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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 18:29:34 UTC

Update Date

2023-02-21 17:23:33 UTC

HMDB ID

HMDB0033733

Secondary Accession Numbers

HMDB33733

Metabolite Identification

Common Name

2,4-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one

Description

2,4-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one 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 has been detected, but not quantified in, a few different foods, such as breakfast cereal, 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. 2,4-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on 2,4-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       2.667   0.000   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    6    9                                                  
CONECT    6    4    5   13                                                  
CONECT    7    8    9   10                                                  
CONECT    8    7   11   13                                                  
CONECT    9    5    7   12                                                  
CONECT   10    7                                                            
CONECT   11    8                                                            
CONECT   12    9                                                            
CONECT   13    6    8                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2,4-Dihydroxy-1,4-benzoxazin-3-one	ChEBI
2,4-Dihydroxy-1,4-benzoxazinone	ChEBI
2,4-Dihydroxy-1,4-benzoxanzin-3(4H)-one	HMDB
DIBOA	HMDB
DIBOA CPD	MeSH, HMDB
2,4-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one	ChEBI

Chemical Formula

C₈H₇NO₄

Average Molecular Weight

181.1455

Monoisotopic Molecular Weight

181.037507717

IUPAC Name

2,4-dihydroxy-3,4-dihydro-2H-1,4-benzoxazin-3-one

Traditional Name

diboa

CAS Registry Number

17359-54-5

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 Key

COVOPZQGJGUPEY-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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzoxazines

Sub Class

Benzoxazinones

Direct Parent

Benzoxazinones

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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

benzoxazine (CHEBI:63558 )
cyclic hydroxamic acid (CHEBI:63558 )
lactol (CHEBI:63558 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Excreta

Biofluid or Excreta

Urine (PMID: 32966057)

Cellular substructure

Extracellular (HMDB: HMDB0033733)
Cytoplasm (HMDB: HMDB0033733)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033733)

Source

Exogenous

Exogenous (HMDB: HMDB0033733)

Food

Food (HMDB: HMDB0033733)

Cereal and cereal product

Cereal product

Breakfast cereal (FooDB: FOOD00270)
Whole grain cereal products (HMDB: HMDB0033733)

Cereals and cereal products (FooDB: FOOD00858)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Endogenous

Plant

Poaceae (HMDB: HMDB0033733)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033733)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	152 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	116 g/L	ALOGPS
logP	-0.08	ALOGPS
logP	0.1	ChemAxon
logS	-0.19	ALOGPS
pKa (Strongest Acidic)	7.89	ChemAxon
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	70 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	42.01 m³·mol⁻¹	ChemAxon
Polarizability	16.18 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	138.577	31661259
DarkChem	[M-H]-	136.716	31661259
DeepCCS	[M+H]+	131.759	30932474
DeepCCS	[M-H]-	127.931	30932474
DeepCCS	[M-2H]-	165.362	30932474
DeepCCS	[M+Na]+	140.876	30932474
AllCCS	[M+H]+	139.4	32859911
AllCCS	[M+H-H2O]+	135.0	32859911
AllCCS	[M+NH4]+	143.6	32859911
AllCCS	[M+Na]+	144.7	32859911
AllCCS	[M-H]-	134.8	32859911
AllCCS	[M+Na-2H]-	135.2	32859911
AllCCS	[M+HCOO]-	135.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,4-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one	OC1OC2=CC=CC=C2N(O)C1=O	3004.1	Standard polar	33892256
2,4-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one	OC1OC2=CC=CC=C2N(O)C1=O	1608.1	Standard non polar	33892256
2,4-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one	OC1OC2=CC=CC=C2N(O)C1=O	1690.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2,4-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one,1TMS,isomer #1	C[Si](C)(C)OC1OC2=CC=CC=C2N(O)C1=O	1721.5	Semi standard non polar	33892256
2,4-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1OC2=CC=CC=C2N(O)C1=O	1976.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2,4-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-2900000000-8cffc6380318868a1cdb	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,4-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one GC-MS (1 TMS) - 70eV, Positive	splash10-00dr-9820000000-da3ad41de177835775c3	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,4-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,4-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one 6V, Positive-QTOF	splash10-01q0-0900000000-3e39a57a4e315e589c0e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,4-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one 6V, Positive-QTOF	splash10-000i-0900000000-787278de81328a591165	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,4-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one 6V, Positive-QTOF	splash10-01q0-0900000000-569a6e583ffd3315894a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,4-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one 6V, Negative-QTOF	splash10-000i-0900000000-f391f2b5f0be7b3cbce2	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one 10V, Positive-QTOF	splash10-001i-0900000000-99528ffc7bd64777a557	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one 20V, Positive-QTOF	splash10-001i-4900000000-fec4f652ebcb126578d9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one 40V, Positive-QTOF	splash10-004i-9100000000-3eb0aa3a751f0a977ab8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one 10V, Negative-QTOF	splash10-0f89-0900000000-b1b2e7e31a7eea725fcd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one 20V, Negative-QTOF	splash10-001i-1900000000-b373bdca736d9fef9184	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one 40V, Negative-QTOF	splash10-0a4i-9100000000-9702b36556d91ed75094	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one 10V, Negative-QTOF	splash10-001i-0900000000-709148915c23d7f31657	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one 20V, Negative-QTOF	splash10-0ab9-9600000000-872305e6d1e0b2b74fda	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one 40V, Negative-QTOF	splash10-00kf-9700000000-7786ebe4630b1c84d736	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one 10V, Positive-QTOF	splash10-001i-0900000000-91ddc7394e22e556eaf3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one 20V, Positive-QTOF	splash10-0089-0900000000-b20ba6d3084f0004280d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one 40V, Positive-QTOF	splash10-0pb9-9800000000-881a981d3f93270be779	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

28495

PDB ID

Not Available

ChEBI ID

63558

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 2,4-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one (HMDB0033733)

MOL for HMDB0033733 (2,4-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one)

3D MOL for HMDB0033733 (2,4-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one)

3D SDF for HMDB0033733 (2,4-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one)

3D-SDF for HMDB0033733 (2,4-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one)

PDB for HMDB0033733 (2,4-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one)

3D PDB for HMDB0033733 (2,4-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one)

SMILES for HMDB0033733 (2,4-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one)

INCHI for HMDB0033733 (2,4-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one)

Structure for HMDB0033733 (2,4-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one)

3D Structure for HMDB0033733 (2,4-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra