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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:34:59 UTC

Update Date

2022-03-07 02:54:12 UTC

HMDB ID

HMDB0034684

Secondary Accession Numbers

HMDB34684

Metabolite Identification

Common Name

Thalictroidine

Description

Thalictroidine belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. Thalictroidine has been detected, but not quantified in, a few different foods, such as arabica coffees (Coffea arabica), coffee and coffee products, and robusta coffees (Coffea canephora). This could make thalictroidine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Thalictroidine.

Structure

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

HMDB0034684
     RDKit          3D
Thalictroidine
 36 37  0  0  0  0  0  0  0  0999 V2000
   -2.4579    2.0565   -0.6570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2303    0.6569   -0.7395 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3807   -0.1701   -0.8704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0345   -0.3535    0.4547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0679   -0.8422    1.4671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6517   -1.0051    0.9680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2071    0.1241    0.0992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0794   -0.3499   -0.8345 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0250   -0.9278   -0.0972 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8525   -1.8865    0.7400 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3887   -0.4734   -0.2435 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6800    0.5623   -1.0914 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9817    1.0463   -1.2535 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9786    0.4430   -0.5273 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2933    0.9013   -0.6650 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7142   -0.5986    0.3292 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4316   -1.0501    0.4684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8735    2.4102    0.3117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0739    2.3697   -1.5221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4856    2.5818   -0.7727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0380   -1.1665   -1.2342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0812    0.3073   -1.5893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4394    0.6350    0.7926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8999   -1.0698    0.3249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3825   -1.8467    1.8561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0761   -0.1824    2.3796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5117   -1.9515    0.4234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0238   -1.0757    1.8904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7826    0.9194    0.7835 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1316    0.5131   -1.4754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5957   -1.0889   -1.5030 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9314    1.0892   -1.6971 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1771    1.8712   -1.9331 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0360    0.4735   -0.1449 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5538   -1.0469    0.8894 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1980   -1.8752    1.1357 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  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
  7  2  1  0
 17 11  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
 12 32  1  0
 13 33  1  0
 15 34  1  0
 16 35  1  0
 17 36  1  0
M  END


  Mrv0541 05061308002D          

 17 18  0  0  0  0            999 V2000
   -2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  4  2  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  2  0  0  0  0
  9  3  1  0  0  0  0
 11  5  2  0  0  0  0
 11  6  1  0  0  0  0
 12  4  1  0  0  0  0
 12 10  1  0  0  0  0
 13  7  2  0  0  0  0
 13  8  1  0  0  0  0
 14 10  1  0  0  0  0
 14 11  1  0  0  0  0
 15  1  1  0  0  0  0
 15  9  1  0  0  0  0
 15 12  1  0  0  0  0
 16 13  1  0  0  0  0
 17 14  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034684

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1CCCCC1CC(=O)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H19NO2/c1-15-9-3-2-4-12(15)10-14(17)11-5-7-13(16)8-6-11/h5-8,12,16H,2-4,9-10H2,1H3

> <INCHI_KEY>
DZUIOQIFAIDHJH-UHFFFAOYSA-N

> <FORMULA>
C14H19NO2

> <MOLECULAR_WEIGHT>
233.3062

> <EXACT_MASS>
233.141578857

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
26.136238452505864

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(4-hydroxyphenyl)-2-(1-methylpiperidin-2-yl)ethan-1-one

> <ALOGPS_LOGP>
1.79

> <JCHEM_LOGP>
1.3069734296387283

> <ALOGPS_LOGS>
-1.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
16.59801322673887

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.500030124943278

> <JCHEM_PKA_STRONGEST_BASIC>
8.65412836885498

> <JCHEM_POLAR_SURFACE_AREA>
40.54

> <JCHEM_REFRACTIVITY>
68.3823

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.03e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-(4-hydroxyphenyl)-2-(1-methylpiperidin-2-yl)ethanone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034684
     RDKit          3D
Thalictroidine
 36 37  0  0  0  0  0  0  0  0999 V2000
   -2.4579    2.0565   -0.6570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2303    0.6569   -0.7395 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3807   -0.1701   -0.8704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0345   -0.3535    0.4547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0679   -0.8422    1.4671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6517   -1.0051    0.9680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2071    0.1241    0.0992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0794   -0.3499   -0.8345 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0250   -0.9278   -0.0972 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8525   -1.8865    0.7400 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3887   -0.4734   -0.2435 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6800    0.5623   -1.0914 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9817    1.0463   -1.2535 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9786    0.4430   -0.5273 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2933    0.9013   -0.6650 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7142   -0.5986    0.3292 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4316   -1.0501    0.4684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8735    2.4102    0.3117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0739    2.3697   -1.5221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4856    2.5818   -0.7727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0380   -1.1665   -1.2342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0812    0.3073   -1.5893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4394    0.6350    0.7926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8999   -1.0698    0.3249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3825   -1.8467    1.8561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0761   -0.1824    2.3796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5117   -1.9515    0.4234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0238   -1.0757    1.8904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7826    0.9194    0.7835 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1316    0.5131   -1.4754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5957   -1.0889   -1.5030 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9314    1.0892   -1.6971 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1771    1.8712   -1.9331 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0360    0.4735   -0.1449 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5538   -1.0469    0.8894 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1980   -1.8752    1.1357 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  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
  7  2  1  0
 17 11  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
 12 32  1  0
 13 33  1  0
 15 34  1  0
 16 35  1  0
 17 36  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      -4.001   8.470   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -8.002  10.780   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -9.336   8.470   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -9.336  11.550   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -10.669   9.240   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -6.668   6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -8.002   9.240   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.335   6.160   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -10.669  10.780   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -6.668   8.470   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0      -4.001   6.930   0.000  0.00  0.00           N+0
HETATM   16  O   UNK     0     -12.003  11.550   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -5.335   9.240   0.000  0.00  0.00           O+0
CONECT    1   15                                                            
CONECT    2    3    4                                                       
CONECT    3    2    9                                                       
CONECT    4    2   12                                                       
CONECT    5    7   11                                                       
CONECT    6    8   11                                                       
CONECT    7    5   13                                                       
CONECT    8    6   13                                                       
CONECT    9    3   15                                                       
CONECT   10   12   14                                                       
CONECT   11    5    6   14                                                  
CONECT   12    4   10   15                                                  
CONECT   13    7    8   16                                                  
CONECT   14   10   11   17                                                  
CONECT   15    1    9   12                                                  
CONECT   16   13                                                            
CONECT   17   14                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0034684
HETATM    1  C1  UNL     1      -2.458   2.056  -0.657  1.00  0.00           C  
HETATM    2  N1  UNL     1      -2.230   0.657  -0.739  1.00  0.00           N  
HETATM    3  C2  UNL     1      -3.381  -0.170  -0.870  1.00  0.00           C  
HETATM    4  C3  UNL     1      -4.034  -0.354   0.455  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.068  -0.842   1.467  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.652  -1.005   0.968  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.207   0.124   0.099  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.079  -0.350  -0.834  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.025  -0.928  -0.097  1.00  0.00           C  
HETATM   10  O1  UNL     1       0.852  -1.886   0.740  1.00  0.00           O  
HETATM   11  C9  UNL     1       2.389  -0.473  -0.243  1.00  0.00           C  
HETATM   12  C10 UNL     1       2.680   0.562  -1.091  1.00  0.00           C  
HETATM   13  C11 UNL     1       3.982   1.046  -1.254  1.00  0.00           C  
HETATM   14  C12 UNL     1       4.979   0.443  -0.527  1.00  0.00           C  
HETATM   15  O2  UNL     1       6.293   0.901  -0.665  1.00  0.00           O  
HETATM   16  C13 UNL     1       4.714  -0.599   0.329  1.00  0.00           C  
HETATM   17  C14 UNL     1       3.432  -1.050   0.468  1.00  0.00           C  
HETATM   18  H1  UNL     1      -2.874   2.410   0.312  1.00  0.00           H  
HETATM   19  H2  UNL     1      -3.074   2.370  -1.522  1.00  0.00           H  
HETATM   20  H3  UNL     1      -1.486   2.582  -0.773  1.00  0.00           H  
HETATM   21  H4  UNL     1      -3.038  -1.167  -1.234  1.00  0.00           H  
HETATM   22  H5  UNL     1      -4.081   0.307  -1.589  1.00  0.00           H  
HETATM   23  H6  UNL     1      -4.439   0.635   0.793  1.00  0.00           H  
HETATM   24  H7  UNL     1      -4.900  -1.070   0.325  1.00  0.00           H  
HETATM   25  H8  UNL     1      -3.383  -1.847   1.856  1.00  0.00           H  
HETATM   26  H9  UNL     1      -3.076  -0.182   2.380  1.00  0.00           H  
HETATM   27  H10 UNL     1      -1.512  -1.951   0.423  1.00  0.00           H  
HETATM   28  H11 UNL     1      -1.024  -1.076   1.890  1.00  0.00           H  
HETATM   29  H12 UNL     1      -0.783   0.919   0.784  1.00  0.00           H  
HETATM   30  H13 UNL     1       0.132   0.513  -1.475  1.00  0.00           H  
HETATM   31  H14 UNL     1      -0.596  -1.089  -1.503  1.00  0.00           H  
HETATM   32  H15 UNL     1       1.931   1.089  -1.697  1.00  0.00           H  
HETATM   33  H16 UNL     1       4.177   1.871  -1.933  1.00  0.00           H  
HETATM   34  H17 UNL     1       7.036   0.474  -0.145  1.00  0.00           H  
HETATM   35  H18 UNL     1       5.554  -1.047   0.889  1.00  0.00           H  
HETATM   36  H19 UNL     1       3.198  -1.875   1.136  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    7
CONECT    3    4   21   22
CONECT    4    5   23   24
CONECT    5    6   25   26
CONECT    6    7   27   28
CONECT    7    8   29
CONECT    8    9   30   31
CONECT    9   10   10   11
CONECT   11   12   12   17
CONECT   12   13   32
CONECT   13   14   14   33
CONECT   14   15   16
CONECT   15   34
CONECT   16   17   17   35
CONECT   17   36
END

