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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:53:40 UTC
Update Date2022-03-07 02:54:17 UTC
HMDB IDHMDB0034960
Secondary Accession Numbers
  • HMDB34960
Metabolite Identification
Common NameEdulone A
DescriptionEdulone A belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system. Edulone A is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, edulone a has been detected, but not quantified in, root vegetables. This could make edulone a a potential biomarker for the consumption of these foods.
Structure
Data?1563862642
Synonyms
ValueSource
2-{3,4,6-trihydroxy-1,12-dimethyl-8,11-dioxo-10-oxatetracyclo[7.6.1.0²,⁷.0¹³,¹⁶]hexadeca-2(7),3,5,9(16),12-pentaen-5-yl}propyl acetic acidGenerator
Chemical FormulaC22H22O8
Average Molecular Weight414.4053
Monoisotopic Molecular Weight414.13146768
IUPAC Name2-{3,4,6-trihydroxy-1,12-dimethyl-8,11-dioxo-10-oxatetracyclo[7.6.1.0²,⁷.0¹³,¹⁶]hexadeca-2(7),3,5,9(16),12-pentaen-5-yl}propyl acetate
Traditional Name2-{3,4,6-trihydroxy-1,12-dimethyl-8,11-dioxo-10-oxatetracyclo[7.6.1.0²,⁷.0¹³,¹⁶]hexadeca-2(7),3,5,9(16),12-pentaen-5-yl}propyl acetate
CAS Registry Number68421-12-5
SMILES
CC(COC(C)=O)C1=C(O)C2=C(C(O)=C1O)C1(C)CCC3=C(C)C(=O)OC(=C13)C2=O
InChI Identifier
InChI=1S/C22H22O8/c1-8(7-29-10(3)23)12-16(24)13-15(19(27)17(12)25)22(4)6-5-11-9(2)21(28)30-20(14(11)22)18(13)26/h8,24-25,27H,5-7H2,1-4H3
InChI KeyMLTCCXPBXYMUMQ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassNaphthopyrans
Sub ClassNaphthopyranones
Direct ParentNaphthopyranones
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point153 - 159 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.057 g/LALOGPS
logP2.67ALOGPS
logP2.81ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)7.62ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area130.36 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity107.14 m³·mol⁻¹ChemAxon
Polarizability41.99 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+196.4131661259
DarkChem[M-H]-193.22931661259
DeepCCS[M-2H]-235.30330932474
DeepCCS[M+Na]+210.72830932474
AllCCS[M+H]+194.532859911
AllCCS[M+H-H2O]+192.032859911
AllCCS[M+NH4]+196.832859911
AllCCS[M+Na]+197.432859911
AllCCS[M-H]-201.032859911
AllCCS[M+Na-2H]-201.232859911
AllCCS[M+HCOO]-201.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Edulone ACC(COC(C)=O)C1=C(O)C2=C(C(O)=C1O)C1(C)CCC3=C(C)C(=O)OC(=C13)C2=O4498.1Standard polar33892256
Edulone ACC(COC(C)=O)C1=C(O)C2=C(C(O)=C1O)C1(C)CCC3=C(C)C(=O)OC(=C13)C2=O2988.0Standard non polar33892256
Edulone ACC(COC(C)=O)C1=C(O)C2=C(C(O)=C1O)C1(C)CCC3=C(C)C(=O)OC(=C13)C2=O3524.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Edulone A,1TMS,isomer #1CC(=O)OCC(C)C1=C(O)C(O)=C2C(=C1O[Si](C)(C)C)C(=O)C1=C3C(=C(C)C(=O)O1)CCC32C3310.8Semi standard non polar33892256
Edulone A,1TMS,isomer #2CC(=O)OCC(C)C1=C(O)C(O[Si](C)(C)C)=C2C(=C1O)C(=O)C1=C3C(=C(C)C(=O)O1)CCC32C3388.4Semi standard non polar33892256
Edulone A,1TMS,isomer #3CC(=O)OCC(C)C1=C(O)C2=C(C(O)=C1O[Si](C)(C)C)C1(C)CCC3=C(C)C(=O)OC(=C31)C2=O3369.8Semi standard non polar33892256
Edulone A,2TMS,isomer #1CC(=O)OCC(C)C1=C(O[Si](C)(C)C)C(O)=C2C(=C1O[Si](C)(C)C)C(=O)C1=C3C(=C(C)C(=O)O1)CCC32C3348.5Semi standard non polar33892256
Edulone A,2TMS,isomer #2CC(=O)OCC(C)C1=C(O)C(O[Si](C)(C)C)=C2C(=C1O[Si](C)(C)C)C(=O)C1=C3C(=C(C)C(=O)O1)CCC32C3382.3Semi standard non polar33892256
Edulone A,2TMS,isomer #3CC(=O)OCC(C)C1=C(O)C2=C(C(O[Si](C)(C)C)=C1O[Si](C)(C)C)C1(C)CCC3=C(C)C(=O)OC(=C31)C2=O3328.8Semi standard non polar33892256
Edulone A,3TMS,isomer #1CC(=O)OCC(C)C1=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2C(=C1O[Si](C)(C)C)C(=O)C1=C3C(=C(C)C(=O)O1)CCC32C3319.3Semi standard non polar33892256
Edulone A,1TBDMS,isomer #1CC(=O)OCC(C)C1=C(O)C(O)=C2C(=C1O[Si](C)(C)C(C)(C)C)C(=O)C1=C3C(=C(C)C(=O)O1)CCC32C3534.8Semi standard non polar33892256
Edulone A,1TBDMS,isomer #2CC(=O)OCC(C)C1=C(O)C(O[Si](C)(C)C(C)(C)C)=C2C(=C1O)C(=O)C1=C3C(=C(C)C(=O)O1)CCC32C3599.3Semi standard non polar33892256
Edulone A,1TBDMS,isomer #3CC(=O)OCC(C)C1=C(O)C2=C(C(O)=C1O[Si](C)(C)C(C)(C)C)C1(C)CCC3=C(C)C(=O)OC(=C31)C2=O3584.6Semi standard non polar33892256
Edulone A,2TBDMS,isomer #1CC(=O)OCC(C)C1=C(O[Si](C)(C)C(C)(C)C)C(O)=C2C(=C1O[Si](C)(C)C(C)(C)C)C(=O)C1=C3C(=C(C)C(=O)O1)CCC32C3817.2Semi standard non polar33892256
Edulone A,2TBDMS,isomer #2CC(=O)OCC(C)C1=C(O)C(O[Si](C)(C)C(C)(C)C)=C2C(=C1O[Si](C)(C)C(C)(C)C)C(=O)C1=C3C(=C(C)C(=O)O1)CCC32C3842.2Semi standard non polar33892256
Edulone A,2TBDMS,isomer #3CC(=O)OCC(C)C1=C(O)C2=C(C(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C)C1(C)CCC3=C(C)C(=O)OC(=C31)C2=O3776.2Semi standard non polar33892256
Edulone A,3TBDMS,isomer #1CC(=O)OCC(C)C1=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C2C(=C1O[Si](C)(C)C(C)(C)C)C(=O)C1=C3C(=C(C)C(=O)O1)CCC32C3957.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Edulone A GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-4309000000-4277e29849e83d4ae9622017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Edulone A GC-MS (3 TMS) - 70eV, Positivesplash10-014i-4110069000-36b937fdf4881724df662017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Edulone A 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 - Edulone A 10V, Positive-QTOFsplash10-066r-0109500000-ef6f1fa669050360a6a92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Edulone A 20V, Positive-QTOFsplash10-0a4i-2209000000-7f4db93aa75e4e1430512016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Edulone A 40V, Positive-QTOFsplash10-000i-2249000000-d82e1f73b55757d8dd822016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Edulone A 10V, Negative-QTOFsplash10-03di-5006900000-c87aff0f61869a5b52412016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Edulone A 20V, Negative-QTOFsplash10-0bt9-9017200000-2e19826287799d7fb3562016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Edulone A 40V, Negative-QTOFsplash10-0a4i-9100000000-cc6cbafc484fe192bfcc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Edulone A 10V, Positive-QTOFsplash10-0aor-0009200000-6aae5f0d59b9c13d146f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Edulone A 20V, Positive-QTOFsplash10-0a4l-0009000000-3ae4a3c0f25023a83e2b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Edulone A 40V, Positive-QTOFsplash10-002u-1009000000-23d259dab3f5e4aa905e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Edulone A 10V, Negative-QTOFsplash10-0pb9-9006000000-157af242b13ddcc6d12c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Edulone A 20V, Negative-QTOFsplash10-0a4l-6009000000-0a7d38276496b10d8cb52021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Edulone A 40V, Negative-QTOFsplash10-0btc-9026000000-d1b129ebe9f470f0419c2021-09-25Wishart 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 IDFDB013555
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound13894316
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.. .