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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:30:55 UTC
Update Date2021-10-13 06:01:03 UTC
HMDB IDHMDB0029521
Secondary Accession Numbers
  • HMDB29521
Metabolite Identification
Common NameNorizalpinin
DescriptionNorizalpinin, also known as teptochrysin, 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. Norizalpinin is found, on average, in the highest concentration within mexican oreganos (Lippia graveolens). Norizalpinin has also been detected, but not quantified in, several different foods, such as cloudberries (Rubus chamaemorus), yellow zucchinis (Cucurbita pepo var. cylindrica), tea leaf willows (Salix pulchra), common thymes (Thymus vulgaris), and pigeon peas (Cajanus cajan). This could make norizalpinin a potential biomarker for the consumption of these foods. Norizalpinin 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 significant number of articles have been published on Norizalpinin.
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

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point217 - 218 °CNot Available
Boiling Point518.64 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility571.9 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP3.322 (est)The Good Scents Company Information System
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available154.914http://allccs.zhulab.cn/database/detail?ID=AllCCS00001413
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
logP10(2.39) g/LALOGPS
logP10(2.76) g/LChemAxon
logS10(-3.4) g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+161.75230932474
DeepCCS[M-H]-159.39430932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
NorizalpininOC1=CC(O)=C2C(OC(=C(O)C2=O)C2=CC=CC=C2)=C14001.1Standard polar33892256
NorizalpininOC1=CC(O)=C2C(OC(=C(O)C2=O)C2=CC=CC=C2)=C12483.1Standard non polar33892256
NorizalpininOC1=CC(O)=C2C(OC(=C(O)C2=O)C2=CC=CC=C2)=C12734.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Norizalpinin,1TMS,isomer #1C[Si](C)(C)OC1=CC(O)=C2C(=O)C(O)=C(C3=CC=CC=C3)OC2=C12819.6Semi standard non polar33892256
Norizalpinin,1TMS,isomer #2C[Si](C)(C)OC1=CC(O)=CC2=C1C(=O)C(O)=C(C1=CC=CC=C1)O22765.4Semi standard non polar33892256
Norizalpinin,1TMS,isomer #3C[Si](C)(C)OC1=C(C2=CC=CC=C2)OC2=CC(O)=CC(O)=C2C1=O2735.1Semi standard non polar33892256
Norizalpinin,2TMS,isomer #1C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C2C(=O)C(O)=C(C3=CC=CC=C3)OC2=C12792.2Semi standard non polar33892256
Norizalpinin,2TMS,isomer #2C[Si](C)(C)OC1=CC(O)=C2C(=O)C(O[Si](C)(C)C)=C(C3=CC=CC=C3)OC2=C12728.1Semi standard non polar33892256
Norizalpinin,2TMS,isomer #3C[Si](C)(C)OC1=C(C2=CC=CC=C2)OC2=CC(O)=CC(O[Si](C)(C)C)=C2C1=O2698.5Semi standard non polar33892256
Norizalpinin,3TMS,isomer #1C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C2C(=O)C(O[Si](C)(C)C)=C(C3=CC=CC=C3)OC2=C12785.0Semi standard non polar33892256
Norizalpinin,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)C(O)=C(C3=CC=CC=C3)OC2=C13068.7Semi standard non polar33892256
Norizalpinin,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC(O)=CC2=C1C(=O)C(O)=C(C1=CC=CC=C1)O23030.0Semi standard non polar33892256
Norizalpinin,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=C(C2=CC=CC=C2)OC2=CC(O)=CC(O)=C2C1=O2998.7Semi standard non polar33892256
Norizalpinin,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C(O)=C(C3=CC=CC=C3)OC2=C13280.4Semi standard non polar33892256
Norizalpinin,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)C(O[Si](C)(C)C(C)(C)C)=C(C3=CC=CC=C3)OC2=C13215.4Semi standard non polar33892256
Norizalpinin,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=C(C2=CC=CC=C2)OC2=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C2C1=O3209.5Semi standard non polar33892256
Norizalpinin,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C(O[Si](C)(C)C(C)(C)C)=C(C3=CC=CC=C3)OC2=C13429.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Norizalpinin GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-0950000000-f80dc86cabb2b5ee7f802017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Norizalpinin GC-MS (3 TMS) - 70eV, Positivesplash10-00di-3433900000-6efc1a666076cec9c8662017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Norizalpinin 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 - Norizalpinin ESI-TOF , Negative-QTOFsplash10-004i-0917700000-5933de30c7285a663ccc2017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norizalpinin ESI-TOF 10V, Negative-QTOFsplash10-004i-0917700000-5933de30c7285a663ccc2017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norizalpinin ESI-TOF 40V, Negative-QTOFsplash10-014i-0980000000-5ead402f53f21ad1bc692017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norizalpinin ESI-TOF 30V, Negative-QTOFsplash10-014i-0980000000-5ead402f53f21ad1bc692017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norizalpinin ESI-TOF 20V, Negative-QTOFsplash10-014i-0980000000-5ead402f53f21ad1bc692017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norizalpinin ESI-TOF , Negative-QTOFsplash10-014i-0090000000-ccad6be83481aed77fa32017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norizalpinin ESI-TOF 10V, Negative-QTOFsplash10-014i-0090000000-a7d187f28c6a27ca6b7c2017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norizalpinin ESI-TOF 40V, Negative-QTOFsplash10-014i-0980000000-5ead402f53f21ad1bc692017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norizalpinin ESI-TOF 30V, Negative-QTOFsplash10-014i-0090000000-573c015550a1005e3b912017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norizalpinin ESI-TOF 20V, Negative-QTOFsplash10-014i-0090000000-041e54bbbd21adb90d8e2017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norizalpinin DI-ESI-qTof , Negative-QTOFsplash10-014i-0970000000-f56d16bf9ffd129227e22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norizalpinin DI-ESI-qTof , Positive-QTOFsplash10-0uk9-0940000000-fcc781cee9aa39b4d2c32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norizalpinin LC-ESI-qTof , Positive-QTOFsplash10-00ov-0941000000-088245d4060300c289132017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norizalpinin Linear Ion Trap , negative-QTOFsplash10-01b9-0090000000-3dca6de83080ab5407382017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norizalpinin Linear Ion Trap , negative-QTOFsplash10-01b9-0090000000-c7a6c4b522f7d1ab344a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norizalpinin Linear Ion Trap , negative-QTOFsplash10-00mk-0690000000-9d8f0b599742e5233f852017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norizalpinin LC-ESI-TOF , negative-QTOFsplash10-014i-0090000000-a7d187f28c6a27ca6b7c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norizalpinin LC-ESI-TOF , negative-QTOFsplash10-014i-0980000000-5ead402f53f21ad1bc692017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norizalpinin LC-ESI-TOF , negative-QTOFsplash10-014i-0090000000-573c015550a1005e3b912017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norizalpinin 10V, Positive-QTOFsplash10-00di-0090000000-a5f26af5c8b5cd0dba262016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norizalpinin 20V, Positive-QTOFsplash10-00di-0090000000-760166b17d32142846722016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norizalpinin 40V, Positive-QTOFsplash10-0udi-6950000000-b847b228161afff1e72a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norizalpinin 10V, Negative-QTOFsplash10-014i-0090000000-54bac69149adc7b5ba6e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norizalpinin 20V, Negative-QTOFsplash10-014i-0190000000-d5a27d2008cc138143012016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norizalpinin 40V, Negative-QTOFsplash10-014i-3930000000-91f995a09835f8ce69532016-08-03Wishart LabView Spectrum
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 IDNot Available
Good Scents IDrw1247821
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