Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 00:11:17 UTC

Update Date

2022-03-07 02:55:57 UTC

HMDB ID

HMDB0038840

Secondary Accession Numbers

HMDB38840

Metabolite Identification

Common Name

Sarmentine

Description

Sarmentine belongs to the class of organic compounds known as n-acylpyrrolidines. These are n-Acylated Pyrrolidine derivatives. Pyrrolidine is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms. Sarmentine has been detected, but not quantified in, herbs and spices and pepper (spice). This could make sarmentine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Sarmentine.

Structure

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

HMDB0038840
     RDKit          3D
Sarmentine
 39 39  0  0  0  0  0  0  0  0999 V2000
   -6.4920   -0.7921   -0.2153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4079    0.2734    0.0052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4676    0.1534   -1.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3262    1.1144   -1.1523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4940    0.9040    0.1125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9871   -0.4563    0.1352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7167   -0.7953    0.1492 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3175    0.2084    0.1423 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5838   -0.1767    0.1580 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6847    0.8100    0.1518 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3708    2.0183    0.1313 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0388    0.3943    0.1686 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1736    1.2950    0.1640 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1193    0.5529    1.1175 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0064   -0.8552    0.5780 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5571   -0.9482    0.1931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4427   -0.4993    0.2727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6709   -0.8644   -1.3282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0882   -1.7537    0.1278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9320   -0.0103    0.9694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8202    1.2810    0.0484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1063    0.3215   -2.0796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1419   -0.8989   -1.2328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6167    2.1632   -1.1615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6692    0.8345   -2.0158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7668    1.7154    0.2278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2384    1.0767    0.9626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7299   -1.2779    0.1461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4478   -1.8788    0.1668 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0785    1.2455    0.1233 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7866   -1.2370    0.1754 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9339    2.2984    0.5167 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6149    1.2530   -0.8450 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6712    0.5521    2.1232 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1354    0.9506    1.0691 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6411   -0.8913   -0.3413 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3054   -1.6243    1.3163 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0531   -1.6008    0.9280 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4902   -1.3596   -0.8488 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  1  0
  5  6  1  0
  6  7  2  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
 16 12  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  7 29  1  0
  8 30  1  0
  9 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
M  END


  Mrv0541 05061310412D          

 16 16  0  0  0  0            999 V2000
    0.8853    5.7877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5998    5.3752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3143    5.7877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0287    5.3752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7432    5.7877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4577    5.3752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1721    5.7877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1721    6.6127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9068    8.5402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4943    9.2547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8866    7.0252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3548    7.9271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6873    9.0831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8866    7.8502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6011    8.2627    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1721    8.2627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  2  0  0  0  0
  8  7  1  0  0  0  0
 10  9  1  0  0  0  0
 11  8  2  0  0  0  0
 12  9  1  0  0  0  0
 13 10  1  0  0  0  0
 14 11  1  0  0  0  0
 15 12  1  0  0  0  0
 15 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 14  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038840

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC\C=C/C=C/C(=O)N1CCCC1

> <INCHI_IDENTIFIER>
InChI=1S/C14H23NO/c1-2-3-4-5-6-7-8-11-14(16)15-12-9-10-13-15/h6-8,11H,2-5,9-10,12-13H2,1H3/b7-6-,11-8+

> <INCHI_KEY>
BFZBGTMIBOQWBA-BQGCWICQSA-N

> <FORMULA>
C14H23NO

> <MOLECULAR_WEIGHT>
221.3385

> <EXACT_MASS>
221.177964363

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
26.976880866958844

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,4Z)-1-(pyrrolidin-1-yl)deca-2,4-dien-1-one

> <ALOGPS_LOGP>
4.15

> <JCHEM_LOGP>
3.271279604999999

> <ALOGPS_LOGS>
-3.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
2.070215683476251

> <JCHEM_POLAR_SURFACE_AREA>
20.310000000000002

> <JCHEM_REFRACTIVITY>
70.8441

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.45e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E,4Z)-1-(pyrrolidin-1-yl)deca-2,4-dien-1-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0038840
     RDKit          3D
Sarmentine
 39 39  0  0  0  0  0  0  0  0999 V2000
   -6.4920   -0.7921   -0.2153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4079    0.2734    0.0052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4676    0.1534   -1.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3262    1.1144   -1.1523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4940    0.9040    0.1125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9871   -0.4563    0.1352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7167   -0.7953    0.1492 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3175    0.2084    0.1423 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5838   -0.1767    0.1580 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6847    0.8100    0.1518 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3708    2.0183    0.1313 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0388    0.3943    0.1686 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1736    1.2950    0.1640 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1193    0.5529    1.1175 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0064   -0.8552    0.5780 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5571   -0.9482    0.1931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4427   -0.4993    0.2727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6709   -0.8644   -1.3282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0882   -1.7537    0.1278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9320   -0.0103    0.9694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8202    1.2810    0.0484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1063    0.3215   -2.0796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1419   -0.8989   -1.2328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6167    2.1632   -1.1615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6692    0.8345   -2.0158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7668    1.7154    0.2278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2384    1.0767    0.9626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7299   -1.2779    0.1461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4478   -1.8788    0.1668 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0785    1.2455    0.1233 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7866   -1.2370    0.1754 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9339    2.2984    0.5167 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6149    1.2530   -0.8450 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6712    0.5521    2.1232 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1354    0.9506    1.0691 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6411   -0.8913   -0.3413 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3054   -1.6243    1.3163 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0531   -1.6008    0.9280 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4902   -1.3596   -0.8488 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  1  0
  5  6  1  0
  6  7  2  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
 16 12  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  7 29  1  0
  8 30  1  0
  9 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  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       1.653  10.804   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.986  10.034   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.320  10.804   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.654  10.034   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.987  10.804   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.321  10.034   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.655  10.804   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.655  12.344   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.759  15.942   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.989  17.275   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.988  13.114   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.729  14.797   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.483  16.955   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.988  14.654   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0      12.322  15.424   0.000  0.00  0.00           N+0
HETATM   16  O   UNK     0       9.655  15.424   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7   11                                                       
CONECT    9   10   12                                                       
CONECT   10    9   13                                                       
CONECT   11    8   14                                                       
CONECT   12    9   15                                                       
CONECT   13   10   15                                                       
CONECT   14   11   15   16                                                  
CONECT   15   12   13   14                                                  
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0038840
HETATM    1  C1  UNL     1      -6.492  -0.792  -0.215  1.00  0.00           C  
HETATM    2  C2  UNL     1      -5.408   0.273   0.005  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.468   0.153  -1.160  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.326   1.114  -1.152  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.494   0.904   0.112  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.987  -0.456   0.135  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.717  -0.795   0.149  1.00  0.00           C  
HETATM    8  C8  UNL     1       0.318   0.208   0.142  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.584  -0.177   0.158  1.00  0.00           C  
HETATM   10  C10 UNL     1       2.685   0.810   0.152  1.00  0.00           C  
HETATM   11  O1  UNL     1       2.371   2.018   0.131  1.00  0.00           O  
HETATM   12  N1  UNL     1       4.039   0.394   0.169  1.00  0.00           N  
HETATM   13  C11 UNL     1       5.174   1.295   0.164  1.00  0.00           C  
HETATM   14  C12 UNL     1       6.119   0.553   1.117  1.00  0.00           C  
HETATM   15  C13 UNL     1       6.006  -0.855   0.578  1.00  0.00           C  
HETATM   16  C14 UNL     1       4.557  -0.948   0.193  1.00  0.00           C  
HETATM   17  H1  UNL     1      -7.443  -0.499   0.273  1.00  0.00           H  
HETATM   18  H2  UNL     1      -6.671  -0.864  -1.328  1.00  0.00           H  
HETATM   19  H3  UNL     1      -6.088  -1.754   0.128  1.00  0.00           H  
HETATM   20  H4  UNL     1      -4.932  -0.010   0.969  1.00  0.00           H  
HETATM   21  H5  UNL     1      -5.820   1.281   0.048  1.00  0.00           H  
HETATM   22  H6  UNL     1      -5.106   0.322  -2.080  1.00  0.00           H  
HETATM   23  H7  UNL     1      -4.142  -0.899  -1.233  1.00  0.00           H  
HETATM   24  H8  UNL     1      -3.617   2.163  -1.162  1.00  0.00           H  
HETATM   25  H9  UNL     1      -2.669   0.835  -2.016  1.00  0.00           H  
HETATM   26  H10 UNL     1      -1.767   1.715   0.228  1.00  0.00           H  
HETATM   27  H11 UNL     1      -3.238   1.077   0.963  1.00  0.00           H  
HETATM   28  H12 UNL     1      -2.730  -1.278   0.146  1.00  0.00           H  
HETATM   29  H13 UNL     1      -0.448  -1.879   0.167  1.00  0.00           H  
HETATM   30  H14 UNL     1       0.078   1.245   0.123  1.00  0.00           H  
HETATM   31  H15 UNL     1       1.787  -1.237   0.175  1.00  0.00           H  
HETATM   32  H16 UNL     1       4.934   2.298   0.517  1.00  0.00           H  
HETATM   33  H17 UNL     1       5.615   1.253  -0.845  1.00  0.00           H  
HETATM   34  H18 UNL     1       5.671   0.552   2.123  1.00  0.00           H  
HETATM   35  H19 UNL     1       7.135   0.951   1.069  1.00  0.00           H  
HETATM   36  H20 UNL     1       6.641  -0.891  -0.341  1.00  0.00           H  
HETATM   37  H21 UNL     1       6.305  -1.624   1.316  1.00  0.00           H  
HETATM   38  H22 UNL     1       4.053  -1.601   0.928  1.00  0.00           H  
HETATM   39  H23 UNL     1       4.490  -1.360  -0.849  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3   20   21
CONECT    3    4   22   23
CONECT    4    5   24   25
CONECT    5    6   26   27
CONECT    6    7    7   28
CONECT    7    8   29
CONECT    8    9    9   30
CONECT    9   10   31
CONECT   10   11   11   12
CONECT   12   13   16
CONECT   13   14   32   33
CONECT   14   15   34   35
CONECT   15   16   36   37
CONECT   16   38   39
END

HMDB0038840
     RDKit          3D
Sarmentine
 39 39  0  0  0  0  0  0  0  0999 V2000
   -6.4920   -0.7921   -0.2153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4079    0.2734    0.0052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4676    0.1534   -1.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3262    1.1144   -1.1523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4940    0.9040    0.1125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9871   -0.4563    0.1352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7167   -0.7953    0.1492 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3175    0.2084    0.1423 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5838   -0.1767    0.1580 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6847    0.8100    0.1518 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3708    2.0183    0.1313 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0388    0.3943    0.1686 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1736    1.2950    0.1640 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1193    0.5529    1.1175 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0064   -0.8552    0.5780 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5571   -0.9482    0.1931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4427   -0.4993    0.2727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6709   -0.8644   -1.3282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0882   -1.7537    0.1278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9320   -0.0103    0.9694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8202    1.2810    0.0484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1063    0.3215   -2.0796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1419   -0.8989   -1.2328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6167    2.1632   -1.1615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6692    0.8345   -2.0158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7668    1.7154    0.2278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2384    1.0767    0.9626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7299   -1.2779    0.1461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4478   -1.8788    0.1668 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0785    1.2455    0.1233 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7866   -1.2370    0.1754 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9339    2.2984    0.5167 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6149    1.2530   -0.8450 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6712    0.5521    2.1232 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1354    0.9506    1.0691 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6411   -0.8913   -0.3413 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3054   -1.6243    1.3163 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0531   -1.6008    0.9280 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4902   -1.3596   -0.8488 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  1  0
  5  6  1  0
  6  7  2  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
 16 12  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  7 29  1  0
  8 30  1  0
  9 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-((2E,4E)-1-oxo-2,4-Decadienyl)-pyrrolidine	HMDB
1-(1-oxo-2,4-Decadienyl)pyrrolidine, 9ci	HMDB
1-(2,4-Decadienoyl)pyrrolidine	HMDB
2,4-Decadienoic acid pyrrolidide	HMDB

Chemical Formula

C₁₄H₂₃NO

Average Molecular Weight

221.3385

Monoisotopic Molecular Weight

221.177964363

IUPAC Name

(2E,4Z)-1-(pyrrolidin-1-yl)deca-2,4-dien-1-one

Traditional Name

(2E,4Z)-1-(pyrrolidin-1-yl)deca-2,4-dien-1-one

CAS Registry Number

78910-33-5

SMILES

CCCCC\C=C/C=C/C(=O)N1CCCC1

InChI Identifier

InChI=1S/C14H23NO/c1-2-3-4-5-6-7-8-11-14(16)15-12-9-10-13-15/h6-8,11H,2-5,9-10,12-13H2,1H3/b7-6-,11-8+

InChI Key

BFZBGTMIBOQWBA-BQGCWICQSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acylpyrrolidines. These are n-Acylated Pyrrolidine derivatives. Pyrrolidine is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrrolidines

Sub Class

N-acylpyrrolidines

Direct Parent

N-acylpyrrolidines

Alternative Parents

Substituents

N-acylpyrrolidine
Tertiary carboxylic acid amide
Carboxamide group
Azacycle
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0038840)
Cell membrane (HMDB: HMDB0038840)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038840)

Source

Exogenous

Exogenous (HMDB: HMDB0038840)

Food

Food (HMDB: HMDB0038840)

Herb and spice

Spice

Pepper (Spice) (FooDB: FOOD00139)

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0038840)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0038840)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	370.00 to 372.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	16.33 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.264 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.054 g/L	ALOGPS
logP	4.15	ALOGPS
logP	3.27	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Basic)	2.07	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	20.31 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	70.84 m³·mol⁻¹	ChemAxon
Polarizability	26.98 Å³	ChemAxon
Number of Rings	1	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]+	160.248	31661259
DarkChem	[M-H]-	157.13	31661259
DeepCCS	[M+H]+	160.386	30932474
DeepCCS	[M-H]-	158.029	30932474
DeepCCS	[M-2H]-	191.93	30932474
DeepCCS	[M+Na]+	167.664	30932474
AllCCS	[M+H]+	154.6	32859911
AllCCS	[M+H-H2O]+	150.9	32859911
AllCCS	[M+NH4]+	158.0	32859911
AllCCS	[M+Na]+	158.9	32859911
AllCCS	[M-H]-	160.6	32859911
AllCCS	[M+Na-2H]-	161.4	32859911
AllCCS	[M+HCOO]-	162.5	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.	7.99 minutes	32390414
Predicted by Siyang on May 30, 2022	17.8832 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.12 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	26.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2415.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	503.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	206.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	307.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	465.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	750.5 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	647.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	96.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1605.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	492.1 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	1485.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	547.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	430.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	325.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	458.2 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	8.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Sarmentine	CCCCC\C=C/C=C/C(=O)N1CCCC1	2527.6	Standard polar	33892256
Sarmentine	CCCCC\C=C/C=C/C(=O)N1CCCC1	1910.3	Standard non polar	33892256
Sarmentine	CCCCC\C=C/C=C/C(=O)N1CCCC1	2132.9	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 - Sarmentine GC-MS (Non-derivatized) - 70eV, Positive	splash10-054o-9600000000-dccb66fb0f1c1c770722	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sarmentine 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 - Sarmentine 10V, Positive-QTOF	splash10-00di-4290000000-746fb6ce7457fe0ab042	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sarmentine 20V, Positive-QTOF	splash10-00di-9520000000-e042410cde0325010c69	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sarmentine 40V, Positive-QTOF	splash10-0596-9000000000-56c0c4ae6738c61e5980	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sarmentine 10V, Negative-QTOF	splash10-00di-0190000000-bb1bfc17c377f35ce5c4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sarmentine 20V, Negative-QTOF	splash10-00di-9680000000-f9b3c0a6aa3cb9ed98e6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sarmentine 40V, Negative-QTOF	splash10-00di-9200000000-17ea35aaeab9b05bec50	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sarmentine 10V, Negative-QTOF	splash10-00di-0090000000-c1fe20ca7550c2bb7082	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sarmentine 20V, Negative-QTOF	splash10-022a-9550000000-3c019dc90a2edef1b374	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sarmentine 40V, Negative-QTOF	splash10-014i-9100000000-9b597547291110df644b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sarmentine 10V, Positive-QTOF	splash10-00di-7590000000-5cf2f27b24fcbab23fc1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sarmentine 20V, Positive-QTOF	splash10-00di-9000000000-feb1501abbb00048edad	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sarmentine 40V, Positive-QTOF	splash10-00di-9000000000-01874a7e56a6b3a7500a	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

FDB018275

KNApSAcK ID

C00031306

Chemspider ID

30777295

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

46935132

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1583671

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 Sarmentine (HMDB0038840)

MOL for HMDB0038840 (Sarmentine)

3D MOL for HMDB0038840 (Sarmentine)

3D SDF for HMDB0038840 (Sarmentine)

3D-SDF for HMDB0038840 (Sarmentine)

PDB for HMDB0038840 (Sarmentine)

3D PDB for HMDB0038840 (Sarmentine)

SMILES for HMDB0038840 (Sarmentine)

INCHI for HMDB0038840 (Sarmentine)

Structure for HMDB0038840 (Sarmentine)

3D Structure for HMDB0038840 (Sarmentine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra