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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:07:22 UTC

Update Date

2023-02-21 17:26:09 UTC

HMDB ID

HMDB0037866

Secondary Accession Numbers

HMDB37866

Metabolite Identification

Common Name

4-Ethyl-2,5-dimethyloxazole

Description

4-Ethyl-2,5-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. 4-Ethyl-2,5-dimethyloxazole is a burnt and roasted tasting compound. 4-Ethyl-2,5-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 4-ethyl-2,5-dimethyloxazole a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 4-Ethyl-2,5-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
4-Ethyl-2,5-dimethyl-1,3-oxazole	HMDB

Chemical Formula

C₇H₁₁NO

Average Molecular Weight

125.1683

Monoisotopic Molecular Weight

125.084063979

IUPAC Name

4-ethyl-2,5-dimethyl-1,3-oxazole

Traditional Name

4-ethyl-2,5-dimethyl-1,3-oxazole

CAS Registry Number

30408-61-8

SMILES

CCC1=C(C)OC(C)=N1

InChI Identifier

InChI=1S/C7H11NO/c1-4-7-5(2)9-6(3)8-7/h4H2,1-3H3

InChI Key

YZZBROGKUWYQOL-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

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

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Cellular substructure

Extracellular (HMDB: HMDB0037866)
Cytoplasm (HMDB: HMDB0037866)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037866)

Source

Exogenous

Food

Food (HMDB: HMDB0037866)

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: HMDB0037866)
Coffea (HMDB: HMDB0037866)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0037866)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	150.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	949.3 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.715 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	5.73 g/L	ALOGPS
logP	2.18	ALOGPS
logP	1.07	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Basic)	1.87	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.03 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	35.58 m³·mol⁻¹	ChemAxon
Polarizability	14.55 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	126.553	31661259
DarkChem	[M-H]-	124.731	31661259
DeepCCS	[M+H]+	133.507	30932474
DeepCCS	[M-H]-	129.807	30932474
DeepCCS	[M-2H]-	166.924	30932474
DeepCCS	[M+Na]+	142.151	30932474
AllCCS	[M+H]+	126.1	32859911
AllCCS	[M+H-H2O]+	121.4	32859911
AllCCS	[M+NH4]+	130.5	32859911
AllCCS	[M+Na]+	131.8	32859911
AllCCS	[M-H]-	127.8	32859911
AllCCS	[M+Na-2H]-	130.0	32859911
AllCCS	[M+HCOO]-	132.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Ethyl-2,5-dimethyloxazole	CCC1=C(C)OC(C)=N1	1204.9	Standard polar	33892256
4-Ethyl-2,5-dimethyloxazole	CCC1=C(C)OC(C)=N1	901.0	Standard non polar	33892256
4-Ethyl-2,5-dimethyloxazole	CCC1=C(C)OC(C)=N1	919.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 4-Ethyl-2,5-dimethyloxazole EI-B (Non-derivatized)	splash10-0403-9700000000-d92f185fefd535fec33e	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 4-Ethyl-2,5-dimethyloxazole EI-B (Non-derivatized)	splash10-0403-9700000000-d92f185fefd535fec33e	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Ethyl-2,5-dimethyloxazole GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-9600000000-b1023bf18a4108ff45a8	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Ethyl-2,5-dimethyloxazole GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0296-9400000000-9a62451f75daf05c71d9	2015-03-01	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethyl-2,5-dimethyloxazole 10V, Positive-QTOF	splash10-004i-0900000000-fe5c492405c11b1647f6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethyl-2,5-dimethyloxazole 20V, Positive-QTOF	splash10-004i-6900000000-68612729affa1b090dd1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethyl-2,5-dimethyloxazole 40V, Positive-QTOF	splash10-014i-9000000000-1ec08f019b97e08a8b96	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethyl-2,5-dimethyloxazole 10V, Negative-QTOF	splash10-00e9-7900000000-4377b673a7c714e773ec	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethyl-2,5-dimethyloxazole 20V, Negative-QTOF	splash10-0089-9300000000-3576db4743eb5b8ec815	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethyl-2,5-dimethyloxazole 40V, Negative-QTOF	splash10-0udl-9000000000-43c5046a9466f2b6efed	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethyl-2,5-dimethyloxazole 10V, Negative-QTOF	splash10-0ff3-9300000000-5db720d1cb8eb067edd6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethyl-2,5-dimethyloxazole 20V, Negative-QTOF	splash10-0006-9000000000-bccf57d303bbb8b5163c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethyl-2,5-dimethyloxazole 40V, Negative-QTOF	splash10-0006-9000000000-e40cb50c33c5ae2f8ca9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethyl-2,5-dimethyloxazole 10V, Positive-QTOF	splash10-004i-3900000000-3b44e41f1b9415bc1c87	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethyl-2,5-dimethyloxazole 20V, Positive-QTOF	splash10-05q9-9300000000-48e40d7b32531349ba22	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethyl-2,5-dimethyloxazole 40V, Positive-QTOF	splash10-00r6-9100000000-216e3b165e240a852ba7	2021-09-24	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

FDB017019

KNApSAcK ID

Not Available

Chemspider ID

108582

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

121694

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1583271

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-Ethyl-2,5-dimethyloxazole (HMDB0037866)

MOL for HMDB0037866 (4-Ethyl-2,5-dimethyloxazole)

3D MOL for HMDB0037866 (4-Ethyl-2,5-dimethyloxazole)

3D SDF for HMDB0037866 (4-Ethyl-2,5-dimethyloxazole)

3D-SDF for HMDB0037866 (4-Ethyl-2,5-dimethyloxazole)

PDB for HMDB0037866 (4-Ethyl-2,5-dimethyloxazole)

3D PDB for HMDB0037866 (4-Ethyl-2,5-dimethyloxazole)

SMILES for HMDB0037866 (4-Ethyl-2,5-dimethyloxazole)

INCHI for HMDB0037866 (4-Ethyl-2,5-dimethyloxazole)

Structure for HMDB0037866 (4-Ethyl-2,5-dimethyloxazole)

3D Structure for HMDB0037866 (4-Ethyl-2,5-dimethyloxazole)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra