5,7,3'-Trihydroxy-4'-methoxyflavanone (CHEM024760)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 21:54:30 UTC
Update Date2016-11-09 01:17:57 UTC
Accession NumberCHEM024760
Identification
Common Name5,7,3'-Trihydroxy-4'-methoxyflavanone
ClassSmall Molecule
DescriptionThe S-form is It is isolated from Brickellia vernicosa, Persica vulgaris (preferred genus name Prunus), Citrus and Mentha species [CCD
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC16H14O6
Average Molecular Mass302.282 g/mol
Monoisotopic Mass302.079 g/mol
CAS Registry NumberNot Available
IUPAC Name5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one
Traditional Namehesperetine
SMILESCOC1=C(O)C=C(C=C1)C1CC(=O)C2=C(O)C=C(O)C=C2O1
InChI IdentifierInChI=1S/C16H14O6/c1-21-13-3-2-8(4-10(13)18)14-7-12(20)16-11(19)5-9(17)6-15(16)22-14/h2-6,14,17-19H,7H2,1H3
InChI KeyAIONOLUJZLIMTK-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 4'-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C4' atom of the flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassO-methylated flavonoids
Direct Parent4'-O-methylated flavonoids
Alternative Parents
Substituents
  • 4p-methoxyflavonoid-skeleton
  • Flavanone
  • Hydroxyflavonoid
  • 7-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • Flavan
  • Chromone
  • Chromane
  • Benzopyran
  • Methoxyphenol
  • 1-benzopyran
  • Methoxybenzene
  • Phenoxy compound
  • Aryl alkyl ketone
  • Anisole
  • Phenol ether
  • Aryl ketone
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Benzenoid
  • Vinylogous acid
  • Ketone
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.14 g/LALOGPS
logP2.52ALOGPS
logP2.68ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)7.86ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area96.22 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity77.75 m³·mol⁻¹ChemAxon
Polarizability30.32 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-052f-1971000000-56754303127301d1b2eaSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000l-2971100000-c6ded90239807f8bb898Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4l-1890100000-d023765b6d478c346388Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-052f-1971000000-56754303127301d1b2eaSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000l-2971100000-c6ded90239807f8bb898Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4l-1890100000-d023765b6d478c346388Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-0792000000-043d1ca82d4702349341Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0udj-3860980000-a1715e067e13bbdada3eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-0udi-0498000000-93e6bf74ac9acf6199dcSpectrum
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-0udi-0900000000-3155fa8cf11cb598c7b8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0udi-0910000000-950b0c394b2535d33d8eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0009000000-e068a12319d0bfd192f1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0693000000-4d820f1d6dcf9d80fc41Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a4r-0910000000-3ba63f0018fc2d3146edSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-000l-0190000000-5929a6a017c13b7d93e6Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-000i-0190000000-eb01c4ad53e16b476f09Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0udi-0169000000-5d9b7fba914d229018a6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-053i-0920000000-b6ab2fed21176a341b28Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0udi-0009000000-32f8b49c4bc1df10782aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0iki-0930000000-20176d350f94ae4a84edSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0907000000-36605ac798a9e373e56cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0ufr-0900000000-de657b62f36904fa4d9eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0900000000-aca6930de1cdc2b44ee3Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-004i-0950000000-3910d5d1943ed6685f2cSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0udi-0910000000-950b0c394b2535d33d8eSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0udi-0901000000-21943a0770755ae8ec60Spectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0udi-0859000000-8990f8b07e70df4050b5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0329000000-4364410cdc5a65b92032Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udr-0944000000-edd7b755d11b9331e6c9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uki-3910000000-9e449d46da8305c0b794Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0109000000-21473197ac3beced4628Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0569000000-1e4d2574c341d9d9124fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pbl-4940000000-c9a717aa36bf4402e6c7Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0030746
FooDB IDFDB002676
Phenol Explorer IDNot Available
KNApSAcK IDC00014343
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID3467
ChEBI ID244674
PubChem Compound ID3593
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Barreca D, Lagana G, Tellone E, Ficarra S, Leuzzi U, Galtieri A, Bellocco E: Influences of flavonoids on erythrocyte membrane and metabolic implication through anionic exchange modulation. J Membr Biol. 2009 Aug;230(3):163-71. doi: 10.1007/s00232-009-9197-x.
2. Choi EJ: Hesperetin induced G1-phase cell cycle arrest in human breast cancer MCF-7 cells: involvement of CDK4 and p21. Nutr Cancer. 2007;59(1):115-9.
3. De Clercq E: Potential antivirals and antiviral strategies against SARS coronavirus infections. Expert Rev Anti Infect Ther. 2006 Apr;4(2):291-302.
4. Jin YR, Han XH, Zhang YH, Lee JJ, Lim Y, Chung JH, Yun YP: Antiplatelet activity of hesperetin, a bioflavonoid, is mainly mediated by inhibition of PLC-gamma2 phosphorylation and cyclooxygenase-1 activity. Atherosclerosis. 2007 Sep;194(1):144-52. Epub 2006 Nov 7.
5. Kuppusamy UR, Das NP: Antilipolytic action of hesperetin in rat adipocytes. Planta Med. 1993 Dec;59(6):508-12.
6. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.