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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:29:34 UTC
Update Date2019-07-23 06:14:12 UTC
HMDB IDHMDB0033733
Secondary Accession Numbers
  • HMDB33733
Metabolite Identification
Common Name2,4-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one
Description2,4-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one, also known as DIBOA, 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-2H-1,4-benzoxazin-3(4H)-one is an extremely weak basic (essentially neutral) compound (based on its pKa). 2,4-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one is a benzoxazinoid precursor of 2-aminophenol sulfate. Outside of the human body, 2,4-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one has been detected, but not quantified in, cereals and cereal products and fats and oils. This could make 2,4-dihydroxy-2H-1,4-benzoxazin-3(4H)-one a potential biomarker for the consumption of these foods. It is a particularly strong biomarker for whole grain rye bread consumption (PMID: 23307617 ). It is a metabolite found in urine of individuals that have consumed whole grains.
Structure
Data?1563862452
Synonyms
ValueSource
2,4-Dihydroxy-1,4-benzoxazin-3-oneChEBI
2,4-Dihydroxy-1,4-benzoxazinoneChEBI
2,4-Dihydroxy-1,4-benzoxanzin-3(4H)-oneHMDB
DIBOAHMDB
DIBOA CPDHMDB
2,4-Dihydroxy-2H-1,4-benzoxazin-3(4H)-oneChEBI
Chemical FormulaC8H7NO4
Average Molecular Weight181.1455
Monoisotopic Molecular Weight181.037507717
IUPAC Name2,4-dihydroxy-3,4-dihydro-2H-1,4-benzoxazin-3-one
Traditional Namediboa
CAS Registry Number17359-54-5
SMILES
OC1OC2=CC=CC=C2N(O)C1=O
InChI Identifier
InChI=1S/C8H7NO4/c10-7-8(11)13-6-4-2-1-3-5(6)9(7)12/h1-4,8,11-12H
InChI KeyCOVOPZQGJGUPEY-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
  • Oxazinane
  • Benzenoid
  • Hemiacetal
  • Hydroxamic acid
  • Carboxylic acid derivative
  • Oxacycle
  • Azacycle
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point152 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility116 g/LALOGPS
logP-0.08ALOGPS
logP0.1ChemAxon
logS-0.19ALOGPS
pKa (Strongest Acidic)7.89ChemAxon
pKa (Strongest Basic)-5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area70 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity42.01 m³·mol⁻¹ChemAxon
Polarizability16.18 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-2900000000-8cffc6380318868a1cdbSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dr-9820000000-da3ad41de177835775c3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-99528ffc7bd64777a557Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-4900000000-fec4f652ebcb126578d9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9100000000-3eb0aa3a751f0a977ab8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f89-0900000000-b1b2e7e31a7eea725fcdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-1900000000-b373bdca736d9fef9184Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9100000000-9702b36556d91ed75094Spectrum
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 IDFDB011857
KNApSAcK IDC00036460
Chemspider ID26511
KEGG Compound IDC15770
BioCyc IDCPD-6365
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound28495
PDB IDNot Available
ChEBI ID63558
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Bondia-Pons I, Barri T, Hanhineva K, Juntunen K, Dragsted LO, Mykkanen H, Poutanen K: UPLC-QTOF/MS metabolic profiling unveils urinary changes in humans after a whole grain rye versus refined wheat bread intervention. Mol Nutr Food Res. 2013 Mar;57(3):412-22. doi: 10.1002/mnfr.201200571. Epub 2013 Jan 10. [PubMed:23307617 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .