxychalconeOC1=CC=C(\C=C/C(=O)C2=CC=CC=C2)C=C13497.0Standard polar33892256
4-HydroxychalconeOC1=CC=C(\C=C/C(=O)C2=CC=CC=C2)C=C12215.6Standard non polar33892256
4-HydroxychalconeOC1=CC=C(\C=C/C(=O)C2=CC=CC=C2)C=C12440.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Hydroxychalcone,1TMS,isomer #1C[Si](C)(C)OC1=CC=C(/C=C\C(=O)C2=CC=CC=C2)C=C12377.5Semi standard non polar33892256
4-Hydroxychalcone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C\C(=O)C2=CC=CC=C2)C=C12657.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxychalcone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-3930000000-6415d1f46bc19424d5ef2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxychalcone GC-MS (1 TMS) - 70eV, Positivesplash10-05fr-6790000000-dd1bff905e4ace545c832017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxychalcone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxychalcone 10V, Positive-QTOFsplash10-004i-0190000000-856391d152b9bfb325e82016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxychalcone 20V, Positive-QTOFsplash10-0a6r-1960000000-bbda4ff7c9df6a3ad0f72016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxychalcone 40V, Positive-QTOFsplash10-0a4i-6900000000-a6343545bc9207565e6e2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxychalcone 10V, Negative-QTOFsplash10-00di-0190000000-ccf4583d231a337887a62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxychalcone 20V, Negative-QTOFsplash10-00di-1590000000-b23de3f7e6cce89dd2802016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxychalcone 40V, Negative-QTOFsplash10-0kxr-4910000000-e2ebf7a23a2ec858be552016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxychalcone 10V, Negative-QTOFsplash10-00di-0090000000-2ee08f480428f62baef52021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxychalcone 20V, Negative-QTOFsplash10-00di-1390000000-cac93dc5ed1c3cba5f632021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxychalcone 40V, Negative-QTOFsplash10-014i-9610000000-a0bcdad78de544c51b9c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxychalcone 10V, Positive-QTOFsplash10-004i-0090000000-0f3790e5e409e7a887c42021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxychalcone 20V, Positive-QTOFsplash10-056s-0940000000-b25fdef880f655e416072021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxychalcone 40V, Positive-QTOFsplash10-0a6r-5900000000-83aa01820b05a1db0c542021-09-25Wishart 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 IDFDB010521
KNApSAcK IDNot Available
Chemspider ID21428166
KEGG Compound IDC14231
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound25021769
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1540681
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.. .