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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:51:54 UTC

Update Date

2022-03-07 02:53:28 UTC

HMDB ID

HMDB0032800

Secondary Accession Numbers

HMDB32800

Metabolite Identification

Common Name

Feruloylcholine

Description

Feruloylcholine belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. Based on a literature review very few articles have been published on Feruloylcholine.

Structure

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

HMDB0032800
     RDKit          3D
Feruloylcholine
 42 42  0  0  0  0  0  0  0  0999 V2000
    5.9042   -2.1565   -0.6271 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3378   -0.8864   -0.1915 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3801    0.0990    0.0013 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0391   -0.1359   -0.2207 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0672    0.8330   -0.0346 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6596    0.5399   -0.2818 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6795    1.3982   -0.1302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7249    1.0494   -0.3940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5809    1.9559   -0.2138 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0991   -0.2025   -0.8175 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4478   -0.4935   -1.0510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2280   -0.3650    0.2083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6417   -0.6592    0.0240 N   0  0  0  0  0  4  0  0  0  0  0  0
   -5.2903   -0.3205    1.2932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1459    0.2525   -0.9886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8852   -2.0259   -0.3215 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5201    2.0638    0.3913 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8604    2.3362    0.6246 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8042    1.3496    0.4299 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1560    1.5541    0.6439 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7836   -2.8589   -0.6025 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4845   -2.0826   -1.6556 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1120   -2.5805    0.0187 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7526   -1.1404   -0.5589 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3948   -0.4492   -0.6129 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9036    2.3929    0.1981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5994   -1.4631   -1.5692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8310    0.2930   -1.7620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8182   -1.1105    0.9337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1609    0.6048    0.6780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9315    0.7155    1.5338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8384   -0.9746    2.0613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3800   -0.3899    1.2375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5900    1.1959   -1.0220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2021    0.5005   -0.7594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0485   -0.2713   -1.9762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0155   -2.6797   -0.2631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2906   -2.0534   -1.3572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6697   -2.4434    0.3474 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8380    2.8682    0.5598 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2142    3.3059    0.9598 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5283    2.4346    0.9540 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  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 13 16  1  0
  5 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19  3  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  6 25  1  0
  7 26  1  0
 11 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 14 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 16 39  1  0
 17 40  1  0
 18 41  1  0
 20 42  1  0
M  CHG  1  13   1
M  END


  Mrv0541 05061306422D          

 20 20  0  0  0  0            999 V2000
   -1.4289   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2539   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  5  2  0  0  0  0
  8  6  2  0  0  0  0
 10  9  1  0  0  0  0
 12  5  1  0  0  0  0
 12  6  1  0  0  0  0
 12 11  2  0  0  0  0
 13  7  1  0  0  0  0
 14 11  1  0  0  0  0
 14 13  2  0  0  0  0
  8 15  1  0  0  0  0
 16  1  1  0  0  0  0
 16  2  1  0  0  0  0
 16  3  1  0  0  0  0
 16  9  1  0  0  0  0
 17 13  1  0  0  0  0
 18 15  2  0  0  0  0
 19  4  1  0  0  0  0
 19 14  1  0  0  0  0
 20 10  1  0  0  0  0
 20 15  1  0  0  0  0
M  CHG  1  16   1
M  END
> <DATABASE_ID>
HMDB0032800

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=CC(\C=C\C(=O)OCC[N+](C)(C)C)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H21NO4/c1-16(2,3)9-10-20-15(18)8-6-12-5-7-13(17)14(11-12)19-4/h5-8,11H,9-10H2,1-4H3/p+1

> <INCHI_KEY>
XHSNXOZZHHJDDX-UHFFFAOYSA-O

> <FORMULA>
C15H22NO4

> <MOLECULAR_WEIGHT>
280.3395

> <EXACT_MASS>
280.154883197

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
31.297192207876243

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}ethyl)trimethylazanium

> <ALOGPS_LOGP>
-1.21

> <JCHEM_LOGP>
-2.0896150321384113

> <ALOGPS_LOGS>
-4.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.867763751859222

> <JCHEM_PKA_STRONGEST_BASIC>
-4.888862772261203

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
90.2058

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.34e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}ethyl)trimethylazanium

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0032800
     RDKit          3D
Feruloylcholine
 42 42  0  0  0  0  0  0  0  0999 V2000
    5.9042   -2.1565   -0.6271 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3378   -0.8864   -0.1915 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3801    0.0990    0.0013 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0391   -0.1359   -0.2207 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0672    0.8330   -0.0346 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6596    0.5399   -0.2818 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6795    1.3982   -0.1302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7249    1.0494   -0.3940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5809    1.9559   -0.2138 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0991   -0.2025   -0.8175 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4478   -0.4935   -1.0510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2280   -0.3650    0.2083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6417   -0.6592    0.0240 N   0  0  0  0  0  4  0  0  0  0  0  0
   -5.2903   -0.3205    1.2932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1459    0.2525   -0.9886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8852   -2.0259   -0.3215 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5201    2.0638    0.3913 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8604    2.3362    0.6246 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8042    1.3496    0.4299 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1560    1.5541    0.6439 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7836   -2.8589   -0.6025 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4845   -2.0826   -1.6556 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1120   -2.5805    0.0187 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7526   -1.1404   -0.5589 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3948   -0.4492   -0.6129 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9036    2.3929    0.1981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5994   -1.4631   -1.5692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8310    0.2930   -1.7620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8182   -1.1105    0.9337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1609    0.6048    0.6780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9315    0.7155    1.5338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8384   -0.9746    2.0613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3800   -0.3899    1.2375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5900    1.1959   -1.0220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2021    0.5005   -0.7594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0485   -0.2713   -1.9762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0155   -2.6797   -0.2631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2906   -2.0534   -1.3572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6697   -2.4434    0.3474 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8380    2.8682    0.5598 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2142    3.3059    0.9598 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5283    2.4346    0.9540 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  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 13 16  1  0
  5 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19  3  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  6 25  1  0
  7 26  1  0
 11 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 14 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 16 39  1  0
 17 40  1  0
 18 41  1  0
 20 42  1  0
M  CHG  1  13   1
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 -10.780   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.127  -9.240   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.207  -9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      -2.667  -9.240   0.000  0.00  0.00           N+1
HETATM   17  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
CONECT    1   16                                                            
CONECT    2   16                                                            
CONECT    3   16                                                            
CONECT    4   19                                                            
CONECT    5    7   12                                                       
CONECT    6    8   12                                                       
CONECT    7    5   13                                                       
CONECT    8    6   15                                                       
CONECT    9   10   16                                                       
CONECT   10    9   20                                                       
CONECT   11   12   14                                                       
CONECT   12    5    6   11                                                  
CONECT   13    7   14   17                                                  
CONECT   14   11   13   19                                                  
CONECT   15    8   18   20                                                  
CONECT   16    1    2    3    9                                             
CONECT   17   13                                                            
CONECT   18   15                                                            
CONECT   19    4   14                                                       
CONECT   20   10   15                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

COMPND    HMDB0032800
HETATM    1  C1  UNL     1       5.904  -2.157  -0.627  1.00  0.00           C  
HETATM    2  O1  UNL     1       6.338  -0.886  -0.191  1.00  0.00           O  
HETATM    3  C2  UNL     1       5.380   0.099   0.001  1.00  0.00           C  
HETATM    4  C3  UNL     1       4.039  -0.136  -0.221  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.067   0.833  -0.035  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.660   0.540  -0.282  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.680   1.398  -0.130  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.725   1.049  -0.394  1.00  0.00           C  
HETATM    9  O2  UNL     1      -1.581   1.956  -0.214  1.00  0.00           O  
HETATM   10  O3  UNL     1      -1.099  -0.202  -0.818  1.00  0.00           O  
HETATM   11  C8  UNL     1      -2.448  -0.493  -1.051  1.00  0.00           C  
HETATM   12  C9  UNL     1      -3.228  -0.365   0.208  1.00  0.00           C  
HETATM   13  N1  UNL     1      -4.642  -0.659   0.024  1.00  0.00           N1+
HETATM   14  C10 UNL     1      -5.290  -0.320   1.293  1.00  0.00           C  
HETATM   15  C11 UNL     1      -5.146   0.253  -0.989  1.00  0.00           C  
HETATM   16  C12 UNL     1      -4.885  -2.026  -0.321  1.00  0.00           C  
HETATM   17  C13 UNL     1       3.520   2.064   0.391  1.00  0.00           C  
HETATM   18  C14 UNL     1       4.860   2.336   0.625  1.00  0.00           C  
HETATM   19  C15 UNL     1       5.804   1.350   0.430  1.00  0.00           C  
HETATM   20  O4  UNL     1       7.156   1.554   0.644  1.00  0.00           O  
HETATM   21  H1  UNL     1       6.784  -2.859  -0.603  1.00  0.00           H  
HETATM   22  H2  UNL     1       5.484  -2.083  -1.656  1.00  0.00           H  
HETATM   23  H3  UNL     1       5.112  -2.580   0.019  1.00  0.00           H  
HETATM   24  H4  UNL     1       3.753  -1.140  -0.559  1.00  0.00           H  
HETATM   25  H5  UNL     1       1.395  -0.449  -0.613  1.00  0.00           H  
HETATM   26  H6  UNL     1       0.904   2.393   0.198  1.00  0.00           H  
HETATM   27  H7  UNL     1      -2.599  -1.463  -1.569  1.00  0.00           H  
HETATM   28  H8  UNL     1      -2.831   0.293  -1.762  1.00  0.00           H  
HETATM   29  H9  UNL     1      -2.818  -1.110   0.934  1.00  0.00           H  
HETATM   30  H10 UNL     1      -3.161   0.605   0.678  1.00  0.00           H  
HETATM   31  H11 UNL     1      -4.932   0.715   1.534  1.00  0.00           H  
HETATM   32  H12 UNL     1      -4.838  -0.975   2.061  1.00  0.00           H  
HETATM   33  H13 UNL     1      -6.380  -0.390   1.238  1.00  0.00           H  
HETATM   34  H14 UNL     1      -4.590   1.196  -1.022  1.00  0.00           H  
HETATM   35  H15 UNL     1      -6.202   0.500  -0.759  1.00  0.00           H  
HETATM   36  H16 UNL     1      -5.049  -0.271  -1.976  1.00  0.00           H  
HETATM   37  H17 UNL     1      -4.015  -2.680  -0.263  1.00  0.00           H  
HETATM   38  H18 UNL     1      -5.291  -2.053  -1.357  1.00  0.00           H  
HETATM   39  H19 UNL     1      -5.670  -2.443   0.347  1.00  0.00           H  
HETATM   40  H20 UNL     1       2.838   2.868   0.560  1.00  0.00           H  
HETATM   41  H21 UNL     1       5.214   3.306   0.960  1.00  0.00           H  
HETATM   42  H22 UNL     1       7.528   2.435   0.954  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3
CONECT    3    4    4   19
CONECT    4    5   24
CONECT    5    6   17   17
CONECT    6    7    7   25
CONECT    7    8   26
CONECT    8    9    9   10
CONECT   10   11
CONECT   11   12   27   28
CONECT   12   13   29   30
CONECT   13   14   15   16
CONECT   14   31   32   33
CONECT   15   34   35   36
CONECT   16   37   38   39
CONECT   17   18   40
CONECT   18   19   19   41
CONECT   19   20
CONECT   20   42
END

HMDB0032800
     RDKit          3D
Feruloylcholine
 42 42  0  0  0  0  0  0  0  0999 V2000
    5.9042   -2.1565   -0.6271 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3378   -0.8864   -0.1915 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3801    0.0990    0.0013 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0391   -0.1359   -0.2207 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0672    0.8330   -0.0346 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6596    0.5399   -0.2818 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6795    1.3982   -0.1302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7249    1.0494   -0.3940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5809    1.9559   -0.2138 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0991   -0.2025   -0.8175 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4478   -0.4935   -1.0510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2280   -0.3650    0.2083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6417   -0.6592    0.0240 N   0  0  0  0  0  4  0  0  0  0  0  0
   -5.2903   -0.3205    1.2932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1459    0.2525   -0.9886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8852   -2.0259   -0.3215 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5201    2.0638    0.3913 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8604    2.3362    0.6246 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8042    1.3496    0.4299 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1560    1.5541    0.6439 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7836   -2.8589   -0.6025 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4845   -2.0826   -1.6556 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1120   -2.5805    0.0187 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7526   -1.1404   -0.5589 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3948   -0.4492   -0.6129 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9036    2.3929    0.1981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5994   -1.4631   -1.5692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8310    0.2930   -1.7620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8182   -1.1105    0.9337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1609    0.6048    0.6780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9315    0.7155    1.5338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8384   -0.9746    2.0613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3800   -0.3899    1.2375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5900    1.1959   -1.0220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2021    0.5005   -0.7594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0485   -0.2713   -1.9762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0155   -2.6797   -0.2631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2906   -2.0534   -1.3572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6697   -2.4434    0.3474 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8380    2.8682    0.5598 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2142    3.3059    0.9598 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5283    2.4346    0.9540 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  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 13 16  1  0
  5 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19  3  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  6 25  1  0
  7 26  1  0
 11 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 14 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 16 39  1  0
 17 40  1  0
 18 41  1  0
 20 42  1  0
M  CHG  1  13   1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₂₂NO₄

Average Molecular Weight

280.3395

Monoisotopic Molecular Weight

280.154883197

IUPAC Name

(2-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}ethyl)trimethylazanium

CAS Registry Number

85927-25-9

SMILES

COC1=C(O)C=CC(\C=C\C(=O)OCC[N+](C)(C)C)=C1

InChI Identifier

InChI=1S/C15H21NO4/c1-16(2,3)9-10-20-15(18)8-6-12-5-7-13(17)14(11-12)19-4/h5-8,11H,9-10H2,1-4H3/p+1

InChI Key

XHSNXOZZHHJDDX-UHFFFAOYSA-O

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acids and derivatives

Alternative Parents

Substituents

Coumaric acid or derivatives
Cinnamic acid ester
Methoxyphenol
Acyl choline
Anisole
Phenoxy compound
Phenol ether
Styrene
Methoxybenzene
Phenol
Alkyl aryl ether
Fatty acid ester
1-hydroxy-2-unsubstituted benzenoid
Fatty acyl
Benzenoid
Monocyclic benzene moiety
Tetraalkylammonium salt
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Quaternary ammonium salt
Carboxylic acid ester
Carboxylic acid derivative
Ether
Monocarboxylic acid or derivatives
Organopnictogen compound
Organic oxide
Organonitrogen compound
Organooxygen compound
Amine
Organic nitrogen compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic salt
Organic cation
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0032800)
Cytoplasm (HMDB: HMDB0032800)

Source

Exogenous

Exogenous (HMDB: HMDB0032800)

Food

Food (HMDB: HMDB0032800)

Endogenous

Plant

Plant (HMDB: HMDB0032800)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0032800)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	203 - 205 °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	0.013 g/L	ALOGPS
logP	-1.2	ALOGPS
logP	-2.1	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	9.87	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	90.21 m³·mol⁻¹	ChemAxon
Polarizability	31.3 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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]+	166.648	31661259
DarkChem	[M-H]-	167.341	31661259
DeepCCS	[M+H]+	168.412	30932474
DeepCCS	[M-H]-	166.053	30932474
DeepCCS	[M-2H]-	198.939	30932474
DeepCCS	[M+Na]+	174.505	30932474
AllCCS	[M+H]+	166.0	32859911
AllCCS	[M+H-H2O]+	162.8	32859911
AllCCS	[M+NH4]+	168.9	32859911
AllCCS	[M+Na]+	169.8	32859911
AllCCS	[M-H]-	175.1	32859911
AllCCS	[M+Na-2H]-	176.0	32859911
AllCCS	[M+HCOO]-	177.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.08 minutes	32390414
Predicted by Siyang on May 30, 2022	10.172 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.12 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1207.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	198.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	133.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	164.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	63.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	372.4 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	318.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	692.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1008.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	201.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1253.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	200.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	262.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	441.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	380.2 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	9.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Feruloylcholine	COC1=C(O)C=CC(\C=C\C(=O)OCC[N+](C)(C)C)=C1	3618.9	Standard polar	33892256
Feruloylcholine	COC1=C(O)C=CC(\C=C\C(=O)OCC[N+](C)(C)C)=C1	2135.2	Standard non polar	33892256
Feruloylcholine	COC1=C(O)C=CC(\C=C\C(=O)OCC[N+](C)(C)C)=C1	2241.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Feruloylcholine,1TMS,isomer #1	COC1=CC(/C=C/C(=O)OCC[N+](C)(C)C)=CC=C1O[Si](C)(C)C	2345.9	Semi standard non polar	33892256
Feruloylcholine,1TBDMS,isomer #1	COC1=CC(/C=C/C(=O)OCC[N+](C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2600.2	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 - Feruloylcholine GC-MS (1 TMS) - 70eV, Positive	splash10-0aca-8092000000-f7dc3029f4844d2ddf14	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Feruloylcholine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	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

FDB010772

KNApSAcK ID

Not Available

Chemspider ID

30776954

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

54470093

PDB ID

Not Available

ChEBI ID

168277

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.. .

Enzymes

Enzyme Details

1. Liver carboxylesterase 1

General function:: Lipid transport and metabolism
Specific function:: Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl-CoA ester. Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine. Catalyzes the transesterification of cocaine to form cocaethylene. Displays fatty acid ethyl ester synthase activity, catalyzing the ethyl esterification of oleic acid to ethyloleate.
Gene Name:: CES1
Uniprot ID:: P23141
Molecular weight:: 62520.62

Reactions

Feruloylcholine → Choline	details

Showing metabocard for Feruloylcholine (HMDB0032800)

MOL for HMDB0032800 (Feruloylcholine)

3D MOL for HMDB0032800 (Feruloylcholine)

3D SDF for HMDB0032800 (Feruloylcholine)

3D-SDF for HMDB0032800 (Feruloylcholine)

PDB for HMDB0032800 (Feruloylcholine)

3D PDB for HMDB0032800 (Feruloylcholine)

SMILES for HMDB0032800 (Feruloylcholine)

INCHI for HMDB0032800 (Feruloylcholine)

Structure for HMDB0032800 (Feruloylcholine)

3D Structure for HMDB0032800 (Feruloylcholine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

NMR Spectra

Enzymes

Reactions