Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 23:52:25 UTC
Update Date2022-03-07 02:55:49 UTC
HMDB IDHMDB0038549
Secondary Accession Numbers
  • HMDB38549
Metabolite Identification
Common NameToralactone
DescriptionToralactone 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. Toralactone has been detected, but not quantified in, several different foods, such as arabica coffees (Coffea arabica), coffee and coffee products, herbs and spices, pulses, and robusta coffees (Coffea canephora). This could make toralactone a potential biomarker for the consumption of these foods. Toralactone 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 significant number of articles have been published on Toralactone.
Structure
Data?1563863216
Synonyms
ValueSource
9,10-Dihydroxy-7-methoxy-3-methyl-1H-naphtho(2,3-c)pyran-1-oneChEBI
9,10-Dihydroxy-7-methoxy-3-methyl-1H-naphtho[2,3-c]pyran-1-one, 9ciHMDB
Chemical FormulaC15H12O5
Average Molecular Weight272.2528
Monoisotopic Molecular Weight272.068473494
IUPAC Name9,10-dihydroxy-7-methoxy-3-methyl-1H-benzo[g]isochromen-1-one
Traditional Name9,10-dihydroxy-7-methoxy-3-methylbenzo[g]isochromen-1-one
CAS Registry Number41743-74-2
SMILES
COC1=CC(O)=C2C(O)=C3C(=O)OC(C)=CC3=CC2=C1
InChI Identifier
InChI=1S/C15H12O5/c1-7-3-8-4-9-5-10(19-2)6-11(16)12(9)14(17)13(8)15(18)20-7/h3-6,16-17H,1-2H3
InChI KeyWEHXAEGTVPWKDY-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 Parents
Substituents
  • Naphthopyranone
  • Isocoumarin
  • 1-naphthol
  • Benzopyran
  • Naphthalene
  • 2-benzopyran
  • Anisole
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous acid
  • Lactone
  • Ether
  • Oxacycle
  • 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 Point252 - 254 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility34.72 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.13 g/LALOGPS
logP2.68ALOGPS
logP3.13ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)8.45ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.99 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity74.18 m³·mol⁻¹ChemAxon
Polarizability27.48 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
DarkChem[M+H]+164.23531661259
DarkChem[M-H]-165.48631661259
DeepCCS[M+H]+163.68330932474
DeepCCS[M-H]-161.32530932474
DeepCCS[M-2H]-194.31330932474
DeepCCS[M+Na]+169.77630932474
AllCCS[M+H]+160.332859911
AllCCS[M+H-H2O]+156.432859911
AllCCS[M+NH4]+163.832859911
AllCCS[M+Na]+164.932859911
AllCCS[M-H]-163.732859911
AllCCS[M+Na-2H]-163.032859911
AllCCS[M+HCOO]-162.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ToralactoneCOC1=CC(O)=C2C(O)=C3C(=O)OC(C)=CC3=CC2=C13981.5Standard polar33892256
ToralactoneCOC1=CC(O)=C2C(O)=C3C(=O)OC(C)=CC3=CC2=C12551.1Standard non polar33892256
ToralactoneCOC1=CC(O)=C2C(O)=C3C(=O)OC(C)=CC3=CC2=C12676.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Toralactone,1TMS,isomer #1COC1=CC(O[Si](C)(C)C)=C2C(O)=C3C(=O)OC(C)=CC3=CC2=C12850.2Semi standard non polar33892256
Toralactone,1TMS,isomer #2COC1=CC(O)=C2C(O[Si](C)(C)C)=C3C(=O)OC(C)=CC3=CC2=C12843.8Semi standard non polar33892256
Toralactone,2TMS,isomer #1COC1=CC(O[Si](C)(C)C)=C2C(O[Si](C)(C)C)=C3C(=O)OC(C)=CC3=CC2=C12925.0Semi standard non polar33892256
Toralactone,1TBDMS,isomer #1COC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(O)=C3C(=O)OC(C)=CC3=CC2=C13059.4Semi standard non polar33892256
Toralactone,1TBDMS,isomer #2COC1=CC(O)=C2C(O[Si](C)(C)C(C)(C)C)=C3C(=O)OC(C)=CC3=CC2=C13053.4Semi standard non polar33892256
Toralactone,2TBDMS,isomer #1COC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(O[Si](C)(C)C(C)(C)C)=C3C(=O)OC(C)=CC3=CC2=C13324.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Toralactone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0abc-0190000000-0b6644937e0069cfba342017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Toralactone GC-MS (2 TMS) - 70eV, Positivesplash10-0uk9-2009400000-28388824cb8fdaf3e7482017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Toralactone 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 - Toralactone 10V, Positive-QTOFsplash10-00di-0090000000-af0e4aa15b772877e7052016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Toralactone 20V, Positive-QTOFsplash10-00di-0090000000-67a31feccf2de0c2d09c2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Toralactone 40V, Positive-QTOFsplash10-002b-0890000000-b766d9ba09c1aa5c07ac2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Toralactone 10V, Negative-QTOFsplash10-00di-0090000000-a304bd0b8e43139378852016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Toralactone 20V, Negative-QTOFsplash10-00di-0090000000-b199e2cdf9b618446ccb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Toralactone 40V, Negative-QTOFsplash10-004j-1980000000-284d4a71b00b8c9cc8c52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Toralactone 10V, Positive-QTOFsplash10-00di-0090000000-031a5312b116bdf1aa4a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Toralactone 20V, Positive-QTOFsplash10-00di-0090000000-e8cad39c3f9c861b9b612021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Toralactone 40V, Positive-QTOFsplash10-0fi9-0490000000-d32339d75f0f0ea867802021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Toralactone 10V, Negative-QTOFsplash10-00di-0090000000-d6b6f6391b4e9f4522f42021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Toralactone 20V, Negative-QTOFsplash10-00di-0090000000-d6b6f6391b4e9f4522f42021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Toralactone 40V, Negative-QTOFsplash10-00dj-3970000000-0694d792101fade0dd102021-09-24Wishart 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 IDFDB017935
KNApSAcK IDC00032364
Chemspider ID4479581
KEGG Compound IDC17673
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5321980
PDB IDNot Available
ChEBI ID78029
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1351071
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.. .