Showing NP-Card for Ethyl crotonate (NP0049452)

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Record Information
Version2.0
Created at2022-03-17 21:12:46 UTC
Updated at2022-03-17 21:12:46 UTC
NP-MRD IDNP0049452
Secondary Accession NumbersNone
Natural Product Identification
Common NameEthyl crotonate
DescriptionEthyl crotonate, also known as fema 3486, belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. Ethyl crotonate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Ethyl crotonate is a sweet, alliaceous, and caramel tasting compound. Outside of the human body, Ethyl crotonate has been detected, but not quantified in, several different foods, such as alcoholic beverages, asian pears, fruits, mollusks, and prickly pears. This could make ethyl crotonate a potential biomarker for the consumption of these foods. Ethyl crotonate is found in Annona reticulata, Dactylanthus taylorii, Mangifera indica , Opuntia ficus-indica, Prunus avium , Psidium guajava , Vasconcellea heilbornii and Vitis rotundifolia. A but-2-enoate ester obtained by the formal condensation of isocrotonic acid with ethanol.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0049452 (Ethyl crotonate)

  Mrv0541 05061311152D          

  8  7  0  0  0  0            999 V2000
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    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
   -1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  6  5  1  0  0  0  0
  7  6  2  0  0  0  0
  8  4  1  0  0  0  0
  8  6  1  0  0  0  0
M  END
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3D MOL for NP0049452 (Ethyl crotonate)

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3D SDF for NP0049452 (Ethyl crotonate)
  Mrv0541 05061311152D          

  8  7  0  0  0  0            999 V2000
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    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
   -1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  6  5  1  0  0  0  0
  7  6  2  0  0  0  0
  8  4  1  0  0  0  0
  8  6  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049452

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCOC(=O)\C=C/C

> <INCHI_IDENTIFIER>
InChI=1S/C6H10O2/c1-3-5-6(7)8-4-2/h3,5H,4H2,1-2H3/b5-3-

> <INCHI_KEY>
ZFDIRQKJPRINOQ-HYXAFXHYSA-N

> <FORMULA>
C6H10O2

> <MOLECULAR_WEIGHT>
114.1424

> <EXACT_MASS>
114.068079564

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
12.345876955632836

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
ethyl (2Z)-but-2-enoate

> <ALOGPS_LOGP>
1.70

> <JCHEM_LOGP>
1.655617631333333

> <ALOGPS_LOGS>
-1.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.789815320886001

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
32.4826

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.25e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ethyl (2Z)-but-2-enoate

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0049452 (Ethyl crotonate)
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PDB for NP0049452 (Ethyl crotonate)
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       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -5.335   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.770  -4.001   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.310  -1.334   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       0.000  -2.667   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2    4                                                            
CONECT    3    1    5                                                       
CONECT    4    2    8                                                       
CONECT    5    3    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    4    6                                                       
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END

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3D PDB for NP0049452 (Ethyl crotonate)
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SMILES for NP0049452 (Ethyl crotonate)
CCOC(=O)\C=C/C
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INCHI for NP0049452 (Ethyl crotonate)
InChI=1S/C6H10O2/c1-3-5-6(7)8-4-2/h3,5H,4H2,1-2H3/b5-3-
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Synonyms
Chemical FormulaC6H10O2
Average Mass114.1424 Da
Monoisotopic Mass114.06808 Da
IUPAC Nameethyl (2Z)-but-2-enoate
Traditional Nameethyl (2Z)-but-2-enoate
CAS Registry Number623-70-1
SMILES
CCOC(=O)\C=C/C
InChI Identifier
InChI=1S/C6H10O2/c1-3-5-6(7)8-4-2/h3,5H,4H2,1-2H3/b5-3-
InChI KeyZFDIRQKJPRINOQ-HYXAFXHYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Chemical Taxonomy
Description Belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassFatty Acyls  
Sub ClassFatty acid esters  
Direct ParentFatty acid esters  
Alternative Parents
Substituents
  • Fatty acid ester
    • 

  • Alpha,beta-unsaturated carboxylic ester
    • 

  • Enoate ester
    • 

  • 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
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
logP1.7ALOGPS
logP1.66ChemAxon
logS-1.1ALOGPS
pKa (Strongest Basic)-6.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity32.48 m³·mol⁻¹ChemAxon
Polarizability12.35 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0039581  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB019204  
KNApSAcK IDNot Available
Chemspider ID4510483  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5354263  
PDB IDNot Available
ChEBI ID87334  
Good Scents IDNot Available
References
General References