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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:30:02 UTC

Update Date

2022-03-07 02:52:08 UTC

HMDB ID

HMDB0029374

Secondary Accession Numbers

HMDB29374

Metabolite Identification

Common Name

(E,E)-Trichostachine

Description

(E,E)-Trichostachine, also known as 1-piperoylpyrrolidine, belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms (E,E)-Trichostachine has been detected, but not quantified in, herbs and spices and pepper (spice). This could make (e,e)-trichostachine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (E,E)-Trichostachine.

Structure

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

HMDB0029374
     RDKit          3D
(E,E)-Trichostachine
 37 39  0  0  0  0  0  0  0  0999 V2000
   -3.4793   -2.7592    0.2176 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9714   -1.5517    0.1089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5437   -1.4681    0.1209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8239   -0.4013    0.0202 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6549   -0.4667    0.0491 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3797    0.6267   -0.0542 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8308    0.5514   -0.0247 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5676    1.7396   -0.1377 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9451    1.7402   -0.1172 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6686    0.5741    0.0153 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9619   -0.6016    0.1275 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5613   -0.6017    0.1066 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9103   -1.6079    0.2467 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1922   -1.1409   -0.1328 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0277    0.2659    0.0678 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9307   -0.5135   -0.0045 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3772   -0.8225   -0.0209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9828    0.3641   -0.7489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1586    1.4816   -0.1598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7708    0.8897   -0.1100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9871   -2.4210    0.2283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2575    0.5481   -0.0900 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0831   -1.4458    0.1578 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8644    1.5776   -0.1612 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9943    2.6590   -0.2422 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5016    2.6692   -0.2058 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0572   -1.5405    0.1970 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4730   -1.3952   -1.1532 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9054   -1.5685    0.6211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5277   -1.7725   -0.5276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8007   -0.8485    0.9942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7601    0.2282   -1.8275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0523    0.4643   -0.5215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4981    1.6439    0.8894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2022    2.4071   -0.7681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2548    1.1620   -1.0647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2000    1.3348    0.7493 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
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
  2 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 12  7  1  0
 20 16  1  0
 15 10  1  0
  3 21  1  0
  4 22  1  0
  5 23  1  0
  6 24  1  0
  8 25  1  0
  9 26  1  0
 12 27  1  0
 14 28  1  0
 14 29  1  0
 17 30  1  0
 17 31  1  0
 18 32  1  0
 18 33  1  0
 19 34  1  0
 19 35  1  0
 20 36  1  0
 20 37  1  0
M  END


  Mrv0541 02241212512D          

 20 22  0  0  0  0            999 V2000
    1.3069    3.3822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0214    3.7947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7359    3.3822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4503    3.7947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1648    3.3822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8793    3.7947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5937    3.3822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3082    3.7947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0227    3.3822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0227    2.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6358    2.0051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3002    1.2515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4797    1.3377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3082    2.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5937    2.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0214    4.6197    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6888    5.1046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4339    5.8892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6089    5.8892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3540    5.1046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 10 14  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
  7 15  1  0  0  0  0
  2 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 20  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029374

> <DATABASE_NAME>
hmdb

> <SMILES>
O=C(\C=C\C=C\C1=CC=C2OCOC2=C1)N1CCCC1

> <INCHI_IDENTIFIER>
InChI=1S/C16H17NO3/c18-16(17-9-3-4-10-17)6-2-1-5-13-7-8-14-15(11-13)20-12-19-14/h1-2,5-8,11H,3-4,9-10,12H2/b5-1+,6-2+

> <INCHI_KEY>
GQIJYUMTOUBHSH-IJIVKGSJSA-N

> <FORMULA>
C16H17NO3

> <MOLECULAR_WEIGHT>
271.3111

> <EXACT_MASS>
271.120843415

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
29.955589395088925

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,4E)-5-(2H-1,3-benzodioxol-5-yl)-1-(pyrrolidin-1-yl)penta-2,4-dien-1-one

> <ALOGPS_LOGP>
3.01

> <JCHEM_LOGP>
2.332742385333334

> <ALOGPS_LOGS>
-2.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
2.06823807404301

> <JCHEM_POLAR_SURFACE_AREA>
38.77

> <JCHEM_REFRACTIVITY>
78.30199999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.35e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
trichostachine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0029374
     RDKit          3D
(E,E)-Trichostachine
 37 39  0  0  0  0  0  0  0  0999 V2000
   -3.4793   -2.7592    0.2176 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9714   -1.5517    0.1089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5437   -1.4681    0.1209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8239   -0.4013    0.0202 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6549   -0.4667    0.0491 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3797    0.6267   -0.0542 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8308    0.5514   -0.0247 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5676    1.7396   -0.1377 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9451    1.7402   -0.1172 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6686    0.5741    0.0153 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9619   -0.6016    0.1275 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5613   -0.6017    0.1066 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9103   -1.6079    0.2467 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1922   -1.1409   -0.1328 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0277    0.2659    0.0678 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9307   -0.5135   -0.0045 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3772   -0.8225   -0.0209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9828    0.3641   -0.7489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1586    1.4816   -0.1598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7708    0.8897   -0.1100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9871   -2.4210    0.2283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2575    0.5481   -0.0900 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0831   -1.4458    0.1578 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8644    1.5776   -0.1612 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9943    2.6590   -0.2422 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5016    2.6692   -0.2058 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0572   -1.5405    0.1970 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4730   -1.3952   -1.1532 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9054   -1.5685    0.6211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5277   -1.7725   -0.5276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8007   -0.8485    0.9942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7601    0.2282   -1.8275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0523    0.4643   -0.5215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4981    1.6439    0.8894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2022    2.4071   -0.7681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2548    1.1620   -1.0647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2000    1.3348    0.7493 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
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
  2 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 12  7  1  0
 20 16  1  0
 15 10  1  0
  3 21  1  0
  4 22  1  0
  5 23  1  0
  6 24  1  0
  8 25  1  0
  9 26  1  0
 12 27  1  0
 14 28  1  0
 14 29  1  0
 17 30  1  0
 17 31  1  0
 18 32  1  0
 18 33  1  0
 19 34  1  0
 19 35  1  0
 20 36  1  0
 20 37  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  O   UNK     0       2.440   6.313   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.773   7.083   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.107   6.313   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.441   7.083   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.774   6.313   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.108   7.083   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.442   6.313   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.775   7.083   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.109   6.313   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.109   4.773   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      14.253   3.743   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      13.627   2.336   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      12.095   2.497   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      11.775   4.003   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.442   4.773   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       3.773   8.623   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       5.019   9.529   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.543  10.993   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.003  10.993   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.527   9.529   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   15                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   14                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   10   13   15                                                  
CONECT   15   14    7                                                       
CONECT   16    2   17   20                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   16   19                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0029374
HETATM    1  O1  UNL     1      -3.479  -2.759   0.218  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.971  -1.552   0.109  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.544  -1.468   0.121  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.824  -0.401   0.020  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.655  -0.467   0.049  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.380   0.627  -0.054  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.831   0.551  -0.025  1.00  0.00           C  
HETATM    8  C7  UNL     1       3.568   1.740  -0.138  1.00  0.00           C  
HETATM    9  C8  UNL     1       4.945   1.740  -0.117  1.00  0.00           C  
HETATM   10  C9  UNL     1       5.669   0.574   0.015  1.00  0.00           C  
HETATM   11  C10 UNL     1       4.962  -0.602   0.127  1.00  0.00           C  
HETATM   12  C11 UNL     1       3.561  -0.602   0.107  1.00  0.00           C  
HETATM   13  O2  UNL     1       5.910  -1.608   0.247  1.00  0.00           O  
HETATM   14  C12 UNL     1       7.192  -1.141  -0.133  1.00  0.00           C  
HETATM   15  O3  UNL     1       7.028   0.266   0.068  1.00  0.00           O  
HETATM   16  N1  UNL     1      -3.931  -0.514  -0.005  1.00  0.00           N  
HETATM   17  C13 UNL     1      -5.377  -0.823  -0.021  1.00  0.00           C  
HETATM   18  C14 UNL     1      -5.983   0.364  -0.749  1.00  0.00           C  
HETATM   19  C15 UNL     1      -5.159   1.482  -0.160  1.00  0.00           C  
HETATM   20  C16 UNL     1      -3.771   0.890  -0.110  1.00  0.00           C  
HETATM   21  H1  UNL     1      -0.987  -2.421   0.228  1.00  0.00           H  
HETATM   22  H2  UNL     1      -1.257   0.548  -0.090  1.00  0.00           H  
HETATM   23  H3  UNL     1       1.083  -1.446   0.158  1.00  0.00           H  
HETATM   24  H4  UNL     1       0.864   1.578  -0.161  1.00  0.00           H  
HETATM   25  H5  UNL     1       2.994   2.659  -0.242  1.00  0.00           H  
HETATM   26  H6  UNL     1       5.502   2.669  -0.206  1.00  0.00           H  
HETATM   27  H7  UNL     1       3.057  -1.540   0.197  1.00  0.00           H  
HETATM   28  H8  UNL     1       7.473  -1.395  -1.153  1.00  0.00           H  
HETATM   29  H9  UNL     1       7.905  -1.569   0.621  1.00  0.00           H  
HETATM   30  H10 UNL     1      -5.528  -1.772  -0.528  1.00  0.00           H  
HETATM   31  H11 UNL     1      -5.801  -0.849   0.994  1.00  0.00           H  
HETATM   32  H12 UNL     1      -5.760   0.228  -1.827  1.00  0.00           H  
HETATM   33  H13 UNL     1      -7.052   0.464  -0.522  1.00  0.00           H  
HETATM   34  H14 UNL     1      -5.498   1.644   0.889  1.00  0.00           H  
HETATM   35  H15 UNL     1      -5.202   2.407  -0.768  1.00  0.00           H  
HETATM   36  H16 UNL     1      -3.255   1.162  -1.065  1.00  0.00           H  
HETATM   37  H17 UNL     1      -3.200   1.335   0.749  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   16
CONECT    3    4    4   21
CONECT    4    5   22
CONECT    5    6    6   23
CONECT    6    7   24
CONECT    7    8    8   12
CONECT    8    9   25
CONECT    9   10   10   26
CONECT   10   11   15
CONECT   11   12   12   13
CONECT   12   27
CONECT   13   14
CONECT   14   15   28   29
CONECT   16   17   20
CONECT   17   18   30   31
CONECT   18   19   32   33
CONECT   19   20   34   35
CONECT   20   36   37
END

HMDB0029374
     RDKit          3D
(E,E)-Trichostachine
 37 39  0  0  0  0  0  0  0  0999 V2000
   -3.4793   -2.7592    0.2176 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9714   -1.5517    0.1089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5437   -1.4681    0.1209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8239   -0.4013    0.0202 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6549   -0.4667    0.0491 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3797    0.6267   -0.0542 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8308    0.5514   -0.0247 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5676    1.7396   -0.1377 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9451    1.7402   -0.1172 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6686    0.5741    0.0153 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9619   -0.6016    0.1275 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5613   -0.6017    0.1066 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9103   -1.6079    0.2467 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1922   -1.1409   -0.1328 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0277    0.2659    0.0678 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9307   -0.5135   -0.0045 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3772   -0.8225   -0.0209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9828    0.3641   -0.7489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1586    1.4816   -0.1598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7708    0.8897   -0.1100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9871   -2.4210    0.2283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2575    0.5481   -0.0900 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0831   -1.4458    0.1578 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8644    1.5776   -0.1612 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9943    2.6590   -0.2422 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5016    2.6692   -0.2058 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0572   -1.5405    0.1970 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4730   -1.3952   -1.1532 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9054   -1.5685    0.6211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5277   -1.7725   -0.5276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8007   -0.8485    0.9942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7601    0.2282   -1.8275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0523    0.4643   -0.5215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4981    1.6439    0.8894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2022    2.4071   -0.7681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2548    1.1620   -1.0647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2000    1.3348    0.7493 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
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
  2 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 12  7  1  0
 20 16  1  0
 15 10  1  0
  3 21  1  0
  4 22  1  0
  5 23  1  0
  6 24  1  0
  8 25  1  0
  9 26  1  0
 12 27  1  0
 14 28  1  0
 14 29  1  0
 17 30  1  0
 17 31  1  0
 18 32  1  0
 18 33  1  0
 19 34  1  0
 19 35  1  0
 20 36  1  0
 20 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Trichostachine	Kegg
(2E,4E)-5-(1,3-Benzodioxol-5-yl)-1-(1-pyrrolidinyl)-2,4-pentadien-1-one	MeSH
1-Piperoylpyrrolidine	MeSH
1-Piperoyl-(e,e)-pyrrolidine	HMDB

Chemical Formula

C₁₆H₁₇NO₃

Average Molecular Weight

271.3111

Monoisotopic Molecular Weight

271.120843415

IUPAC Name

(2E,4E)-5-(2H-1,3-benzodioxol-5-yl)-1-(pyrrolidin-1-yl)penta-2,4-dien-1-one

Traditional Name

trichostachine

CAS Registry Number

25924-78-1

SMILES

O=C(\C=C\C=C\C1=CC=C2OCOC2=C1)N1CCCC1

InChI Identifier

InChI=1S/C16H17NO3/c18-16(17-9-3-4-10-17)6-2-1-5-13-7-8-14-15(11-13)20-12-19-14/h1-2,5-8,11H,3-4,9-10,12H2/b5-1+,6-2+

InChI Key

GQIJYUMTOUBHSH-IJIVKGSJSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodioxoles

Sub Class

Not Available

Direct Parent

Benzodioxoles

Alternative Parents

Substituents

Benzodioxole
N-acylpyrrolidine
Styrene
Benzenoid
Pyrrolidine
Tertiary carboxylic acid amide
Carboxamide group
Acetal
Carboxylic acid derivative
Oxacycle
Azacycle
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organic nitrogen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

benzodioxoles (CHEBI:9691 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0029374)
Cell membrane (HMDB: HMDB0029374)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0029374)

Source

Endogenous

Endogenous (HMDB: HMDB0029374)

Plant

Plant (HMDB: HMDB0029374)

Exogenous

Food

Food (HMDB: HMDB0029374)

Herb and spice

Spice

Pepper (Spice) (FooDB: FOOD00139)

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0029374)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	143 - 145 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	33.37 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	0.44 g/L	ALOGPS
logP	3.01	ALOGPS
logP	2.33	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Basic)	2.07	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	38.77 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	78.3 m³·mol⁻¹	ChemAxon
Polarizability	29.96 Å³	ChemAxon
Number of Rings	3	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]+	167.386	31661259
DarkChem	[M-H]-	166.79	31661259
DeepCCS	[M+H]+	163.784	30932474
DeepCCS	[M-H]-	161.426	30932474
DeepCCS	[M-2H]-	194.473	30932474
DeepCCS	[M+Na]+	169.878	30932474
AllCCS	[M+H]+	164.4	32859911
AllCCS	[M+H-H2O]+	160.6	32859911
AllCCS	[M+NH4]+	167.9	32859911
AllCCS	[M+Na]+	168.9	32859911
AllCCS	[M-H]-	169.0	32859911
AllCCS	[M+Na-2H]-	168.8	32859911
AllCCS	[M+HCOO]-	168.7	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.	6.96 minutes	32390414
Predicted by Siyang on May 30, 2022	14.8026 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.3 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	24.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2269.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	382.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	187.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	216.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	209.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	586.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	614.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	114.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1323.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	456.2 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	1463.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	425.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	410.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	352.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	341.1 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	8.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(E,E)-Trichostachine	O=C(\C=C\C=C\C1=CC=C2OCOC2=C1)N1CCCC1	3726.3	Standard polar	33892256
(E,E)-Trichostachine	O=C(\C=C\C=C\C1=CC=C2OCOC2=C1)N1CCCC1	2516.7	Standard non polar	33892256
(E,E)-Trichostachine	O=C(\C=C\C=C\C1=CC=C2OCOC2=C1)N1CCCC1	2843.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - (E,E)-Trichostachine EI-B (Non-derivatized)	splash10-0fk9-0290000000-e92fc9516c43a7ad9514	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - (E,E)-Trichostachine EI-B (Non-derivatized)	splash10-0fk9-0290000000-e92fc9516c43a7ad9514	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (E,E)-Trichostachine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fkc-5390000000-7bfda9369e555bb06d54	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (E,E)-Trichostachine 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - (E,E)-Trichostachine LC-ESI-qTof , Positive-QTOF	splash10-0udi-0950000000-9f2d88b978f2237a85eb	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (E,E)-Trichostachine , positive-QTOF	splash10-0udi-0950000000-9f2d88b978f2237a85eb	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-Trichostachine 10V, Positive-QTOF	splash10-00di-2290000000-76c18ea5a1e2c576a5c6	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-Trichostachine 20V, Positive-QTOF	splash10-00di-7970000000-51fe56f246b2ec5bcfd4	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-Trichostachine 40V, Positive-QTOF	splash10-00dl-9400000000-afe354c3cddf61b9ca10	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-Trichostachine 10V, Negative-QTOF	splash10-00di-0090000000-f50f2646b634026f3fce	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-Trichostachine 20V, Negative-QTOF	splash10-00di-7390000000-37c90a22e5a28a53acdc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-Trichostachine 40V, Negative-QTOF	splash10-00di-9200000000-f330d100a34c7f7d5f46	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-Trichostachine 10V, Positive-QTOF	splash10-00di-0090000000-0ebdc69de0cc3f27706a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-Trichostachine 20V, Positive-QTOF	splash10-00di-1490000000-41beceda8fe1f339c740	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-Trichostachine 40V, Positive-QTOF	splash10-00dr-6920000000-1c0a5bf853f9d1356bb8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-Trichostachine 10V, Negative-QTOF	splash10-00di-0090000000-19dbfadd3d4c17868278	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-Trichostachine 20V, Negative-QTOF	splash10-00di-0290000000-6470a49610102798f868	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-Trichostachine 40V, Negative-QTOF	splash10-014m-0590000000-1f0196154dc55f844b03	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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

636537

PDB ID

Not Available

ChEBI ID

715057

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1628131

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)-Trichostachine (HMDB0029374)

MOL for HMDB0029374 ((E,E)-Trichostachine)

3D MOL for HMDB0029374 ((E,E)-Trichostachine)

3D SDF for HMDB0029374 ((E,E)-Trichostachine)

3D-SDF for HMDB0029374 ((E,E)-Trichostachine)

PDB for HMDB0029374 ((E,E)-Trichostachine)

3D PDB for HMDB0029374 ((E,E)-Trichostachine)

SMILES for HMDB0029374 ((E,E)-Trichostachine)

INCHI for HMDB0029374 ((E,E)-Trichostachine)

Structure for HMDB0029374 ((E,E)-Trichostachine)

3D Structure for HMDB0029374 ((E,E)-Trichostachine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra