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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-12 00:15:11 UTC
Update Date2022-09-22 18:34:58 UTC
HMDB IDHMDB0038905
Secondary Accession Numbers
  • HMDB38905
Metabolite Identification
Common NameIsoangustone A
DescriptionIsoangustone A 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, isoangustone a is considered to be a flavonoid. Isoangustone A has been detected, but not quantified in, herbs and spices. This could make isoangustone a a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Isoangustone A.
Structure
Data?1563863278
Synonyms
ValueSource
3-[3,4-Dihydroxy-5-(3-methyl-2-butenyl)phenyl]-5,7-dihydroxy-6-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one, 9ciHMDB
5,7,3',4'-Tetrahydroxy-6,5'-diprenylisoflavoneHMDB
Chemical FormulaC25H26O6
Average Molecular Weight422.4703
Monoisotopic Molecular Weight422.172938564
IUPAC Name3-[3,4-dihydroxy-5-(3-methylbut-2-en-1-yl)phenyl]-5,7-dihydroxy-6-(3-methylbut-2-en-1-yl)-4H-chromen-4-one
Traditional Nameisoangustone A
CAS Registry Number129280-34-8
SMILES
CC(C)=CCC1=CC(=CC(O)=C1O)C1=COC2=C(C(O)=C(CC=C(C)C)C(O)=C2)C1=O
InChI Identifier
InChI=1S/C25H26O6/c1-13(2)5-7-15-9-16(10-20(27)23(15)28)18-12-31-21-11-19(26)17(8-6-14(3)4)24(29)22(21)25(18)30/h5-6,9-12,26-29H,7-8H2,1-4H3
InChI KeyQNLGNISMYMFVHP-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
  • Isoflavone
  • Hydroxyisoflavonoid
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Catechol
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Pyranone
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Vinylogous acid
  • Oxacycle
  • Organoheterocyclic compound
  • 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
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point191 - 193 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0058 g/LALOGPS
logP4.6ALOGPS
logP6.23ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)6.42ChemAxon
pKa (Strongest Basic)-5.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area107.22 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity122.15 m³·mol⁻¹ChemAxon
Polarizability46.8 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]+197.6730932474
DeepCCS[M-H]-195.27530932474
DeepCCS[M-2H]-228.34930932474
DeepCCS[M+Na]+203.61730932474
AllCCS[M+H]+205.532859911
AllCCS[M+H-H2O]+202.932859911
AllCCS[M+NH4]+208.032859911
AllCCS[M+Na]+208.732859911
AllCCS[M-H]-197.232859911
AllCCS[M+Na-2H]-197.332859911
AllCCS[M+HCOO]-197.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Isoangustone ACC(C)=CCC1=CC(=CC(O)=C1O)C1=COC2=C(C(O)=C(CC=C(C)C)C(O)=C2)C1=O5603.4Standard polar33892256
Isoangustone ACC(C)=CCC1=CC(=CC(O)=C1O)C1=COC2=C(C(O)=C(CC=C(C)C)C(O)=C2)C1=O3568.7Standard non polar33892256
Isoangustone ACC(C)=CCC1=CC(=CC(O)=C1O)C1=COC2=C(C(O)=C(CC=C(C)C)C(O)=C2)C1=O3818.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Isoangustone A,1TMS,isomer #1CC(C)=CCC1=CC(C2=COC3=CC(O)=C(CC=C(C)C)C(O)=C3C2=O)=CC(O[Si](C)(C)C)=C1O3802.6Semi standard non polar33892256
Isoangustone A,1TMS,isomer #2CC(C)=CCC1=CC(C2=COC3=CC(O)=C(CC=C(C)C)C(O)=C3C2=O)=CC(O)=C1O[Si](C)(C)C3785.7Semi standard non polar33892256
Isoangustone A,1TMS,isomer #3CC(C)=CCC1=CC(C2=COC3=CC(O)=C(CC=C(C)C)C(O[Si](C)(C)C)=C3C2=O)=CC(O)=C1O3766.2Semi standard non polar33892256
Isoangustone A,1TMS,isomer #4CC(C)=CCC1=CC(C2=COC3=CC(O[Si](C)(C)C)=C(CC=C(C)C)C(O)=C3C2=O)=CC(O)=C1O3807.3Semi standard non polar33892256
Isoangustone A,2TMS,isomer #1CC(C)=CCC1=CC(C2=COC3=CC(O[Si](C)(C)C)=C(CC=C(C)C)C(O)=C3C2=O)=CC(O[Si](C)(C)C)=C1O3647.7Semi standard non polar33892256
Isoangustone A,2TMS,isomer #2CC(C)=CCC1=CC(C2=COC3=CC(O)=C(CC=C(C)C)C(O[Si](C)(C)C)=C3C2=O)=CC(O[Si](C)(C)C)=C1O3613.2Semi standard non polar33892256
Isoangustone A,2TMS,isomer #3CC(C)=CCC1=CC(C2=COC3=CC(O)=C(CC=C(C)C)C(O)=C3C2=O)=CC(O[Si](C)(C)C)=C1O[Si](C)(C)C3679.2Semi standard non polar33892256
Isoangustone A,2TMS,isomer #4CC(C)=CCC1=CC(C2=COC3=CC(O[Si](C)(C)C)=C(CC=C(C)C)C(O)=C3C2=O)=CC(O)=C1O[Si](C)(C)C3641.9Semi standard non polar33892256
Isoangustone A,2TMS,isomer #5CC(C)=CCC1=CC(C2=COC3=CC(O)=C(CC=C(C)C)C(O[Si](C)(C)C)=C3C2=O)=CC(O)=C1O[Si](C)(C)C3609.4Semi standard non polar33892256
Isoangustone A,2TMS,isomer #6CC(C)=CCC1=CC(C2=COC3=CC(O[Si](C)(C)C)=C(CC=C(C)C)C(O[Si](C)(C)C)=C3C2=O)=CC(O)=C1O3626.8Semi standard non polar33892256
Isoangustone A,3TMS,isomer #1CC(C)=CCC1=CC(C2=COC3=CC(O[Si](C)(C)C)=C(CC=C(C)C)C(O[Si](C)(C)C)=C3C2=O)=CC(O[Si](C)(C)C)=C1O3579.4Semi standard non polar33892256
Isoangustone A,3TMS,isomer #2CC(C)=CCC1=CC(C2=COC3=CC(O[Si](C)(C)C)=C(CC=C(C)C)C(O)=C3C2=O)=CC(O[Si](C)(C)C)=C1O[Si](C)(C)C3580.7Semi standard non polar33892256
Isoangustone A,3TMS,isomer #3CC(C)=CCC1=CC(C2=COC3=CC(O)=C(CC=C(C)C)C(O[Si](C)(C)C)=C3C2=O)=CC(O[Si](C)(C)C)=C1O[Si](C)(C)C3552.9Semi standard non polar33892256
Isoangustone A,3TMS,isomer #4CC(C)=CCC1=CC(C2=COC3=CC(O[Si](C)(C)C)=C(CC=C(C)C)C(O[Si](C)(C)C)=C3C2=O)=CC(O)=C1O[Si](C)(C)C3573.0Semi standard non polar33892256
Isoangustone A,4TMS,isomer #1CC(C)=CCC1=CC(C2=COC3=CC(O[Si](C)(C)C)=C(CC=C(C)C)C(O[Si](C)(C)C)=C3C2=O)=CC(O[Si](C)(C)C)=C1O[Si](C)(C)C3567.8Semi standard non polar33892256
Isoangustone A,1TBDMS,isomer #1CC(C)=CCC1=CC(C2=COC3=CC(O)=C(CC=C(C)C)C(O)=C3C2=O)=CC(O[Si](C)(C)C(C)(C)C)=C1O4061.2Semi standard non polar33892256
Isoangustone A,1TBDMS,isomer #2CC(C)=CCC1=CC(C2=COC3=CC(O)=C(CC=C(C)C)C(O)=C3C2=O)=CC(O)=C1O[Si](C)(C)C(C)(C)C4055.0Semi standard non polar33892256
Isoangustone A,1TBDMS,isomer #3CC(C)=CCC1=CC(C2=COC3=CC(O)=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=C3C2=O)=CC(O)=C1O4044.0Semi standard non polar33892256
Isoangustone A,1TBDMS,isomer #4CC(C)=CCC1=CC(C2=COC3=CC(O[Si](C)(C)C(C)(C)C)=C(CC=C(C)C)C(O)=C3C2=O)=CC(O)=C1O4079.2Semi standard non polar33892256
Isoangustone A,2TBDMS,isomer #1CC(C)=CCC1=CC(C2=COC3=CC(O[Si](C)(C)C(C)(C)C)=C(CC=C(C)C)C(O)=C3C2=O)=CC(O[Si](C)(C)C(C)(C)C)=C1O4157.5Semi standard non polar33892256
Isoangustone A,2TBDMS,isomer #2CC(C)=CCC1=CC(C2=COC3=CC(O)=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=C3C2=O)=CC(O[Si](C)(C)C(C)(C)C)=C1O4125.8Semi standard non polar33892256
Isoangustone A,2TBDMS,isomer #3CC(C)=CCC1=CC(C2=COC3=CC(O)=C(CC=C(C)C)C(O)=C3C2=O)=CC(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C4214.4Semi standard non polar33892256
Isoangustone A,2TBDMS,isomer #4CC(C)=CCC1=CC(C2=COC3=CC(O[Si](C)(C)C(C)(C)C)=C(CC=C(C)C)C(O)=C3C2=O)=CC(O)=C1O[Si](C)(C)C(C)(C)C4169.8Semi standard non polar33892256
Isoangustone A,2TBDMS,isomer #5CC(C)=CCC1=CC(C2=COC3=CC(O)=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=C3C2=O)=CC(O)=C1O[Si](C)(C)C(C)(C)C4129.7Semi standard non polar33892256
Isoangustone A,2TBDMS,isomer #6CC(C)=CCC1=CC(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)=CC(O)=C1O4155.9Semi standard non polar33892256
Isoangustone A,3TBDMS,isomer #1CC(C)=CCC1=CC(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)=CC(O[Si](C)(C)C(C)(C)C)=C1O4250.6Semi standard non polar33892256
Isoangustone A,3TBDMS,isomer #2CC(C)=CCC1=CC(C2=COC3=CC(O[Si](C)(C)C(C)(C)C)=C(CC=C(C)C)C(O)=C3C2=O)=CC(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C4309.3Semi standard non polar33892256
Isoangustone A,3TBDMS,isomer #3CC(C)=CCC1=CC(C2=COC3=CC(O)=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=C3C2=O)=CC(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C4244.1Semi standard non polar33892256
Isoangustone A,3TBDMS,isomer #4CC(C)=CCC1=CC(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)=CC(O)=C1O[Si](C)(C)C(C)(C)C4249.7Semi standard non polar33892256
Isoangustone A,4TBDMS,isomer #1CC(C)=CCC1=CC(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)=CC(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C4381.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Isoangustone A GC-MS (Non-derivatized) - 70eV, Positivesplash10-0aou-2009400000-fcc396668b12f9ceed4a2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isoangustone A GC-MS (3 TMS) - 70eV, Positivesplash10-00di-1000049000-1330420e504cefb1031d2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isoangustone 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 - Isoangustone A 6V, Positive-QTOFsplash10-02mi-0119500000-08d34dd8a9db84f2de072021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoangustone A 10V, Positive-QTOFsplash10-00di-0105900000-09af23c5e1012e3c14402016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoangustone A 20V, Positive-QTOFsplash10-01di-1209300000-c54ae2bd75de8b82f4ad2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoangustone A 40V, Positive-QTOFsplash10-01b9-3914200000-6e5d397729c4460abc6f2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoangustone A 10V, Negative-QTOFsplash10-00di-0000900000-7df5cb1698b4620c80292016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoangustone A 20V, Negative-QTOFsplash10-00di-0155900000-3db7cc32dcda61519cd72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoangustone A 40V, Negative-QTOFsplash10-0pdi-0943100000-b9dafd57755304a4c4ee2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoangustone A 10V, Negative-QTOFsplash10-00di-0000900000-1a0e5664f3fc8624ecf12021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoangustone A 20V, Negative-QTOFsplash10-00di-0005900000-727ef5b91ad52e9f747d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoangustone A 40V, Negative-QTOFsplash10-003u-7159100000-eed20fb3bc7bfc2475f52021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoangustone A 10V, Positive-QTOFsplash10-02mi-0019500000-98eab69e0764a08751ad2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoangustone A 20V, Positive-QTOFsplash10-08fs-0039100000-db90cccb2448cd99f0f42021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoangustone A 40V, Positive-QTOFsplash10-06r2-3249000000-29ef362b74f8ed282c892021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB018369
KNApSAcK IDC00009922
Chemspider ID10211375
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound21591148
PDB IDNot Available
ChEBI IDNot Available
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.. .