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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 00:29:31 UTC

Update Date

2022-03-07 02:56:05 UTC

HMDB ID

HMDB0039125

Secondary Accession Numbers

HMDB39125

Metabolite Identification

Common Name

Coumaperine

Description

Coumaperine belongs to the class of organic compounds known as n-acylpiperidines. N-acylpiperidines are compounds containing an N-acyethanolamine moiety, which is characterized by an acyl group is linked to the nitrogen atom of a piperidine. Coumaperine has been detected, but not quantified in, herbs and spices. This could make coumaperine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Coumaperine.

Structure

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

HMDB0039125
     RDKit          3D
Coumaperine
 38 39  0  0  0  0  0  0  0  0999 V2000
   -0.7542    0.8632   -1.3879 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2898    0.1943   -0.4676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4839   -0.5247    0.5256 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8628   -0.4586    0.4382 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5958   -1.1748    1.4276 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8820   -1.2013    1.5117 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7937   -0.5106    0.6488 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0883   -1.0618    0.5062 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0961   -0.4812   -0.2039 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8744    0.7278   -0.8407 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9166    1.2904   -1.5547 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6441    1.3135   -0.7399 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6270    0.6843    0.0043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6998    0.1164   -0.3641 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3663   -0.6381    0.6729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7865   -0.9576    0.2554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5793    0.2415   -0.1571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7066    1.3992   -0.5798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5165    0.8153   -1.3281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9513   -1.0897    1.3033 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1956    0.0938   -0.4050 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0239   -1.7601    2.1905 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3582   -1.8142    2.3383 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2779   -1.9893    0.9859 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0730   -0.9633   -0.2727 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8688    2.1536   -2.0496 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4309    2.2568   -1.2220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7006    1.2170    0.1146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3658   -0.0984    1.6456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8725   -1.6112    0.8659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7026   -1.6782   -0.6017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2487   -1.5108    1.1062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3309    0.5484    0.6175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2106   -0.0367   -1.0508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3030    2.0584   -1.2312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2894    1.9358    0.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9283    1.5997   -1.8396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9238    0.0513   -2.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
  2 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 13  7  1  0
 19 14  1  0
  3 20  1  0
  4 21  1  0
  5 22  1  0
  6 23  1  0
  8 24  1  0
  9 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 15 29  1  0
 15 30  1  0
 16 31  1  0
 16 32  1  0
 17 33  1  0
 17 34  1  0
 18 35  1  0
 18 36  1  0
 19 37  1  0
 19 38  1  0
M  END


  Mrv0541 02241219022D          

 19 20  0  0  0  0            999 V2000
    0.7421   -0.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7421    0.2066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4021    0.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1446    0.2066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1446   -0.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4846   -1.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4846   -1.8558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4021    1.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7421    1.8558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0004    1.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7421    1.8558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4021    1.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1446    1.8558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1446   -0.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4021   -1.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7421   -0.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7421    0.2066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4021    0.6184    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1446    0.2066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  8  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  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
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 18  1  0  0  0  0
 14 15  1  0  0  0  0
 14 19  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0039125

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC=C(\C=C/C=C/C(=O)N2CCCCC2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H19NO2/c18-15-10-8-14(9-11-15)6-2-3-7-16(19)17-12-4-1-5-13-17/h2-3,6-11,18H,1,4-5,12-13H2/b6-2-,7-3+

> <INCHI_KEY>
QDAARMDLSCDBFU-MFDSWNTHSA-N

> <FORMULA>
C16H19NO2

> <MOLECULAR_WEIGHT>
257.3276

> <EXACT_MASS>
257.141578857

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
29.35753744669158

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,4Z)-5-(4-hydroxyphenyl)-1-(piperidin-1-yl)penta-2,4-dien-1-one

> <ALOGPS_LOGP>
3.52

> <JCHEM_LOGP>
2.850512261

> <ALOGPS_LOGS>
-3.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.5066117108892

> <JCHEM_PKA_STRONGEST_BASIC>
2.368301167072483

> <JCHEM_POLAR_SURFACE_AREA>
40.54

> <JCHEM_REFRACTIVITY>
79.117

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.36e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E,4Z)-5-(4-hydroxyphenyl)-1-(piperidin-1-yl)penta-2,4-dien-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0039125
     RDKit          3D
Coumaperine
 38 39  0  0  0  0  0  0  0  0999 V2000
   -0.7542    0.8632   -1.3879 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2898    0.1943   -0.4676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4839   -0.5247    0.5256 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8628   -0.4586    0.4382 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5958   -1.1748    1.4276 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8820   -1.2013    1.5117 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7937   -0.5106    0.6488 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0883   -1.0618    0.5062 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0961   -0.4812   -0.2039 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8744    0.7278   -0.8407 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9166    1.2904   -1.5547 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6441    1.3135   -0.7399 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6270    0.6843    0.0043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6998    0.1164   -0.3641 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3663   -0.6381    0.6729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7865   -0.9576    0.2554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5793    0.2415   -0.1571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7066    1.3992   -0.5798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5165    0.8153   -1.3281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9513   -1.0897    1.3033 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1956    0.0938   -0.4050 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0239   -1.7601    2.1905 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3582   -1.8142    2.3383 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2779   -1.9893    0.9859 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0730   -0.9633   -0.2727 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8688    2.1536   -2.0496 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4309    2.2568   -1.2220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7006    1.2170    0.1146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3658   -0.0984    1.6456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8725   -1.6112    0.8659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7026   -1.6782   -0.6017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2487   -1.5108    1.1062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3309    0.5484    0.6175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2106   -0.0367   -1.0508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3030    2.0584   -1.2312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2894    1.9358    0.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9283    1.5997   -1.8396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9238    0.0513   -2.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
  2 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 13  7  1  0
 19 14  1  0
  3 20  1  0
  4 21  1  0
  5 22  1  0
  6 23  1  0
  8 24  1  0
  9 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 15 29  1  0
 15 30  1  0
 16 31  1  0
 16 32  1  0
 17 33  1  0
 17 34  1  0
 18 35  1  0
 18 36  1  0
 19 37  1  0
 19 38  1  0
M  END

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  C   UNK     0       1.385  -1.154   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.385   0.386   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.617   1.154   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.003   0.386   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.003  -1.154   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.771  -1.924   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.771  -3.464   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.617   2.694   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.385   3.464   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.001   2.694   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.385   3.464   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.617   2.694   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -4.003   3.464   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -4.003  -1.154   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.617  -1.924   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.385  -1.154   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.385   0.386   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0      -2.617   1.154   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0      -4.003   0.386   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5    7                                                  
CONECT    7    6                                                            
CONECT    8    3    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12                                                            
CONECT   14   15   19                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   12   17   19                                                  
CONECT   19   14   18                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0039125
HETATM    1  O1  UNL     1      -0.754   0.863  -1.388  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.290   0.194  -0.468  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.484  -0.525   0.526  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.863  -0.459   0.438  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.596  -1.175   1.428  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.882  -1.201   1.512  1.00  0.00           C  
HETATM    7  C6  UNL     1       3.794  -0.511   0.649  1.00  0.00           C  
HETATM    8  C7  UNL     1       5.088  -1.062   0.506  1.00  0.00           C  
HETATM    9  C8  UNL     1       6.096  -0.481  -0.204  1.00  0.00           C  
HETATM   10  C9  UNL     1       5.874   0.728  -0.841  1.00  0.00           C  
HETATM   11  O2  UNL     1       6.917   1.290  -1.555  1.00  0.00           O  
HETATM   12  C10 UNL     1       4.644   1.314  -0.740  1.00  0.00           C  
HETATM   13  C11 UNL     1       3.627   0.684   0.004  1.00  0.00           C  
HETATM   14  N1  UNL     1      -2.700   0.116  -0.364  1.00  0.00           N  
HETATM   15  C12 UNL     1      -3.366  -0.638   0.673  1.00  0.00           C  
HETATM   16  C13 UNL     1      -4.786  -0.958   0.255  1.00  0.00           C  
HETATM   17  C14 UNL     1      -5.579   0.241  -0.157  1.00  0.00           C  
HETATM   18  C15 UNL     1      -4.707   1.399  -0.580  1.00  0.00           C  
HETATM   19  C16 UNL     1      -3.516   0.815  -1.328  1.00  0.00           C  
HETATM   20  H1  UNL     1      -0.951  -1.090   1.303  1.00  0.00           H  
HETATM   21  H2  UNL     1       1.196   0.094  -0.405  1.00  0.00           H  
HETATM   22  H3  UNL     1       1.024  -1.760   2.190  1.00  0.00           H  
HETATM   23  H4  UNL     1       3.358  -1.814   2.338  1.00  0.00           H  
HETATM   24  H5  UNL     1       5.278  -1.989   0.986  1.00  0.00           H  
HETATM   25  H6  UNL     1       7.073  -0.963  -0.273  1.00  0.00           H  
HETATM   26  H7  UNL     1       6.869   2.154  -2.050  1.00  0.00           H  
HETATM   27  H8  UNL     1       4.431   2.257  -1.222  1.00  0.00           H  
HETATM   28  H9  UNL     1       2.701   1.217   0.115  1.00  0.00           H  
HETATM   29  H10 UNL     1      -3.366  -0.098   1.646  1.00  0.00           H  
HETATM   30  H11 UNL     1      -2.873  -1.611   0.866  1.00  0.00           H  
HETATM   31  H12 UNL     1      -4.703  -1.678  -0.602  1.00  0.00           H  
HETATM   32  H13 UNL     1      -5.249  -1.511   1.106  1.00  0.00           H  
HETATM   33  H14 UNL     1      -6.331   0.548   0.617  1.00  0.00           H  
HETATM   34  H15 UNL     1      -6.211  -0.037  -1.051  1.00  0.00           H  
HETATM   35  H16 UNL     1      -5.303   2.058  -1.231  1.00  0.00           H  
HETATM   36  H17 UNL     1      -4.289   1.936   0.296  1.00  0.00           H  
HETATM   37  H18 UNL     1      -2.928   1.600  -1.840  1.00  0.00           H  
HETATM   38  H19 UNL     1      -3.924   0.051  -2.024  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   14
CONECT    3    4    4   20
CONECT    4    5   21
CONECT    5    6    6   22
CONECT    6    7   23
CONECT    7    8    8   13
CONECT    8    9   24
CONECT    9   10   10   25
CONECT   10   11   12
CONECT   11   26
CONECT   12   13   13   27
CONECT   13   28
CONECT   14   15   19
CONECT   15   16   29   30
CONECT   16   17   31   32
CONECT   17   18   33   34
CONECT   18   19   35   36
CONECT   19   37   38
END

HMDB0039125
     RDKit          3D
Coumaperine
 38 39  0  0  0  0  0  0  0  0999 V2000
   -0.7542    0.8632   -1.3879 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2898    0.1943   -0.4676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4839   -0.5247    0.5256 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8628   -0.4586    0.4382 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5958   -1.1748    1.4276 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8820   -1.2013    1.5117 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7937   -0.5106    0.6488 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0883   -1.0618    0.5062 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0961   -0.4812   -0.2039 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8744    0.7278   -0.8407 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9166    1.2904   -1.5547 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6441    1.3135   -0.7399 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6270    0.6843    0.0043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6998    0.1164   -0.3641 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3663   -0.6381    0.6729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7865   -0.9576    0.2554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5793    0.2415   -0.1571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7066    1.3992   -0.5798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5165    0.8153   -1.3281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9513   -1.0897    1.3033 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1956    0.0938   -0.4050 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0239   -1.7601    2.1905 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3582   -1.8142    2.3383 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2779   -1.9893    0.9859 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0730   -0.9633   -0.2727 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8688    2.1536   -2.0496 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4309    2.2568   -1.2220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7006    1.2170    0.1146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3658   -0.0984    1.6456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8725   -1.6112    0.8659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7026   -1.6782   -0.6017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2487   -1.5108    1.1062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3309    0.5484    0.6175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2106   -0.0367   -1.0508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3030    2.0584   -1.2312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2894    1.9358    0.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9283    1.5997   -1.8396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9238    0.0513   -2.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
  2 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 13  7  1  0
 19 14  1  0
  3 20  1  0
  4 21  1  0
  5 22  1  0
  6 23  1  0
  8 24  1  0
  9 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 15 29  1  0
 15 30  1  0
 16 31  1  0
 16 32  1  0
 17 33  1  0
 17 34  1  0
 18 35  1  0
 18 36  1  0
 19 37  1  0
 19 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-[5-(4-Hydroxyphenyl)-1-oxo-2,4-pentadienyl]piperidine, 9ci	HMDB
5-(4-Hydroxyphenyl)-2,4-pentadienoic acid piperidide	HMDB
N-[5-(4-Hydroxyphenyl)-2,4-pentadienoyl]piperidine	HMDB
N-5-(4-Hydroxyphenyl)-2E,4E-pentadienoylpiperidine	MeSH

Chemical Formula

C₁₆H₁₉NO₂

Average Molecular Weight

257.3276

Monoisotopic Molecular Weight

257.141578857

IUPAC Name

(2E,4Z)-5-(4-hydroxyphenyl)-1-(piperidin-1-yl)penta-2,4-dien-1-one

Traditional Name

(2E,4Z)-5-(4-hydroxyphenyl)-1-(piperidin-1-yl)penta-2,4-dien-1-one

CAS Registry Number

76733-91-0

SMILES

OC1=CC=C(\C=C/C=C/C(=O)N2CCCCC2)C=C1

InChI Identifier

InChI=1S/C16H19NO2/c18-15-10-8-14(9-11-15)6-2-3-7-16(19)17-12-4-1-5-13-17/h2-3,6-11,18H,1,4-5,12-13H2/b6-2-,7-3+

InChI Key

QDAARMDLSCDBFU-MFDSWNTHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acylpiperidines. N-acylpiperidines are compounds containing an N-acyethanolamine moiety, which is characterized by an acyl group is linked to the nitrogen atom of a piperidine.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Piperidines

Sub Class

N-acylpiperidines

Direct Parent

N-acylpiperidines

Alternative Parents

Substituents

N-acyl-piperidine
Styrene
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Tertiary carboxylic acid amide
Carboxamide group
Carboxylic acid derivative
Azacycle
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0039125)
Cell membrane (HMDB: HMDB0039125)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0039125)

Source

Exogenous

Exogenous (HMDB: HMDB0039125)

Food

Food (HMDB: HMDB0039125)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0039125)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0039125)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	199.5 - 200.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	168.2 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.24 g/L	ALOGPS
logP	3.52	ALOGPS
logP	2.85	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	9.51	ChemAxon
pKa (Strongest Basic)	2.37	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	40.54 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	79.12 m³·mol⁻¹	ChemAxon
Polarizability	29.36 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	166.946	30932474
DeepCCS	[M-H]-	164.588	30932474
DeepCCS	[M-2H]-	197.474	30932474
DeepCCS	[M+Na]+	173.04	30932474
AllCCS	[M+H]+	161.9	32859911
AllCCS	[M+H-H2O]+	158.2	32859911
AllCCS	[M+NH4]+	165.4	32859911
AllCCS	[M+Na]+	166.5	32859911
AllCCS	[M-H]-	166.5	32859911
AllCCS	[M+Na-2H]-	166.6	32859911
AllCCS	[M+HCOO]-	166.9	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.	6.95 minutes	32390414
Predicted by Siyang on May 30, 2022	14.3024 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.43 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2170.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	334.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	180.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	192.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	394.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	641.3 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	545.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	113.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1319.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	444.7 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	1352.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	408.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	397.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	327.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	213.6 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	8.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Coumaperine	OC1=CC=C(\C=C/C=C/C(=O)N2CCCCC2)C=C1	3630.3	Standard polar	33892256
Coumaperine	OC1=CC=C(\C=C/C=C/C(=O)N2CCCCC2)C=C1	2575.6	Standard non polar	33892256
Coumaperine	OC1=CC=C(\C=C/C=C/C(=O)N2CCCCC2)C=C1	2844.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Coumaperine,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C(/C=C\C=C\C(=O)N2CCCCC2)C=C1	2693.1	Semi standard non polar	33892256
Coumaperine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C\C=C\C(=O)N2CCCCC2)C=C1	2961.8	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 - Coumaperine GC-MS (Non-derivatized) - 70eV, Positive	splash10-059y-5940000000-6aae430daf96ceb7fe93	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Coumaperine GC-MS (1 TMS) - 70eV, Positive	splash10-0229-7594000000-16655b7e5bccaab5610e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Coumaperine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Coumaperine 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 - Coumaperine 10V, Positive-QTOF	splash10-0a4i-3390000000-b56f7bbf7b1fcff6314d	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coumaperine 20V, Positive-QTOF	splash10-052s-4920000000-fa86bb26d42c16f42a46	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coumaperine 40V, Positive-QTOF	splash10-0670-9300000000-9a30b8a7d75c668b5dd9	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coumaperine 10V, Negative-QTOF	splash10-0a4i-0190000000-22a2bfea2cfbb245939b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coumaperine 20V, Negative-QTOF	splash10-0a59-7790000000-b67d1458b656c74d1f71	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coumaperine 40V, Negative-QTOF	splash10-001i-9200000000-7ba3dfbcf6dd3e42ae45	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coumaperine 10V, Negative-QTOF	splash10-0a4i-0090000000-e3e3cf7ed0e20649e8c8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coumaperine 20V, Negative-QTOF	splash10-0a59-0950000000-75d3451b88cb015bb6a0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coumaperine 40V, Negative-QTOF	splash10-014i-3910000000-61e3a92412ef440b9eb3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coumaperine 10V, Positive-QTOF	splash10-0a4i-0190000000-47c5b16203862c202aaf	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coumaperine 20V, Positive-QTOF	splash10-0api-0960000000-7a08a0ed2bce447eb3bb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coumaperine 40V, Positive-QTOF	splash10-0a6r-1900000000-be8fda645e4d88c6fc1c	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

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

FDB018637

KNApSAcK ID

C00055009

Chemspider ID

30777321

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131752556

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1874451

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 Coumaperine (HMDB0039125)

MOL for HMDB0039125 (Coumaperine)

3D MOL for HMDB0039125 (Coumaperine)

3D SDF for HMDB0039125 (Coumaperine)

3D-SDF for HMDB0039125 (Coumaperine)

PDB for HMDB0039125 (Coumaperine)

3D PDB for HMDB0039125 (Coumaperine)

SMILES for HMDB0039125 (Coumaperine)

INCHI for HMDB0039125 (Coumaperine)

Structure for HMDB0039125 (Coumaperine)

3D Structure for HMDB0039125 (Coumaperine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra