Record Information
Version1.0
Creation date2010-04-08 22:04:39 UTC
Update date2020-09-17 15:40:58 UTC
Primary IDFDB000657
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGalangin
DescriptionNorizalpinin, also known as teptochrysin or galangin, belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position. Thus, norizalpinin is considered to be a flavonoid lipid molecule. Norizalpinin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Norizalpinin is found, on average, in the highest concentration within mexican oregano. Norizalpinin has also been detected, but not quantified in, several different foods, such as lingonberries, garden onion (var.), herbs and spices, parsley, and apples. This could make norizalpinin a potential biomarker for the consumption of these foods. A 7-hydroxyflavonol with additional hydroxy groups at positions 3 and 5 respectively; a growth inhibitor of breast tumor cells.
CAS Number548-83-4
Structure
Thumb
Synonyms
SynonymSource
3,5,7-Trihydroxy-2-phenyl-4H-benzopyran-4-oneChEBI
3,5,7-TrihydroxyflavoneChEBI
3,5,7-TriOH-flavoneChEBI
TeptochrysinChEBI
3,5,7-Trihydroxy-2-phenyl-4-benzopyroneHMDB
3,5,7-Trihydroxy-2-phenyl-4H-1-benzopyran-4-oneHMDB
3,5,7-Trihydroxy-2-phenyl-4H-1-benzopyran-4-one, 9ciHMDB
3,5,7-Trihydroxy-2-phenyl-4H-chromen-4-oneHMDB
3,5,7-Trihydroxy-flavoneHMDB
4H-1-Benzopyran-4-one, 3,5,7-trihydroxy-2-phenyl- (9ci)HMDB
5,7-DihydroxyflavonolHMDB
GalanginHMDB
NorizalpininChEBI
3,5,7-Trihydroxy-2-phenyl-4H-1-benzopyran-4-one, 9CIdb_source
Predicted Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
logP2.39ALOGPS
logP2.76ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)6.38ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity72.9 m³·mol⁻¹ChemAxon
Polarizability26.54 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC15H10O5
IUPAC name3,5,7-trihydroxy-2-phenyl-4H-chromen-4-one
InChI IdentifierInChI=1S/C15H10O5/c16-9-6-10(17)12-11(7-9)20-15(14(19)13(12)18)8-4-2-1-3-5-8/h1-7,16-17,19H
InChI KeyVCCRNZQBSJXYJD-UHFFFAOYSA-N
Isomeric SMILESOC1=CC(O)=C2C(OC(=C(O)C2=O)C2=CC=CC=C2)=C1
Average Molecular Weight270.2369
Monoisotopic Molecular Weight270.05282343
Classification
Description Belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavones
Direct ParentFlavonols
Alternative Parents
Substituents
  • 3-hydroxyflavone
  • 3-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Vinylogous acid
  • Heteroaromatic compound
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Organooxygen compound
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 66.67%; H 3.73%; O 29.60%DFC
Melting PointMp 217-218°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSGalangin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000i-0950000000-f80dc86cabb2b5ee7f80Spectrum
Predicted GC-MSGalangin, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-3433900000-6efc1a666076cec9c866Spectrum
Predicted GC-MSGalangin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-004i-0917700000-5933de30c7285a663cccSpectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0917700000-5933de30c7285a663cccSpectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-014i-0980000000-5ead402f53f21ad1bc69Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-014i-0980000000-5ead402f53f21ad1bc69Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-014i-0980000000-5ead402f53f21ad1bc69Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-014i-0090000000-ccad6be83481aed77fa3Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-014i-0090000000-a7d187f28c6a27ca6b7cSpectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-014i-0980000000-5ead402f53f21ad1bc69Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-014i-0090000000-573c015550a1005e3b91Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-014i-0090000000-041e54bbbd21adb90d8eSpectrum
MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-014i-0970000000-f56d16bf9ffd129227e2Spectrum
MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-0uk9-0940000000-fcc781cee9aa39b4d2c3Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00ov-0941000000-088245d4060300c28913Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-01b9-0090000000-3dca6de83080ab540738Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-01b9-0090000000-c7a6c4b522f7d1ab344aSpectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00mk-0690000000-9d8f0b599742e5233f85Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-014i-0090000000-a7d187f28c6a27ca6b7cSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-014i-0980000000-5ead402f53f21ad1bc69Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-014i-0090000000-573c015550a1005e3b91Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0090000000-a5f26af5c8b5cd0dba26Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0090000000-760166b17d3214284672Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-6950000000-b847b228161afff1e72aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-54bac69149adc7b5ba6eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0190000000-d5a27d2008cc13814301Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-3930000000-91f995a09835f8ce6953Spectrum
NMRNot Available
ChemSpider ID4444935
ChEMBL IDCHEMBL309490
KEGG Compound IDC10044
Pubchem Compound ID5281616
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID317
DrugBank IDNot Available
HMDB IDHMDB29521
CRC / DFC (Dictionary of Food Compounds) IDBFL05-Z:BFL05-Z
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00004533
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia ID3,5,7-Trihydroxyflavone
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti microbial33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.CHEBI
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.