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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 23:48:28 UTC
Update Date2022-03-07 02:55:47 UTC
HMDB IDHMDB0038488
Secondary Accession Numbers
  • HMDB38488
Metabolite Identification
Common NameGancaonin B
DescriptionGancaonin B belongs to the class of organic compounds known as 6-prenylated isoflavanones. These are isoflavanones featuring a C5-isoprenoid unit at the 6-position. Thus, gancaonin b is considered to be a flavonoid. Gancaonin B has been detected, but not quantified in, herbs and spices. This could make gancaonin b a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Gancaonin B.
Structure
Data?1563863206
Synonyms
ValueSource
3',5,7-Trihydroxy-4'-methoxy-6-prenylisoflavoneHMDB
5,7,3'-Trihydroxy-4'-methoxy-6-prenylisoflavoneHMDB
Chemical FormulaC21H20O6
Average Molecular Weight368.3799
Monoisotopic Molecular Weight368.125988372
IUPAC Name5,7-dihydroxy-3-(3-hydroxy-4-methoxyphenyl)-6-(3-methylbut-2-en-1-yl)-4H-chromen-4-one
Traditional Namegancaonin B
CAS Registry Number124596-86-7
SMILES
COC1=C(O)C=C(C=C1)C1=COC2=C(C(O)=C(CC=C(C)C)C(O)=C2)C1=O
InChI Identifier
InChI=1S/C21H20O6/c1-11(2)4-6-13-15(22)9-18-19(20(13)24)21(25)14(10-27-18)12-5-7-17(26-3)16(23)8-12/h4-5,7-10,22-24H,6H2,1-3H3
InChI KeyYQEPOQVRUDADPH-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 6-prenylated isoflavanones. These are isoflavanones featuring a C5-isoprenoid unit at the 6-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassIsoflavans
Direct Parent6-prenylated isoflavanones
Alternative Parents
Substituents
  • 6-prenylated isoflavanone
  • 4p-o-methylisoflavone
  • 3'-hydroxy,4'-methoxyisoflavonoid
  • Isoflavone
  • Hydroxyisoflavonoid
  • Chromone
  • Methoxyphenol
  • 1-benzopyran
  • Benzopyran
  • Phenoxy compound
  • Anisole
  • Phenol ether
  • Methoxybenzene
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Pyranone
  • Pyran
  • Monocyclic benzene moiety
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous acid
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point206 - 209 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.94 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.014 g/LALOGPS
logP3.74ALOGPS
logP4.65ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)6.42ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area96.22 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity102.39 m³·mol⁻¹ChemAxon
Polarizability39.14 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]+190.56330932474
DeepCCS[M-H]-188.20530932474
DeepCCS[M-2H]-221.60930932474
DeepCCS[M+Na]+196.83730932474
AllCCS[M+H]+188.932859911
AllCCS[M+H-H2O]+185.832859911
AllCCS[M+NH4]+191.832859911
AllCCS[M+Na]+192.632859911
AllCCS[M-H]-187.432859911
AllCCS[M+Na-2H]-187.032859911
AllCCS[M+HCOO]-186.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Gancaonin BCOC1=C(O)C=C(C=C1)C1=COC2=C(C(O)=C(CC=C(C)C)C(O)=C2)C1=O5077.5Standard polar33892256
Gancaonin BCOC1=C(O)C=C(C=C1)C1=COC2=C(C(O)=C(CC=C(C)C)C(O)=C2)C1=O3185.9Standard non polar33892256
Gancaonin BCOC1=C(O)C=C(C=C1)C1=COC2=C(C(O)=C(CC=C(C)C)C(O)=C2)C1=O3469.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Gancaonin B,1TMS,isomer #1COC1=CC=C(C2=COC3=CC(O)=C(CC=C(C)C)C(O)=C3C2=O)C=C1O[Si](C)(C)C3430.7Semi standard non polar33892256
Gancaonin B,1TMS,isomer #2COC1=CC=C(C2=COC3=CC(O)=C(CC=C(C)C)C(O[Si](C)(C)C)=C3C2=O)C=C1O3401.9Semi standard non polar33892256
Gancaonin B,1TMS,isomer #3COC1=CC=C(C2=COC3=CC(O[Si](C)(C)C)=C(CC=C(C)C)C(O)=C3C2=O)C=C1O3430.0Semi standard non polar33892256
Gancaonin B,2TMS,isomer #1COC1=CC=C(C2=COC3=CC(O[Si](C)(C)C)=C(CC=C(C)C)C(O)=C3C2=O)C=C1O[Si](C)(C)C3276.8Semi standard non polar33892256
Gancaonin B,2TMS,isomer #2COC1=CC=C(C2=COC3=CC(O)=C(CC=C(C)C)C(O[Si](C)(C)C)=C3C2=O)C=C1O[Si](C)(C)C3250.0Semi standard non polar33892256
Gancaonin B,2TMS,isomer #3COC1=CC=C(C2=COC3=CC(O[Si](C)(C)C)=C(CC=C(C)C)C(O[Si](C)(C)C)=C3C2=O)C=C1O3266.4Semi standard non polar33892256
Gancaonin B,3TMS,isomer #1COC1=CC=C(C2=COC3=CC(O[Si](C)(C)C)=C(CC=C(C)C)C(O[Si](C)(C)C)=C3C2=O)C=C1O[Si](C)(C)C3211.8Semi standard non polar33892256
Gancaonin B,1TBDMS,isomer #1COC1=CC=C(C2=COC3=CC(O)=C(CC=C(C)C)C(O)=C3C2=O)C=C1O[Si](C)(C)C(C)(C)C3691.6Semi standard non polar33892256
Gancaonin B,1TBDMS,isomer #2COC1=CC=C(C2=COC3=CC(O)=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=C3C2=O)C=C1O3666.7Semi standard non polar33892256
Gancaonin B,1TBDMS,isomer #3COC1=CC=C(C2=COC3=CC(O[Si](C)(C)C(C)(C)C)=C(CC=C(C)C)C(O)=C3C2=O)C=C1O3695.3Semi standard non polar33892256
Gancaonin B,2TBDMS,isomer #1COC1=CC=C(C2=COC3=CC(O[Si](C)(C)C(C)(C)C)=C(CC=C(C)C)C(O)=C3C2=O)C=C1O[Si](C)(C)C(C)(C)C3798.0Semi standard non polar33892256
Gancaonin B,2TBDMS,isomer #2COC1=CC=C(C2=COC3=CC(O)=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=C3C2=O)C=C1O[Si](C)(C)C(C)(C)C3756.1Semi standard non polar33892256
Gancaonin B,2TBDMS,isomer #3COC1=CC=C(C2=COC3=CC(O[Si](C)(C)C(C)(C)C)=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=C3C2=O)C=C1O3769.3Semi standard non polar33892256
Gancaonin B,3TBDMS,isomer #1COC1=CC=C(C2=COC3=CC(O[Si](C)(C)C(C)(C)C)=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=C3C2=O)C=C1O[Si](C)(C)C(C)(C)C3893.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Gancaonin B GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udu-1109000000-c3e03b8f9b047e82d2ef2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gancaonin B GC-MS (3 TMS) - 70eV, Positivesplash10-01b9-1000090000-95e1b3bccacbb123e0892017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gancaonin 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 - Gancaonin B 10V, Positive-QTOFsplash10-014i-0009000000-fb712ef4a8e8793dc8e72015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gancaonin B 20V, Positive-QTOFsplash10-02t9-2009000000-d17ba71b440f5bc7c3172015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gancaonin B 40V, Positive-QTOFsplash10-0gb9-9563000000-28fb8184a5be1ada68492015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gancaonin B 10V, Negative-QTOFsplash10-014i-0009000000-84927c7763b8e293318f2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gancaonin B 20V, Negative-QTOFsplash10-014i-0019000000-3ab66104eb0698ec0fbd2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gancaonin B 40V, Negative-QTOFsplash10-0ab9-2955000000-f5deb078b54033ed6f0d2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gancaonin B 10V, Positive-QTOFsplash10-03di-0009000000-c013acf407d50c5d0ce92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gancaonin B 20V, Positive-QTOFsplash10-03di-0039000000-9051ab6db4ba0e6980582021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gancaonin B 40V, Positive-QTOFsplash10-001l-0191000000-3ee9057435a8d45962862021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gancaonin B 10V, Negative-QTOFsplash10-014i-0009000000-53fb202c32e20191eab92021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gancaonin B 20V, Negative-QTOFsplash10-014i-0009000000-f72b1f109db8b58438c72021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gancaonin B 40V, Negative-QTOFsplash10-014i-2297000000-eeb5e7e7409eb001c76c2021-09-23Wishart 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 IDFDB017860
KNApSAcK IDC00009891
Chemspider ID4476334
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5317479
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1868771
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.. .