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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:47:29 UTC
Update Date2019-07-23 06:17:06 UTC
HMDB IDHMDB0034864
Secondary Accession Numbers
  • HMDB34864
Metabolite Identification
Common Name2,4-Dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one
Description2,4-Dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one, also known as DIMBOA or HBO, 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. 2,4-Dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 2,4-Dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one has been detected, but not quantified in, several different foods, such as sorghums, wild rices, ryes, oats, and hard wheats. This could make 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one a potential biomarker for the consumption of these foods. A lactol that is DIBOA in which the hydrogen at position 7 is replaced by a methoxy group.
Structure
Data?1563862626
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 Weight211.1715
Monoisotopic Molecular Weight211.048072403
IUPAC Name2,4-dihydroxy-7-methoxy-3,4-dihydro-2H-1,4-benzoxazin-3-one
Traditional Namedimboa
CAS Registry Number15893-52-4
SMILES
COC1=CC2=C(C=C1)N(O)C(=O)C(O)O2
InChI Identifier
InChI=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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point168 - 169 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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 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
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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
FoodDB IDFDB013434
KNApSAcK IDC00026498
Chemspider ID2268
KEGG Compound IDC04720
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDIMBOA
METLIN IDNot Available
PubChem Compound2358
PDB IDNot Available
ChEBI ID18048
Food Biomarker OntologyNot Available
VMH 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.. .