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Showing NP-Card for Ethyl levulinate (NP0338079)

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Record Information
Version2.0
Created at2024-09-11 13:44:35 UTC
Updated at2024-09-11 13:44:36 UTC
NP-MRD IDNP0338079
Secondary Accession NumbersNone
Natural Product Identification
Common NameEthyl levulinate
DescriptionEthyl levulinate, also known as ethyl 4-oxovalerate or fema 2442, 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. It is an ester derived from the keto acid levulinic acid. These two synthesis options make ethyl levulinate a viable biofuel option, since both precursors can be obtained from biomass: Levulinic acid from 6-carbon polymerized sugars such as cellulose, and furfural from 5-carbon polymerized sugars such as xylan and arabinan. Ethyl levulinate is an extremely weak basic (essentially neutral) compound (based on its pKa). Ethyl levulinate is a sweet, berry, and floral tasting compound. Outside of the human body, Ethyl levulinate has been detected, but not quantified in, evergreen blackberries. This could make ethyl levulinate a potential biomarker for the consumption of these foods. Ethyl levulinate can also be obtained by reaction between ethanol and furfuryl alcohol. Ethyl levulinate is an organic compound with the formula CH3C(O)CH2CH2C(O)OC2H5.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0338079 (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 NP0338079 (Ethyl levulinate)

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3D SDF for NP0338079 (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>
NP0338079

> <DATABASE_NAME>
NP-MRD

> <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 NP0338079 (Ethyl levulinate)
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PDB for NP0338079 (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 NP0338079 (Ethyl levulinate)
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SMILES for NP0338079 (Ethyl levulinate)
CCOC(=O)CCC(C)=O
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INCHI for NP0338079 (Ethyl levulinate)
InChI=1S/C7H12O3/c1-3-10-7(9)5-4-6(2)8/h3-5H2,1-2H3
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Synonyms
ValueSource
Ethyl levulinic acidGenerator
Ethyl 3-acetylpropionateHMDB
Ethyl 4-ketovalerateHMDB
Ethyl 4-oxopentanoateHMDB
Ethyl 4-oxovalerateHMDB
Ethyl acetylpropanoateHMDB
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 Mass144.1684 Da
Monoisotopic Mass144.07864 Da
IUPAC Nameethyl 4-oxopentanoate
Traditional Nameethyl levulinate
CAS Registry NumberNot Available
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
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.38ALOGPS
logP0.43ChemAxon
logS-0.8ALOGPS
pKa (Strongest Acidic)17.54ChemAxon
pKa (Strongest Basic)-6.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity36.61 m³·mol⁻¹ChemAxon
Polarizability15.4 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0040433  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
Good Scents IDNot Available
References
General ReferencesNot Available