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Showing metabocard for Ethyl levulinate (HMDB0040433)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 01:58:30 UTC
Update Date2023-02-21 17:28:16 UTC
HMDB IDHMDB0040433
Secondary Accession Numbers
  • HMDB40433
Metabolite Identification
Common NameEthyl levulinate
DescriptionEthyl levulinate belongs to the class of organic compounds known as gamma-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom. Ethyl levulinate is a sweet, berry, and floral tasting compound. Ethyl levulinate has been detected, but not quantified in, blackberries (Rubus) and evergreen blackberries (Rubus laciniatus). This could make ethyl levulinate a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Ethyl levulinate.
Structure
Data?1677000496
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0040433 (Ethyl levulinate)

  Mrv0541 05061311502D          

 10  9  0  0  0  0            999 V2000
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 C   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
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   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
    2.8579   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   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
  3  1  1  0  0  0  0
  5  4  1  0  0  0  0
  6  2  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  2  0  0  0  0
  9  7  2  0  0  0  0
 10  3  1  0  0  0  0
 10  7  1  0  0  0  0
M  END
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3D MOL for HMDB0040433 (Ethyl levulinate)

HMDB0040433
     RDKit          3D
Ethyl levulinate
 22 21  0  0  0  0  0  0  0  0999 V2000
    3.5184    0.2701   -0.6430 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1325   -0.2414    0.7112 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8210    0.1199    1.0980 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7368   -0.2894    0.3319 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9897   -0.9784   -0.6909 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6673    0.0801    0.7175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5763   -0.5277   -0.3319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9955   -0.2597   -0.1055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6848    0.7596   -0.9305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6057   -0.8640    0.7485 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6681    0.5278   -1.2928 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1911   -0.4736   -1.1376 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1608    1.1774   -0.5014 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8547    0.0690    1.4961 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2161   -1.3651    0.6817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7840    1.1795    0.7952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8338   -0.3606    1.7281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2102   -0.1337   -1.3169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3370   -1.6266   -0.3399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9464    0.2576   -1.8964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6366    1.0550   -0.4527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0117    1.6244   -1.0758 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
  8  9  1  0
  8 10  2  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  0
  2 15  1  0
  6 16  1  0
  6 17  1  0
  7 18  1  0
  7 19  1  0
  9 20  1  0
  9 21  1  0
  9 22  1  0
M  END
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3D SDF for HMDB0040433 (Ethyl levulinate)

  Mrv0541 05061311502D          

 10  9  0  0  0  0            999 V2000
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 C   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
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   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
    2.8579   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   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
  3  1  1  0  0  0  0
  5  4  1  0  0  0  0
  6  2  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  2  0  0  0  0
  9  7  2  0  0  0  0
 10  3  1  0  0  0  0
 10  7  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0040433

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C7H12O3/c1-3-10-7(9)5-4-6(2)8/h3-5H2,1-2H3

> <INCHI_KEY>
GMEONFUTDYJSNV-UHFFFAOYSA-N

> <FORMULA>
C7H12O3

> <MOLECULAR_WEIGHT>
144.1684

> <EXACT_MASS>
144.07864425

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
15.398990539156973

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
ethyl 4-oxopentanoate

> <ALOGPS_LOGP>
0.38

> <JCHEM_LOGP>
0.433844566

> <ALOGPS_LOGS>
-0.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.543002183073213

> <JCHEM_PKA_STRONGEST_BASIC>
-6.841609891237484

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
36.6058

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.27e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ethyl levulinate

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0040433 (Ethyl levulinate)

HMDB0040433
     RDKit          3D
Ethyl levulinate
 22 21  0  0  0  0  0  0  0  0999 V2000
    3.5184    0.2701   -0.6430 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1325   -0.2414    0.7112 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8210    0.1199    1.0980 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7368   -0.2894    0.3319 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9897   -0.9784   -0.6909 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6673    0.0801    0.7175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5763   -0.5277   -0.3319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9955   -0.2597   -0.1055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6848    0.7596   -0.9305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6057   -0.8640    0.7485 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6681    0.5278   -1.2928 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1911   -0.4736   -1.1376 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1608    1.1774   -0.5014 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8547    0.0690    1.4961 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2161   -1.3651    0.6817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7840    1.1795    0.7952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8338   -0.3606    1.7281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2102   -0.1337   -1.3169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3370   -1.6266   -0.3399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9464    0.2576   -1.8964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6366    1.0550   -0.4527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0117    1.6244   -1.0758 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
  8  9  1  0
  8 10  2  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  0
  2 15  1  0
  6 16  1  0
  6 17  1  0
  7 18  1  0
  7 19  1  0
  9 20  1  0
  9 21  1  0
  9 22  1  0
M  END
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PDB for HMDB0040433 (Ethyl levulinate)

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      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.335  -1.540   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2    6                                                            
CONECT    3    1   10                                                       
CONECT    4    5    6                                                       
CONECT    5    4    7                                                       
CONECT    6    2    4    8                                                  
CONECT    7    5    9   10                                                  
CONECT    8    6                                                            
CONECT    9    7                                                            
CONECT   10    3    7                                                       
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END
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3D PDB for HMDB0040433 (Ethyl levulinate)

COMPND    HMDB0040433
HETATM    1  C1  UNL     1       3.518   0.270  -0.643  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.133  -0.241   0.711  1.00  0.00           C  
HETATM    3  O1  UNL     1       1.821   0.120   1.098  1.00  0.00           O  
HETATM    4  C3  UNL     1       0.737  -0.289   0.332  1.00  0.00           C  
HETATM    5  O2  UNL     1       0.990  -0.978  -0.691  1.00  0.00           O  
HETATM    6  C4  UNL     1      -0.667   0.080   0.718  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.576  -0.528  -0.332  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.995  -0.260  -0.105  1.00  0.00           C  
HETATM    9  C7  UNL     1      -3.685   0.760  -0.931  1.00  0.00           C  
HETATM   10  O3  UNL     1      -3.606  -0.864   0.748  1.00  0.00           O  
HETATM   11  H1  UNL     1       2.668   0.528  -1.293  1.00  0.00           H  
HETATM   12  H2  UNL     1       4.191  -0.474  -1.138  1.00  0.00           H  
HETATM   13  H3  UNL     1       4.161   1.177  -0.501  1.00  0.00           H  
HETATM   14  H4  UNL     1       3.855   0.069   1.496  1.00  0.00           H  
HETATM   15  H5  UNL     1       3.216  -1.365   0.682  1.00  0.00           H  
HETATM   16  H6  UNL     1      -0.784   1.179   0.795  1.00  0.00           H  
HETATM   17  H7  UNL     1      -0.834  -0.361   1.728  1.00  0.00           H  
HETATM   18  H8  UNL     1      -1.210  -0.134  -1.317  1.00  0.00           H  
HETATM   19  H9  UNL     1      -1.337  -1.627  -0.340  1.00  0.00           H  
HETATM   20  H10 UNL     1      -3.946   0.258  -1.896  1.00  0.00           H  
HETATM   21  H11 UNL     1      -4.637   1.055  -0.453  1.00  0.00           H  
HETATM   22  H12 UNL     1      -3.012   1.624  -1.076  1.00  0.00           H  
CONECT    1    2   11   12   13
CONECT    2    3   14   15
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7   16   17
CONECT    7    8   18   19
CONECT    8    9   10   10
CONECT    9   20   21   22
END
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SMILES for HMDB0040433 (Ethyl levulinate)

CCOC(=O)CCC(C)=O
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INCHI for HMDB0040433 (Ethyl levulinate)

InChI=1S/C7H12O3/c1-3-10-7(9)5-4-6(2)8/h3-5H2,1-2H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
Ethyl levulinic acidGenerator
Ethyl 3-acetylpropionateHMDB
Ethyl 4-ketovalerateHMDB, MeSH
Ethyl 4-oxopentanoateHMDB, MeSH
Ethyl 4-oxovalerateHMDB
Ethyl acetylpropanoateHMDB, MeSH
Ethyl ketovalerateHMDB
Ethyl laevulinateHMDB
Ethyl levulateHMDB
FEMA 2442HMDB
Levulinic acid, ethyl esterHMDB
Pentanoic acid, 4-oxo-, ethyl esterHMDB
Ethyl 4-oxopentanoic acidGenerator
Ethyl levulinateMeSH
Chemical FormulaC7H12O3
Average Molecular Weight144.1684
Monoisotopic Molecular Weight144.07864425
IUPAC Nameethyl 4-oxopentanoate
Traditional Nameethyl levulinate
CAS Registry Number539-88-8
SMILES
CCOC(=O)CCC(C)=O
InChI Identifier
InChI=1S/C7H12O3/c1-3-10-7(9)5-4-6(2)8/h3-5H2,1-2H3
InChI KeyGMEONFUTDYJSNV-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as gamma-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassGamma-keto acids and derivatives
Direct ParentGamma-keto acids and derivatives
Alternative Parents
Substituents
  • Gamma-keto acid
  • Fatty acid ester
  • Fatty acyl
  • 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 DescriptorsNot Available
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationSource
ProcessNot Available
Role
Industrial applicationBiological role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point< 25 °CNot Available
Boiling Point93.00 to 94.00 °C. @ 18.00 mm HgThe Good Scents Company Information System
Water Solubility45660 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP0.400 (est)The Good Scents Company Information System
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 IDFDB020166
KNApSAcK IDNot Available
Chemspider ID13853514
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEthyl levulinate
METLIN IDNot Available
PubChem Compound10883
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1024311
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.. .