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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:30:49 UTC
Update Date2022-03-07 02:52:11 UTC
HMDB IDHMDB0029506
Secondary Accession Numbers
  • HMDB29506
Metabolite Identification
Common NameKuwanon B
DescriptionKuwanon B belongs to the class of organic compounds known as 3-prenylated flavones. These are flavones that features a C5-isoprenoid substituent at the 3-position. Thus, kuwanon b is considered to be a flavonoid. Based on a literature review very few articles have been published on Kuwanon B.
Structure
Data?1582753428
Synonyms
ValueSource
5,7-Dihydroxy-2-(5-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-yl)-3-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one, 9ciHMDB
Chemical FormulaC25H24O6
Average Molecular Weight420.4545
Monoisotopic Molecular Weight420.1572885
IUPAC Name5,7-dihydroxy-2-(5-hydroxy-2,2-dimethyl-2H-chromen-6-yl)-3-(3-methylbut-2-en-1-yl)-4H-chromen-4-one
Traditional Namekuwanon B
CAS Registry Number62949-78-4
SMILES
CC(C)=CCC1=C(OC2=CC(O)=CC(O)=C2C1=O)C1=C(O)C2=C(OC(C)(C)C=C2)C=C1
InChI Identifier
InChI=1S/C25H24O6/c1-13(2)5-6-17-23(29)21-18(27)11-14(26)12-20(21)30-24(17)16-7-8-19-15(22(16)28)9-10-25(3,4)31-19/h5,7-12,26-28H,6H2,1-4H3
InChI KeyGHYDRKXFHRBWGZ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 3-prenylated flavones. These are flavones that features a C5-isoprenoid substituent at the 3-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavones
Direct Parent3-prenylated flavones
Alternative Parents
Substituents
  • 3-prenylated flavone
  • Pyranoflavonoid
  • Hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • 2,2-dimethyl-1-benzopyran
  • Chromone
  • 1-benzopyran
  • Benzopyran
  • 1-hydroxy-4-unsubstituted benzenoid
  • Pyranone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous acid
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point250 - 254 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.012 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0044 g/LALOGPS
logP4.93ALOGPS
logP5.22ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)6.6ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area96.22 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity120.87 m³·mol⁻¹ChemAxon
Polarizability45.45 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+200.12230932474
DeepCCS[M-H]-197.72730932474
DeepCCS[M-2H]-230.6130932474
DeepCCS[M+Na]+206.03530932474
AllCCS[M+H]+201.832859911
AllCCS[M+H-H2O]+199.032859911
AllCCS[M+NH4]+204.332859911
AllCCS[M+Na]+205.032859911
AllCCS[M-H]-199.132859911
AllCCS[M+Na-2H]-198.732859911
AllCCS[M+HCOO]-198.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Kuwanon BCC(C)=CCC1=C(OC2=CC(O)=CC(O)=C2C1=O)C1=C(O)C2=C(OC(C)(C)C=C2)C=C15015.9Standard polar33892256
Kuwanon BCC(C)=CCC1=C(OC2=CC(O)=CC(O)=C2C1=O)C1=C(O)C2=C(OC(C)(C)C=C2)C=C13562.7Standard non polar33892256
Kuwanon BCC(C)=CCC1=C(OC2=CC(O)=CC(O)=C2C1=O)C1=C(O)C2=C(OC(C)(C)C=C2)C=C13685.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Kuwanon B,1TMS,isomer #1CC(C)=CCC1=C(C2=CC=C3OC(C)(C)C=CC3=C2O)OC2=CC(O[Si](C)(C)C)=CC(O)=C2C1=O3510.5Semi standard non polar33892256
Kuwanon B,1TMS,isomer #2CC(C)=CCC1=C(C2=CC=C3OC(C)(C)C=CC3=C2O)OC2=CC(O)=CC(O[Si](C)(C)C)=C2C1=O3475.1Semi standard non polar33892256
Kuwanon B,1TMS,isomer #3CC(C)=CCC1=C(C2=CC=C3OC(C)(C)C=CC3=C2O[Si](C)(C)C)OC2=CC(O)=CC(O)=C2C1=O3492.3Semi standard non polar33892256
Kuwanon B,2TMS,isomer #1CC(C)=CCC1=C(C2=CC=C3OC(C)(C)C=CC3=C2O[Si](C)(C)C)OC2=CC(O[Si](C)(C)C)=CC(O)=C2C1=O3419.5Semi standard non polar33892256
Kuwanon B,2TMS,isomer #2CC(C)=CCC1=C(C2=CC=C3OC(C)(C)C=CC3=C2O)OC2=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C2C1=O3406.6Semi standard non polar33892256
Kuwanon B,2TMS,isomer #3CC(C)=CCC1=C(C2=CC=C3OC(C)(C)C=CC3=C2O[Si](C)(C)C)OC2=CC(O)=CC(O[Si](C)(C)C)=C2C1=O3387.6Semi standard non polar33892256
Kuwanon B,3TMS,isomer #1CC(C)=CCC1=C(C2=CC=C3OC(C)(C)C=CC3=C2O[Si](C)(C)C)OC2=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C2C1=O3403.7Semi standard non polar33892256
Kuwanon B,1TBDMS,isomer #1CC(C)=CCC1=C(C2=CC=C3OC(C)(C)C=CC3=C2O)OC2=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C2C1=O3770.9Semi standard non polar33892256
Kuwanon B,1TBDMS,isomer #2CC(C)=CCC1=C(C2=CC=C3OC(C)(C)C=CC3=C2O)OC2=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C2C1=O3730.5Semi standard non polar33892256
Kuwanon B,1TBDMS,isomer #3CC(C)=CCC1=C(C2=CC=C3OC(C)(C)C=CC3=C2O[Si](C)(C)C(C)(C)C)OC2=CC(O)=CC(O)=C2C1=O3737.7Semi standard non polar33892256
Kuwanon B,2TBDMS,isomer #1CC(C)=CCC1=C(C2=CC=C3OC(C)(C)C=CC3=C2O[Si](C)(C)C(C)(C)C)OC2=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C2C1=O3879.3Semi standard non polar33892256
Kuwanon B,2TBDMS,isomer #2CC(C)=CCC1=C(C2=CC=C3OC(C)(C)C=CC3=C2O)OC2=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C2C1=O3869.7Semi standard non polar33892256
Kuwanon B,2TBDMS,isomer #3CC(C)=CCC1=C(C2=CC=C3OC(C)(C)C=CC3=C2O[Si](C)(C)C(C)(C)C)OC2=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C2C1=O3838.3Semi standard non polar33892256
Kuwanon B,3TBDMS,isomer #1CC(C)=CCC1=C(C2=CC=C3OC(C)(C)C=CC3=C2O[Si](C)(C)C(C)(C)C)OC2=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C2C1=O4024.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Kuwanon B GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4l-4209700000-407e44854a8344973bee2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kuwanon B GC-MS (3 TMS) - 70eV, Positivesplash10-00di-2100049000-611c5714eb7a8fce24212017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kuwanon B 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 - Kuwanon B 10V, Positive-QTOFsplash10-00di-1013900000-1e3ff6f555254fc6e7a02015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kuwanon B 20V, Positive-QTOFsplash10-014i-2019300000-e2c26514a400201e0b152015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kuwanon B 40V, Positive-QTOFsplash10-0gdj-5294000000-e96332206e798add116c2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kuwanon B 10V, Negative-QTOFsplash10-014i-0000900000-bd81d1902893635aa3142015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kuwanon B 20V, Negative-QTOFsplash10-014i-0006900000-acc18d01dc5801b0413e2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kuwanon B 40V, Negative-QTOFsplash10-0k9i-1937100000-5e0f7b9a253d7a0f24bd2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kuwanon B 10V, Positive-QTOFsplash10-00di-0000900000-2c722d7f3ff1673a173f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kuwanon B 20V, Positive-QTOFsplash10-00di-0000900000-2c722d7f3ff1673a173f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kuwanon B 40V, Positive-QTOFsplash10-0uk9-0960600000-58be6e708439ce7389d12021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kuwanon B 10V, Negative-QTOFsplash10-014i-0000900000-e89f00937a4f746a0b2c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kuwanon B 20V, Negative-QTOFsplash10-014i-0000900000-e89f00937a4f746a0b2c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kuwanon B 40V, Negative-QTOFsplash10-0a4i-0609200000-67f18785bb351f49916e2021-09-24Wishart 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 IDFDB000641
KNApSAcK IDC00004056
Chemspider ID24843909
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound44258295
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1810041
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.. .