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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 00:11:14 UTC

Update Date

2022-03-07 02:55:57 UTC

HMDB ID

HMDB0038839

Secondary Accession Numbers

HMDB38839

Metabolite Identification

Common Name

1-(m-Methoxycinnamoyl)pyrrolidine

Description

1-(m-Methoxycinnamoyl)pyrrolidine belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. 1-(m-Methoxycinnamoyl)pyrrolidine has been detected, but not quantified in, beverages. This could make 1-(m-methoxycinnamoyl)pyrrolidine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 1-(m-Methoxycinnamoyl)pyrrolidine.

Structure

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

HMDB0038839
     RDKit          3D
1-(m-Methoxycinnamoyl)pyrrolidine
 34 35  0  0  0  0  0  0  0  0999 V2000
   -5.7082    0.9267    0.8738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5958   -0.3194    0.1911 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3132   -0.7232   -0.1488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1339   -1.9227   -0.8128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8850   -2.3639   -1.1697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7688   -1.5972   -0.8626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9129   -0.4074   -0.2071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7877    0.4336    0.1392 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4775    0.1692   -0.1240 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5493    1.1073    0.2798 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2351    2.1617    0.8785 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8956    0.8205   -0.0033 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0159    1.6586    0.3420 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1819    0.7385    0.5409 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6607   -0.6644    0.2282 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4816   -0.3245   -0.6769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1867   -0.0016    0.1330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7460    1.1673    1.1075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0561    0.8365    1.7732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2221    1.6890    0.2213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9863   -2.5546   -1.0723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7314   -3.3175   -1.6985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8044   -1.9445   -1.1417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9721    1.3876    0.6714 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7065   -0.7469   -0.6400 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8062    2.2818    1.2452 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2222    2.3284   -0.5095 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0183    0.9617   -0.1843 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5082    0.7948    1.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2667   -1.1657    1.1152 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4423   -1.2310   -0.3143 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9022    0.0379   -1.6369 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7815   -1.1651   -0.7852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3411    0.9484    0.6600 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
  7 17  2  0
 17  3  1  0
 16 12  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  5 22  1  0
  6 23  1  0
  8 24  1  0
  9 25  1  0
 13 26  1  0
 13 27  1  0
 14 28  1  0
 14 29  1  0
 15 30  1  0
 15 31  1  0
 16 32  1  0
 16 33  1  0
 17 34  1  0
M  END


  Mrv0541 05061310412D          

 17 18  0  0  0  0            999 V2000
    9.1814    1.0527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7676   -1.4544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5926   -1.4544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0380    2.2902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3235    1.8777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7525    1.8777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6091    0.6402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8946    1.0527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5127   -0.6697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8476   -0.6697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0380    0.6402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3235    1.0527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7525    1.0527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1801    0.6402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1801   -0.1848    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    1.0527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4669    0.6402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  8  7  2  0  0  0  0
  9  2  1  0  0  0  0
 10  3  1  0  0  0  0
 12  5  1  0  0  0  0
 12  7  1  0  0  0  0
 12 11  2  0  0  0  0
 13  6  2  0  0  0  0
 13 11  1  0  0  0  0
 14  8  1  0  0  0  0
 15  9  1  0  0  0  0
 15 10  1  0  0  0  0
 15 14  1  0  0  0  0
 16 14  2  0  0  0  0
 17  1  1  0  0  0  0
 17 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038839

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC=CC(\C=C\C(=O)N2CCCC2)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H17NO2/c1-17-13-6-4-5-12(11-13)7-8-14(16)15-9-2-3-10-15/h4-8,11H,2-3,9-10H2,1H3/b8-7+

> <INCHI_KEY>
LAPTWLCIZWFMJK-BQYQJAHWSA-N

> <FORMULA>
C14H17NO2

> <MOLECULAR_WEIGHT>
231.2903

> <EXACT_MASS>
231.125928793

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
26.13181063552024

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-3-(3-methoxyphenyl)-1-(pyrrolidin-1-yl)prop-2-en-1-one

> <ALOGPS_LOGP>
2.42

> <JCHEM_LOGP>
2.0246219786666666

> <ALOGPS_LOGS>
-2.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
1.6368968641007542

> <JCHEM_POLAR_SURFACE_AREA>
29.540000000000003

> <JCHEM_REFRACTIVITY>
68.67970000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.50e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-3-(3-methoxyphenyl)-1-(pyrrolidin-1-yl)prop-2-en-1-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0038839
     RDKit          3D
1-(m-Methoxycinnamoyl)pyrrolidine
 34 35  0  0  0  0  0  0  0  0999 V2000
   -5.7082    0.9267    0.8738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5958   -0.3194    0.1911 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3132   -0.7232   -0.1488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1339   -1.9227   -0.8128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8850   -2.3639   -1.1697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7688   -1.5972   -0.8626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9129   -0.4074   -0.2071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7877    0.4336    0.1392 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4775    0.1692   -0.1240 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5493    1.1073    0.2798 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2351    2.1617    0.8785 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8956    0.8205   -0.0033 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0159    1.6586    0.3420 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1819    0.7385    0.5409 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6607   -0.6644    0.2282 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4816   -0.3245   -0.6769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1867   -0.0016    0.1330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7460    1.1673    1.1075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0561    0.8365    1.7732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2221    1.6890    0.2213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9863   -2.5546   -1.0723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7314   -3.3175   -1.6985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8044   -1.9445   -1.1417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9721    1.3876    0.6714 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7065   -0.7469   -0.6400 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8062    2.2818    1.2452 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2222    2.3284   -0.5095 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0183    0.9617   -0.1843 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5082    0.7948    1.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2667   -1.1657    1.1152 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4423   -1.2310   -0.3143 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9022    0.0379   -1.6369 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7815   -1.1651   -0.7852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3411    0.9484    0.6600 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
  7 17  2  0
 17  3  1  0
 16 12  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  5 22  1  0
  6 23  1  0
  8 24  1  0
  9 25  1  0
 13 26  1  0
 13 27  1  0
 14 28  1  0
 14 29  1  0
 15 30  1  0
 15 31  1  0
 16 32  1  0
 16 33  1  0
 17 34  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      17.139   1.965   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.033  -2.715   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.573  -2.715   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.138   4.275   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.804   3.505   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.471   3.505   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.470   1.195   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.137   1.965   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.557  -1.250   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.049  -1.250   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.138   1.195   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.804   1.965   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.471   1.965   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.803   1.195   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       7.803  -0.345   0.000  0.00  0.00           N+0
HETATM   16  O   UNK     0       6.469   1.965   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      15.805   1.195   0.000  0.00  0.00           O+0
CONECT    1   17                                                            
CONECT    2    3    9                                                       
CONECT    3    2   10                                                       
CONECT    4    5    6                                                       
CONECT    5    4   12                                                       
CONECT    6    4   13                                                       
CONECT    7    8   12                                                       
CONECT    8    7   14                                                       
CONECT    9    2   15                                                       
CONECT   10    3   15                                                       
CONECT   11   12   13                                                       
CONECT   12    5    7   11                                                  
CONECT   13    6   11   17                                                  
CONECT   14    8   15   16                                                  
CONECT   15    9   10   14                                                  
CONECT   16   14                                                            
CONECT   17    1   13                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0038839
HETATM    1  C1  UNL     1      -5.708   0.927   0.874  1.00  0.00           C  
HETATM    2  O1  UNL     1      -5.596  -0.319   0.191  1.00  0.00           O  
HETATM    3  C2  UNL     1      -4.313  -0.723  -0.149  1.00  0.00           C  
HETATM    4  C3  UNL     1      -4.134  -1.923  -0.813  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.885  -2.364  -1.170  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.769  -1.597  -0.863  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.913  -0.407  -0.207  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.788   0.434   0.139  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.478   0.169  -0.124  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.549   1.107   0.280  1.00  0.00           C  
HETATM   11  O2  UNL     1       1.235   2.162   0.879  1.00  0.00           O  
HETATM   12  N1  UNL     1       2.896   0.820  -0.003  1.00  0.00           N  
HETATM   13  C10 UNL     1       4.016   1.659   0.342  1.00  0.00           C  
HETATM   14  C11 UNL     1       5.182   0.738   0.541  1.00  0.00           C  
HETATM   15  C12 UNL     1       4.661  -0.664   0.228  1.00  0.00           C  
HETATM   16  C13 UNL     1       3.482  -0.325  -0.677  1.00  0.00           C  
HETATM   17  C14 UNL     1      -3.187  -0.002   0.133  1.00  0.00           C  
HETATM   18  H1  UNL     1      -6.746   1.167   1.108  1.00  0.00           H  
HETATM   19  H2  UNL     1      -5.056   0.837   1.773  1.00  0.00           H  
HETATM   20  H3  UNL     1      -5.222   1.689   0.221  1.00  0.00           H  
HETATM   21  H4  UNL     1      -4.986  -2.555  -1.072  1.00  0.00           H  
HETATM   22  H5  UNL     1      -2.731  -3.317  -1.699  1.00  0.00           H  
HETATM   23  H6  UNL     1      -0.804  -1.945  -1.142  1.00  0.00           H  
HETATM   24  H7  UNL     1      -0.972   1.388   0.671  1.00  0.00           H  
HETATM   25  H8  UNL     1       0.707  -0.747  -0.640  1.00  0.00           H  
HETATM   26  H9  UNL     1       3.806   2.282   1.245  1.00  0.00           H  
HETATM   27  H10 UNL     1       4.222   2.328  -0.509  1.00  0.00           H  
HETATM   28  H11 UNL     1       6.018   0.962  -0.184  1.00  0.00           H  
HETATM   29  H12 UNL     1       5.508   0.795   1.588  1.00  0.00           H  
HETATM   30  H13 UNL     1       4.267  -1.166   1.115  1.00  0.00           H  
HETATM   31  H14 UNL     1       5.442  -1.231  -0.314  1.00  0.00           H  
HETATM   32  H15 UNL     1       3.902   0.038  -1.637  1.00  0.00           H  
HETATM   33  H16 UNL     1       2.782  -1.165  -0.785  1.00  0.00           H  
HETATM   34  H17 UNL     1      -3.341   0.948   0.660  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3
CONECT    3    4    4   17
CONECT    4    5   21
CONECT    5    6    6   22
CONECT    6    7   23
CONECT    7    8   17   17
CONECT    8    9    9   24
CONECT    9   10   25
CONECT   10   11   11   12
CONECT   12   13   16
CONECT   13   14   26   27
CONECT   14   15   28   29
CONECT   15   16   30   31
CONECT   16   32   33
CONECT   17   34
END

HMDB0038839
     RDKit          3D
1-(m-Methoxycinnamoyl)pyrrolidine
 34 35  0  0  0  0  0  0  0  0999 V2000
   -5.7082    0.9267    0.8738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5958   -0.3194    0.1911 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3132   -0.7232   -0.1488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1339   -1.9227   -0.8128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8850   -2.3639   -1.1697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7688   -1.5972   -0.8626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9129   -0.4074   -0.2071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7877    0.4336    0.1392 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4775    0.1692   -0.1240 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5493    1.1073    0.2798 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2351    2.1617    0.8785 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8956    0.8205   -0.0033 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0159    1.6586    0.3420 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1819    0.7385    0.5409 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6607   -0.6644    0.2282 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4816   -0.3245   -0.6769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1867   -0.0016    0.1330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7460    1.1673    1.1075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0561    0.8365    1.7732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2221    1.6890    0.2213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9863   -2.5546   -1.0723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7314   -3.3175   -1.6985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8044   -1.9445   -1.1417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9721    1.3876    0.6714 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7065   -0.7469   -0.6400 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8062    2.2818    1.2452 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2222    2.3284   -0.5095 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0183    0.9617   -0.1843 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5082    0.7948    1.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2667   -1.1657    1.1152 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4423   -1.2310   -0.3143 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9022    0.0379   -1.6369 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7815   -1.1651   -0.7852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3411    0.9484    0.6600 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
  7 17  2  0
 17  3  1  0
 16 12  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  5 22  1  0
  6 23  1  0
  8 24  1  0
  9 25  1  0
 13 26  1  0
 13 27  1  0
 14 28  1  0
 14 29  1  0
 15 30  1  0
 15 31  1  0
 16 32  1  0
 16 33  1  0
 17 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-(m-Methoxycinnamoyl)pyrrolidine, 8ci	HMDB
m-Methoxycinnamic acid pyrrolidide	HMDB

Chemical Formula

C₁₄H₁₇NO₂

Average Molecular Weight

231.2903

Monoisotopic Molecular Weight

231.125928793

IUPAC Name

(2E)-3-(3-methoxyphenyl)-1-(pyrrolidin-1-yl)prop-2-en-1-one

Traditional Name

(2E)-3-(3-methoxyphenyl)-1-(pyrrolidin-1-yl)prop-2-en-1-one

CAS Registry Number

29647-01-6

SMILES

COC1=CC=CC(\C=C\C(=O)N2CCCC2)=C1

InChI Identifier

InChI=1S/C14H17NO2/c1-17-13-6-4-5-12(11-13)7-8-14(16)15-9-2-3-10-15/h4-8,11H,2-3,9-10H2,1H3/b8-7+

InChI Key

LAPTWLCIZWFMJK-BQYQJAHWSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acids and derivatives

Alternative Parents

Substituents

Coumaric acid or derivatives
Phenoxy compound
Anisole
N-acylpyrrolidine
Methoxybenzene
Phenol ether
Styrene
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Tertiary carboxylic acid amide
Pyrrolidine
Carboxamide group
Carboxylic acid derivative
Ether
Azacycle
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Organic oxide
Carbonyl group
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0038839)
Cytoplasm (HMDB: HMDB0038839)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038839)

Source

Exogenous

Food

Food (HMDB: HMDB0038839)

Beverage

Beverages (FooDB: FOOD00870)

Endogenous

Plant

Plant (HMDB: HMDB0038839)

Not Available

Nutrient (HMDB: HMDB0038839)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	90 - 93 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.5 g/L	ALOGPS
logP	2.42	ALOGPS
logP	2.02	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Basic)	1.64	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	29.54 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	68.68 m³·mol⁻¹	ChemAxon
Polarizability	26.13 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]+	156.511	31661259
DarkChem	[M-H]-	156.872	31661259
DeepCCS	[M+H]+	159.94	30932474
DeepCCS	[M-H]-	157.582	30932474
DeepCCS	[M-2H]-	190.469	30932474
DeepCCS	[M+Na]+	166.034	30932474
AllCCS	[M+H]+	153.4	32859911
AllCCS	[M+H-H2O]+	149.4	32859911
AllCCS	[M+NH4]+	157.2	32859911
AllCCS	[M+Na]+	158.2	32859911
AllCCS	[M-H]-	158.5	32859911
AllCCS	[M+Na-2H]-	158.7	32859911
AllCCS	[M+HCOO]-	159.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1-(m-Methoxycinnamoyl)pyrrolidine	COC1=CC=CC(\C=C\C(=O)N2CCCC2)=C1	3123.0	Standard polar	33892256
1-(m-Methoxycinnamoyl)pyrrolidine	COC1=CC=CC(\C=C\C(=O)N2CCCC2)=C1	2154.2	Standard non polar	33892256
1-(m-Methoxycinnamoyl)pyrrolidine	COC1=CC=CC(\C=C\C(=O)N2CCCC2)=C1	2355.8	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 - 1-(m-Methoxycinnamoyl)pyrrolidine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0hr0-9870000000-608b01bc89f74a539e7f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-(m-Methoxycinnamoyl)pyrrolidine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-(m-Methoxycinnamoyl)pyrrolidine 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 - 1-(m-Methoxycinnamoyl)pyrrolidine 10V, Negative-QTOF	splash10-001i-0090000000-c287c7982eed044607c3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(m-Methoxycinnamoyl)pyrrolidine 20V, Negative-QTOF	splash10-0089-7490000000-b4d9ea391271098ced16	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(m-Methoxycinnamoyl)pyrrolidine 40V, Negative-QTOF	splash10-00di-9300000000-56b5bb3c03841207cb6f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(m-Methoxycinnamoyl)pyrrolidine 10V, Negative-QTOF	splash10-001i-0090000000-219884484b7e41d6161e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(m-Methoxycinnamoyl)pyrrolidine 20V, Negative-QTOF	splash10-0159-2950000000-c57baf9fb68f6647dc77	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(m-Methoxycinnamoyl)pyrrolidine 40V, Negative-QTOF	splash10-01b9-0900000000-75795fe4187dcffc54c1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(m-Methoxycinnamoyl)pyrrolidine 10V, Positive-QTOF	splash10-001i-2190000000-ee659fae3071a622b221	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(m-Methoxycinnamoyl)pyrrolidine 20V, Positive-QTOF	splash10-0089-7950000000-50f418a9718405d92d26	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(m-Methoxycinnamoyl)pyrrolidine 40V, Positive-QTOF	splash10-05fu-9400000000-fad8489909ac4e06ea48	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(m-Methoxycinnamoyl)pyrrolidine 10V, Positive-QTOF	splash10-01q9-0590000000-398492c34cfbe2f26908	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(m-Methoxycinnamoyl)pyrrolidine 20V, Positive-QTOF	splash10-0089-4940000000-50473043a7da2f7d1827	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(m-Methoxycinnamoyl)pyrrolidine 40V, Positive-QTOF	splash10-001i-6910000000-e973adc46ec09cd91ee1	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

FDB018274

KNApSAcK ID

Not Available

Chemspider ID

4523676

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5373710

PDB ID

Not Available

ChEBI ID

157735

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

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 1-(m-Methoxycinnamoyl)pyrrolidine (HMDB0038839)

MOL for HMDB0038839 (1-(m-Methoxycinnamoyl)pyrrolidine)

3D MOL for HMDB0038839 (1-(m-Methoxycinnamoyl)pyrrolidine)

3D SDF for HMDB0038839 (1-(m-Methoxycinnamoyl)pyrrolidine)

3D-SDF for HMDB0038839 (1-(m-Methoxycinnamoyl)pyrrolidine)

PDB for HMDB0038839 (1-(m-Methoxycinnamoyl)pyrrolidine)

3D PDB for HMDB0038839 (1-(m-Methoxycinnamoyl)pyrrolidine)

SMILES for HMDB0038839 (1-(m-Methoxycinnamoyl)pyrrolidine)

INCHI for HMDB0038839 (1-(m-Methoxycinnamoyl)pyrrolidine)

Structure for HMDB0038839 (1-(m-Methoxycinnamoyl)pyrrolidine)

3D Structure for HMDB0038839 (1-(m-Methoxycinnamoyl)pyrrolidine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra