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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 02:44:44 UTC
Update Date2022-03-07 02:56:53 UTC
HMDB IDHMDB0041100
Secondary Accession Numbers
  • HMDB41100
Metabolite Identification
Common NameKanzonol N
DescriptionKanzonol N belongs to the class of organic compounds known as 5-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C5 atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one. Kanzonol N has been detected, but not quantified in, herbs and spices. This could make kanzonol N a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Kanzonol N.
Structure
Data?1563863623
Synonyms
ValueSource
(3R)-8-Carboxyaldehyde-7,2',4'-trihydroxy-5-methoxy-3'-prenylisoflavanHMDB
Chemical FormulaC22H24O6
Average Molecular Weight384.4224
Monoisotopic Molecular Weight384.1572885
IUPAC Name3-[2,4-dihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]-7-hydroxy-5-methoxy-3,4-dihydro-2H-1-benzopyran-8-carbaldehyde
Traditional Name3-[2,4-dihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]-7-hydroxy-5-methoxy-3,4-dihydro-2H-1-benzopyran-8-carbaldehyde
CAS Registry Number156250-71-4
SMILES
COC1=C2CC(COC2=C(C=O)C(O)=C1)C1=C(O)C(CC=C(C)C)=C(O)C=C1
InChI Identifier
InChI=1S/C22H24O6/c1-12(2)4-5-15-18(24)7-6-14(21(15)26)13-8-16-20(27-3)9-19(25)17(10-23)22(16)28-11-13/h4,6-7,9-10,13,24-26H,5,8,11H2,1-3H3
InChI KeyANRYVYXUTFJPOR-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 5-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C5 atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassO-methylated isoflavonoids
Direct Parent5-O-methylated isoflavonoids
Alternative Parents
Substituents
  • 5-methoxyisoflavonoid-skeleton
  • Isoflavanol
  • Hydroxyisoflavonoid
  • Isoflavan
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Anisole
  • Resorcinol
  • Aryl-aldehyde
  • Alkyl aryl ether
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Aldehyde
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.012 g/LALOGPS
logP3.57ALOGPS
logP4.82ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)8.65ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area96.22 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity108.23 m³·mol⁻¹ChemAxon
Polarizability41.05 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
DarkChem[M+H]+193.03931661259
DarkChem[M-H]-194.27631661259
DeepCCS[M+H]+197.9130932474
DeepCCS[M-H]-195.55230932474
DeepCCS[M-2H]-229.07430932474
DeepCCS[M+Na]+204.30330932474
AllCCS[M+H]+193.632859911
AllCCS[M+H-H2O]+190.732859911
AllCCS[M+NH4]+196.332859911
AllCCS[M+Na]+197.132859911
AllCCS[M-H]-195.332859911
AllCCS[M+Na-2H]-195.332859911
AllCCS[M+HCOO]-195.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Kanzonol NCOC1=C2CC(COC2=C(C=O)C(O)=C1)C1=C(O)C(CC=C(C)C)=C(O)C=C14195.2Standard polar33892256
Kanzonol NCOC1=C2CC(COC2=C(C=O)C(O)=C1)C1=C(O)C(CC=C(C)C)=C(O)C=C13322.1Standard non polar33892256
Kanzonol NCOC1=C2CC(COC2=C(C=O)C(O)=C1)C1=C(O)C(CC=C(C)C)=C(O)C=C13611.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Kanzonol N,1TMS,isomer #1COC1=CC(O[Si](C)(C)C)=C(C=O)C2=C1CC(C1=CC=C(O)C(CC=C(C)C)=C1O)CO23407.6Semi standard non polar33892256
Kanzonol N,1TMS,isomer #2COC1=CC(O)=C(C=O)C2=C1CC(C1=CC=C(O)C(CC=C(C)C)=C1O[Si](C)(C)C)CO23309.1Semi standard non polar33892256
Kanzonol N,1TMS,isomer #3COC1=CC(O)=C(C=O)C2=C1CC(C1=CC=C(O[Si](C)(C)C)C(CC=C(C)C)=C1O)CO23344.0Semi standard non polar33892256
Kanzonol N,2TMS,isomer #1COC1=CC(O[Si](C)(C)C)=C(C=O)C2=C1CC(C1=CC=C(O[Si](C)(C)C)C(CC=C(C)C)=C1O)CO23285.8Semi standard non polar33892256
Kanzonol N,2TMS,isomer #2COC1=CC(O[Si](C)(C)C)=C(C=O)C2=C1CC(C1=CC=C(O)C(CC=C(C)C)=C1O[Si](C)(C)C)CO23251.0Semi standard non polar33892256
Kanzonol N,2TMS,isomer #3COC1=CC(O)=C(C=O)C2=C1CC(C1=CC=C(O[Si](C)(C)C)C(CC=C(C)C)=C1O[Si](C)(C)C)CO23232.4Semi standard non polar33892256
Kanzonol N,3TMS,isomer #1COC1=CC(O[Si](C)(C)C)=C(C=O)C2=C1CC(C1=CC=C(O[Si](C)(C)C)C(CC=C(C)C)=C1O[Si](C)(C)C)CO23213.5Semi standard non polar33892256
Kanzonol N,1TBDMS,isomer #1COC1=CC(O[Si](C)(C)C(C)(C)C)=C(C=O)C2=C1CC(C1=CC=C(O)C(CC=C(C)C)=C1O)CO23676.1Semi standard non polar33892256
Kanzonol N,1TBDMS,isomer #2COC1=CC(O)=C(C=O)C2=C1CC(C1=CC=C(O)C(CC=C(C)C)=C1O[Si](C)(C)C(C)(C)C)CO23573.7Semi standard non polar33892256
Kanzonol N,1TBDMS,isomer #3COC1=CC(O)=C(C=O)C2=C1CC(C1=CC=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C1O)CO23620.8Semi standard non polar33892256
Kanzonol N,2TBDMS,isomer #1COC1=CC(O[Si](C)(C)C(C)(C)C)=C(C=O)C2=C1CC(C1=CC=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C1O)CO23770.5Semi standard non polar33892256
Kanzonol N,2TBDMS,isomer #2COC1=CC(O[Si](C)(C)C(C)(C)C)=C(C=O)C2=C1CC(C1=CC=C(O)C(CC=C(C)C)=C1O[Si](C)(C)C(C)(C)C)CO23699.2Semi standard non polar33892256
Kanzonol N,2TBDMS,isomer #3COC1=CC(O)=C(C=O)C2=C1CC(C1=CC=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C1O[Si](C)(C)C(C)(C)C)CO23670.7Semi standard non polar33892256
Kanzonol N,3TBDMS,isomer #1COC1=CC(O[Si](C)(C)C(C)(C)C)=C(C=O)C2=C1CC(C1=CC=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C1O[Si](C)(C)C(C)(C)C)CO23834.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Kanzonol N GC-MS (Non-derivatized) - 70eV, Positivesplash10-014l-1309000000-83e3c688392da33fc3092017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kanzonol N GC-MS (3 TMS) - 70eV, Positivesplash10-000i-1000090000-4d65f917c834ce6418e52017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kanzonol N 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 - Kanzonol N 10V, Positive-QTOFsplash10-001r-0918000000-c70464323e7dbb6e83702015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kanzonol N 20V, Positive-QTOFsplash10-0159-1933000000-d72eca9e0760d9db3b972015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kanzonol N 40V, Positive-QTOFsplash10-014j-3901000000-0fb7b298ee08de94f7412015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kanzonol N 10V, Negative-QTOFsplash10-001i-0219000000-24bf582e9e40b909e0e12015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kanzonol N 20V, Negative-QTOFsplash10-0059-0936000000-901795ab3c451e04edb82015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kanzonol N 40V, Negative-QTOFsplash10-004r-1911000000-7f7c6584addde30a5c9d2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kanzonol N 10V, Positive-QTOFsplash10-004r-0009000000-c1ec17d8dcc5f67055312021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kanzonol N 20V, Positive-QTOFsplash10-004i-0129000000-ea2f4023adca3110c2472021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kanzonol N 40V, Positive-QTOFsplash10-0a6r-0976000000-a5ee2eb1fc15a122bc4b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kanzonol N 10V, Negative-QTOFsplash10-001i-0009000000-30d2b8786aad6ec803f72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kanzonol N 20V, Negative-QTOFsplash10-053i-0009000000-19637e075671c917fc1e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kanzonol N 40V, Negative-QTOFsplash10-0f80-0739000000-45b40ab0a60a9b8649142021-09-22Wishart 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 IDFDB020982
KNApSAcK IDC00019327
Chemspider ID35015104
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131753028
PDB IDNot Available
ChEBI ID175909
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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.. .