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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:45:04 UTC

Update Date

2022-03-07 02:53:05 UTC

HMDB ID

HMDB0031729

Secondary Accession Numbers

HMDB31729

Metabolite Identification

Common Name

Phenylmethylglycidic ester

Description

Phenylmethylglycidic ester, also known as aldehyde C-16 or aldehyde C16 (misleading), belongs to the class of organic compounds known as oxirane carboxylic acids. Oxirane carboxylic acids are compounds containing an oxirane ring bearing a carboxylic acid group. Based on a literature review very few articles have been published on Phenylmethylglycidic ester.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0031729
     RDKit          3D
Phenylmethylglycidic ester
 29 30  0  0  0  0  0  0  0  0999 V2000
    5.2068    1.2919    0.1366 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2248    0.2393   -0.2054 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8763    0.6370    0.0947 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8177   -0.2703   -0.1188 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1126   -1.3590   -0.5564 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4284    0.1934    0.2415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0756   -0.7592    1.3026 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6968   -0.7203    0.0535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5464   -1.8472   -0.9279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1096   -0.1497    0.1613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5282    0.6601   -0.8009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8472    1.1376   -0.7205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6203    0.7410    0.3484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1594   -0.0854    1.3230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8458   -0.5647    1.2472 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1333    0.8093    0.5367 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8207    1.8676    1.0171 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5148    1.9585   -0.7113 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4598   -0.6675    0.4296 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3029   -0.0881   -1.2315 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2971    1.2323    0.5947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5408   -1.9863   -1.4285 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1659   -1.6614   -1.7509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3386   -2.8202   -0.4366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9189    0.9614   -1.6501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2209    1.7741   -1.4694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6647    1.0923    0.3856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7814   -0.3670    2.1494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4666   -1.2495    1.9864 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  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  8  6  1  0
 15 10  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  6 21  1  0
  9 22  1  0
  9 23  1  0
  9 24  1  0
 11 25  1  0
 12 26  1  0
 13 27  1  0
 14 28  1  0
 15 29  1  0
M  END


  Mrv0541 05061306062D          

 15 16  0  0  0  0            999 V2000
    4.4324   -1.6386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2230    2.0812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4324   -0.8136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6950    3.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5518    2.3293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4703    3.4240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1838    1.7990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1023    2.8937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9590    2.0812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0035    0.8364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7180    0.4239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5910    1.5509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4324    0.8364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7180   -0.4011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1785    0.8364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  5  4  2  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
  9  8  1  0  0  0  0
 11 10  1  0  0  0  0
 12  2  1  0  0  0  0
 12  9  1  0  0  0  0
 12 10  1  0  0  0  0
 13 11  2  0  0  0  0
 14  3  1  0  0  0  0
 14 11  1  0  0  0  0
 15 10  1  0  0  0  0
 15 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031729

> <DATABASE_NAME>
hmdb

> <SMILES>
CCOC(=O)C1OC1(C)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C12H14O3/c1-3-14-11(13)10-12(2,15-10)9-7-5-4-6-8-9/h4-8,10H,3H2,1-2H3

> <INCHI_KEY>
LQKRYVGRPXFFAV-UHFFFAOYSA-N

> <FORMULA>
C12H14O3

> <MOLECULAR_WEIGHT>
206.2378

> <EXACT_MASS>
206.094294314

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
22.057354455318617

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
ethyl 3-methyl-3-phenyloxirane-2-carboxylate

> <ALOGPS_LOGP>
2.40

> <JCHEM_LOGP>
2.2104829539999997

> <ALOGPS_LOGS>
-2.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.333337675217929

> <JCHEM_POLAR_SURFACE_AREA>
38.83

> <JCHEM_REFRACTIVITY>
55.31210000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.68e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ethyl methylphenylglycidate

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0031729
     RDKit          3D
Phenylmethylglycidic ester
 29 30  0  0  0  0  0  0  0  0999 V2000
    5.2068    1.2919    0.1366 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2248    0.2393   -0.2054 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8763    0.6370    0.0947 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8177   -0.2703   -0.1188 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1126   -1.3590   -0.5564 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4284    0.1934    0.2415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0756   -0.7592    1.3026 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6968   -0.7203    0.0535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5464   -1.8472   -0.9279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1096   -0.1497    0.1613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5282    0.6601   -0.8009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8472    1.1376   -0.7205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6203    0.7410    0.3484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1594   -0.0854    1.3230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8458   -0.5647    1.2472 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1333    0.8093    0.5367 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8207    1.8676    1.0171 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5148    1.9585   -0.7113 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4598   -0.6675    0.4296 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3029   -0.0881   -1.2315 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2971    1.2323    0.5947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5408   -1.9863   -1.4285 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1659   -1.6614   -1.7509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3386   -2.8202   -0.4366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9189    0.9614   -1.6501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2209    1.7741   -1.4694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6647    1.0923    0.3856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7814   -0.3670    2.1494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4666   -1.2495    1.9864 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  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  8  6  1  0
 15 10  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  6 21  1  0
  9 22  1  0
  9 23  1  0
  9 24  1  0
 11 25  1  0
 12 26  1  0
 13 27  1  0
 14 28  1  0
 15 29  1  0
M  END

