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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 21:44:25 UTC

Update Date

2023-02-21 17:25:25 UTC

HMDB ID

HMDB0036582

Secondary Accession Numbers

HMDB36582

Metabolite Identification

Common Name

6-Methoxy-2(3H)-benzoxazolone

Description

6-Methoxy-2(3H)-benzoxazolone, also known as 6-MBOA, belongs to the class of organic compounds known as benzoxazolones. These are organic compounds containing a benzene fused to an oxazole ring (a five-member aliphatic ring with three carbon atoms, one oxygen atom, and one nitrogen atom) bearing a ketone group. 6-Methoxy-2(3H)-benzoxazolone has been detected, but not quantified in, several different foods, such as flour, common wheats (Triticum aestivum), wild rice (Zizania), teas (Camellia sinensis), and alcoholic beverages. This could make 6-methoxy-2(3H)-benzoxazolone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 6-Methoxy-2(3H)-benzoxazolone.

Structure

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

HEADER    PROTEIN                                 10-JAN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-JAN-13         0                                  
HETATM    1  C   UNK     0      -5.280  -3.905   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.614  -4.675   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.614  -6.215   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.280  -6.985   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      -2.482  -4.199   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      -3.946  -4.675   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.946  -6.215   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.482  -6.691   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.577  -5.445   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -7.947  -6.985   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -9.281  -6.215   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.037  -5.445   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    7                                                       
CONECT    5    6    9                                                       
CONECT    6    1    5    7                                                  
CONECT    7    4    8    6                                                  
CONECT    8    7    9                                                       
CONECT    9    8    5   12                                                  
CONECT   10    3   11                                                       
CONECT   11   10                                                            
CONECT   12    9                                                            
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
6-MBOA	MeSH
6-Methoxy-2-benzoxazolinone	MeSH
6-Methoxybenzoxazolinone	MeSH
2(3H)-Benzoxazolone, 6-methoxy- (9ci)	HMDB
6-Methoxy-1,3-benzoxazol-2(3H)-one	HMDB
6-Methoxy-2-benzoxazolinone, 8ci	HMDB
6-Methoxy-3H-benzooxazol-2-one	HMDB
6-Methoxy-benzoxazolin-2(3H)-one	HMDB
6-Methoxybenzoxazolin-2(3H)-one	HMDB
Coixol	HMDB
MBOA	HMDB

Chemical Formula

C₈H₇NO₃

Average Molecular Weight

165.1461

Monoisotopic Molecular Weight

165.042593095

IUPAC Name

6-methoxy-2,3-dihydro-1,3-benzoxazol-2-one

Traditional Name

6-methoxy-3H-1,3-benzoxazol-2-one

CAS Registry Number

532-91-2

SMILES

COC1=CC=C2NC(=O)OC2=C1

InChI Identifier

InChI=1S/C8H7NO3/c1-11-5-2-3-6-7(4-5)12-8(10)9-6/h2-4H,1H3,(H,9,10)

InChI Key

MKMCJLMBVKHUMS-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoxazolones. These are organic compounds containing a benzene fused to an oxazole ring (a five-member aliphatic ring with three carbon atoms, one oxygen atom, and one nitrogen atom) bearing a ketone group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzoxazoles

Sub Class

Benzoxazolones

Direct Parent

Benzoxazolones

Alternative Parents

Substituents

Benzoxazolone
Anisole
Alkyl aryl ether
Benzenoid
Heteroaromatic compound
Oxazole
Azole
Oxacycle
Azacycle
Ether
Hydrocarbon derivative
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Excreta

Biofluid or Excreta

Urine (PMID: 32966057)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036582)

Source

Exogenous

Exogenous (HMDB: HMDB0036582)

Food

Food (HMDB: HMDB0036582)

Cereal and cereal product

Cereal

Cereal product

Breakfast cereal (FooDB: FOOD00270)
Whole grain cereal products (HMDB: HMDB0036582)
Flour (FooDB: FOOD00799)
Bulgur (FooDB: FOOD00741)

Cereals and cereal products (FooDB: FOOD00858)

Soy

Soy bean (FooDB: FOOD00085)

Tea

Herb and spice

Herb

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

Other seed

Quinoa (FooDB: FOOD00441)

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Coffee and coffee products (FooDB: FOOD00861)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Not Available

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

Antipsychotic (HMDB: HMDB0036582)

Antipyretic (HMDB: HMDB0036582)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	160 - 161 °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	10.1 g/L	ALOGPS
logP	1.21	ALOGPS
logP	1.17	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	9.66	ChemAxon
pKa (Strongest Basic)	-1.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	47.56 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	42.73 m³·mol⁻¹	ChemAxon
Polarizability	15.7 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]+	136.248	31661259
DarkChem	[M-H]-	134.68	31661259
DeepCCS	[M+H]+	132.655	30932474
DeepCCS	[M-H]-	128.884	30932474
DeepCCS	[M-2H]-	166.403	30932474
DeepCCS	[M+Na]+	141.941	30932474
AllCCS	[M+H]+	134.0	32859911
AllCCS	[M+H-H2O]+	129.5	32859911
AllCCS	[M+NH4]+	138.3	32859911
AllCCS	[M+Na]+	139.5	32859911
AllCCS	[M-H]-	132.8	32859911
AllCCS	[M+Na-2H]-	133.5	32859911
AllCCS	[M+HCOO]-	134.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
6-Methoxy-2(3H)-benzoxazolone	COC1=CC=C2NC(=O)OC2=C1	2734.8	Standard polar	33892256
6-Methoxy-2(3H)-benzoxazolone	COC1=CC=C2NC(=O)OC2=C1	1683.9	Standard non polar	33892256
6-Methoxy-2(3H)-benzoxazolone	COC1=CC=C2NC(=O)OC2=C1	1807.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
6-Methoxy-2(3H)-benzoxazolone,1TMS,isomer #1	COC1=CC=C2C(=C1)OC(=O)N2[Si](C)(C)C	1768.9	Semi standard non polar	33892256
6-Methoxy-2(3H)-benzoxazolone,1TMS,isomer #1	COC1=CC=C2C(=C1)OC(=O)N2[Si](C)(C)C	1788.9	Standard non polar	33892256
6-Methoxy-2(3H)-benzoxazolone,1TBDMS,isomer #1	COC1=CC=C2C(=C1)OC(=O)N2[Si](C)(C)C(C)(C)C	1990.4	Semi standard non polar	33892256
6-Methoxy-2(3H)-benzoxazolone,1TBDMS,isomer #1	COC1=CC=C2C(=C1)OC(=O)N2[Si](C)(C)C(C)(C)C	2001.0	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 6-Methoxy-2(3H)-benzoxazolone GC-MS (Non-derivatized) - 70eV, Positive	splash10-00xr-1900000000-ae55931a6532474213eb	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6-Methoxy-2(3H)-benzoxazolone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6-Methoxy-2(3H)-benzoxazolone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-1000-9800000000-b7f572346c850aedd8ad	2015-03-01	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - 6-Methoxy-2(3H)-benzoxazolone 6V, Negative-QTOF	splash10-0002-0900000000-fffb3a4c848b2a0dd10a	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Methoxy-2(3H)-benzoxazolone 10V, Positive-QTOF	splash10-014i-0900000000-e82eff1b272d62124d45	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Methoxy-2(3H)-benzoxazolone 20V, Positive-QTOF	splash10-014i-0900000000-6719525fa8c09d546ab8	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Methoxy-2(3H)-benzoxazolone 40V, Positive-QTOF	splash10-0uxu-5900000000-339ef11a0a1b20fab447	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Methoxy-2(3H)-benzoxazolone 10V, Negative-QTOF	splash10-03di-0900000000-2eafa61b506b198e6d87	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Methoxy-2(3H)-benzoxazolone 20V, Negative-QTOF	splash10-03di-0900000000-b8aeb67e44838d074a0a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Methoxy-2(3H)-benzoxazolone 40V, Negative-QTOF	splash10-0005-5900000000-421d3edef6a74ac871c6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Methoxy-2(3H)-benzoxazolone 10V, Positive-QTOF	splash10-014i-0900000000-52879b1c24e4e827f43a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Methoxy-2(3H)-benzoxazolone 20V, Positive-QTOF	splash10-014i-0900000000-39903a20e890e6c55a27	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Methoxy-2(3H)-benzoxazolone 40V, Positive-QTOF	splash10-01xw-9500000000-04fb799eee300bb0ff59	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Methoxy-2(3H)-benzoxazolone 10V, Negative-QTOF	splash10-03di-0900000000-65490e650f013cfe115e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Methoxy-2(3H)-benzoxazolone 20V, Negative-QTOF	splash10-03di-1900000000-25a1dd3e12969e3c6451	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Methoxy-2(3H)-benzoxazolone 40V, Negative-QTOF	splash10-006x-9500000000-738460d14bd58c753814	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
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, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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
Predicted 1D NMR	¹H 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+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

Not Available

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

FDB015492

KNApSAcK ID

C00036627

Chemspider ID

10317

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10772

PDB ID

Not Available

ChEBI ID

Not Available

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 6-Methoxy-2(3H)-benzoxazolone (HMDB0036582)

MOL for HMDB0036582 (6-Methoxy-2(3H)-benzoxazolone)

3D MOL for HMDB0036582 (6-Methoxy-2(3H)-benzoxazolone)

3D SDF for HMDB0036582 (6-Methoxy-2(3H)-benzoxazolone)

3D-SDF for HMDB0036582 (6-Methoxy-2(3H)-benzoxazolone)

PDB for HMDB0036582 (6-Methoxy-2(3H)-benzoxazolone)

3D PDB for HMDB0036582 (6-Methoxy-2(3H)-benzoxazolone)

SMILES for HMDB0036582 (6-Methoxy-2(3H)-benzoxazolone)

INCHI for HMDB0036582 (6-Methoxy-2(3H)-benzoxazolone)

Structure for HMDB0036582 (6-Methoxy-2(3H)-benzoxazolone)

3D Structure for HMDB0036582 (6-Methoxy-2(3H)-benzoxazolone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra