Hmdb loader
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 21:44:25 UTC
Update Date2023-02-21 17:25:25 UTC
HMDB IDHMDB0036582
Secondary Accession Numbers
  • HMDB36582
Metabolite Identification
Common Name6-Methoxy-2(3H)-benzoxazolone
Description6-Methoxy-2(3H)-benzoxazolone, also known as 6-MBOA, belongs to the class of organic compounds known as benzoxazolones. These are organic compounds containing a benzene fused to an oxazole ring (a five-member aliphatic ring with three carbon atoms, one oxygen atom, and one nitrogen atom) bearing a ketone group. 6-Methoxy-2(3H)-benzoxazolone has been detected, but not quantified in, several different foods, such as flour, common wheats (Triticum aestivum), wild rice (Zizania), teas (Camellia sinensis), and alcoholic beverages. This could make 6-methoxy-2(3H)-benzoxazolone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 6-Methoxy-2(3H)-benzoxazolone.
Structure
Data?1677000325
Synonyms
ValueSource
6-MBOAMeSH
6-Methoxy-2-benzoxazolinoneMeSH
6-MethoxybenzoxazolinoneMeSH
2(3H)-Benzoxazolone, 6-methoxy- (9ci)HMDB
6-Methoxy-1,3-benzoxazol-2(3H)-oneHMDB
6-Methoxy-2-benzoxazolinone, 8ciHMDB
6-Methoxy-3H-benzooxazol-2-oneHMDB
6-Methoxy-benzoxazolin-2(3H)-oneHMDB
6-Methoxybenzoxazolin-2(3H)-oneHMDB
CoixolHMDB
MBOAHMDB
Chemical FormulaC8H7NO3
Average Molecular Weight165.1461
Monoisotopic Molecular Weight165.042593095
IUPAC Name6-methoxy-2,3-dihydro-1,3-benzoxazol-2-one
Traditional Name6-methoxy-3H-1,3-benzoxazol-2-one
CAS Registry Number532-91-2
SMILES
COC1=CC=C2NC(=O)OC2=C1
InChI Identifier
InChI=1S/C8H7NO3/c1-11-5-2-3-6-7(4-5)12-8(10)9-6/h2-4H,1H3,(H,9,10)
InChI KeyMKMCJLMBVKHUMS-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzoxazolones. These are organic compounds containing a benzene fused to an oxazole ring (a five-member aliphatic ring with three carbon atoms, one oxygen atom, and one nitrogen atom) bearing a ketone group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzoxazoles
Sub ClassBenzoxazolones
Direct ParentBenzoxazolones
Alternative Parents
Substituents
  • Benzoxazolone
  • Anisole
  • Alkyl aryl ether
  • Benzenoid
  • Heteroaromatic compound
  • Oxazole
  • Azole
  • Oxacycle
  • Azacycle
  • Ether
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point160 - 161 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility10.1 g/LALOGPS
logP1.21ALOGPS
logP1.17ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)9.66ChemAxon
pKa (Strongest Basic)-1.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area47.56 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity42.73 m³·mol⁻¹ChemAxon
Polarizability15.7 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+136.24831661259
DarkChem[M-H]-134.6831661259
DeepCCS[M+H]+132.65530932474
DeepCCS[M-H]-128.88430932474
DeepCCS[M-2H]-166.40330932474
DeepCCS[M+Na]+141.94130932474
AllCCS[M+H]+134.032859911
AllCCS[M+H-H2O]+129.532859911
AllCCS[M+NH4]+138.332859911
AllCCS[M+Na]+139.532859911
AllCCS[M-H]-132.832859911
AllCCS[M+Na-2H]-133.532859911
AllCCS[M+HCOO]-134.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
6-Methoxy-2(3H)-benzoxazoloneCOC1=CC=C2NC(=O)OC2=C12734.8Standard polar33892256
6-Methoxy-2(3H)-benzoxazoloneCOC1=CC=C2NC(=O)OC2=C11683.9Standard non polar33892256
6-Methoxy-2(3H)-benzoxazoloneCOC1=CC=C2NC(=O)OC2=C11807.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
6-Methoxy-2(3H)-benzoxazolone,1TMS,isomer #1COC1=CC=C2C(=C1)OC(=O)N2[Si](C)(C)C1768.9Semi standard non polar33892256
6-Methoxy-2(3H)-benzoxazolone,1TMS,isomer #1COC1=CC=C2C(=C1)OC(=O)N2[Si](C)(C)C1788.9Standard non polar33892256
6-Methoxy-2(3H)-benzoxazolone,1TBDMS,isomer #1COC1=CC=C2C(=C1)OC(=O)N2[Si](C)(C)C(C)(C)C1990.4Semi standard non polar33892256
6-Methoxy-2(3H)-benzoxazolone,1TBDMS,isomer #1COC1=CC=C2C(=C1)OC(=O)N2[Si](C)(C)C(C)(C)C2001.0Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 6-Methoxy-2(3H)-benzoxazolone GC-MS (Non-derivatized) - 70eV, Positivesplash10-00xr-1900000000-ae55931a6532474213eb2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6-Methoxy-2(3H)-benzoxazolone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6-Methoxy-2(3H)-benzoxazolone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-1000-9800000000-b7f572346c850aedd8ad2015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 6-Methoxy-2(3H)-benzoxazolone 6V, Negative-QTOFsplash10-0002-0900000000-fffb3a4c848b2a0dd10a2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Methoxy-2(3H)-benzoxazolone 10V, Positive-QTOFsplash10-014i-0900000000-e82eff1b272d62124d452016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Methoxy-2(3H)-benzoxazolone 20V, Positive-QTOFsplash10-014i-0900000000-6719525fa8c09d546ab82016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Methoxy-2(3H)-benzoxazolone 40V, Positive-QTOFsplash10-0uxu-5900000000-339ef11a0a1b20fab4472016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Methoxy-2(3H)-benzoxazolone 10V, Negative-QTOFsplash10-03di-0900000000-2eafa61b506b198e6d872016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Methoxy-2(3H)-benzoxazolone 20V, Negative-QTOFsplash10-03di-0900000000-b8aeb67e44838d074a0a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Methoxy-2(3H)-benzoxazolone 40V, Negative-QTOFsplash10-0005-5900000000-421d3edef6a74ac871c62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Methoxy-2(3H)-benzoxazolone 10V, Positive-QTOFsplash10-014i-0900000000-52879b1c24e4e827f43a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Methoxy-2(3H)-benzoxazolone 20V, Positive-QTOFsplash10-014i-0900000000-39903a20e890e6c55a272021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Methoxy-2(3H)-benzoxazolone 40V, Positive-QTOFsplash10-01xw-9500000000-04fb799eee300bb0ff592021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Methoxy-2(3H)-benzoxazolone 10V, Negative-QTOFsplash10-03di-0900000000-65490e650f013cfe115e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Methoxy-2(3H)-benzoxazolone 20V, Negative-QTOFsplash10-03di-1900000000-25a1dd3e12969e3c64512021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Methoxy-2(3H)-benzoxazolone 40V, Negative-QTOFsplash10-006x-9500000000-738460d14bd58c7538142021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB015492
KNApSAcK IDC00036627
Chemspider ID10317
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10772
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.. .