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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:52:14 UTC

Update Date

2023-02-21 17:22:40 UTC

HMDB ID

HMDB0032846

Secondary Accession Numbers

HMDB32846

Metabolite Identification

Common Name

5-Chloro-6-methoxy-2(3H)-benzoxazolone

Description

5-Chloro-6-methoxy-2(3H)-benzoxazolone 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. 5-Chloro-6-methoxy-2(3H)-benzoxazolone has been detected, but not quantified in, breakfast cereal and cereals and cereal products. This could make 5-chloro-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 5-Chloro-6-methoxy-2(3H)-benzoxazolone.

Structure

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

HEADER    PROTEIN                                 04-APR-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-APR-13         0                                  
HETATM    1  C   UNK     0       0.600  -5.224   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.733  -5.994   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.733  -7.534   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.600  -8.304   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       3.399  -5.518   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       1.934  -5.994   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.934  -7.534   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       3.399  -8.010   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.304  -6.764   0.000  0.00  0.00           C+0
HETATM   10 Cl   UNK     0      -2.067  -5.224   0.000  0.00  0.00          Cl+0
HETATM   11  O   UNK     0      -2.067  -8.304   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.067  -9.844   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.844  -6.764   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   10                                                  
CONECT    3    2    4   11                                                  
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   13                                                  
CONECT   10    2                                                            
CONECT   11    3   12                                                       
CONECT   12   11                                                            
CONECT   13    9                                                            
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
5-chloro-6-Methoxy-2-benzoxazolinone	HMDB

Chemical Formula

C₈H₆ClNO₃

Average Molecular Weight

199.591

Monoisotopic Molecular Weight

199.00362077

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

COC1=C(Cl)C=C2NC(=O)OC2=C1

InChI Identifier

InChI=1S/C8H6ClNO3/c1-12-6-3-7-5(2-4(6)9)10-8(11)13-7/h2-3H,1H3,(H,10,11)

InChI Key

QQQYQWNSMUHSCK-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
Aryl chloride
Aryl halide
Benzenoid
Azole
Oxazole
Heteroaromatic compound
Ether
Azacycle
Oxacycle
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Hydrocarbon derivative
Organic nitrogen compound
Organic oxide
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Ingestion (HMDB: HMDB0032846)

Source

Exogenous

Food

Food (HMDB: HMDB0032846)

Cereal and cereal product

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Cereals and cereal products (FooDB: FOOD00858)

Endogenous

Plant

Poaceae (HMDB: HMDB0032846)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0032846)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	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	2.11 g/L	ALOGPS
logP	2.01	ALOGPS
logP	1.78	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	9.56	ChemAxon
pKa (Strongest Basic)	-1.9	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	47.53 m³·mol⁻¹	ChemAxon
Polarizability	17.87 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
DeepCCS	[M+H]+	138.831	30932474
DeepCCS	[M-H]-	135.413	30932474
DeepCCS	[M-2H]-	172.272	30932474
DeepCCS	[M+Na]+	147.811	30932474
AllCCS	[M+H]+	139.4	32859911
AllCCS	[M+H-H2O]+	135.1	32859911
AllCCS	[M+NH4]+	143.3	32859911
AllCCS	[M+Na]+	144.5	32859911
AllCCS	[M-H]-	136.0	32859911
AllCCS	[M+Na-2H]-	136.3	32859911
AllCCS	[M+HCOO]-	136.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5-Chloro-6-methoxy-2(3H)-benzoxazolone	COC1=C(Cl)C=C2NC(=O)OC2=C1	2761.0	Standard polar	33892256
5-Chloro-6-methoxy-2(3H)-benzoxazolone	COC1=C(Cl)C=C2NC(=O)OC2=C1	1836.2	Standard non polar	33892256
5-Chloro-6-methoxy-2(3H)-benzoxazolone	COC1=C(Cl)C=C2NC(=O)OC2=C1	1969.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5-Chloro-6-methoxy-2(3H)-benzoxazolone,1TMS,isomer #1	COC1=CC2=C(C=C1Cl)N([Si](C)(C)C)C(=O)O2	1912.9	Semi standard non polar	33892256
5-Chloro-6-methoxy-2(3H)-benzoxazolone,1TMS,isomer #1	COC1=CC2=C(C=C1Cl)N([Si](C)(C)C)C(=O)O2	1860.9	Standard non polar	33892256
5-Chloro-6-methoxy-2(3H)-benzoxazolone,1TBDMS,isomer #1	COC1=CC2=C(C=C1Cl)N([Si](C)(C)C(C)(C)C)C(=O)O2	2135.8	Semi standard non polar	33892256
5-Chloro-6-methoxy-2(3H)-benzoxazolone,1TBDMS,isomer #1	COC1=CC2=C(C=C1Cl)N([Si](C)(C)C(C)(C)C)C(=O)O2	2061.9	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Chloro-6-methoxy-2(3H)-benzoxazolone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4j-1900000000-47d76ce9a24926cfc293	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Chloro-6-methoxy-2(3H)-benzoxazolone 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 - 5-Chloro-6-methoxy-2(3H)-benzoxazolone 10V, Positive-QTOF	splash10-0udi-0090000000-9d481ce6d834f682cdd4	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Chloro-6-methoxy-2(3H)-benzoxazolone 20V, Positive-QTOF	splash10-0udi-0090000000-a4323bb568a1db492587	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Chloro-6-methoxy-2(3H)-benzoxazolone 40V, Positive-QTOF	splash10-0ff0-0910000000-9d2280288b4bd777e3b2	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Chloro-6-methoxy-2(3H)-benzoxazolone 10V, Negative-QTOF	splash10-0002-0900000000-db3bc7de39ee6e088727	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Chloro-6-methoxy-2(3H)-benzoxazolone 20V, Negative-QTOF	splash10-0002-0900000000-8c536fb3a9019d6947cc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Chloro-6-methoxy-2(3H)-benzoxazolone 40V, Negative-QTOF	splash10-001i-2900000000-04670dc11305b01b1fc2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Chloro-6-methoxy-2(3H)-benzoxazolone 10V, Negative-QTOF	splash10-0002-0900000000-4afc2c0d5a6f94969264	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Chloro-6-methoxy-2(3H)-benzoxazolone 20V, Negative-QTOF	splash10-000t-8900000000-e3c1d2176051e207f58b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Chloro-6-methoxy-2(3H)-benzoxazolone 40V, Negative-QTOF	splash10-001i-9000000000-8e3e779f63bc23dd9387	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Chloro-6-methoxy-2(3H)-benzoxazolone 10V, Positive-QTOF	splash10-0udi-0090000000-cc602e410a54a6bd5a54	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Chloro-6-methoxy-2(3H)-benzoxazolone 20V, Positive-QTOF	splash10-0udi-0190000000-b9f27cb9940f6edd19bb	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Chloro-6-methoxy-2(3H)-benzoxazolone 40V, Positive-QTOF	splash10-084m-3900000000-4d43213736573e30512a	2021-09-24	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+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

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

FDB010823

KNApSAcK ID

Not Available

Chemspider ID

14874

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15636

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 5-Chloro-6-methoxy-2(3H)-benzoxazolone (HMDB0032846)

MOL for HMDB0032846 (5-Chloro-6-methoxy-2(3H)-benzoxazolone)

3D MOL for HMDB0032846 (5-Chloro-6-methoxy-2(3H)-benzoxazolone)

3D SDF for HMDB0032846 (5-Chloro-6-methoxy-2(3H)-benzoxazolone)

3D-SDF for HMDB0032846 (5-Chloro-6-methoxy-2(3H)-benzoxazolone)

PDB for HMDB0032846 (5-Chloro-6-methoxy-2(3H)-benzoxazolone)

3D PDB for HMDB0032846 (5-Chloro-6-methoxy-2(3H)-benzoxazolone)

SMILES for HMDB0032846 (5-Chloro-6-methoxy-2(3H)-benzoxazolone)

INCHI for HMDB0032846 (5-Chloro-6-methoxy-2(3H)-benzoxazolone)

Structure for HMDB0032846 (5-Chloro-6-methoxy-2(3H)-benzoxazolone)

3D Structure for HMDB0032846 (5-Chloro-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