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       8.274  -3.059   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.016   3.885   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.274  -1.519   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.297   5.865   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.030   4.348   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.745   6.391   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.210   3.358   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.924   5.402   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.657   3.885   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.607   1.561   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.940   0.791   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.837   2.895   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       8.274   1.561   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       6.940  -0.749   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       4.067   1.561   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2   12                                                            
CONECT    3    1   14                                                       
CONECT    4    5    6                                                       
CONECT    5    4    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5    9                                                       
CONECT    8    6    9                                                       
CONECT    9    7    8   12                                                  
CONECT   10   11   12   15                                                  
CONECT   11   10   13   14                                                  
CONECT   12    2    9   10   15                                             
CONECT   13   11                                                            
CONECT   14    3   11                                                       
CONECT   15   10   12                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

COMPND    HMDB0031729
HETATM    1  C1  UNL     1       5.207   1.292   0.137  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.225   0.239  -0.205  1.00  0.00           C  
HETATM    3  O1  UNL     1       2.876   0.637   0.095  1.00  0.00           O  
HETATM    4  C3  UNL     1       1.818  -0.270  -0.119  1.00  0.00           C  
HETATM    5  O2  UNL     1       2.113  -1.359  -0.556  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.428   0.193   0.242  1.00  0.00           C  
HETATM    7  O3  UNL     1      -0.076  -0.759   1.303  1.00  0.00           O  
HETATM    8  C5  UNL     1      -0.697  -0.720   0.053  1.00  0.00           C  
HETATM    9  C6  UNL     1      -0.546  -1.847  -0.928  1.00  0.00           C  
HETATM   10  C7  UNL     1      -2.110  -0.150   0.161  1.00  0.00           C  
HETATM   11  C8  UNL     1      -2.528   0.660  -0.801  1.00  0.00           C  
HETATM   12  C9  UNL     1      -3.847   1.138  -0.720  1.00  0.00           C  
HETATM   13  C10 UNL     1      -4.620   0.741   0.348  1.00  0.00           C  
HETATM   14  C11 UNL     1      -4.159  -0.085   1.323  1.00  0.00           C  
HETATM   15  C12 UNL     1      -2.846  -0.565   1.247  1.00  0.00           C  
HETATM   16  H1  UNL     1       6.133   0.809   0.537  1.00  0.00           H  
HETATM   17  H2  UNL     1       4.821   1.868   1.017  1.00  0.00           H  
HETATM   18  H3  UNL     1       5.515   1.958  -0.711  1.00  0.00           H  
HETATM   19  H4  UNL     1       4.460  -0.668   0.430  1.00  0.00           H  
HETATM   20  H5  UNL     1       4.303  -0.088  -1.232  1.00  0.00           H  
HETATM   21  H6  UNL     1       0.297   1.232   0.595  1.00  0.00           H  
HETATM   22  H7  UNL     1      -1.541  -1.986  -1.428  1.00  0.00           H  
HETATM   23  H8  UNL     1       0.166  -1.661  -1.751  1.00  0.00           H  
HETATM   24  H9  UNL     1      -0.339  -2.820  -0.437  1.00  0.00           H  
HETATM   25  H10 UNL     1      -1.919   0.961  -1.650  1.00  0.00           H  
HETATM   26  H11 UNL     1      -4.221   1.774  -1.469  1.00  0.00           H  
HETATM   27  H12 UNL     1      -5.665   1.092   0.386  1.00  0.00           H  
HETATM   28  H13 UNL     1      -4.781  -0.367   2.149  1.00  0.00           H  
HETATM   29  H14 UNL     1      -2.467  -1.250   1.986  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3   19   20
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7    8   21
CONECT    7    8
CONECT    8    9   10
CONECT    9   22   23   24
CONECT   10   11   11   15
CONECT   11   12   25
CONECT   12   13   13   26
CONECT   13   14   27
CONECT   14   15   15   28
CONECT   15   29
END

HMDB0031729
     RDKit          3D
Phenylmethylglycidic ester
 29 30  0  0  0  0  0  0  0  0999 V2000
    5.2068    1.2919    0.1366 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2248    0.2393   -0.2054 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8763    0.6370    0.0947 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8177   -0.2703   -0.1188 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1126   -1.3590   -0.5564 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4284    0.1934    0.2415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0756   -0.7592    1.3026 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6968   -0.7203    0.0535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5464   -1.8472   -0.9279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1096   -0.1497    0.1613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5282    0.6601   -0.8009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8472    1.1376   -0.7205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6203    0.7410    0.3484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1594   -0.0854    1.3230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8458   -0.5647    1.2472 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1333    0.8093    0.5367 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8207    1.8676    1.0171 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5148    1.9585   -0.7113 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4598   -0.6675    0.4296 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3029   -0.0881   -1.2315 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2971    1.2323    0.5947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5408   -1.9863   -1.4285 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1659   -1.6614   -1.7509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3386   -2.8202   -0.4366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9189    0.9614   -1.6501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2209    1.7741   -1.4694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6647    1.0923    0.3856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7814   -0.3670    2.1494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4666   -1.2495    1.9864 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  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  8  6  1  0
 15 10  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  6 21  1  0
  9 22  1  0
  9 23  1  0
  9 24  1  0
 11 25  1  0
 12 26  1  0
 13 27  1  0
 14 28  1  0
 15 29  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2, 3-Epoxy-3-phenylbutyric acid, ethyl ester	HMDB
2,3-Epoxy-3-phenylbutyric acid, ethyl ester	HMDB
2-Oxiranecarboxylic acid, 3-methyl-3-phenyl-, ethyl ester	HMDB
3-METHYL-3-phenyl glycidIC ACID ethyl ester	HMDB
3-Methyl-3-phenylglycidic acid ethyl ester	HMDB
3-Methyl-3-phenylglycidic acid, ethyl ester	HMDB
3-Methyl-3-phenyloxiranecarboxylic acid, ethyl ester	HMDB
Aldehyde C-16	HMDB
Aldehyde C16	HMDB
Aldehyde C16 (misleading)	HMDB
alpha,beta-Epoxy-beta-methylhydrocinnamic acid, ethyl ester	HMDB
Butanoic acid, 2,3-epoxy-3-phenyl-, ethyl ester	HMDB
C-16 Aldehyde	HMDB
cis-Ethyl 3-methyl-3-phenylglycidate	HMDB
EMPG	HMDB
Ethyl 2,3-epoxy-2-methyl-3-phenylpropionate	HMDB
Ethyl 2,3-epoxy-3-methyl-3-phenylpropionate	HMDB
Ethyl 2,3-epoxy-3-phenylbutyrate	HMDB
Ethyl 3-methyl-3-phenyl-2-oxiranecarboxylate	HMDB
Ethyl 3-methyl-3-phenylglycidate	HMDB
Ethyl 3-methyl-3-phenyloxirane-2-carboxylate	HMDB
Ethyl 3-methyl-3-phenyloxiranecarboxylate	HMDB
Ethyl alpha ,beta -epoxy-beta -methylhydrocinnamate	HMDB
Ethyl alpha,beta-epoxy-beta-methylhydrocinnamate	HMDB
Ethyl alpha,beta-epoxy-beta-methylphenylpropionate	HMDB
Ethyl beta -methyl-beta -phenylglycidate	HMDB
Ethyl beta-methyl-beta-phenylglycidate	HMDB
Ethyl ester OF 2,3-epoxy-3-phenylbutanoic acid	HMDB
Ethyl methylphenylglycidate	HMDB
Ethyl(methylphenyl)glycidate	HMDB
Ethyl-3-methyl-3-phenylglycidate	HMDB
FEMA 2444	HMDB
Fraeseol	HMDB
Fraise pure	HMDB
Oxiranecarboxylic acid, 3-methyl-3-phenyl-, ethyl ester	HMDB
Strawberry aldehyde	HMDB
trans-Ethyl 3-methyl-3-phenylglycidate	HMDB
Ethyl 3-methyl-3-phenyloxirane-2-carboxylic acid	HMDB

Chemical Formula

C₁₂H₁₄O₃

Average Molecular Weight

206.2378

Monoisotopic Molecular Weight

206.094294314

IUPAC Name

ethyl 3-methyl-3-phenyloxirane-2-carboxylate

Traditional Name

ethyl methylphenylglycidate

CAS Registry Number

77-83-8

SMILES

CCOC(=O)C1OC1(C)C1=CC=CC=C1

InChI Identifier

InChI=1S/C12H14O3/c1-3-14-11(13)10-12(2,15-10)9-7-5-4-6-8-9/h4-8,10H,3H2,1-2H3

InChI Key

LQKRYVGRPXFFAV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxirane carboxylic acids. Oxirane carboxylic acids are compounds containing an oxirane ring bearing a carboxylic acid group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Epoxides

Sub Class

Oxirane carboxylic acids and derivatives

Direct Parent

Oxirane carboxylic acids

Alternative Parents

Substituents

Benzenoid
Oxirane carboxylic acid
Monocyclic benzene moiety
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Organoleptic effect

Taste

Sweet

Odor

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0031729)
Cytoplasm (HMDB: HMDB0031729)

Source

Endogenous

Endogenous (HMDB: HMDB0031729)

Exogenous

Food

Food (HMDB: HMDB0031729)

Exogenous (HMDB: HMDB0031729)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	272.00 to 275.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	111.3 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.655 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.87 g/L	ALOGPS
logP	2.4	ALOGPS
logP	2.21	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	38.83 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	55.31 m³·mol⁻¹	ChemAxon
Polarizability	22.06 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	148.567	31661259
DarkChem	[M-H]-	146.284	31661259
DeepCCS	[M+H]+	146.57	30932474
DeepCCS	[M-H]-	144.212	30932474
DeepCCS	[M-2H]-	178.423	30932474
DeepCCS	[M+Na]+	153.743	30932474
AllCCS	[M+H]+	146.0	32859911
AllCCS	[M+H-H2O]+	141.9	32859911
AllCCS	[M+NH4]+	149.9	32859911
AllCCS	[M+Na]+	151.0	32859911
AllCCS	[M-H]-	150.1	32859911
AllCCS	[M+Na-2H]-	150.4	32859911
AllCCS	[M+HCOO]-	150.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.72 minutes	32390414
Predicted by Siyang on May 30, 2022	15.6847 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.18 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2279.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	513.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	192.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	302.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	199.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	640.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	805.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	90.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1327.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	496.6 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1504.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	419.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	439.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	446.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	411.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	33.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Phenylmethylglycidic ester	CCOC(=O)C1OC1(C)C1=CC=CC=C1	2181.0	Standard polar	33892256
Phenylmethylglycidic ester	CCOC(=O)C1OC1(C)C1=CC=CC=C1	1428.2	Standard non polar	33892256
Phenylmethylglycidic ester	CCOC(=O)C1OC1(C)C1=CC=CC=C1	1508.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Phenylmethylglycidic ester GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ugi-3900000000-95a88776da33a25e0316	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenylmethylglycidic ester GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenylmethylglycidic ester GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylmethylglycidic ester 10V, Positive-QTOF	splash10-0a4i-0490000000-045556589e2fef30db0a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylmethylglycidic ester 20V, Positive-QTOF	splash10-08i1-3920000000-3bfaf226d5cd7582d13a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylmethylglycidic ester 40V, Positive-QTOF	splash10-102a-8900000000-91e198f0e73a81fcdc77	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylmethylglycidic ester 10V, Negative-QTOF	splash10-0a4i-6970000000-13ad9025ea0a65b6e3e0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylmethylglycidic ester 20V, Negative-QTOF	splash10-0a4j-6910000000-b9e5a815007e987bf77f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylmethylglycidic ester 40V, Negative-QTOF	splash10-054k-9400000000-57be8ada1f8bb8c5d78d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylmethylglycidic ester 10V, Negative-QTOF	splash10-0a4i-1920000000-bc117f5bde914eaa13af	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylmethylglycidic ester 20V, Negative-QTOF	splash10-0pb9-4900000000-83bd8c382753db224804	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylmethylglycidic ester 40V, Negative-QTOF	splash10-0fk9-9400000000-0ef05d802f8e9d2e39bf	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylmethylglycidic ester 10V, Positive-QTOF	splash10-0a59-3910000000-b5e8f43a8c575ed921e5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylmethylglycidic ester 20V, Positive-QTOF	splash10-0a4i-5900000000-69e0cf80dc416c15574d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylmethylglycidic ester 40V, Positive-QTOF	splash10-0zi0-9800000000-832771e853b6b228341b	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB008392

KNApSAcK ID

Not Available

Chemspider ID

6255

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6501

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1001602

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Phenylmethylglycidic ester (HMDB0031729)

MOL for HMDB0031729 (Phenylmethylglycidic ester)

3D MOL for HMDB0031729 (Phenylmethylglycidic ester)

3D SDF for HMDB0031729 (Phenylmethylglycidic ester)

3D-SDF for HMDB0031729 (Phenylmethylglycidic ester)

PDB for HMDB0031729 (Phenylmethylglycidic ester)

3D PDB for HMDB0031729 (Phenylmethylglycidic ester)

SMILES for HMDB0031729 (Phenylmethylglycidic ester)

INCHI for HMDB0031729 (Phenylmethylglycidic ester)

Structure for HMDB0031729 (Phenylmethylglycidic ester)

3D Structure for HMDB0031729 (Phenylmethylglycidic ester)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra