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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:48:11 UTC

Update Date

2023-02-21 17:28:05 UTC

HMDB ID

HMDB0040268

Secondary Accession Numbers

HMDB40268

Metabolite Identification

Common Name

Ethyl 3-oxo-3-phenylpropanoate

Description

Ethyl 3-oxo-3-phenylpropanoate belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. Ethyl 3-oxo-3-phenylpropanoate is a sweet, acetophenone, and bitter tasting compound. Based on a literature review very few articles have been published on Ethyl 3-oxo-3-phenylpropanoate.

Structure

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


  Mrv0541 05061311432D          

 14 14  0  0  0  0            999 V2000
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
  9  6  2  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11  8  1  0  0  0  0
 12 10  2  0  0  0  0
 13 11  2  0  0  0  0
 14  2  1  0  0  0  0
 14 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0040268

> <DATABASE_NAME>
hmdb

> <SMILES>
CCOC(=O)CC(=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C11H12O3/c1-2-14-11(13)8-10(12)9-6-4-3-5-7-9/h3-7H,2,8H2,1H3

> <INCHI_KEY>
GKKZMYDNDDMXSE-UHFFFAOYSA-N

> <FORMULA>
C11H12O3

> <MOLECULAR_WEIGHT>
192.2112

> <EXACT_MASS>
192.07864425

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
19.614335551320238

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
ethyl 3-oxo-3-phenylpropanoate

> <ALOGPS_LOGP>
1.71

> <JCHEM_LOGP>
1.9258237913333331

> <ALOGPS_LOGS>
-2.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.808267374597783

> <JCHEM_PKA_STRONGEST_BASIC>
-7.001490588767577

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
52.32260000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.34e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ethyl benzoylacetate

> <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       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      16.004   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      16.004   6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.671   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.671   6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.337   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.337   6.160   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.003   6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      12.003   8.470   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       9.336   8.470   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       8.002   6.160   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1   14                                                       
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4    9                                                       
CONECT    7    5    9                                                       
CONECT    8   10   11                                                       
CONECT    9    6    7   10                                                  
CONECT   10    8    9   12                                                  
CONECT   11    8   13   14                                                  
CONECT   12   10                                                            
CONECT   13   11                                                            
CONECT   14    2   11                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

COMPND    HMDB0040268
HETATM    1  C1  UNL     1      -4.436  -0.468   0.527  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.758   0.759  -0.018  1.00  0.00           C  
HETATM    3  O1  UNL     1      -2.361   0.545  -0.073  1.00  0.00           O  
HETATM    4  C3  UNL     1      -1.843  -0.488  -0.841  1.00  0.00           C  
HETATM    5  O2  UNL     1      -2.562  -1.269  -1.512  1.00  0.00           O  
HETATM    6  C4  UNL     1      -0.376  -0.705  -0.892  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.312   0.294  -0.052  1.00  0.00           C  
HETATM    8  O3  UNL     1      -0.315   1.159   0.576  1.00  0.00           O  
HETATM    9  C6  UNL     1       1.765   0.242   0.025  1.00  0.00           C  
HETATM   10  C7  UNL     1       2.502  -0.704  -0.658  1.00  0.00           C  
HETATM   11  C8  UNL     1       3.878  -0.745  -0.578  1.00  0.00           C  
HETATM   12  C9  UNL     1       4.585   0.160   0.189  1.00  0.00           C  
HETATM   13  C10 UNL     1       3.835   1.100   0.866  1.00  0.00           C  
HETATM   14  C11 UNL     1       2.461   1.151   0.794  1.00  0.00           C  
HETATM   15  H1  UNL     1      -5.414  -0.665   0.024  1.00  0.00           H  
HETATM   16  H2  UNL     1      -4.692  -0.311   1.611  1.00  0.00           H  
HETATM   17  H3  UNL     1      -3.781  -1.340   0.481  1.00  0.00           H  
HETATM   18  H4  UNL     1      -4.093   0.964  -1.072  1.00  0.00           H  
HETATM   19  H5  UNL     1      -3.915   1.653   0.629  1.00  0.00           H  
HETATM   20  H6  UNL     1       0.022  -0.593  -1.933  1.00  0.00           H  
HETATM   21  H7  UNL     1      -0.095  -1.713  -0.520  1.00  0.00           H  
HETATM   22  H8  UNL     1       1.941  -1.419  -1.264  1.00  0.00           H  
HETATM   23  H9  UNL     1       4.429  -1.504  -1.129  1.00  0.00           H  
HETATM   24  H10 UNL     1       5.666   0.143   0.263  1.00  0.00           H  
HETATM   25  H11 UNL     1       4.356   1.841   1.489  1.00  0.00           H  
HETATM   26  H12 UNL     1       1.888   1.913   1.345  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3   18   19
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7   20   21
CONECT    7    8    8    9
CONECT    9   10   10   14
CONECT   10   11   22
CONECT   11   12   12   23
CONECT   12   13   24
CONECT   13   14   14   25
CONECT   14   26
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Ethyl 3-oxo-3-phenylpropanoic acid	Generator
1-Ethoxy-3-phenylpropane-1,3-dione	HMDB
3-oxo,3-PHENYL-propanoIC ACID,ethyl ester	HMDB
Acetic acid, benzoyl-, ethyl ester	HMDB
Benzenepropanoic acid, beta-oxo-, ethyl ester	HMDB
Benzoylacetic acid ethyl ester	HMDB
Benzoylacetic acid, ethyl ester	HMDB
Ethyl 3-oxo-3-phenylpropionate	HMDB
Ethyl 3-phenyl-3-oxopropanoate	HMDB
Ethyl benzoyl acetate	HMDB
Ethyl benzoylacetate	HMDB
Ethyl beta-oxobenzenepropanoate	HMDB
FEMA 2423	HMDB

Chemical Formula

C₁₁H₁₂O₃

Average Molecular Weight

192.2112

Monoisotopic Molecular Weight

192.07864425

IUPAC Name

ethyl 3-oxo-3-phenylpropanoate

Traditional Name

ethyl benzoylacetate

CAS Registry Number

94-02-0

SMILES

CCOC(=O)CC(=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C11H12O3/c1-2-14-11(13)8-10(12)9-6-4-3-5-7-9/h3-7H,2,8H2,1H3

InChI Key

GKKZMYDNDDMXSE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Benzoyl
Aryl alkyl ketone
Beta-keto acid
Fatty acid ester
Monocyclic benzene moiety
Fatty acyl
Benzenoid
1,3-dicarbonyl compound
Keto acid
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Cellular substructure

Extracellular (HMDB: HMDB0040268)
Cytoplasm (HMDB: HMDB0040268)

Source

Exogenous

Food

Food (HMDB: HMDB0040268)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0040268)

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0040268)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	< 0 °C	Not Available
Boiling Point	265.00 to 270.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	1212 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.87	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.63 g/L	ALOGPS
logP	1.71	ALOGPS
logP	1.93	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	10.81	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	52.32 m³·mol⁻¹	ChemAxon
Polarizability	19.61 Å³	ChemAxon
Number of Rings	1	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]+	142.99	30932474
DeepCCS	[M-H]-	140.474	30932474
DeepCCS	[M-2H]-	176.181	30932474
DeepCCS	[M+Na]+	151.72	30932474
AllCCS	[M+H]+	141.6	32859911
AllCCS	[M+H-H2O]+	137.5	32859911
AllCCS	[M+NH4]+	145.5	32859911
AllCCS	[M+Na]+	146.6	32859911
AllCCS	[M-H]-	143.8	32859911
AllCCS	[M+Na-2H]-	144.5	32859911
AllCCS	[M+HCOO]-	145.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ethyl 3-oxo-3-phenylpropanoate	CCOC(=O)CC(=O)C1=CC=CC=C1	2458.8	Standard polar	33892256
Ethyl 3-oxo-3-phenylpropanoate	CCOC(=O)CC(=O)C1=CC=CC=C1	1472.2	Standard non polar	33892256
Ethyl 3-oxo-3-phenylpropanoate	CCOC(=O)CC(=O)C1=CC=CC=C1	1542.0	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 - Ethyl 3-oxo-3-phenylpropanoate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-3900000000-2dbccd06400330834c16	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyl 3-oxo-3-phenylpropanoate 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 - Ethyl 3-oxo-3-phenylpropanoate 10V, Positive-QTOF	splash10-0006-1900000000-e43781da67735dc72505	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 3-oxo-3-phenylpropanoate 20V, Positive-QTOF	splash10-052b-3900000000-3d299b530b2aa1c9d517	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 3-oxo-3-phenylpropanoate 40V, Positive-QTOF	splash10-0pbc-9600000000-a44288d3df4cfba5c67b	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 3-oxo-3-phenylpropanoate 10V, Negative-QTOF	splash10-0007-1900000000-00e1c4cd4b1bf7d8d612	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 3-oxo-3-phenylpropanoate 20V, Negative-QTOF	splash10-00kb-6900000000-9c2e25c0eaf2c6e44e70	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 3-oxo-3-phenylpropanoate 40V, Negative-QTOF	splash10-05oy-9400000000-45bf3558c1be86788d7f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 3-oxo-3-phenylpropanoate 10V, Negative-QTOF	splash10-00kf-1900000000-22cf77027e7f3e819a64	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 3-oxo-3-phenylpropanoate 20V, Negative-QTOF	splash10-016u-9800000000-543f6a69e1dba188ea2f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 3-oxo-3-phenylpropanoate 40V, Negative-QTOF	splash10-002f-9200000000-01b993924dea6f9f53ca	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 3-oxo-3-phenylpropanoate 10V, Positive-QTOF	splash10-00kg-2900000000-78fc97bfb5fc2e54fee0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 3-oxo-3-phenylpropanoate 20V, Positive-QTOF	splash10-0a4i-2900000000-bcb2486eb946aea06d4d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 3-oxo-3-phenylpropanoate 40V, Positive-QTOF	splash10-004i-9100000000-c0481b5a3ae960b5453a	2021-09-23	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

FDB019986

KNApSAcK ID

Not Available

Chemspider ID

6902

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

7170

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1022301

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 Ethyl 3-oxo-3-phenylpropanoate (HMDB0040268)

MOL for HMDB0040268 (Ethyl 3-oxo-3-phenylpropanoate)

3D MOL for HMDB0040268 (Ethyl 3-oxo-3-phenylpropanoate)

3D SDF for HMDB0040268 (Ethyl 3-oxo-3-phenylpropanoate)

3D-SDF for HMDB0040268 (Ethyl 3-oxo-3-phenylpropanoate)

PDB for HMDB0040268 (Ethyl 3-oxo-3-phenylpropanoate)

3D PDB for HMDB0040268 (Ethyl 3-oxo-3-phenylpropanoate)

SMILES for HMDB0040268 (Ethyl 3-oxo-3-phenylpropanoate)

INCHI for HMDB0040268 (Ethyl 3-oxo-3-phenylpropanoate)

Structure for HMDB0040268 (Ethyl 3-oxo-3-phenylpropanoate)

3D Structure for HMDB0040268 (Ethyl 3-oxo-3-phenylpropanoate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra