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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:30:55 UTC
Update Date2020-02-26 21:43:50 UTC
HMDB IDHMDB0029521
Secondary Accession Numbers
  • HMDB29521
Metabolite Identification
Common NameNorizalpinin
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.
Structure
Data?1582753430
Synonyms
ValueSource
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
Chemical FormulaC15H10O5
Average Molecular Weight270.2369
Monoisotopic Molecular Weight270.05282343
IUPAC Name3,5,7-trihydroxy-2-phenyl-4H-chromen-4-one
Traditional Namegalangin
CAS Registry Number548-83-4
SMILES
OC1=CC(O)=C2C(OC(=C(O)C2=O)C2=CC=CC=C2)=C1
InChI Identifier
InChI=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
Chemical Taxonomy
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:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point217 - 218 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
logP2.39ALOGPS
logP2.76ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)6.45ChemAxon
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
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-0950000000-f80dc86cabb2b5ee7f80Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00di-3433900000-6efc1a666076cec9c866Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-004i-0917700000-5933de30c7285a663cccSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0917700000-5933de30c7285a663cccSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-014i-0980000000-5ead402f53f21ad1bc69Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-014i-0980000000-5ead402f53f21ad1bc69Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-014i-0980000000-5ead402f53f21ad1bc69Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-014i-0090000000-ccad6be83481aed77fa3Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-014i-0090000000-a7d187f28c6a27ca6b7cSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-014i-0980000000-5ead402f53f21ad1bc69Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-014i-0090000000-573c015550a1005e3b91Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-014i-0090000000-041e54bbbd21adb90d8eSpectrum
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-014i-0970000000-f56d16bf9ffd129227e2Spectrum
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-0uk9-0940000000-fcc781cee9aa39b4d2c3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00ov-0941000000-088245d4060300c28913Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-01b9-0090000000-3dca6de83080ab540738Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-01b9-0090000000-c7a6c4b522f7d1ab344aSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00mk-0690000000-9d8f0b599742e5233f85Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-014i-0090000000-a7d187f28c6a27ca6b7cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-014i-0980000000-5ead402f53f21ad1bc69Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-014i-0090000000-573c015550a1005e3b91Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0090000000-a5f26af5c8b5cd0dba26Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0090000000-760166b17d3214284672Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-6950000000-b847b228161afff1e72aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-54bac69149adc7b5ba6eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0190000000-d5a27d2008cc13814301Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-3930000000-91f995a09835f8ce6953Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 ID317
FooDB IDFDB000657
KNApSAcK IDC00004533
Chemspider ID4444935
KEGG Compound IDC10044
BioCyc IDCPD-13502
BiGG IDNot Available
Wikipedia LinkGalangin
METLIN IDNot Available
PubChem Compound5281616
PDB IDNot Available
ChEBI ID5262
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
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.. .

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Norizalpinin → 6-[(3,7-dihydroxy-4-oxo-2-phenyl-4H-chromen-5-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Norizalpinin → 6-[(3,5-dihydroxy-4-oxo-2-phenyl-4H-chromen-7-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Norizalpinin → 6-[(5,7-dihydroxy-4-oxo-2-phenyl-4H-chromen-3-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails