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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 00:13:25 UTC
Update Date2022-03-07 02:55:58 UTC
HMDB IDHMDB0038875
Secondary Accession Numbers
  • HMDB38875
Metabolite Identification
Common NameGancaonin Q
DescriptionGancaonin Q belongs to the class of organic compounds known as 6-prenylated flavones. These are flavones that features a C5-isoprenoid substituent at the 6-position. Thus, gancaonin Q is considered to be a flavonoid. Gancaonin Q has been detected, but not quantified in, herbs and spices. This could make gancaonin Q a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on Gancaonin Q.
Structure
Data?1563863273
Synonyms
ValueSource
5,7-Dihydroxy-2-[4-hydroxy-3-(3-methyl-2-butenyl)phenyl]-6-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one, 9ciHMDB
Chemical FormulaC25H26O5
Average Molecular Weight406.4709
Monoisotopic Molecular Weight406.178023942
IUPAC Name5,7-dihydroxy-2-[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]-6-(3-methylbut-2-en-1-yl)-4H-chromen-4-one
Traditional Namegancaonin Q
CAS Registry Number134958-52-4
SMILES
CC(C)=CCC1=CC(=CC=C1O)C1=CC(=O)C2=C(O1)C=C(O)C(CC=C(C)C)=C2O
InChI Identifier
InChI=1S/C25H26O5/c1-14(2)5-7-16-11-17(8-10-19(16)26)22-13-21(28)24-23(30-22)12-20(27)18(25(24)29)9-6-15(3)4/h5-6,8,10-13,26-27,29H,7,9H2,1-4H3
InChI KeyWGNIVAMNAWBYRO-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 6-prenylated flavones. These are flavones that features a C5-isoprenoid substituent at the 6-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavones
Direct Parent6-prenylated flavones
Alternative Parents
Substituents
  • 3'-prenylated flavone
  • 6-prenylated flavone
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • Benzenoid
  • Pyran
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Vinylogous acid
  • Oxacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • 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 Point212 - 214 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0038 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0028 g/LALOGPS
logP5.06ALOGPS
logP6.16ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)6.45ChemAxon
pKa (Strongest Basic)-5.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity121.4 m³·mol⁻¹ChemAxon
Polarizability46.13 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+196.06430932474
DeepCCS[M-H]-193.70630932474
DeepCCS[M-2H]-227.51730932474
DeepCCS[M+Na]+202.68530932474
AllCCS[M+H]+203.732859911
AllCCS[M+H-H2O]+201.032859911
AllCCS[M+NH4]+206.332859911
AllCCS[M+Na]+207.132859911
AllCCS[M-H]-192.632859911
AllCCS[M+Na-2H]-192.632859911
AllCCS[M+HCOO]-192.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Gancaonin QCC(C)=CCC1=CC(=CC=C1O)C1=CC(=O)C2=C(O1)C=C(O)C(CC=C(C)C)=C2O5439.6Standard polar33892256
Gancaonin QCC(C)=CCC1=CC(=CC=C1O)C1=CC(=O)C2=C(O1)C=C(O)C(CC=C(C)C)=C2O3556.3Standard non polar33892256
Gancaonin QCC(C)=CCC1=CC(=CC=C1O)C1=CC(=O)C2=C(O1)C=C(O)C(CC=C(C)C)=C2O3834.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Gancaonin Q,1TMS,isomer #1CC(C)=CCC1=CC(C2=CC(=O)C3=C(O)C(CC=C(C)C)=C(O)C=C3O2)=CC=C1O[Si](C)(C)C3838.5Semi standard non polar33892256
Gancaonin Q,1TMS,isomer #2CC(C)=CCC1=CC(C2=CC(=O)C3=C(O)C(CC=C(C)C)=C(O[Si](C)(C)C)C=C3O2)=CC=C1O3864.1Semi standard non polar33892256
Gancaonin Q,1TMS,isomer #3CC(C)=CCC1=CC(C2=CC(=O)C3=C(O[Si](C)(C)C)C(CC=C(C)C)=C(O)C=C3O2)=CC=C1O3829.5Semi standard non polar33892256
Gancaonin Q,2TMS,isomer #1CC(C)=CCC1=CC(C2=CC(=O)C3=C(O[Si](C)(C)C)C(CC=C(C)C)=C(O)C=C3O2)=CC=C1O[Si](C)(C)C3686.3Semi standard non polar33892256
Gancaonin Q,2TMS,isomer #2CC(C)=CCC1=CC(C2=CC(=O)C3=C(O)C(CC=C(C)C)=C(O[Si](C)(C)C)C=C3O2)=CC=C1O[Si](C)(C)C3724.7Semi standard non polar33892256
Gancaonin Q,2TMS,isomer #3CC(C)=CCC1=CC(C2=CC(=O)C3=C(O[Si](C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C)C=C3O2)=CC=C1O3754.7Semi standard non polar33892256
Gancaonin Q,3TMS,isomer #1CC(C)=CCC1=CC(C2=CC(=O)C3=C(O[Si](C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C)C=C3O2)=CC=C1O[Si](C)(C)C3688.8Semi standard non polar33892256
Gancaonin Q,1TBDMS,isomer #1CC(C)=CCC1=CC(C2=CC(=O)C3=C(O)C(CC=C(C)C)=C(O)C=C3O2)=CC=C1O[Si](C)(C)C(C)(C)C4074.9Semi standard non polar33892256
Gancaonin Q,1TBDMS,isomer #2CC(C)=CCC1=CC(C2=CC(=O)C3=C(O)C(CC=C(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C3O2)=CC=C1O4097.5Semi standard non polar33892256
Gancaonin Q,1TBDMS,isomer #3CC(C)=CCC1=CC(C2=CC(=O)C3=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C(O)C=C3O2)=CC=C1O4070.5Semi standard non polar33892256
Gancaonin Q,2TBDMS,isomer #1CC(C)=CCC1=CC(C2=CC(=O)C3=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C(O)C=C3O2)=CC=C1O[Si](C)(C)C(C)(C)C4186.1Semi standard non polar33892256
Gancaonin Q,2TBDMS,isomer #2CC(C)=CCC1=CC(C2=CC(=O)C3=C(O)C(CC=C(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C3O2)=CC=C1O[Si](C)(C)C(C)(C)C4234.1Semi standard non polar33892256
Gancaonin Q,2TBDMS,isomer #3CC(C)=CCC1=CC(C2=CC(=O)C3=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C3O2)=CC=C1O4234.9Semi standard non polar33892256
Gancaonin Q,3TBDMS,isomer #1CC(C)=CCC1=CC(C2=CC(=O)C3=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C3O2)=CC=C1O[Si](C)(C)C(C)(C)C4342.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Gancaonin Q GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-2019000000-4fcfe1b843a248aaed6c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gancaonin Q GC-MS (3 TMS) - 70eV, Positivesplash10-0a4i-2000059000-09123a766d35d6284e6e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gancaonin Q 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 Q 10V, Positive-QTOFsplash10-0a4i-1009800000-afddb628e205a7ca90242016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gancaonin Q 20V, Positive-QTOFsplash10-0ldi-2009100000-9a873155229be4e857482016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gancaonin Q 40V, Positive-QTOFsplash10-014i-9716000000-394b0e534716db4a137e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gancaonin Q 10V, Negative-QTOFsplash10-0a4i-0001900000-0831847ac709b3c62f752016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gancaonin Q 20V, Negative-QTOFsplash10-0a4i-0115900000-f2aa0177a44a6df3ef902016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gancaonin Q 40V, Negative-QTOFsplash10-0550-0923000000-1567910f2e7f0d1dac9f2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gancaonin Q 10V, Positive-QTOFsplash10-0a4i-0000900000-18eb98d75246f8994f012021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gancaonin Q 20V, Positive-QTOFsplash10-0a4i-0000900000-18eb98d75246f8994f012021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gancaonin Q 40V, Positive-QTOFsplash10-05fr-0491600000-5edbd4293023540762a62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gancaonin Q 10V, Negative-QTOFsplash10-0a4i-0000900000-4beb10611eb4ba1142872021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gancaonin Q 20V, Negative-QTOFsplash10-0a4i-0000900000-881a9d71e0d8ed60c7e02021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gancaonin Q 40V, Negative-QTOFsplash10-004i-0190100000-ffa7a248f330cba4485e2021-09-23Wishart 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 IDFDB018321
KNApSAcK IDC00004017
Chemspider ID421872
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound480802
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1872261
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.. .