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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 23:36:40 UTC

Update Date

2023-02-21 17:26:30 UTC

HMDB ID

HMDB0038318

Secondary Accession Numbers

HMDB38318

Metabolite Identification

Common Name

(R)-2-Hydroxy-2H-1,4-benzoxazin-3(4H)-one

Description

(R)-2-Hydroxy-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 (R)-2-Hydroxy-2H-1,4-benzoxazin-3(4H)-one has been detected, but not quantified in, several different foods, such as red rice (Oryza rufipogon), soy beans (Glycine max), oriental wheats (Triticum turanicum), common buckwheats (Fagopyrum esculentum), and oats (Avena sativa). This could make (R)-2-hydroxy-2H-1,4-benzoxazin-3(4H)-one a potential biomarker for the consumption of these foods (R)-2-Hydroxy-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 (R)-2-Hydroxy-2H-1,4-benzoxazin-3(4H)-one.

Structure

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

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -2.016   1.586   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.309   0.927   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.365  -0.658   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.045  -1.450   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.670  -0.658   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.696   0.794   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.647  -1.450   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.939  -0.793   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.260  -1.586   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       3.365   1.586   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.993   0.794   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       0.675   1.586   0.000  0.00  0.00           N+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    1    5   12                                                  
CONECT    7    5    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8                                                            
CONECT   10   11                                                            
CONECT   11    8   10   12                                                  
CONECT   12    6   11                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-Hydroxy-1,4-benzoxazin-3-one	ChEBI
2-Hydroxy-2H-1,4-benzoxazin-3(4H)-one	ChEBI
HBOA CPD	MeSH, HMDB

Chemical Formula

C₈H₇NO₃

Average Molecular Weight

165.1461

Monoisotopic Molecular Weight

165.042593095

IUPAC Name

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

Traditional Name

HBOA

CAS Registry Number

Not Available

SMILES

OC1OC2=CC=CC=C2NC1=O

InChI Identifier

InChI=1S/C8H7NO3/c10-7-8(11)12-6-4-2-1-3-5(6)9-7/h1-4,8,11H,(H,9,10)

InChI Key

VMQBFYRBJKDACN-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
Carboxamide group
Hemiacetal
Lactam
Secondary carboxylic acid amide
Carboxylic acid derivative
Oxacycle
Azacycle
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organooxygen compound
Organic nitrogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

lactam (CHEBI:63559 )
benzoxazine (CHEBI:63559 )
lactol (CHEBI:63559 )
an indole derivative (CPD-6364 )

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: HMDB0038318)
Cytoplasm (HMDB: HMDB0038318)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038318)

Source

Exogenous

Exogenous (HMDB: HMDB0038318)

Food

Food (HMDB: HMDB0038318)

Cereal and cereal product

Cereal

Cereal product

Breakfast cereal (FooDB: FOOD00270)
Whole grain cereal products (HMDB: HMDB0038318)
Flour (FooDB: FOOD00799)
Bulgur (FooDB: FOOD00741)

Cereals and cereal products (FooDB: FOOD00858)

Soy

Soy bean (FooDB: FOOD00085)

Herb and spice

Herb

Amaranth (FooDB: FOOD00288)
Teff (FooDB: FOOD00489)

Other seed

Quinoa (FooDB: FOOD00441)

Endogenous

Plant

Poaceae (HMDB: HMDB0038318)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0038318)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	207 °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	47.9 g/L	ALOGPS
logP	0.48	ALOGPS
logP	0.47	ChemAxon
logS	-0.54	ALOGPS
pKa (Strongest Acidic)	10.05	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.56 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	42.02 m³·mol⁻¹	ChemAxon
Polarizability	15.34 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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]+	135.191	31661259
DarkChem	[M-H]-	130.48	31661259
DeepCCS	[M+H]+	126.543	30932474
DeepCCS	[M-H]-	122.713	30932474
DeepCCS	[M-2H]-	160.104	30932474
DeepCCS	[M+Na]+	135.507	30932474
AllCCS	[M+H]+	135.7	32859911
AllCCS	[M+H-H2O]+	131.1	32859911
AllCCS	[M+NH4]+	140.0	32859911
AllCCS	[M+Na]+	141.2	32859911
AllCCS	[M-H]-	132.1	32859911
AllCCS	[M+Na-2H]-	132.7	32859911
AllCCS	[M+HCOO]-	133.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(R)-2-Hydroxy-2H-1,4-benzoxazin-3(4H)-one	OC1OC2=CC=CC=C2NC1=O	2639.0	Standard polar	33892256
(R)-2-Hydroxy-2H-1,4-benzoxazin-3(4H)-one	OC1OC2=CC=CC=C2NC1=O	1501.8	Standard non polar	33892256
(R)-2-Hydroxy-2H-1,4-benzoxazin-3(4H)-one	OC1OC2=CC=CC=C2NC1=O	1712.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(R)-2-Hydroxy-2H-1,4-benzoxazin-3(4H)-one,1TMS,isomer #1	C[Si](C)(C)OC1OC2=CC=CC=C2NC1=O	1704.4	Semi standard non polar	33892256
(R)-2-Hydroxy-2H-1,4-benzoxazin-3(4H)-one,1TMS,isomer #2	C[Si](C)(C)N1C(=O)C(O)OC2=CC=CC=C21	1580.2	Semi standard non polar	33892256
(R)-2-Hydroxy-2H-1,4-benzoxazin-3(4H)-one,2TMS,isomer #1	C[Si](C)(C)OC1OC2=CC=CC=C2N([Si](C)(C)C)C1=O	1607.9	Semi standard non polar	33892256
(R)-2-Hydroxy-2H-1,4-benzoxazin-3(4H)-one,2TMS,isomer #1	C[Si](C)(C)OC1OC2=CC=CC=C2N([Si](C)(C)C)C1=O	1711.7	Standard non polar	33892256
(R)-2-Hydroxy-2H-1,4-benzoxazin-3(4H)-one,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1OC2=CC=CC=C2NC1=O	1943.3	Semi standard non polar	33892256
(R)-2-Hydroxy-2H-1,4-benzoxazin-3(4H)-one,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C(=O)C(O)OC2=CC=CC=C21	1843.7	Semi standard non polar	33892256
(R)-2-Hydroxy-2H-1,4-benzoxazin-3(4H)-one,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1OC2=CC=CC=C2N([Si](C)(C)C(C)(C)C)C1=O	2075.5	Semi standard non polar	33892256
(R)-2-Hydroxy-2H-1,4-benzoxazin-3(4H)-one,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1OC2=CC=CC=C2N([Si](C)(C)C(C)(C)C)C1=O	2193.9	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-2-Hydroxy-2H-1,4-benzoxazin-3(4H)-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4r-2900000000-c017a81ddc28a67c4af4	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-2-Hydroxy-2H-1,4-benzoxazin-3(4H)-one GC-MS (1 TMS) - 70eV, Positive	splash10-00dr-9410000000-6643cf0567459e7c462c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-2-Hydroxy-2H-1,4-benzoxazin-3(4H)-one GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-2-Hydroxy-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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-2-Hydroxy-2H-1,4-benzoxazin-3(4H)-one 10V, Positive-QTOF	splash10-014i-0900000000-f601fc34ae5a072303f8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-2-Hydroxy-2H-1,4-benzoxazin-3(4H)-one 20V, Positive-QTOF	splash10-0670-3900000000-e38150b54799641d4bfa	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-2-Hydroxy-2H-1,4-benzoxazin-3(4H)-one 40V, Positive-QTOF	splash10-0006-9200000000-5f498046cbbf930ce4e4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-2-Hydroxy-2H-1,4-benzoxazin-3(4H)-one 10V, Negative-QTOF	splash10-02t9-0900000000-294ce897b099ffccc871	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-2-Hydroxy-2H-1,4-benzoxazin-3(4H)-one 20V, Negative-QTOF	splash10-014i-0900000000-073dc783dddee3d4d4ca	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-2-Hydroxy-2H-1,4-benzoxazin-3(4H)-one 40V, Negative-QTOF	splash10-0006-9200000000-26934471e913677e7e4f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-2-Hydroxy-2H-1,4-benzoxazin-3(4H)-one 10V, Positive-QTOF	splash10-014i-0900000000-6a9b37931e7c93914c66	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-2-Hydroxy-2H-1,4-benzoxazin-3(4H)-one 20V, Positive-QTOF	splash10-014i-0900000000-9ee49a3213a0a7f1d055	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-2-Hydroxy-2H-1,4-benzoxazin-3(4H)-one 40V, Positive-QTOF	splash10-0ku6-9200000000-8defc88fd8cc29dfb538	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-2-Hydroxy-2H-1,4-benzoxazin-3(4H)-one 10V, Negative-QTOF	splash10-03di-0900000000-b379fcc43b54a3c613bf	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-2-Hydroxy-2H-1,4-benzoxazin-3(4H)-one 20V, Negative-QTOF	splash10-03dl-2900000000-7242fe9d91ea25e92a09	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-2-Hydroxy-2H-1,4-benzoxazin-3(4H)-one 40V, Negative-QTOF	splash10-0a4l-9500000000-445e5c051b5626ea7c50	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	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+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

322636

PDB ID

Not Available

ChEBI ID

63559

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

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

Showing metabocard for (R)-2-Hydroxy-2H-1,4-benzoxazin-3(4H)-one (HMDB0038318)

MOL for HMDB0038318 ((R)-2-Hydroxy-2H-1,4-benzoxazin-3(4H)-one)

3D MOL for HMDB0038318 ((R)-2-Hydroxy-2H-1,4-benzoxazin-3(4H)-one)

3D SDF for HMDB0038318 ((R)-2-Hydroxy-2H-1,4-benzoxazin-3(4H)-one)

3D-SDF for HMDB0038318 ((R)-2-Hydroxy-2H-1,4-benzoxazin-3(4H)-one)

PDB for HMDB0038318 ((R)-2-Hydroxy-2H-1,4-benzoxazin-3(4H)-one)

3D PDB for HMDB0038318 ((R)-2-Hydroxy-2H-1,4-benzoxazin-3(4H)-one)

SMILES for HMDB0038318 ((R)-2-Hydroxy-2H-1,4-benzoxazin-3(4H)-one)

INCHI for HMDB0038318 ((R)-2-Hydroxy-2H-1,4-benzoxazin-3(4H)-one)

Structure for HMDB0038318 ((R)-2-Hydroxy-2H-1,4-benzoxazin-3(4H)-one)

3D Structure for HMDB0038318 ((R)-2-Hydroxy-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