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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:10:20 UTC

Update Date

2023-02-21 17:28:25 UTC

HMDB ID

HMDB0040612

Secondary Accession Numbers

HMDB40612

Metabolite Identification

Common Name

4-Acetyl-2(3H)-benzoxazolone

Description

4-Acetyl-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. 4-Acetyl-2(3H)-benzoxazolone is found, on average, in the highest concentration within corns (Zea mays). 4-Acetyl-2(3H)-benzoxazolone has also 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 4-acetyl-2(3H)-benzoxazolone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 4-Acetyl-2(3H)-benzoxazolone.

Structure

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


  Mrv0541 05061311592D          

 13 14  0  0  0  0            999 V2000
    3.3523    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    3.5854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  1  1  0  0  0  0
  6  3  1  0  0  0  0
  6  5  1  0  0  0  0
  7  4  2  0  0  0  0
  8  6  2  0  0  0  0
  8  7  1  0  0  0  0
 10  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11  5  2  0  0  0  0
 12  9  2  0  0  0  0
 13  7  1  0  0  0  0
 13  9  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0040612

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)C1=C2NC(=O)OC2=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C9H7NO3/c1-5(11)6-3-2-4-7-8(6)10-9(12)13-7/h2-4H,1H3,(H,10,12)

> <INCHI_KEY>
FZAQRVWPQCXSPC-UHFFFAOYSA-N

> <FORMULA>
C9H7NO3

> <MOLECULAR_WEIGHT>
177.1568

> <EXACT_MASS>
177.042593095

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
16.787523706067653

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-acetyl-2,3-dihydro-1,3-benzoxazol-2-one

> <ALOGPS_LOGP>
1.02

> <JCHEM_LOGP>
0.8892741373333333

> <ALOGPS_LOGS>
-1.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.030300628038276

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.085136509124213

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6283331028838406

> <JCHEM_POLAR_SURFACE_AREA>
55.400000000000006

> <JCHEM_REFRACTIVITY>
46.667

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.20e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-acetyl-3H-1,3-benzoxazol-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

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       6.258   6.693   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.924   5.923   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       2.126   4.089   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0       3.590   6.693   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -0.320   2.843   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       2.126   1.597   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2    3    4                                                       
CONECT    3    2    6                                                       
CONECT    4    2    7                                                       
CONECT    5    1    6   11                                                  
CONECT    6    3    5    8                                                  
CONECT    7    4    8   13                                                  
CONECT    8    6    7   10                                                  
CONECT    9   10   12   13                                                  
CONECT   10    8    9                                                       
CONECT   11    5                                                            
CONECT   12    9                                                            
CONECT   13    7    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
4-Acetylbenzoxazolin-2-one	HMDB

Chemical Formula

C₉H₇NO₃

Average Molecular Weight

177.1568

Monoisotopic Molecular Weight

177.042593095

IUPAC Name

4-acetyl-2,3-dihydro-1,3-benzoxazol-2-one

Traditional Name

4-acetyl-3H-1,3-benzoxazol-2-one

CAS Registry Number

70735-79-4

SMILES

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

InChI Identifier

InChI=1S/C9H7NO3/c1-5(11)6-3-2-4-7-8(6)10-9(12)13-7/h2-4H,1H3,(H,10,12)

InChI Key

FZAQRVWPQCXSPC-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
Acetophenone
Aryl alkyl ketone
Aryl ketone
Benzenoid
Azole
Oxazole
Heteroaromatic compound
Vinylogous amide
Ketone
Oxacycle
Azacycle
Organic nitrogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0040612)
Cytoplasm (HMDB: HMDB0040612)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040612)

Source

Exogenous

Food

Food (HMDB: HMDB0040612)

Cereal and cereal product

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Cereal

Corn (FooDB: FOOD00205)

Cereals and cereal products (FooDB: FOOD00858)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Endogenous

Plant

Poaceae (HMDB: HMDB0040612)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0040612)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	217 - 218 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	3354 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.2 g/L	ALOGPS
logP	1.02	ALOGPS
logP	0.89	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	9.09	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.4 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	46.67 m³·mol⁻¹	ChemAxon
Polarizability	16.79 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]+	139.392	31661259
DarkChem	[M-H]-	135.298	31661259
DeepCCS	[M+H]+	134.485	30932474
DeepCCS	[M-H]-	132.089	30932474
DeepCCS	[M-2H]-	166.965	30932474
DeepCCS	[M+Na]+	141.424	30932474
AllCCS	[M+H]+	135.8	32859911
AllCCS	[M+H-H2O]+	131.3	32859911
AllCCS	[M+NH4]+	140.0	32859911
AllCCS	[M+Na]+	141.2	32859911
AllCCS	[M-H]-	134.9	32859911
AllCCS	[M+Na-2H]-	135.2	32859911
AllCCS	[M+HCOO]-	135.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Acetyl-2(3H)-benzoxazolone	CC(=O)C1=C2NC(=O)OC2=CC=C1	2652.2	Standard polar	33892256
4-Acetyl-2(3H)-benzoxazolone	CC(=O)C1=C2NC(=O)OC2=CC=C1	1842.1	Standard non polar	33892256
4-Acetyl-2(3H)-benzoxazolone	CC(=O)C1=C2NC(=O)OC2=CC=C1	1705.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Acetyl-2(3H)-benzoxazolone,1TMS,isomer #1	CC(=O)C1=CC=CC2=C1N([Si](C)(C)C)C(=O)O2	1813.5	Semi standard non polar	33892256
4-Acetyl-2(3H)-benzoxazolone,1TMS,isomer #1	CC(=O)C1=CC=CC2=C1N([Si](C)(C)C)C(=O)O2	1843.6	Standard non polar	33892256
4-Acetyl-2(3H)-benzoxazolone,1TBDMS,isomer #1	CC(=O)C1=CC=CC2=C1N([Si](C)(C)C(C)(C)C)C(=O)O2	2026.6	Semi standard non polar	33892256
4-Acetyl-2(3H)-benzoxazolone,1TBDMS,isomer #1	CC(=O)C1=CC=CC2=C1N([Si](C)(C)C(C)(C)C)C(=O)O2	2043.9	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Acetyl-2(3H)-benzoxazolone GC-MS (Non-derivatized) - 70eV, Positive	splash10-03gi-2900000000-c2e3d7ec94f486a4ca64	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Acetyl-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 - 4-Acetyl-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
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Acetyl-2(3H)-benzoxazolone 6V, Positive-QTOF	splash10-0ufr-0900000000-5202a5379e9ca936690d	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Acetyl-2(3H)-benzoxazolone 10V, Positive-QTOF	splash10-004i-0900000000-e4da8963e4cf5324f078	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Acetyl-2(3H)-benzoxazolone 20V, Positive-QTOF	splash10-004i-0900000000-756537f4ff75c2cb6bc3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Acetyl-2(3H)-benzoxazolone 40V, Positive-QTOF	splash10-03xu-1900000000-fbcf931425554c2864d9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Acetyl-2(3H)-benzoxazolone 10V, Negative-QTOF	splash10-004i-0900000000-faab935ec5f31e381b56	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Acetyl-2(3H)-benzoxazolone 20V, Negative-QTOF	splash10-0059-0900000000-a1436c4ec8d3d2fb309c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Acetyl-2(3H)-benzoxazolone 40V, Negative-QTOF	splash10-001i-1900000000-808b5c6ce7d271edcf15	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Acetyl-2(3H)-benzoxazolone 10V, Positive-QTOF	splash10-004i-0900000000-4441fde08ad1a50e1f59	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Acetyl-2(3H)-benzoxazolone 20V, Positive-QTOF	splash10-004i-0900000000-852d088d603a47a2d733	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Acetyl-2(3H)-benzoxazolone 40V, Positive-QTOF	splash10-05mo-5900000000-9dbe039a4255693a5f4e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Acetyl-2(3H)-benzoxazolone 10V, Negative-QTOF	splash10-004j-0900000000-a4f24ec9f9880e1e900b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Acetyl-2(3H)-benzoxazolone 20V, Negative-QTOF	splash10-004j-0900000000-7a4b54387bc05f6a6cbb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Acetyl-2(3H)-benzoxazolone 40V, Negative-QTOF	splash10-0a4j-2900000000-3ef3eeb26ad3ab1d43b5	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)	2021-09-24	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

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

FDB020403

KNApSAcK ID

C00054437

Chemspider ID

8165361

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9989779

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1884731

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 4-Acetyl-2(3H)-benzoxazolone (HMDB0040612)

MOL for HMDB0040612 (4-Acetyl-2(3H)-benzoxazolone)

3D MOL for HMDB0040612 (4-Acetyl-2(3H)-benzoxazolone)

3D SDF for HMDB0040612 (4-Acetyl-2(3H)-benzoxazolone)

3D-SDF for HMDB0040612 (4-Acetyl-2(3H)-benzoxazolone)

PDB for HMDB0040612 (4-Acetyl-2(3H)-benzoxazolone)

3D PDB for HMDB0040612 (4-Acetyl-2(3H)-benzoxazolone)

SMILES for HMDB0040612 (4-Acetyl-2(3H)-benzoxazolone)

INCHI for HMDB0040612 (4-Acetyl-2(3H)-benzoxazolone)

Structure for HMDB0040612 (4-Acetyl-2(3H)-benzoxazolone)

3D Structure for HMDB0040612 (4-Acetyl-2(3H)-benzoxazolone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra