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Showing metabocard for Ethyl acetoacetate (HMDB0031216)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:41:40 UTC
Update Date2023-02-21 17:20:05 UTC
HMDB IDHMDB0031216
Secondary Accession Numbers
  • HMDB0031218
  • HMDB31216
  • HMDB31218
Metabolite Identification
Common NameEthyl acetoacetate
DescriptionEthyl acetoacetate (EAA) is found in coffee and coffee products as well as in strawberry and yellow passion fruit juice. Ethyl acetoacetate is a flavouring agent. The organic compound ethyl acetoacetate is the ethyl ester of acetoacetic acid. It is mainly used as a chemical intermediate in the production of a wide variety of compounds, such as amino acids, analgesics, antibiotics, antimalarial agents, antipyrine, aminopyrine, and vitamin B1, as well as in the manufacture of dyes, inks, lacquers, perfumes, plastics, and yellow paint pigments (Wikipedia ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0031216 (Ethyl acetoacetate)

  Mrv0541 05061305482D          

  9  8  0  0  0  0            999 V2000
   -1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1599   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7309   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  5  2  1  0  0  0  0
  5  4  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
  8  6  2  0  0  0  0
  9  3  1  0  0  0  0
  9  6  1  0  0  0  0
M  END
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3D MOL for HMDB0031216 (Ethyl acetoacetate)

HMDB0031216
     RDKit          3D
Ethyl acetoacetate
 19 18  0  0  0  0  0  0  0  0999 V2000
    3.5327    0.6188    0.2739 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2474    0.4146   -0.4443 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2068   -0.0391    0.4016 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0512   -0.2745   -0.1853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1759   -0.0724   -1.4161 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2097   -0.7415    0.5762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3657   -0.8951   -0.3437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3789    0.2131   -0.4479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4651   -1.9262   -0.9962 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5217    1.5361    0.8581 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7679   -0.2929    0.8586 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3373    0.7140   -0.4813 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4184   -0.3042   -1.2740 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9130    1.3992   -0.8946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9351   -1.7497    1.0040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4893   -0.0780    1.4169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8641    0.3922    0.5357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1308   -0.0565   -1.2213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8795    1.1421   -0.8115 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  2 13  1  0
  2 14  1  0
  6 15  1  0
  6 16  1  0
  8 17  1  0
  8 18  1  0
  8 19  1  0
M  END
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3D SDF for HMDB0031216 (Ethyl acetoacetate)

  Mrv0541 05061305482D          

  9  8  0  0  0  0            999 V2000
   -1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1599   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7309   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  5  2  1  0  0  0  0
  5  4  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
  8  6  2  0  0  0  0
  9  3  1  0  0  0  0
  9  6  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031216

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H10O3/c1-3-9-6(8)4-5(2)7/h3-4H2,1-2H3

> <INCHI_KEY>
XYIBRDXRRQCHLP-UHFFFAOYSA-N

> <FORMULA>
C6H10O3

> <MOLECULAR_WEIGHT>
130.1418

> <EXACT_MASS>
130.062994186

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
13.195555294032767

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
ethyl 3-oxobutanoate

> <ALOGPS_LOGP>
0.19

> <JCHEM_LOGP>
0.5012102650000003

> <ALOGPS_LOGS>
-0.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.930990013895958

> <JCHEM_PKA_STRONGEST_BASIC>
-6.959626497436529

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
32.0566

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.86e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ethyl acetoacetate

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0031216 (Ethyl acetoacetate)

HMDB0031216
     RDKit          3D
Ethyl acetoacetate
 19 18  0  0  0  0  0  0  0  0999 V2000
    3.5327    0.6188    0.2739 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2474    0.4146   -0.4443 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2068   -0.0391    0.4016 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0512   -0.2745   -0.1853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1759   -0.0724   -1.4161 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2097   -0.7415    0.5762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3657   -0.8951   -0.3437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3789    0.2131   -0.4479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4651   -1.9262   -0.9962 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5217    1.5361    0.8581 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7679   -0.2929    0.8586 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3373    0.7140   -0.4813 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4184   -0.3042   -1.2740 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9130    1.3992   -0.8946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9351   -1.7497    1.0040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4893   -0.0780    1.4169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8641    0.3922    0.5357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1308   -0.0565   -1.2213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8795    1.1421   -0.8115 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  2 13  1  0
  2 14  1  0
  6 15  1  0
  6 16  1  0
  8 17  1  0
  8 18  1  0
  8 19  1  0
M  END
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PDB for HMDB0031216 (Ethyl acetoacetate)

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      -2.104  -0.564   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.898  -0.564   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.231  -0.564   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.565  -1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.897  -1.334   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.565  -2.874   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       1.897  -2.874   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       0.564  -0.564   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2    5                                                            
CONECT    3    1    9                                                       
CONECT    4    5    6                                                       
CONECT    5    2    4    7                                                  
CONECT    6    4    8    9                                                  
CONECT    7    5                                                            
CONECT    8    6                                                            
CONECT    9    3    6                                                       
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END
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3D PDB for HMDB0031216 (Ethyl acetoacetate)

COMPND    HMDB0031216
HETATM    1  C1  UNL     1       3.533   0.619   0.274  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.247   0.415  -0.444  1.00  0.00           C  
HETATM    3  O1  UNL     1       1.207  -0.039   0.402  1.00  0.00           O  
HETATM    4  C3  UNL     1      -0.051  -0.275  -0.185  1.00  0.00           C  
HETATM    5  O2  UNL     1      -0.176  -0.072  -1.416  1.00  0.00           O  
HETATM    6  C4  UNL     1      -1.210  -0.742   0.576  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.366  -0.895  -0.344  1.00  0.00           C  
HETATM    8  C6  UNL     1      -3.379   0.213  -0.448  1.00  0.00           C  
HETATM    9  O3  UNL     1      -2.465  -1.926  -0.996  1.00  0.00           O  
HETATM   10  H1  UNL     1       3.522   1.536   0.858  1.00  0.00           H  
HETATM   11  H2  UNL     1       3.768  -0.293   0.859  1.00  0.00           H  
HETATM   12  H3  UNL     1       4.337   0.714  -0.481  1.00  0.00           H  
HETATM   13  H4  UNL     1       2.418  -0.304  -1.274  1.00  0.00           H  
HETATM   14  H5  UNL     1       1.913   1.399  -0.895  1.00  0.00           H  
HETATM   15  H6  UNL     1      -0.935  -1.750   1.004  1.00  0.00           H  
HETATM   16  H7  UNL     1      -1.489  -0.078   1.417  1.00  0.00           H  
HETATM   17  H8  UNL     1      -3.864   0.392   0.536  1.00  0.00           H  
HETATM   18  H9  UNL     1      -4.131  -0.057  -1.221  1.00  0.00           H  
HETATM   19  H10 UNL     1      -2.880   1.142  -0.812  1.00  0.00           H  
CONECT    1    2   10   11   12
CONECT    2    3   13   14
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7   15   16
CONECT    7    8    9    9
CONECT    8   17   18   19
END
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SMILES for HMDB0031216 (Ethyl acetoacetate)

CCOC(=O)CC(C)=O
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INCHI for HMDB0031216 (Ethyl acetoacetate)

InChI=1S/C6H10O3/c1-3-9-6(8)4-5(2)7/h3-4H2,1-2H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC6H10O3
Average Molecular Weight130.1418
Monoisotopic Molecular Weight130.062994186
IUPAC Nameethyl 3-oxobutanoate
Traditional Nameethyl acetoacetate
CAS Registry Number141-97-9
SMILES
CCOC(=O)CC(C)=O
InChI Identifier
InChI=1S/C6H10O3/c1-3-9-6(8)4-5(2)7/h3-4H2,1-2H3
InChI KeyXYIBRDXRRQCHLP-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as beta-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C3 carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassBeta-keto acids and derivatives
Direct ParentBeta-keto acids and derivatives
Alternative Parents
Substituents
  • Fatty acid ester
  • Beta-keto acid
  • Fatty acyl
  • 1,3-dicarbonyl compound
  • Ketone
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-45 °CNot Available
Boiling Point180.00 to 181.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility110 mg/mL at 17 °CNot Available
LogP0.25Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB003241
KNApSAcK IDNot Available
Chemspider ID13865426
KEGG Compound IDC03500
BioCyc IDETHYL-ACETOACETATE
BiGG IDNot Available
Wikipedia LinkEthyl_acetoacetate
METLIN IDNot Available
PubChem Compound8868
PDB IDNot Available
ChEBI ID4893
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1001852
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .