Showing metabocard for Ethylcinnamate (MMDBc0033638)

Record Information
Version2.0
StatusDetected and Quantified
Creation Date2021-11-19 04:56:58 UTC
Update Date2025-10-07 16:08:02 UTC
Metabolite IDMMDBc0033638
Metabolite Identification
Common NameEthylcinnamate
DescriptionEthylcinnamate is a member of the chemical class of cinnamate esters, characterized by its ethyl ester of cinnamic acid. Its chemical structure features a phenyl group attached to a vinyl group, which is further esterified with an ethyl group, contributing to its unique properties. Ethylcinnamate is involved in various chemical interactions, including the formation of complexes with hydrogen bond donors such as phenol and thiophenol, as studied under ambient conditions (PMID:40859766 ). Additionally, it has been identified as one of six antifungal components in a study of essential oils, demonstrating significant binding affinity to various biological targets, including AKR1B1 and CYP51A1 (PMID:37729978 ). Spectroscopic investigations have also explored the nonradiative decay pathways of ethylcinnamate derivatives, revealing insights into their photophysical behavior (PMID:27657500 ). Furthermore, research has examined the UV absorption properties of ethylcinnamate in formulations, particularly in relation to its effectiveness in sunscreens (PMID:16824709 ). Lastly, ethylcinnamate has been utilized in the synthesis of metal complexes, showcasing its versatility and application in coordination chemistry (PMID:15249033 ).
Structure
MOLSDFPDBSMILESInChI

MOL for #<Metabolite:0x00005624ca236690>


  Mrv0541 02241223222D          

 13 13  0  0  0  0            999 V2000
   -0.7145    3.7125    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    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
    0.7145   -0.4125    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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
M  CHG  1   1  -1
M  END
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3D MOL for #<Metabolite:0x00005624ca236690>

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3D SDF for #<Metabolite:0x00005624ca236690>

  Mrv0541 02241223222D          

 13 13  0  0  0  0            999 V2000
   -0.7145    3.7125    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    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
    0.7145   -0.4125    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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
M  CHG  1   1  -1
M  END
> <DATABASE_ID>
MMDBc0033638

> <DATABASE_NAME>
MIME

> <SMILES>
CCC1=CC=CC=C1\C=C\C([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H12O2/c1-2-9-5-3-4-6-10(9)7-8-11(12)13/h3-8H,2H2,1H3,(H,12,13)/p-1/b8-7+

> <INCHI_KEY>
PPDRIRGALQZEPP-BQYQJAHWSA-M

> <FORMULA>
C11H11O2

> <MOLECULAR_WEIGHT>
175.2038

> <EXACT_MASS>
175.075904596

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
18.85285824480446

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-3-(2-ethylphenyl)prop-2-enoate

> <ALOGPS_LOGP>
3.34

> <JCHEM_LOGP>
3.094076314333333

> <ALOGPS_LOGS>
-3.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.703264737852219

> <JCHEM_POLAR_SURFACE_AREA>
40.129999999999995

> <JCHEM_REFRACTIVITY>
63.539200000000015

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.46e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-3-(2-ethylphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for #<Metabolite:0x00005624ca236690>
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PDB for #<Metabolite:0x00005624ca236690>
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0      -1.334   6.930   0.000  0.00  0.00           O-1
HETATM    2  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    6   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

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3D PDB for #<Metabolite:0x00005624ca236690>
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SMILES for #<Metabolite:0x00005624ca236690>
CCC1=CC=CC=C1\C=C\C([O-])=O
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INCHI for #<Metabolite:0x00005624ca236690>
InChI=1S/C11H12O2/c1-2-9-5-3-4-6-10(9)7-8-11(12)13/h3-8H,2H2,1H3,(H,12,13)/p-1/b8-7+
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Synonyms
ValueSource
Ethylcinnamic acidGenerator
Molecular FormulaC11H11O2
Average Mass175.2038
Monoisotopic Mass175.075904596
IUPAC Name(2E)-3-(2-ethylphenyl)prop-2-enoate
Traditional Name(2E)-3-(2-ethylphenyl)prop-2-enoate
CAS Registry Number103-36-6
SMILES
CCC1=CC=CC=C1\C=C\C([O-])=O
InChI Identifier
InChI=1S/C11H12O2/c1-2-9-5-3-4-6-10(9)7-8-11(12)13/h3-8H,2H2,1H3,(H,12,13)/p-1/b8-7+
InChI KeyPPDRIRGALQZEPP-BQYQJAHWSA-M