HMDB0034684
     RDKit          3D
Thalictroidine
 36 37  0  0  0  0  0  0  0  0999 V2000
   -2.4579    2.0565   -0.6570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2303    0.6569   -0.7395 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3807   -0.1701   -0.8704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0345   -0.3535    0.4547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0679   -0.8422    1.4671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6517   -1.0051    0.9680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2071    0.1241    0.0992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0794   -0.3499   -0.8345 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0250   -0.9278   -0.0972 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8525   -1.8865    0.7400 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3887   -0.4734   -0.2435 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6800    0.5623   -1.0914 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9817    1.0463   -1.2535 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9786    0.4430   -0.5273 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2933    0.9013   -0.6650 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7142   -0.5986    0.3292 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4316   -1.0501    0.4684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8735    2.4102    0.3117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0739    2.3697   -1.5221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4856    2.5818   -0.7727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0380   -1.1665   -1.2342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0812    0.3073   -1.5893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4394    0.6350    0.7926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8999   -1.0698    0.3249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3825   -1.8467    1.8561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0761   -0.1824    2.3796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5117   -1.9515    0.4234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0238   -1.0757    1.8904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7826    0.9194    0.7835 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1316    0.5131   -1.4754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5957   -1.0889   -1.5030 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9314    1.0892   -1.6971 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1771    1.8712   -1.9331 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0360    0.4735   -0.1449 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5538   -1.0469    0.8894 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1980   -1.8752    1.1357 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  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
  7  2  1  0
 17 11  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
 12 32  1  0
 13 33  1  0
 15 34  1  0
 16 35  1  0
 17 36  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
4'-Hydroxy-2-(1-methylpiperidin-2-yl)acetophenone	HMDB

Chemical Formula

C₁₄H₁₉NO₂

Average Molecular Weight

233.3062

Monoisotopic Molecular Weight

233.141578857

IUPAC Name

1-(4-hydroxyphenyl)-2-(1-methylpiperidin-2-yl)ethan-1-one

Traditional Name

1-(4-hydroxyphenyl)-2-(1-methylpiperidin-2-yl)ethanone

CAS Registry Number

248259-06-5

SMILES

CN1CCCCC1CC(=O)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C14H19NO2/c1-15-9-3-2-4-12(15)10-14(17)11-5-7-13(16)8-6-11/h5-8,12,16H,2-4,9-10H2,1H3

InChI Key

DZUIOQIFAIDHJH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Benzoyl
Aryl alkyl ketone
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Beta-aminoketone
Piperidine
Benzenoid
Tertiary aliphatic amine
Tertiary amine
Organoheterocyclic compound
Azacycle
Organic nitrogen compound
Amine
Organopnictogen compound
Organonitrogen compound
Organic oxide
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0034684)
Cytoplasm (HMDB: HMDB0034684)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034684)

Source

Exogenous

Food

Food (HMDB: HMDB0034684)

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Coffee and coffee products (FooDB: FOOD00861)

Endogenous

Plant

Coffea (HMDB: HMDB0034684)

Not Available

Nutrient (HMDB: HMDB0034684)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	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	4.03 g/L	ALOGPS
logP	1.79	ALOGPS
logP	1.31	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	7.5	ChemAxon
pKa (Strongest Basic)	8.65	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	40.54 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	68.38 m³·mol⁻¹	ChemAxon
Polarizability	26.14 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	156.055	31661259
DarkChem	[M-H]-	155.836	31661259
DeepCCS	[M+H]+	155.624	30932474
DeepCCS	[M-H]-	153.266	30932474
DeepCCS	[M-2H]-	187.234	30932474
DeepCCS	[M+Na]+	162.479	30932474
AllCCS	[M+H]+	155.9	32859911
AllCCS	[M+H-H2O]+	151.8	32859911
AllCCS	[M+NH4]+	159.7	32859911
AllCCS	[M+Na]+	160.8	32859911
AllCCS	[M-H]-	161.1	32859911
AllCCS	[M+Na-2H]-	161.4	32859911
AllCCS	[M+HCOO]-	161.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Thalictroidine	CN1CCCCC1CC(=O)C1=CC=C(O)C=C1	2915.1	Standard polar	33892256
Thalictroidine	CN1CCCCC1CC(=O)C1=CC=C(O)C=C1	2091.2	Standard non polar	33892256
Thalictroidine	CN1CCCCC1CC(=O)C1=CC=C(O)C=C1	2170.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Thalictroidine,1TMS,isomer #1	CN1CCCCC1CC(=O)C1=CC=C(O[Si](C)(C)C)C=C1	2093.1	Semi standard non polar	33892256
Thalictroidine,1TBDMS,isomer #1	CN1CCCCC1CC(=O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	2355.5	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 - Thalictroidine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0092-9110000000-ce14d0087734c41b1da2	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Thalictroidine GC-MS (1 TMS) - 70eV, Positive	splash10-0007-9230000000-0637af8e5ddc22ceae8c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Thalictroidine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Thalictroidine 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 - Thalictroidine 10V, Negative-QTOF	splash10-001i-0090000000-d307898c484ff22e47f8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thalictroidine 20V, Negative-QTOF	splash10-001i-2290000000-97b346e8ca0e22f577ff	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thalictroidine 40V, Negative-QTOF	splash10-00ko-9830000000-731d0ebdaf3be00532bc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thalictroidine 10V, Negative-QTOF	splash10-001i-0090000000-9dcf26b75789781b52de	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thalictroidine 20V, Negative-QTOF	splash10-001r-4690000000-51e7eae1dd0da9d5b912	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thalictroidine 40V, Negative-QTOF	splash10-0006-9810000000-faf3e823b95a413080ee	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thalictroidine 10V, Positive-QTOF	splash10-001i-0190000000-25032eec989bffab2e3c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thalictroidine 20V, Positive-QTOF	splash10-00dj-5920000000-2173a4db2d66e3f3530e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thalictroidine 40V, Positive-QTOF	splash10-00dl-9600000000-8ddec635e70825d180ad	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thalictroidine 10V, Positive-QTOF	splash10-001j-5090000000-1d8da3c37c75daaa83a6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thalictroidine 20V, Positive-QTOF	splash10-000t-9540000000-45df9b131087180cb82a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thalictroidine 40V, Positive-QTOF	splash10-0002-9100000000-a7e9306bf1bcef347a28	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB013213

KNApSAcK ID

C00049539

Chemspider ID

8665237

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10489834

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 Thalictroidine (HMDB0034684)

MOL for HMDB0034684 (Thalictroidine)

3D MOL for HMDB0034684 (Thalictroidine)

3D SDF for HMDB0034684 (Thalictroidine)

3D-SDF for HMDB0034684 (Thalictroidine)

PDB for HMDB0034684 (Thalictroidine)

3D PDB for HMDB0034684 (Thalictroidine)

SMILES for HMDB0034684 (Thalictroidine)

INCHI for HMDB0034684 (Thalictroidine)

Structure for HMDB0034684 (Thalictroidine)

3D Structure for HMDB0034684 (Thalictroidine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra