You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2019-07-16 17:10:23 UTC
Update Date2019-10-24 17:45:44 UTC
HMDB IDHMDB0240376
Secondary Accession NumbersNone
Metabolite Identification
Common NameDIBOA sulfate
Description2,4-Dihydroxy-1,4-benzoxazin-3-one sulfate (DIBOA sulfate) is a benzoxazinoid metabolite. It is a potential plasma and urinary biomarker of whole grain intake (PMID: 23650214 ).
Structure
Data?1563892758
Synonyms
ValueSource
DIBOA sulfuric acidGenerator
DIBOA sulphateGenerator
DIBOA sulphuric acidGenerator
(R)-2,4-Dihydroxy-1,4-benzoxazin-3-one sulfateHMDB
(R)-DIBOA sulfateHMDB
2,4-Dihydroxy-1,4-benzoxazin-3-one sulfateHMDB
DIBOA sulfateHMDB
Chemical FormulaC8H7NO7S
Average Molecular Weight261.2
Monoisotopic Molecular Weight260.994322743
IUPAC Name[(2R)-4-hydroxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl]oxidanesulfonic acid
Traditional Name[(2R)-4-hydroxy-3-oxo-2H-1,4-benzoxazin-2-yl]oxidanesulfonic acid
CAS Registry NumberNot Available
SMILES
ON1C(=O)[C@@H](OS(O)(=O)=O)OC2=CC=CC=C12
InChI Identifier
InChI=1S/C8H7NO7S/c10-7-8(16-17(12,13)14)15-6-4-2-1-3-5(6)9(7)11/h1-4,8,11H,(H,12,13,14)/t8-/m1/s1
InChI KeyGNPNIYVSUDXFAF-MRVPVSSYSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Benzenoid
  • Sulfuric acid ester
  • Alkyl sulfate
  • Sulfate-ester
  • Sulfuric acid monoester
  • Oxazinane
  • Organic sulfuric acid or derivatives
  • Hydroxamic acid
  • Oxacycle
  • Azacycle
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Not Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.89ALOGPS
logP0.16ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)-2.3ChemAxon
pKa (Strongest Basic)-5.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area113.37 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity52 m³·mol⁻¹ChemAxon
Polarizability21.74 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineDetected but not Quantified Adult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Adhikari KB, Laursen BB, Gregersen PL, Schnoor HJ, Witten M, Poulsen LK, Jensen BM, Fomsgaard IS: Absorption and metabolic fate of bioactive dietary benzoxazinoids in humans. Mol Nutr Food Res. 2013 Oct;57(10):1847-58. doi: 10.1002/mnfr.201300107. Epub 2013 May 3. [PubMed:23650214 ]
  2. Koistinen VM (2019). Effects of Food Processing and Gut Microbial Metabolism on Whole Grain Phytochemicals: A Metabolomics Approach. In Publications of the University of Eastern Finland. Dissertations in Health Sciences., no 510 (pp. 26-58). University of Eastern Finland. [ISBN:978-952-61-3088-0 ]