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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 09:48:03 UTC

Update Date

2021-09-26 23:04:31 UTC

HMDB ID

HMDB0252118

Secondary Accession Numbers

None

Metabolite Identification

Common Name

4-Ethoxymethylene-2-phenyl-2-oxazolin-5-one

Description

4-(ethoxymethylene)-2-phenyloxazol-5-one, also known as 2-phenyl-4-(ethoxymethylene)-5(4H)-oxazolone or 2-phenyl-oxazolone, belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. Based on a literature review a significant number of articles have been published on 4-(ethoxymethylene)-2-phenyloxazol-5-one. This compound has been identified in human blood as reported by (PMID: 31557052 ). 4-ethoxymethylene-2-phenyl-2-oxazolin-5-one is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 4-Ethoxymethylene-2-phenyl-2-oxazolin-5-one is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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


  Mrv1652309112111482D          

 16 17  0  0  0  0            999 V2000
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3819   -1.7224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1665   -1.4675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -2.5070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -2.5070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0470   -1.7224    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1830   -3.1745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1526   -3.9282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3323   -4.5956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1528   -4.5094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4884   -3.7557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0034   -3.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  4  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  5 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0252118

> <DATABASE_NAME>
hmdb

> <SMILES>
CCOC=C1N=C(OC1=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C12H11NO3/c1-2-15-8-10-12(14)16-11(13-10)9-6-4-3-5-7-9/h3-8H,2H2,1H3

> <INCHI_KEY>
SJHPCNCNNSSLPL-UHFFFAOYSA-N

> <FORMULA>
C12H11NO3

> <MOLECULAR_WEIGHT>
217.224

> <EXACT_MASS>
217.073893218

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
22.594676908774733

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(ethoxymethylidene)-2-phenyl-4,5-dihydro-1,3-oxazol-5-one

> <ALOGPS_LOGP>
2.41

> <JCHEM_LOGP>
2.1164620853333336

> <ALOGPS_LOGS>
-3.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6881270962427264

> <JCHEM_POLAR_SURFACE_AREA>
47.89

> <JCHEM_REFRACTIVITY>
59.53760000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.97e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
oxazolone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.000  -0.000   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.580  -3.215   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.044  -2.739   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       2.104  -4.680   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.564  -4.680   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       0.088  -3.215   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      -0.342  -5.926   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.285  -7.333   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.620  -8.578   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.152  -8.417   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.778  -7.011   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.873  -5.765   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9    5                                                       
CONECT   11    9   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   11                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

COMPND    HMDB0252118
HETATM    1  C1  UNL     1      -4.776  -0.105   1.027  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.345  -0.273  -0.423  1.00  0.00           C  
HETATM    3  O1  UNL     1      -3.441  -1.347  -0.530  1.00  0.00           O  
HETATM    4  C3  UNL     1      -2.258  -1.324   0.158  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.160  -0.821  -0.339  1.00  0.00           C  
HETATM    6  N1  UNL     1       0.114  -0.744   0.280  1.00  0.00           N  
HETATM    7  C5  UNL     1       0.989  -0.186  -0.486  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.379   0.029  -0.122  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.873  -0.352   1.089  1.00  0.00           C  
HETATM   10  C8  UNL     1       4.210  -0.149   1.451  1.00  0.00           C  
HETATM   11  C9  UNL     1       5.002   0.459   0.514  1.00  0.00           C  
HETATM   12  C10 UNL     1       4.542   0.862  -0.727  1.00  0.00           C  
HETATM   13  C11 UNL     1       3.206   0.637  -1.035  1.00  0.00           C  
HETATM   14  O2  UNL     1       0.362   0.154  -1.684  1.00  0.00           O  
HETATM   15  C12 UNL     1      -0.974  -0.213  -1.657  1.00  0.00           C  
HETATM   16  O3  UNL     1      -1.877  -0.087  -2.521  1.00  0.00           O  
HETATM   17  H1  UNL     1      -3.868   0.291   1.570  1.00  0.00           H  
HETATM   18  H2  UNL     1      -5.136  -1.046   1.464  1.00  0.00           H  
HETATM   19  H3  UNL     1      -5.524   0.721   1.081  1.00  0.00           H  
HETATM   20  H4  UNL     1      -3.822   0.650  -0.713  1.00  0.00           H  
HETATM   21  H5  UNL     1      -5.215  -0.394  -1.103  1.00  0.00           H  
HETATM   22  H6  UNL     1      -2.247  -1.744   1.156  1.00  0.00           H  
HETATM   23  H7  UNL     1       2.244  -0.840   1.844  1.00  0.00           H  
HETATM   24  H8  UNL     1       4.600  -0.452   2.410  1.00  0.00           H  
HETATM   25  H9  UNL     1       6.056   0.642   0.744  1.00  0.00           H  
HETATM   26  H10 UNL     1       5.216   1.344  -1.441  1.00  0.00           H  
HETATM   27  H11 UNL     1       2.851   0.954  -2.007  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3   20   21
CONECT    3    4
CONECT    4    5    5   22
CONECT    5    6   15
CONECT    6    7    7
CONECT    7    8   14
CONECT    8    9    9   13
CONECT    9   10   23
CONECT   10   11   11   24
CONECT   11   12   25
CONECT   12   13   13   26
CONECT   13   27
CONECT   14   15
CONECT   15   16   16
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Phenyl-4-(ethoxymethylene)-5(4H)-oxazolone	ChEBI
2-Phenyl-4-ethoxymethylene-5(4H)-oxazolone	ChEBI
2-Phenyl-4-ethoxymethylene-5-oxazolone	ChEBI
2-Phenyl-oxazolone	ChEBI
4-(Ethoxymethylene)-2-phenyloxazol-5(4H)-one	ChEBI
4-Ethoxymethylene-2-phenyl-2-oxazoline-5-one	ChEBI
4-Ethoxymethylene-2-phenyl-4H-1,3-oxazol-5-one	ChEBI
EtOX	ChEBI
OXA	ChEBI
Oxazolone	ChEBI
Phenyl ox	ChEBI
PhOx	ChEBI
Pxazolone	ChEBI
2-Phenyl-4-(ethoxymethylene)oxazol-5-one	MeSH
4 Ethoxymethylene 2 phenyloxazolone	MeSH
4-Ethoxymethylene-2-phenyloxazolone	MeSH

Chemical Formula

C₁₂H₁₁NO₃

Average Molecular Weight

217.224

Monoisotopic Molecular Weight

217.073893218

IUPAC Name

4-(ethoxymethylidene)-2-phenyl-4,5-dihydro-1,3-oxazol-5-one

Traditional Name

oxazolone

CAS Registry Number

Not Available

SMILES

CCOC=C1N=C(OC1=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C12H11NO3/c1-2-15-8-10-12(14)16-11(13-10)9-6-4-3-5-7-9/h3-8H,2H2,1H3

InChI Key

SJHPCNCNNSSLPL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids and derivatives

Alternative Parents

Substituents

Alpha-amino acid or derivatives
4-hydrocarbylideneazlactone
Monocyclic benzene moiety
Benzenoid
Oxazoline
Vinylogous ester
Monocarboxylic acid or derivatives
Oxacycle
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

1,3-oxazoles (CHEBI:53076 )
gamma-lactone (CHEBI:53076 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

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
logP	2.41	ALOGPS
logP	2.12	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Basic)	-1.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	47.89 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	59.54 m³·mol⁻¹	ChemAxon
Polarizability	22.59 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
DeepCCS	[M+H]+	148.556	30932474
DeepCCS	[M-H]-	146.183	30932474
DeepCCS	[M-2H]-	179.689	30932474
DeepCCS	[M+Na]+	154.634	30932474
AllCCS	[M+H]+	148.7	32859911
AllCCS	[M+H-H2O]+	144.6	32859911
AllCCS	[M+NH4]+	152.4	32859911
AllCCS	[M+Na]+	153.5	32859911
AllCCS	[M-H]-	151.4	32859911
AllCCS	[M+Na-2H]-	151.4	32859911
AllCCS	[M+HCOO]-	151.6	32859911

Predicted Kovats Retention Indices

Not Available

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Ethoxymethylene-2-phenyl-2-oxazolin-5-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-9810000000-40d0d61fcdfafdf7997a	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Ethoxymethylene-2-phenyl-2-oxazolin-5-one GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Ethoxymethylene-2-phenyl-2-oxazolin-5-one 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 - 4-Ethoxymethylene-2-phenyl-2-oxazolin-5-one 10V, Positive-QTOF	splash10-014i-0090000000-598ce6e34e1defc5db0a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethoxymethylene-2-phenyl-2-oxazolin-5-one 20V, Positive-QTOF	splash10-07or-2920000000-74c463983ddb9d5726e0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethoxymethylene-2-phenyl-2-oxazolin-5-one 40V, Positive-QTOF	splash10-0kdl-5900000000-0472e50230c44f639e33	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethoxymethylene-2-phenyl-2-oxazolin-5-one 10V, Negative-QTOF	splash10-014i-0190000000-f5d148bf741b436d6dde	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethoxymethylene-2-phenyl-2-oxazolin-5-one 20V, Negative-QTOF	splash10-03di-0910000000-ce21fd0318501923c70d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethoxymethylene-2-phenyl-2-oxazolin-5-one 40V, Negative-QTOF	splash10-004i-8900000000-0f57fe445128d74c4fd7	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

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	Not Specified	Not Specified	Normal	31557052	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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

25530

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Oxazolone

METLIN ID

Not Available

PubChem Compound

27435

PDB ID

Not Available

ChEBI ID

53076

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for 4-Ethoxymethylene-2-phenyl-2-oxazolin-5-one (HMDB0252118)

MOL for HMDB0252118 (4-Ethoxymethylene-2-phenyl-2-oxazolin-5-one)

3D MOL for HMDB0252118 (4-Ethoxymethylene-2-phenyl-2-oxazolin-5-one)

3D SDF for HMDB0252118 (4-Ethoxymethylene-2-phenyl-2-oxazolin-5-one)

3D-SDF for HMDB0252118 (4-Ethoxymethylene-2-phenyl-2-oxazolin-5-one)

PDB for HMDB0252118 (4-Ethoxymethylene-2-phenyl-2-oxazolin-5-one)

3D PDB for HMDB0252118 (4-Ethoxymethylene-2-phenyl-2-oxazolin-5-one)

SMILES for HMDB0252118 (4-Ethoxymethylene-2-phenyl-2-oxazolin-5-one)

INCHI for HMDB0252118 (4-Ethoxymethylene-2-phenyl-2-oxazolin-5-one)

Structure for HMDB0252118 (4-Ethoxymethylene-2-phenyl-2-oxazolin-5-one)

3D Structure for HMDB0252118 (4-Ethoxymethylene-2-phenyl-2-oxazolin-5-one)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

GC-MS Spectra

MS/MS Spectra