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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:27:24 UTC

Update Date

2023-02-21 17:26:22 UTC

HMDB ID

HMDB0038174

Secondary Accession Numbers

HMDB38174

Metabolite Identification

Common Name

5-Acetyl-2,4-dimethyloxazole

Description

5-Acetyl-2,4-dimethyloxazole belongs to the class of organic compounds known as 2,4,5-trisubstituted oxazoles. 2,4,5-trisubstituted oxazoles are compounds containing an oxazole ring substituted at positions 2, 4 and 5 only. Oxazole is a five-membered aromatic heterocycle with one oxygen, one nitrogen, and three carbon atoms. Isomers include 1,2-oxazole and 1,3-oxazole. 5-Acetyl-2,4-dimethyloxazole has been detected, but not quantified in, several different foods, such as arabica coffees (Coffea arabica), coffee and coffee products, potatos (Solanum tuberosum), and robusta coffees (Coffea canephora). This could make 5-acetyl-2,4-dimethyloxazole a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 5-Acetyl-2,4-dimethyloxazole.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1-(2,4-Dimethyl-5-oxazolyl)ethanone, 9ci	HMDB

Chemical Formula

C₇H₉NO₂

Average Molecular Weight

139.1519

Monoisotopic Molecular Weight

139.063328537

IUPAC Name

1-(dimethyl-1,3-oxazol-5-yl)ethan-1-one

Traditional Name

1-(dimethyl-1,3-oxazol-5-yl)ethanone

CAS Registry Number

23012-25-1

SMILES

CC(=O)C1=C(C)N=C(C)O1

InChI Identifier

InChI=1S/C7H9NO2/c1-4-7(5(2)9)10-6(3)8-4/h1-3H3

InChI Key

YJWCNOMJKJYKLQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2,4,5-trisubstituted oxazoles. 2,4,5-Trisubstituted oxazoles are compounds containing an oxazole ring substituted at positions 2, 4 and 5 only. Oxazole is a five-membered aromatic heterocycle with one oxygen, one nitrogen, and three carbon atoms. Isomers include 1,2-oxazole and 1,3-oxazole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azoles

Sub Class

Oxazoles

Direct Parent

2,4,5-trisubstituted oxazoles

Alternative Parents

Substituents

Aryl alkyl ketone
Aryl ketone
2,4,5-trisubstituted 1,3-oxazole
Heteroaromatic compound
Ketone
Oxacycle
Azacycle
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0038174)
Cytoplasm (HMDB: HMDB0038174)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038174)

Source

Exogenous

Exogenous (HMDB: HMDB0038174)

Food

Food (HMDB: HMDB0038174)

Vegetable

Tuber

Potato (FooDB: FOOD00175)

Coffee and coffee product

Coffee

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

Coffee and coffee products (FooDB: FOOD00861)

Endogenous

Plant

Plant (HMDB: HMDB0038174)
Coffea (HMDB: HMDB0038174)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0038174)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	212.00 to 213.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	19620 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	-0.738 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	17.4 g/L	ALOGPS
logP	0.83	ALOGPS
logP	-0.35	ChemAxon
logS	-0.9	ALOGPS
pKa (Strongest Acidic)	14.36	ChemAxon
pKa (Strongest Basic)	-0.072	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.1 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	36.08 m³·mol⁻¹	ChemAxon
Polarizability	14.67 Å³	ChemAxon
Number of Rings	1	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]+	130.41	31661259
DarkChem	[M-H]-	128.755	31661259
DeepCCS	[M+H]+	135.511	30932474
DeepCCS	[M-H]-	133.001	30932474
DeepCCS	[M-2H]-	168.843	30932474
DeepCCS	[M+Na]+	143.956	30932474
AllCCS	[M+H]+	129.1	32859911
AllCCS	[M+H-H2O]+	124.6	32859911
AllCCS	[M+NH4]+	133.4	32859911
AllCCS	[M+Na]+	134.6	32859911
AllCCS	[M-H]-	128.0	32859911
AllCCS	[M+Na-2H]-	129.8	32859911
AllCCS	[M+HCOO]-	131.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5-Acetyl-2,4-dimethyloxazole	CC(=O)C1=C(C)N=C(C)O1	1593.1	Standard polar	33892256
5-Acetyl-2,4-dimethyloxazole	CC(=O)C1=C(C)N=C(C)O1	1031.0	Standard non polar	33892256
5-Acetyl-2,4-dimethyloxazole	CC(=O)C1=C(C)N=C(C)O1	1056.0	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 - 5-Acetyl-2,4-dimethyloxazole GC-MS (Non-derivatized) - 70eV, Positive	splash10-00tn-9200000000-44c1d0834f59ab7687e1	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Acetyl-2,4-dimethyloxazole 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-Acetyl-2,4-dimethyloxazole 10V, Positive-QTOF	splash10-006x-0900000000-3fb161c4e081e5fc544e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Acetyl-2,4-dimethyloxazole 20V, Positive-QTOF	splash10-00dl-0900000000-a74577243c84471b52cf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Acetyl-2,4-dimethyloxazole 40V, Positive-QTOF	splash10-00dl-9800000000-fdda74f2cb1d4efddb6a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Acetyl-2,4-dimethyloxazole 10V, Negative-QTOF	splash10-000i-0900000000-8b4b39babc6e03a04bfe	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Acetyl-2,4-dimethyloxazole 20V, Negative-QTOF	splash10-0002-9200000000-847da9344b9b75c3ff05	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Acetyl-2,4-dimethyloxazole 40V, Negative-QTOF	splash10-0006-9100000000-a24292fc25ff1557bfc7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Acetyl-2,4-dimethyloxazole 10V, Positive-QTOF	splash10-0007-6900000000-5f0008b0bd71e1d3ad59	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Acetyl-2,4-dimethyloxazole 20V, Positive-QTOF	splash10-000w-9200000000-d692598ec1f3a98d9c83	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Acetyl-2,4-dimethyloxazole 40V, Positive-QTOF	splash10-001l-9000000000-d3652865fad0694aa147	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Acetyl-2,4-dimethyloxazole 10V, Negative-QTOF	splash10-000i-3900000000-6018b0169959a92347a9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Acetyl-2,4-dimethyloxazole 20V, Negative-QTOF	splash10-0006-9100000000-e5e5b85bf831f254ecc9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Acetyl-2,4-dimethyloxazole 40V, Negative-QTOF	splash10-0006-9000000000-575faadbcf1537a60f4f	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

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

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

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

FDB017413

KNApSAcK ID

Not Available

Chemspider ID

281857

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

318418

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1637751

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-Acetyl-2,4-dimethyloxazole (HMDB0038174)

MOL for HMDB0038174 (5-Acetyl-2,4-dimethyloxazole)

3D MOL for HMDB0038174 (5-Acetyl-2,4-dimethyloxazole)

3D SDF for HMDB0038174 (5-Acetyl-2,4-dimethyloxazole)

3D-SDF for HMDB0038174 (5-Acetyl-2,4-dimethyloxazole)

PDB for HMDB0038174 (5-Acetyl-2,4-dimethyloxazole)

3D PDB for HMDB0038174 (5-Acetyl-2,4-dimethyloxazole)

SMILES for HMDB0038174 (5-Acetyl-2,4-dimethyloxazole)

INCHI for HMDB0038174 (5-Acetyl-2,4-dimethyloxazole)

Structure for HMDB0038174 (5-Acetyl-2,4-dimethyloxazole)

3D Structure for HMDB0038174 (5-Acetyl-2,4-dimethyloxazole)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra