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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 23:47:51 UTC

Update Date

2021-09-26 22:56:05 UTC

HMDB ID

HMDB0246785

Secondary Accession Numbers

None

Metabolite Identification

Common Name

5-Ethyl-5-phenyl-1,3-oxazolidine-2,4-dione

Description

5-Ethyl-5-phenyl-1,3-oxazolidine-2,4-dione, also known as EPO-5,5, belongs to the class of organic compounds known as oxazolidinediones. Oxazolidinediones are compounds containing an oxazolidine ring which bears two ketones. Based on a literature review very few articles have been published on 5-Ethyl-5-phenyl-1,3-oxazolidine-2,4-dione. This compound has been identified in human blood as reported by (PMID: 31557052 ). 5-ethyl-5-phenyl-1,3-oxazolidine-2,4-dione is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 5-Ethyl-5-phenyl-1,3-oxazolidine-2,4-dione 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


  Mrv1652309112101482D          

 15 16  0  0  0  0            999 V2000
   -0.1749   -0.6157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6320   -0.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1841   -1.0572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8515   -1.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6361   -1.2872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5966   -2.3268    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7716   -2.3268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2866   -2.9942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5166   -1.5422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7361   -0.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4812    0.3405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0332    0.9536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8402    0.7820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0951   -0.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5431   -0.6157    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
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  3  9  1  0  0  0  0
  3 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 10 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0246785

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC1(OC(=O)NC1=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C11H11NO3/c1-2-11(8-6-4-3-5-7-8)9(13)12-10(14)15-11/h3-7H,2H2,1H3,(H,12,13,14)

> <INCHI_KEY>
SGQOVJBGRJMVJR-UHFFFAOYSA-N

> <FORMULA>
C11H11NO3

> <MOLECULAR_WEIGHT>
205.213

> <EXACT_MASS>
205.073893218

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
20.191709009937476

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-ethyl-5-phenyl-1,3-oxazolidine-2,4-dione

> <ALOGPS_LOGP>
2.17

> <JCHEM_LOGP>
2.1706578223333333

> <ALOGPS_LOGS>
-2.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.54052583381576

> <JCHEM_POLAR_SURFACE_AREA>
55.400000000000006

> <JCHEM_REFRACTIVITY>
52.69150000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.45e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-ethyl-5-phenyl-1,3-oxazolidine-2,4-dione

> <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      -0.327  -1.149   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.180  -0.829   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.210  -1.974   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.456  -2.879   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       4.921  -2.403   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       2.980  -4.343   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       1.440  -4.343   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.535  -5.589   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       0.964  -2.879   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.241  -0.829   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.765   0.636   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.795   1.780   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.302   1.460   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.778  -0.005   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.747  -1.149   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9   10                                             
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7    3                                                       
CONECT   10    3   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   10                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

COMPND    HMDB0246785
HETATM    1  C1  UNL     1      -1.581  -1.825  -0.540  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.592  -0.849   0.603  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.775   0.388   0.318  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.621   0.037   0.062  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.555   0.114   1.077  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.887  -0.202   0.904  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.331  -0.621  -0.349  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.423  -0.705  -1.375  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.098  -0.385  -1.178  1.00  0.00           C  
HETATM   10  O1  UNL     1      -0.842   1.197   1.494  1.00  0.00           O  
HETATM   11  C10 UNL     1      -1.628   2.297   1.296  1.00  0.00           C  
HETATM   12  O2  UNL     1      -2.016   3.159   2.135  1.00  0.00           O  
HETATM   13  N1  UNL     1      -1.985   2.360  -0.075  1.00  0.00           N  
HETATM   14  C11 UNL     1      -1.380   1.241  -0.719  1.00  0.00           C  
HETATM   15  O3  UNL     1      -1.406   1.088  -1.967  1.00  0.00           O  
HETATM   16  H1  UNL     1      -1.765  -1.315  -1.514  1.00  0.00           H  
HETATM   17  H2  UNL     1      -0.685  -2.477  -0.557  1.00  0.00           H  
HETATM   18  H3  UNL     1      -2.457  -2.522  -0.410  1.00  0.00           H  
HETATM   19  H4  UNL     1      -2.606  -0.616   0.961  1.00  0.00           H  
HETATM   20  H5  UNL     1      -1.076  -1.366   1.463  1.00  0.00           H  
HETATM   21  H6  UNL     1       1.242   0.437   2.068  1.00  0.00           H  
HETATM   22  H7  UNL     1       3.619  -0.142   1.700  1.00  0.00           H  
HETATM   23  H8  UNL     1       4.378  -0.875  -0.509  1.00  0.00           H  
HETATM   24  H9  UNL     1       2.792  -1.037  -2.352  1.00  0.00           H  
HETATM   25  H10 UNL     1       0.425  -0.464  -2.000  1.00  0.00           H  
HETATM   26  H11 UNL     1      -2.580   3.084  -0.537  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3   19   20
CONECT    3    4   10   14
CONECT    4    5    5    9
CONECT    5    6   21
CONECT    6    7    7   22
CONECT    7    8   23
CONECT    8    9    9   24
CONECT    9   25
CONECT   10   11
CONECT   11   12   12   13
CONECT   13   14   26
CONECT   14   15   15
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5-Ethyl-5-phenyloxazolidinedione	MeSH
5-Ethyl-5-phenyloxazolidinedione, (+-)-isomer	MeSH
5-Ethyl-5-phenyloxazolidinedione, (R)-isomer	MeSH
5-Ethyl-5-phenyloxazolidinedione, (S)-isomer	MeSH
5-Ethyl-5-phenyloxazolidinedione, sodium salt	MeSH
EPO-5,5	MeSH

Chemical Formula

C₁₁H₁₁NO₃

Average Molecular Weight

205.213

Monoisotopic Molecular Weight

205.073893218

IUPAC Name

5-ethyl-5-phenyl-1,3-oxazolidine-2,4-dione

Traditional Name

5-ethyl-5-phenyl-1,3-oxazolidine-2,4-dione

CAS Registry Number

Not Available

SMILES

CCC1(OC(=O)NC1=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C11H11NO3/c1-2-11(8-6-4-3-5-7-8)9(13)12-10(14)15-11/h3-7H,2H2,1H3,(H,12,13,14)

InChI Key

SGQOVJBGRJMVJR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxazolidinediones. Oxazolidinediones are compounds containing an oxazolidine ring which bears two ketones.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azolidines

Sub Class

Oxazolidines

Direct Parent

Oxazolidinediones

Alternative Parents

Substituents

Oxazolidinedione
Monocyclic benzene moiety
Benzenoid
Dicarboximide
Carbamic acid ester
Carbonic acid derivative
Oxacycle
Azacycle
Carboxylic acid derivative
Organopnictogen compound
Organic nitrogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

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	2.17	ALOGPS
logP	2.17	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	6.54	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.4 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	52.69 m³·mol⁻¹	ChemAxon
Polarizability	20.19 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]+	151.582	30932474
DeepCCS	[M-H]-	149.224	30932474
DeepCCS	[M-2H]-	182.903	30932474
DeepCCS	[M+Na]+	157.855	30932474
AllCCS	[M+H]+	144.5	32859911
AllCCS	[M+H-H2O]+	140.2	32859911
AllCCS	[M+NH4]+	148.6	32859911
AllCCS	[M+Na]+	149.7	32859911
AllCCS	[M-H]-	146.0	32859911
AllCCS	[M+Na-2H]-	146.1	32859911
AllCCS	[M+HCOO]-	146.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5-Ethyl-5-phenyl-1,3-oxazolidine-2,4-dione	CCC1(OC(=O)NC1=O)C1=CC=CC=C1	2983.8	Standard polar	33892256
5-Ethyl-5-phenyl-1,3-oxazolidine-2,4-dione	CCC1(OC(=O)NC1=O)C1=CC=CC=C1	1801.8	Standard non polar	33892256
5-Ethyl-5-phenyl-1,3-oxazolidine-2,4-dione	CCC1(OC(=O)NC1=O)C1=CC=CC=C1	1774.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5-Ethyl-5-phenyl-1,3-oxazolidine-2,4-dione,1TMS,isomer #1	CCC1(C2=CC=CC=C2)OC(=O)N([Si](C)(C)C)C1=O	1825.5	Semi standard non polar	33892256
5-Ethyl-5-phenyl-1,3-oxazolidine-2,4-dione,1TMS,isomer #1	CCC1(C2=CC=CC=C2)OC(=O)N([Si](C)(C)C)C1=O	1803.4	Standard non polar	33892256
5-Ethyl-5-phenyl-1,3-oxazolidine-2,4-dione,1TMS,isomer #1	CCC1(C2=CC=CC=C2)OC(=O)N([Si](C)(C)C)C1=O	2258.5	Standard polar	33892256
5-Ethyl-5-phenyl-1,3-oxazolidine-2,4-dione,1TBDMS,isomer #1	CCC1(C2=CC=CC=C2)OC(=O)N([Si](C)(C)C(C)(C)C)C1=O	2068.6	Semi standard non polar	33892256
5-Ethyl-5-phenyl-1,3-oxazolidine-2,4-dione,1TBDMS,isomer #1	CCC1(C2=CC=CC=C2)OC(=O)N([Si](C)(C)C(C)(C)C)C1=O	2037.9	Standard non polar	33892256
5-Ethyl-5-phenyl-1,3-oxazolidine-2,4-dione,1TBDMS,isomer #1	CCC1(C2=CC=CC=C2)OC(=O)N([Si](C)(C)C(C)(C)C)C1=O	2341.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Ethyl-5-phenyl-1,3-oxazolidine-2,4-dione GC-MS (Non-derivatized) - 70eV, Positive	splash10-06vi-2900000000-af56426f2039e28eb21c	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Ethyl-5-phenyl-1,3-oxazolidine-2,4-dione 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-Ethyl-5-phenyl-1,3-oxazolidine-2,4-dione 10V, Positive-QTOF	splash10-0a4i-0590000000-cbcb0dc6d8b4a52917be	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Ethyl-5-phenyl-1,3-oxazolidine-2,4-dione 20V, Positive-QTOF	splash10-014i-2910000000-41ad3d3c91efb44b8e02	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Ethyl-5-phenyl-1,3-oxazolidine-2,4-dione 40V, Positive-QTOF	splash10-016u-9700000000-eaa6b343eaeba2295a9b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Ethyl-5-phenyl-1,3-oxazolidine-2,4-dione 10V, Negative-QTOF	splash10-0udl-6390000000-73eca81f2c28144fdeb2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Ethyl-5-phenyl-1,3-oxazolidine-2,4-dione 20V, Negative-QTOF	splash10-0006-9300000000-68679f427dea1af10473	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Ethyl-5-phenyl-1,3-oxazolidine-2,4-dione 40V, Negative-QTOF	splash10-0006-9100000000-356ff9139110421c4db2	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

103503

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

115735

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

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 5-Ethyl-5-phenyl-1,3-oxazolidine-2,4-dione (HMDB0246785)

MOL for HMDB0246785 (5-Ethyl-5-phenyl-1,3-oxazolidine-2,4-dione)

3D MOL for HMDB0246785 (5-Ethyl-5-phenyl-1,3-oxazolidine-2,4-dione)

3D SDF for HMDB0246785 (5-Ethyl-5-phenyl-1,3-oxazolidine-2,4-dione)

3D-SDF for HMDB0246785 (5-Ethyl-5-phenyl-1,3-oxazolidine-2,4-dione)

PDB for HMDB0246785 (5-Ethyl-5-phenyl-1,3-oxazolidine-2,4-dione)

3D PDB for HMDB0246785 (5-Ethyl-5-phenyl-1,3-oxazolidine-2,4-dione)

SMILES for HMDB0246785 (5-Ethyl-5-phenyl-1,3-oxazolidine-2,4-dione)

INCHI for HMDB0246785 (5-Ethyl-5-phenyl-1,3-oxazolidine-2,4-dione)

Structure for HMDB0246785 (5-Ethyl-5-phenyl-1,3-oxazolidine-2,4-dione)

3D Structure for HMDB0246785 (5-Ethyl-5-phenyl-1,3-oxazolidine-2,4-dione)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra