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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:35:21 UTC

Update Date

2022-03-07 02:52:27 UTC

HMDB ID

HMDB0030190

Secondary Accession Numbers

HMDB30190

Metabolite Identification

Common Name

(E,E)-Lansamide I

Description

(E,E)-Lansamide I, also known as lansiumamide b, belongs to the class of organic compounds known as cinnamic acids and derivatives. These are organic aromatic compounds containing a benzene and a carboxylic acid group (or a derivative thereof) forming 3-phenylprop-2-enoic acid. Based on a literature review very few articles have been published on (E,E)-Lansamide I.

Structure

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

HMDB0030190
     RDKit          3D
(E,E)-Lansamide I
 37 38  0  0  0  0  0  0  0  0999 V2000
   -1.3992   -2.7996    2.5125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6111   -1.7489    1.8056 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7163   -0.4580    2.3222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4040    0.5059    1.7463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1683    0.4530    0.5313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5801   -0.6309   -0.1750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2533   -0.5512   -1.3904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5378    0.6640   -1.9387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1399    1.7895   -1.2544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4744    1.6935   -0.0541 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0959   -2.1488    0.6675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1134   -3.3841    0.2543 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0272   -1.3940   -0.1175 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4636   -0.1835    0.0757 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4091    0.5147   -0.7735 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8157    1.8150   -0.4818 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6980    2.4993   -1.2526 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2153    1.8950   -2.3649 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8388    0.6268   -2.6773 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9353   -0.0580   -1.8774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7068   -3.2582    3.2431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2796   -2.3446    2.9873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7545   -3.5441    1.7698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1873   -0.2131    3.2870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3545    1.4662    2.3270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4350   -1.6037    0.2015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5543   -1.4475   -1.9064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0610    0.7345   -2.8836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3779    2.7359   -1.7138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1865    2.6131    0.4383 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4343   -1.9013   -1.0101 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1302    0.3614    0.9556 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3857    2.2652    0.4085 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9904    3.5151   -0.9897 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9171    2.4238   -2.9883 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2493    0.1486   -3.5590 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6893   -1.0510   -2.1894 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  2  0
  8  9  1  0
  9 10  2  0
  2 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 10  5  1  0
 20 15  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  4 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
  9 29  1  0
 10 30  1  0
 13 31  1  0
 14 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
 19 36  1  0
 20 37  1  0
M  END


  Mrv0541 05061305042D          

 20 21  0  0  0  0            999 V2000
    1.4289    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    9.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    9.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    9.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    8.6625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  2  0  0  0  0
  5  2  1  0  0  0  0
  6  3  2  0  0  0  0
  7  3  1  0  0  0  0
  8  4  1  0  0  0  0
  9  5  2  0  0  0  0
 10  6  1  0  0  0  0
 11  7  2  0  0  0  0
 13 12  2  0  0  0  0
 15 14  2  0  0  0  0
 16  8  2  0  0  0  0
 16  9  1  0  0  0  0
 16 12  1  0  0  0  0
 17 10  2  0  0  0  0
 17 11  1  0  0  0  0
 17 14  1  0  0  0  0
 18 13  1  0  0  0  0
 19  1  1  0  0  0  0
 19 15  1  0  0  0  0
 19 18  1  0  0  0  0
 20 18  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030190

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H17NO/c1-19(15-14-17-10-6-3-7-11-17)18(20)13-12-16-8-4-2-5-9-16/h2-15H,1H3/b13-12+,15-14-

> <INCHI_KEY>
VJGRWRRIAJQNFU-NQDQBVNISA-N

> <FORMULA>
C18H17NO

> <MOLECULAR_WEIGHT>
263.3337

> <EXACT_MASS>
263.131014171

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
30.163689522813968

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-N-methyl-3-phenyl-N-[(Z)-2-phenylethenyl]prop-2-enamide

> <ALOGPS_LOGP>
3.83

> <JCHEM_LOGP>
3.8843091450000005

> <ALOGPS_LOGS>
-4.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7688101669739393

> <JCHEM_POLAR_SURFACE_AREA>
20.310000000000002

> <JCHEM_REFRACTIVITY>
84.13619999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.33e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-N-methyl-3-phenyl-N-[(Z)-2-phenylethenyl]prop-2-enamide

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0030190
     RDKit          3D
(E,E)-Lansamide I
 37 38  0  0  0  0  0  0  0  0999 V2000
   -1.3992   -2.7996    2.5125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6111   -1.7489    1.8056 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7163   -0.4580    2.3222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4040    0.5059    1.7463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1683    0.4530    0.5313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5801   -0.6309   -0.1750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2533   -0.5512   -1.3904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5378    0.6640   -1.9387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1399    1.7895   -1.2544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4744    1.6935   -0.0541 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0959   -2.1488    0.6675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1134   -3.3841    0.2543 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0272   -1.3940   -0.1175 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4636   -0.1835    0.0757 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4091    0.5147   -0.7735 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8157    1.8150   -0.4818 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6980    2.4993   -1.2526 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2153    1.8950   -2.3649 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8388    0.6268   -2.6773 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9353   -0.0580   -1.8774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7068   -3.2582    3.2431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2796   -2.3446    2.9873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7545   -3.5441    1.7698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1873   -0.2131    3.2870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3545    1.4662    2.3270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4350   -1.6037    0.2015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5543   -1.4475   -1.9064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0610    0.7345   -2.8836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3779    2.7359   -1.7138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1865    2.6131    0.4383 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4343   -1.9013   -1.0101 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1302    0.3614    0.9556 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3857    2.2652    0.4085 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9904    3.5151   -0.9897 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9171    2.4238   -2.9883 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2493    0.1486   -3.5590 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6893   -1.0510   -2.1894 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  2  0
  8  9  1  0
  9 10  2  0
  2 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 10  5  1  0
 20 15  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  4 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
  9 29  1  0
 10 30  1  0
 13 31  1  0
 14 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
 19 36  1  0
 20 37  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       2.667  15.400   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668  16.170   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  17.710   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335  15.400   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  10.780   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667  10.780   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335  18.480   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  16.170   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334  13.090   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000  13.860   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667  18.480   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334  17.710   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.334  11.550   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  17.710   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000  15.400   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       1.334  16.170   0.000  0.00  0.00           N+0
HETATM   20  O   UNK     0      -1.334  16.170   0.000  0.00  0.00           O+0
CONECT    1   19                                                            
CONECT    2    4    5                                                       
CONECT    3    6    7                                                       
CONECT    4    2    8                                                       
CONECT    5    2    9                                                       
CONECT    6    3   10                                                       
CONECT    7    3   11                                                       
CONECT    8    4   16                                                       
CONECT    9    5   16                                                       
CONECT   10    6   17                                                       
CONECT   11    7   17                                                       
CONECT   12   13   16                                                       
CONECT   13   12   18                                                       
CONECT   14   15   17                                                       
CONECT   15   14   19                                                       
CONECT   16    8    9   12                                                  
CONECT   17   10   11   14                                                  
CONECT   18   13   19   20                                                  
CONECT   19    1   15   18                                                  
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0030190
HETATM    1  C1  UNL     1      -1.399  -2.800   2.513  1.00  0.00           C  
HETATM    2  N1  UNL     1      -0.611  -1.749   1.806  1.00  0.00           N  
HETATM    3  C2  UNL     1      -0.716  -0.458   2.322  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.404   0.506   1.746  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.168   0.453   0.531  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.580  -0.631  -0.175  1.00  0.00           C  
HETATM    7  C6  UNL     1      -3.253  -0.551  -1.390  1.00  0.00           C  
HETATM    8  C7  UNL     1      -3.538   0.664  -1.939  1.00  0.00           C  
HETATM    9  C8  UNL     1      -3.140   1.790  -1.254  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.474   1.694  -0.054  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.096  -2.149   0.667  1.00  0.00           C  
HETATM   12  O1  UNL     1      -0.113  -3.384   0.254  1.00  0.00           O  
HETATM   13  C11 UNL     1       1.027  -1.394  -0.117  1.00  0.00           C  
HETATM   14  C12 UNL     1       1.464  -0.183   0.076  1.00  0.00           C  
HETATM   15  C13 UNL     1       2.409   0.515  -0.773  1.00  0.00           C  
HETATM   16  C14 UNL     1       2.816   1.815  -0.482  1.00  0.00           C  
HETATM   17  C15 UNL     1       3.698   2.499  -1.253  1.00  0.00           C  
HETATM   18  C16 UNL     1       4.215   1.895  -2.365  1.00  0.00           C  
HETATM   19  C17 UNL     1       3.839   0.627  -2.677  1.00  0.00           C  
HETATM   20  C18 UNL     1       2.935  -0.058  -1.877  1.00  0.00           C  
HETATM   21  H1  UNL     1      -0.707  -3.258   3.243  1.00  0.00           H  
HETATM   22  H2  UNL     1      -2.280  -2.345   2.987  1.00  0.00           H  
HETATM   23  H3  UNL     1      -1.754  -3.544   1.770  1.00  0.00           H  
HETATM   24  H4  UNL     1      -0.187  -0.213   3.287  1.00  0.00           H  
HETATM   25  H5  UNL     1      -1.354   1.466   2.327  1.00  0.00           H  
HETATM   26  H6  UNL     1      -2.435  -1.604   0.202  1.00  0.00           H  
HETATM   27  H7  UNL     1      -3.554  -1.447  -1.906  1.00  0.00           H  
HETATM   28  H8  UNL     1      -4.061   0.734  -2.884  1.00  0.00           H  
HETATM   29  H9  UNL     1      -3.378   2.736  -1.714  1.00  0.00           H  
HETATM   30  H10 UNL     1      -2.187   2.613   0.438  1.00  0.00           H  
HETATM   31  H11 UNL     1       1.434  -1.901  -1.010  1.00  0.00           H  
HETATM   32  H12 UNL     1       1.130   0.361   0.956  1.00  0.00           H  
HETATM   33  H13 UNL     1       2.386   2.265   0.408  1.00  0.00           H  
HETATM   34  H14 UNL     1       3.990   3.515  -0.990  1.00  0.00           H  
HETATM   35  H15 UNL     1       4.917   2.424  -2.988  1.00  0.00           H  
HETATM   36  H16 UNL     1       4.249   0.149  -3.559  1.00  0.00           H  
HETATM   37  H17 UNL     1       2.689  -1.051  -2.189  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3   11
CONECT    3    4    4   24
CONECT    4    5   25
CONECT    5    6    6   10
CONECT    6    7   26
CONECT    7    8    8   27
CONECT    8    9   28
CONECT    9   10   10   29
CONECT   10   30
CONECT   11   12   12   13
CONECT   13   14   14   31
CONECT   14   15   32
CONECT   15   16   16   20
CONECT   16   17   33
CONECT   17   18   18   34
CONECT   18   19   35
CONECT   19   20   20   36
CONECT   20   37
END

HMDB0030190
     RDKit          3D
(E,E)-Lansamide I
 37 38  0  0  0  0  0  0  0  0999 V2000
   -1.3992   -2.7996    2.5125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6111   -1.7489    1.8056 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7163   -0.4580    2.3222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4040    0.5059    1.7463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1683    0.4530    0.5313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5801   -0.6309   -0.1750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2533   -0.5512   -1.3904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5378    0.6640   -1.9387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1399    1.7895   -1.2544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4744    1.6935   -0.0541 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0959   -2.1488    0.6675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1134   -3.3841    0.2543 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0272   -1.3940   -0.1175 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4636   -0.1835    0.0757 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4091    0.5147   -0.7735 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8157    1.8150   -0.4818 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6980    2.4993   -1.2526 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2153    1.8950   -2.3649 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8388    0.6268   -2.6773 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9353   -0.0580   -1.8774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7068   -3.2582    3.2431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2796   -2.3446    2.9873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7545   -3.5441    1.7698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1873   -0.2131    3.2870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3545    1.4662    2.3270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4350   -1.6037    0.2015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5543   -1.4475   -1.9064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0610    0.7345   -2.8836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3779    2.7359   -1.7138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1865    2.6131    0.4383 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4343   -1.9013   -1.0101 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1302    0.3614    0.9556 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3857    2.2652    0.4085 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9904    3.5151   -0.9897 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9171    2.4238   -2.9883 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2493    0.1486   -3.5590 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6893   -1.0510   -2.1894 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  2  0
  8  9  1  0
  9 10  2  0
  2 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 10  5  1  0
 20 15  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  4 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
  9 29  1  0
 10 30  1  0
 13 31  1  0
 14 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
 19 36  1  0
 20 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
N-Methyl-N-styrylcinnamamide	HMDB
Lansiumamide b	HMDB

Chemical Formula

C₁₈H₁₇NO

Average Molecular Weight

263.3337

Monoisotopic Molecular Weight

263.131014171

IUPAC Name

(2E)-N-methyl-3-phenyl-N-[(Z)-2-phenylethenyl]prop-2-enamide

Traditional Name

(2E)-N-methyl-3-phenyl-N-[(Z)-2-phenylethenyl]prop-2-enamide

CAS Registry Number

77527-97-0

SMILES

CN(\C=C/C1=CC=CC=C1)C(=O)\C=C\C1=CC=CC=C1

InChI Identifier

InChI=1S/C18H17NO/c1-19(15-14-17-10-6-3-7-11-17)18(20)13-12-16-8-4-2-5-9-16/h2-15H,1H3/b13-12+,15-14-

InChI Key

VJGRWRRIAJQNFU-NQDQBVNISA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cinnamic acids and derivatives. These are organic aromatic compounds containing a benzene and a carboxylic acid group (or a derivative thereof) forming 3-phenylprop-2-enoic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Not Available

Direct Parent

Cinnamic acids and derivatives

Alternative Parents

Substituents

Cinnamic acid or derivatives
Styrene
Monocyclic benzene moiety
Benzenoid
Tertiary carboxylic acid amide
Carboxamide group
Carboxylic acid derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0030190)
Cell membrane (HMDB: HMDB0030190)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030190)

Source

Endogenous

Endogenous (HMDB: HMDB0030190)

Plant

Plant (HMDB: HMDB0030190)

Exogenous

Food

Food (HMDB: HMDB0030190)

Fruit

Fruits (FooDB: FOOD00871)

Exogenous (HMDB: HMDB0030190)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	124 - 125 °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	0.0073 g/L	ALOGPS
logP	3.83	ALOGPS
logP	3.88	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Basic)	-2.8	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	4	ChemAxon
Refractivity	84.14 m³·mol⁻¹	ChemAxon
Polarizability	30.16 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]+	163.92	31661259
DarkChem	[M-H]-	162.716	31661259
DeepCCS	[M+H]+	161.448	30932474
DeepCCS	[M-H]-	159.09	30932474
DeepCCS	[M-2H]-	191.976	30932474
DeepCCS	[M+Na]+	167.541	30932474
AllCCS	[M+H]+	164.1	32859911
AllCCS	[M+H-H2O]+	160.3	32859911
AllCCS	[M+NH4]+	167.7	32859911
AllCCS	[M+Na]+	168.7	32859911
AllCCS	[M-H]-	168.5	32859911
AllCCS	[M+Na-2H]-	168.2	32859911
AllCCS	[M+HCOO]-	168.1	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.	8.73 minutes	32390414
Predicted by Siyang on May 30, 2022	15.9486 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.9 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	25.6 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2886.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	479.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	204.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	249.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	338.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	707.6 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	695.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	71.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1602.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	546.8 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	1508.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	382.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	435.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	307.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	271.6 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	7.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(E,E)-Lansamide I	CN(\C=C/C1=CC=CC=C1)C(=O)\C=C\C1=CC=CC=C1	3447.3	Standard polar	33892256
(E,E)-Lansamide I	CN(\C=C/C1=CC=CC=C1)C(=O)\C=C\C1=CC=CC=C1	2181.2	Standard non polar	33892256
(E,E)-Lansamide I	CN(\C=C/C1=CC=CC=C1)C(=O)\C=C\C1=CC=CC=C1	2636.2	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 - (E,E)-Lansamide I GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-2930000000-4193845f583e7fc545f8	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (E,E)-Lansamide I 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 - (E,E)-Lansamide I 10V, Positive-QTOF	splash10-03di-0690000000-72f7154f3d439a4e17bb	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-Lansamide I 20V, Positive-QTOF	splash10-001i-0910000000-3eeabd56e65a77c1db34	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-Lansamide I 40V, Positive-QTOF	splash10-0udi-2900000000-987178a365a979a6c03e	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-Lansamide I 10V, Negative-QTOF	splash10-03di-0190000000-bbfaf1ca5fc139404b8e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-Lansamide I 20V, Negative-QTOF	splash10-03di-1960000000-4b87867be1ee9267e147	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-Lansamide I 40V, Negative-QTOF	splash10-0ffx-4900000000-1ba222bed5fb67af9357	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-Lansamide I 10V, Negative-QTOF	splash10-03di-0090000000-897fd6fd89cc6eff86e8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-Lansamide I 20V, Negative-QTOF	splash10-03di-1490000000-34bdf98d9cbe93665beb	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-Lansamide I 40V, Negative-QTOF	splash10-0imi-7980000000-d1759c5866e27b2daaf2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-Lansamide I 10V, Positive-QTOF	splash10-03di-0190000000-2283a69128d625fa7dbe	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-Lansamide I 20V, Positive-QTOF	splash10-0gx0-1920000000-cec26906d43365e98a51	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-Lansamide I 40V, Positive-QTOF	splash10-0uec-4900000000-b05a9148139d0aa30845	2021-09-24	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

FDB002008

KNApSAcK ID

C00056657

Chemspider ID

9532444

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11357517

PDB ID

Not Available

ChEBI ID

Not Available

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 (E,E)-Lansamide I (HMDB0030190)

MOL for HMDB0030190 ((E,E)-Lansamide I)

3D MOL for HMDB0030190 ((E,E)-Lansamide I)

3D SDF for HMDB0030190 ((E,E)-Lansamide I)

3D-SDF for HMDB0030190 ((E,E)-Lansamide I)

PDB for HMDB0030190 ((E,E)-Lansamide I)

3D PDB for HMDB0030190 ((E,E)-Lansamide I)

SMILES for HMDB0030190 ((E,E)-Lansamide I)

INCHI for HMDB0030190 ((E,E)-Lansamide I)

Structure for HMDB0030190 ((E,E)-Lansamide I)

3D Structure for HMDB0030190 ((E,E)-Lansamide I)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra