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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:55:16 UTC
Update Date2022-03-07 02:53:59 UTC
HMDB IDHMDB0034125
Secondary Accession Numbers
  • HMDB34125
Metabolite Identification
Common NameLicoisoflavone A
DescriptionLicoisoflavone A, also known as phaseoluteone, belongs to the class of organic compounds known as isoflavones. These are polycyclic compounds containing a 2-isoflavene skeleton which bears a ketone group at the C4 carbon atom. Thus, licoisoflavone a is considered to be a flavonoid. Licoisoflavone A has been detected, but not quantified in, several different foods, such as teffs (Eragrostis tef), corns (Zea mays), triticales (X Triticosecale rimpaui), common wheats (Triticum aestivum), and bulgur. This could make licoisoflavone a a potential biomarker for the consumption of these foods. Licoisoflavone A is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a small amount of articles have been published on Licoisoflavone A.
Structure
Data?1563862514
Synonyms
ValueSource
2',4',5,7-Tetrahydroxy-3'-(3,3-dimethylallyl)isoflavoneChEBI
PhaseoluteoneChEBI
3'-Isopentenyl-2',4',5,7-tetrahydroxyisoflavoneHMDB
LicoisoflavoneHMDB
[2,4-Dihydroxy-3-(3-methyl-2-butenyl)phenyl]-5,7-dihydroxy-4H-1-benzopyran-4-one, 9ciHMDB
Chemical FormulaC20H18O6
Average Molecular Weight354.358
Monoisotopic Molecular Weight354.1103383
IUPAC Name3-[2,4-dihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]-5,7-dihydroxy-4H-chromen-4-one
Traditional Namelicoisoflavone A
CAS Registry Number66056-19-7
SMILES
CC(C)=CCC1=C(O)C(=CC=C1O)C1=COC2=C(C(O)=CC(O)=C2)C1=O
InChI Identifier
InChI=1S/C20H18O6/c1-10(2)3-4-13-15(22)6-5-12(19(13)24)14-9-26-17-8-11(21)7-16(23)18(17)20(14)25/h3,5-9,21-24H,4H2,1-2H3
InChI KeyKCUZCRLRQVRBBV-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as isoflavones. These are polycyclic compounds containing a 2-isoflavene skeleton which bears a ketone group at the C4 carbon atom.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassIsoflav-2-enes
Direct ParentIsoflavones
Alternative Parents
Substituents
  • Isoflavone
  • Hydroxyisoflavonoid
  • Chromone
  • 1-benzopyran
  • Benzopyran
  • Resorcinol
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Pyranone
  • Phenol
  • Benzenoid
  • Pyran
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Vinylogous acid
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.08 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.019 g/LALOGPS
logP3.29ALOGPS
logP4.5ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)6.54ChemAxon
pKa (Strongest Basic)-5.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area107.22 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity97.91 m³·mol⁻¹ChemAxon
Polarizability36.83 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]+182.97630932474
DeepCCS[M-H]-180.61830932474
DeepCCS[M-2H]-214.87530932474
DeepCCS[M+Na]+191.06630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Licoisoflavone ACC(C)=CCC1=C(O)C(=CC=C1O)C1=COC2=C(C(O)=CC(O)=C2)C1=O5095.4Standard polar33892256
Licoisoflavone ACC(C)=CCC1=C(O)C(=CC=C1O)C1=COC2=C(C(O)=CC(O)=C2)C1=O2971.4Standard non polar33892256
Licoisoflavone ACC(C)=CCC1=C(O)C(=CC=C1O)C1=COC2=C(C(O)=CC(O)=C2)C1=O3415.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Licoisoflavone A,1TMS,isomer #1CC(C)=CCC1=C(O)C=CC(C2=COC3=CC(O)=CC(O)=C3C2=O)=C1O[Si](C)(C)C3322.2Semi standard non polar33892256
Licoisoflavone A,1TMS,isomer #2CC(C)=CCC1=C(O[Si](C)(C)C)C=CC(C2=COC3=CC(O)=CC(O)=C3C2=O)=C1O3359.3Semi standard non polar33892256
Licoisoflavone A,1TMS,isomer #3CC(C)=CCC1=C(O)C=CC(C2=COC3=CC(O)=CC(O[Si](C)(C)C)=C3C2=O)=C1O3380.0Semi standard non polar33892256
Licoisoflavone A,1TMS,isomer #4CC(C)=CCC1=C(O)C=CC(C2=COC3=CC(O[Si](C)(C)C)=CC(O)=C3C2=O)=C1O3402.7Semi standard non polar33892256
Licoisoflavone A,2TMS,isomer #1CC(C)=CCC1=C(O[Si](C)(C)C)C=CC(C2=COC3=CC(O)=CC(O)=C3C2=O)=C1O[Si](C)(C)C3263.7Semi standard non polar33892256
Licoisoflavone A,2TMS,isomer #2CC(C)=CCC1=C(O)C=CC(C2=COC3=CC(O[Si](C)(C)C)=CC(O)=C3C2=O)=C1O[Si](C)(C)C3231.3Semi standard non polar33892256
Licoisoflavone A,2TMS,isomer #3CC(C)=CCC1=C(O)C=CC(C2=COC3=CC(O)=CC(O[Si](C)(C)C)=C3C2=O)=C1O[Si](C)(C)C3232.3Semi standard non polar33892256
Licoisoflavone A,2TMS,isomer #4CC(C)=CCC1=C(O[Si](C)(C)C)C=CC(C2=COC3=CC(O[Si](C)(C)C)=CC(O)=C3C2=O)=C1O3229.7Semi standard non polar33892256
Licoisoflavone A,2TMS,isomer #5CC(C)=CCC1=C(O[Si](C)(C)C)C=CC(C2=COC3=CC(O)=CC(O[Si](C)(C)C)=C3C2=O)=C1O3246.5Semi standard non polar33892256
Licoisoflavone A,2TMS,isomer #6CC(C)=CCC1=C(O)C=CC(C2=COC3=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3C2=O)=C1O3248.3Semi standard non polar33892256
Licoisoflavone A,3TMS,isomer #1CC(C)=CCC1=C(O[Si](C)(C)C)C=CC(C2=COC3=CC(O[Si](C)(C)C)=CC(O)=C3C2=O)=C1O[Si](C)(C)C3165.1Semi standard non polar33892256
Licoisoflavone A,3TMS,isomer #2CC(C)=CCC1=C(O[Si](C)(C)C)C=CC(C2=COC3=CC(O)=CC(O[Si](C)(C)C)=C3C2=O)=C1O[Si](C)(C)C3170.9Semi standard non polar33892256
Licoisoflavone A,3TMS,isomer #3CC(C)=CCC1=C(O)C=CC(C2=COC3=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3C2=O)=C1O[Si](C)(C)C3162.8Semi standard non polar33892256
Licoisoflavone A,3TMS,isomer #4CC(C)=CCC1=C(O[Si](C)(C)C)C=CC(C2=COC3=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3C2=O)=C1O3165.6Semi standard non polar33892256
Licoisoflavone A,4TMS,isomer #1CC(C)=CCC1=C(O[Si](C)(C)C)C=CC(C2=COC3=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3C2=O)=C1O[Si](C)(C)C3173.6Semi standard non polar33892256
Licoisoflavone A,1TBDMS,isomer #1CC(C)=CCC1=C(O)C=CC(C2=COC3=CC(O)=CC(O)=C3C2=O)=C1O[Si](C)(C)C(C)(C)C3625.9Semi standard non polar33892256
Licoisoflavone A,1TBDMS,isomer #2CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=CC(C2=COC3=CC(O)=CC(O)=C3C2=O)=C1O3657.5Semi standard non polar33892256
Licoisoflavone A,1TBDMS,isomer #3CC(C)=CCC1=C(O)C=CC(C2=COC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)=C1O3674.2Semi standard non polar33892256
Licoisoflavone A,1TBDMS,isomer #4CC(C)=CCC1=C(O)C=CC(C2=COC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C3C2=O)=C1O3681.0Semi standard non polar33892256
Licoisoflavone A,2TBDMS,isomer #1CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=CC(C2=COC3=CC(O)=CC(O)=C3C2=O)=C1O[Si](C)(C)C(C)(C)C3746.5Semi standard non polar33892256
Licoisoflavone A,2TBDMS,isomer #2CC(C)=CCC1=C(O)C=CC(C2=COC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C3C2=O)=C1O[Si](C)(C)C(C)(C)C3753.7Semi standard non polar33892256
Licoisoflavone A,2TBDMS,isomer #3CC(C)=CCC1=C(O)C=CC(C2=COC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)=C1O[Si](C)(C)C(C)(C)C3743.8Semi standard non polar33892256
Licoisoflavone A,2TBDMS,isomer #4CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=CC(C2=COC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C3C2=O)=C1O3781.8Semi standard non polar33892256
Licoisoflavone A,2TBDMS,isomer #5CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=CC(C2=COC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)=C1O3780.0Semi standard non polar33892256
Licoisoflavone A,2TBDMS,isomer #6CC(C)=CCC1=C(O)C=CC(C2=COC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)=C1O3809.3Semi standard non polar33892256
Licoisoflavone A,3TBDMS,isomer #1CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=CC(C2=COC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C3C2=O)=C1O[Si](C)(C)C(C)(C)C3846.8Semi standard non polar33892256
Licoisoflavone A,3TBDMS,isomer #2CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=CC(C2=COC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)=C1O[Si](C)(C)C(C)(C)C3840.0Semi standard non polar33892256
Licoisoflavone A,3TBDMS,isomer #3CC(C)=CCC1=C(O)C=CC(C2=COC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)=C1O[Si](C)(C)C(C)(C)C3845.0Semi standard non polar33892256
Licoisoflavone A,3TBDMS,isomer #4CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=CC(C2=COC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)=C1O3881.5Semi standard non polar33892256
Licoisoflavone A,4TBDMS,isomer #1CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=CC(C2=COC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)=C1O[Si](C)(C)C(C)(C)C4000.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Licoisoflavone A GC-MS (Non-derivatized) - 70eV, Positivesplash10-004u-2019000000-2f739f3452171f905be22017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Licoisoflavone A GC-MS (4 TMS) - 70eV, Positivesplash10-004i-1000049000-7018f194d1008ff5433d2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Licoisoflavone A GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Licoisoflavone A 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 - Licoisoflavone A 6V, Positive-QTOFsplash10-0a4i-0259000000-495f77efc5f1a3a3f53e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Licoisoflavone A 6V, Positive-QTOFsplash10-0a4j-0379000000-8433cfe87c1ae275bcd42021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Licoisoflavone A 6V, Negative-QTOFsplash10-0udi-0229000000-359d0281bb2960df18ab2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Licoisoflavone A 6V, Positive-QTOFsplash10-0a4j-0379000000-164d4415475e4af9dc352021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Licoisoflavone A 6V, Positive-QTOFsplash10-0a4i-0259000000-0aaedb95807e7419c45e2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licoisoflavone A 10V, Positive-QTOFsplash10-0a4i-0009000000-62f92498db843c9e58582015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licoisoflavone A 20V, Positive-QTOFsplash10-05ot-3349000000-ed8805f32a0bbcd8f2352015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licoisoflavone A 40V, Positive-QTOFsplash10-0gba-8952000000-6c41fa9ae3eca464c67b2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licoisoflavone A 10V, Negative-QTOFsplash10-0udi-0109000000-be91e8e91b4067f6ed222015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licoisoflavone A 20V, Negative-QTOFsplash10-0fb9-0918000000-fb711c0f7e6d3a6949fe2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licoisoflavone A 40V, Negative-QTOFsplash10-0pki-2921000000-ec8a5e470e5efab9b7102015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licoisoflavone A 10V, Positive-QTOFsplash10-0002-0090000000-0e40d1dc69d66b6011272021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licoisoflavone A 20V, Positive-QTOFsplash10-0002-0090000000-64cb783d19451782d0e72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licoisoflavone A 40V, Positive-QTOFsplash10-00l2-0191000000-f709c80b15ac681aff912021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licoisoflavone A 10V, Negative-QTOFsplash10-0udi-0009000000-b3503695056246b53ddc2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licoisoflavone A 20V, Negative-QTOFsplash10-0udi-0029000000-4100593e7262216dd6272021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licoisoflavone A 40V, Negative-QTOFsplash10-0n4u-2394000000-819b2b3d4c43b48961112021-09-22Wishart 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 IDFDB012398
KNApSAcK IDC00002542
Chemspider ID4445102
KEGG Compound IDC10486
BioCyc IDCPD-6643
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5281789
PDB IDNot Available
ChEBI ID28620
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1840681
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.. .