(R)-2,4-Dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one (CHEM028829)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 00:44:05 UTC
Update Date2016-11-09 01:18:46 UTC
Accession NumberCHEM028829
Identification
Common Name(R)-2,4-Dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one
ClassSmall Molecule
DescriptionA lactol that is DIBOA in which the hydrogen at position 7 is replaced by a methoxy group. It has been isolated from the maize plants.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
2,4-Dihydroxy-7-methoxy-1,4-benzoxazin-3-oneChEBI
(+/-)-2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-oneHMDB
(2R)-2,4-Dihydroxy-7-methoxy-1,4-benzoxazin-3-oneHMDB
2,4-Dihydroxy-7-(methyloxy)-2H-1,4-benzoxazin-3(4H)-oneHMDB
2,4-Dihydroxy-7-methoxy-1,4-benzoxazinoneHMDB
2,4-Dihydroxy-7-methoxy-2H,1,4-benzoxazin-3(4H)oneHMDB
DIMBOAHMDB
HBOHMDB
2,4-Dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-oneChEBI
Chemical FormulaC9H9NO5
Average Molecular Mass211.172 g/mol
Monoisotopic Mass211.048 g/mol
CAS Registry Number15893-52-4
IUPAC Name2,4-dihydroxy-7-methoxy-3,4-dihydro-2H-1,4-benzoxazin-3-one
Traditional Namedimboa
SMILESCOC1=CC2=C(C=C1)N(O)C(=O)C(O)O2
InChI IdentifierInChI=1S/C9H9NO5/c1-14-5-2-3-6-7(4-5)15-9(12)8(11)10(6)13/h2-4,9,12-13H,1H3
InChI KeyGDNZNIJPBQATCZ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzoxazinones. These are organic compounds containing a benzene fused to an oxazine ring (a six-member aliphatic ring with four carbon atoms, one oxygen atom, and one nitrogen atom) bearing a ketone group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzoxazines
Sub ClassBenzoxazinones
Direct ParentBenzoxazinones
Alternative Parents
Substituents
  • Benzoxazinone
  • Benzomorpholine
  • Anisole
  • Alkyl aryl ether
  • Benzenoid
  • Oxazinane
  • Hemiacetal
  • Hydroxamic acid
  • Carboxylic acid derivative
  • Oxacycle
  • Azacycle
  • Ether
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility24.6 g/LALOGPS
logP0.13ALOGPS
logP-0.055ChemAxon
logS-0.93ALOGPS
pKa (Strongest Acidic)7.85ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area79.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity48.47 m³·mol⁻¹ChemAxon
Polarizability19.29 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-0900000000-53c2f5e27646045288afSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0079-8940000000-d0f9b43343833c9e053bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-000i-0900000000-c15b25220502d9d185ddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0190000000-81645df47c3fed0bd3a9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1290000000-4b18989a9733b9c9128dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pc0-8900000000-af10c52b30b91b018343Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0190000000-ff36b9f2da9a370e6f45Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-1960000000-ee23275c26b88778ad93Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9200000000-180699a2eeca136cc131Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0190000000-b79fb45b6c22516246bcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-0950000000-3be199a9f3a68e9917c8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0079-2900000000-10292325a80698ff13dfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ik9-0970000000-e9ff6d06efbb72e08f61Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-3900000000-6245e31fd6f132da0c39Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06tf-6900000000-fdae439c7d67fc93bf97Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0034864
FooDB IDFDB013434
Phenol Explorer IDNot Available
KNApSAcK IDC00026498
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkDIMBOA
Chemspider ID2268
ChEBI ID18048
PubChem Compound ID2358
Kegg Compound IDC04720
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=23647315
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=23771234
3. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.