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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:35:22 UTC

Update Date

2022-03-07 02:52:27 UTC

HMDB ID

HMDB0030191

Secondary Accession Numbers

HMDB30191

Metabolite Identification

Common Name

N-[2-Hydroxy-2-(4-hydroxyphenyl)ethyl]cinnamide

Description

N-[2-Hydroxy-2-(4-hydroxyphenyl)ethyl]cinnamide, also known as N-cinnamoyl-2,4'-dihydroxyphenethylamine or N-cinnamoyloctopamine, belongs to the class of organic compounds known as styrenes. These are organic compounds containing an ethenylbenzene moiety. Based on a literature review very few articles have been published on N-[2-Hydroxy-2-(4-hydroxyphenyl)ethyl]cinnamide.

Structure

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

HMDB0030191
     RDKit          3D
N-[2-Hydroxy-2-(4-hydroxyphenyl)ethyl]cinnamide
 38 39  0  0  0  0  0  0  0  0999 V2000
    1.6416    0.7686    0.7807 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8028   -0.0267    0.0484 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1013   -1.1387   -0.8140 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2621   -1.6442   -1.0120 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5000   -1.2406   -0.4132 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6095   -1.2883   -1.2855 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8509   -1.0456   -0.7756 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0808   -0.7549    0.5524 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9839   -0.7171    1.3781 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6879   -0.9581    0.9171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4767    0.3301    0.1947 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8588    1.4373    1.0428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0008    2.1625    0.3178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4352    3.2549    1.0720 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1223    1.2245    0.0536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3234    0.6905   -1.1989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3519   -0.1737   -1.4543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2244   -0.5392   -0.4597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2606   -1.4183   -0.7449 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0269   -0.0061    0.7990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9931    0.8595    1.0455 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5556    0.9897    1.7620 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2281   -1.6161   -1.3744 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2961   -2.5119   -1.7445 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4810   -1.5140   -2.3453 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7305   -1.0773   -1.4367 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0950   -0.5661    0.9139 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1082   -0.4927    2.4343 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8809   -0.9851    1.6678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3021    1.0928    2.0095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0454    2.1249    1.2854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6599    2.5588   -0.6587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9854    3.3130    1.9522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6554    0.9479   -2.0343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5214   -0.6064   -2.4530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0716   -2.4020   -0.6283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7119   -0.2864    1.6018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8687    1.2544    2.0330 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  2 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 10  5  1  0
 21 15  1  0
  1 22  1  0
  3 23  1  0
  4 24  1  0
  6 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 16 34  1  0
 17 35  1  0
 19 36  1  0
 20 37  1  0
 21 38  1  0
M  END

  Mrv0541 05061305042D          

 21 22  0  0  0  0            999 V2000
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    7.4250    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
   -6.4302    7.0125    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
   -1.4289    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    7.4250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    8.2500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  9  7  1  0  0  0  0
 10  8  2  0  0  0  0
 11  6  2  0  0  0  0
 13  4  2  0  0  0  0
 13  5  1  0  0  0  0
 13  6  1  0  0  0  0
 14  7  2  0  0  0  0
 14  8  1  0  0  0  0
 15  9  2  0  0  0  0
 15 10  1  0  0  0  0
 16 12  1  0  0  0  0
 16 14  1  0  0  0  0
 17 11  1  0  0  0  0
 18 12  1  0  0  0  0
 18 17  2  0  0  0  0
 19 15  1  0  0  0  0
 20 16  1  0  0  0  0
 21 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030191

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C17H17NO3/c19-15-9-7-14(8-10-15)16(20)12-18-17(21)11-6-13-4-2-1-3-5-13/h1-11,16,19-20H,12H2,(H,18,21)/b11-6-

> <INCHI_KEY>
CWMOJJSULWWJSO-WDZFZDKYSA-N

> <FORMULA>
C17H17NO3

> <MOLECULAR_WEIGHT>
283.3218

> <EXACT_MASS>
283.120843415

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
30.52974237700999

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(Z,2Z)-N-[2-hydroxy-2-(4-hydroxyphenyl)ethyl]-3-phenylpropa-2-enimidic acid

> <ALOGPS_LOGP>
2.39

> <JCHEM_LOGP>
3.162996692666667

> <ALOGPS_LOGS>
-3.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.481186924179498

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.779419171773264

> <JCHEM_PKA_STRONGEST_BASIC>
4.2323926583189335

> <JCHEM_POLAR_SURFACE_AREA>
73.05000000000001

> <JCHEM_REFRACTIVITY>
82.8565

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.48e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(Z,2Z)-N-[2-hydroxy-2-(4-hydroxyphenyl)ethyl]-3-phenylpropa-2-enimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030191
     RDKit          3D
N-[2-Hydroxy-2-(4-hydroxyphenyl)ethyl]cinnamide
 38 39  0  0  0  0  0  0  0  0999 V2000
    1.6416    0.7686    0.7807 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8028   -0.0267    0.0484 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1013   -1.1387   -0.8140 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2621   -1.6442   -1.0120 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5000   -1.2406   -0.4132 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6095   -1.2883   -1.2855 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8509   -1.0456   -0.7756 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0808   -0.7549    0.5524 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9839   -0.7171    1.3781 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6879   -0.9581    0.9171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4767    0.3301    0.1947 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8588    1.4373    1.0428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0008    2.1625    0.3178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4352    3.2549    1.0720 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1223    1.2245    0.0536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3234    0.6905   -1.1989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3519   -0.1737   -1.4543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2244   -0.5392   -0.4597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2606   -1.4183   -0.7449 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0269   -0.0061    0.7990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9931    0.8595    1.0455 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5556    0.9897    1.7620 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2281   -1.6161   -1.3744 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2961   -2.5119   -1.7445 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4810   -1.5140   -2.3453 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7305   -1.0773   -1.4367 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0950   -0.5661    0.9139 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1082   -0.4927    2.4343 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8809   -0.9851    1.6678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3021    1.0928    2.0095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0454    2.1249    1.2854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6599    2.5588   -0.6587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9854    3.3130    1.9522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6554    0.9479   -2.0343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5214   -0.6064   -2.4530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0716   -2.4020   -0.6283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7119   -0.2864    1.6018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8687    1.2544    2.0330 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  2 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 10  5  1  0
 21 15  1  0
  1 22  1  0
  3 23  1  0
  4 24  1  0
  6 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 16 34  1  0
 17 35  1  0
 19 36  1  0
 20 37  1  0
 21 38  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  10.780   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667  10.780   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  13.090   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -10.669  13.860   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -9.336  11.550   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -12.003  13.090   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -10.669  10.780   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667  13.860   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -6.668  13.090   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334  11.550   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -9.336  13.090   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0     -12.003  11.550   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -8.002  13.860   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.001  13.090   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0      -5.335  13.860   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0     -13.337  10.780   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -8.002  15.400   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -4.001  11.550   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2   13                                                       
CONECT    5    3   13                                                       
CONECT    6   11   13                                                       
CONECT    7    9   14                                                       
CONECT    8   10   14                                                       
CONECT    9    7   15                                                       
CONECT   10    8   15                                                       
CONECT   11    6   17                                                       
CONECT   12   16   18                                                       
CONECT   13    4    5    6                                                  
CONECT   14    7    8   16                                                  
CONECT   15    9   10   19                                                  
CONECT   16   12   14   20                                                  
CONECT   17   11   18   21                                                  
CONECT   18   12   17                                                       
CONECT   19   15                                                            
CONECT   20   16                                                            
CONECT   21   17                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

COMPND    HMDB0030191
HETATM    1  O1  UNL     1       1.642   0.769   0.781  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.803  -0.027   0.048  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.101  -1.139  -0.814  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.262  -1.644  -1.012  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.500  -1.241  -0.413  1.00  0.00           C  
HETATM    6  C5  UNL     1       4.609  -1.288  -1.285  1.00  0.00           C  
HETATM    7  C6  UNL     1       5.851  -1.046  -0.776  1.00  0.00           C  
HETATM    8  C7  UNL     1       6.081  -0.755   0.552  1.00  0.00           C  
HETATM    9  C8  UNL     1       4.984  -0.717   1.378  1.00  0.00           C  
HETATM   10  C9  UNL     1       3.688  -0.958   0.917  1.00  0.00           C  
HETATM   11  N1  UNL     1      -0.477   0.330   0.195  1.00  0.00           N  
HETATM   12  C10 UNL     1      -0.859   1.437   1.043  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.001   2.162   0.318  1.00  0.00           C  
HETATM   14  O2  UNL     1      -2.435   3.255   1.072  1.00  0.00           O  
HETATM   15  C12 UNL     1      -3.122   1.224   0.054  1.00  0.00           C  
HETATM   16  C13 UNL     1      -3.323   0.691  -1.199  1.00  0.00           C  
HETATM   17  C14 UNL     1      -4.352  -0.174  -1.454  1.00  0.00           C  
HETATM   18  C15 UNL     1      -5.224  -0.539  -0.460  1.00  0.00           C  
HETATM   19  O3  UNL     1      -6.261  -1.418  -0.745  1.00  0.00           O  
HETATM   20  C16 UNL     1      -5.027  -0.006   0.799  1.00  0.00           C  
HETATM   21  C17 UNL     1      -3.993   0.860   1.046  1.00  0.00           C  
HETATM   22  H1  UNL     1       1.556   0.990   1.762  1.00  0.00           H  
HETATM   23  H2  UNL     1       0.228  -1.616  -1.374  1.00  0.00           H  
HETATM   24  H3  UNL     1       2.296  -2.512  -1.745  1.00  0.00           H  
HETATM   25  H4  UNL     1       4.481  -1.514  -2.345  1.00  0.00           H  
HETATM   26  H5  UNL     1       6.730  -1.077  -1.437  1.00  0.00           H  
HETATM   27  H6  UNL     1       7.095  -0.566   0.914  1.00  0.00           H  
HETATM   28  H7  UNL     1       5.108  -0.493   2.434  1.00  0.00           H  
HETATM   29  H8  UNL     1       2.881  -0.985   1.668  1.00  0.00           H  
HETATM   30  H9  UNL     1      -1.302   1.093   2.010  1.00  0.00           H  
HETATM   31  H10 UNL     1      -0.045   2.125   1.285  1.00  0.00           H  
HETATM   32  H11 UNL     1      -1.660   2.559  -0.659  1.00  0.00           H  
HETATM   33  H12 UNL     1      -1.985   3.313   1.952  1.00  0.00           H  
HETATM   34  H13 UNL     1      -2.655   0.948  -2.034  1.00  0.00           H  
HETATM   35  H14 UNL     1      -4.521  -0.606  -2.453  1.00  0.00           H  
HETATM   36  H15 UNL     1      -6.072  -2.402  -0.628  1.00  0.00           H  
HETATM   37  H16 UNL     1      -5.712  -0.286   1.602  1.00  0.00           H  
HETATM   38  H17 UNL     1      -3.869   1.254   2.033  1.00  0.00           H  
CONECT    1    2   22
CONECT    2    3   11   11
CONECT    3    4    4   23
CONECT    4    5   24
CONECT    5    6    6   10
CONECT    6    7   25
CONECT    7    8    8   26
CONECT    8    9   27
CONECT    9   10   10   28
CONECT   10   29
CONECT   11   12
CONECT   12   13   30   31
CONECT   13   14   15   32
CONECT   14   33
CONECT   15   16   16   21
CONECT   16   17   34
CONECT   17   18   18   35
CONECT   18   19   20
CONECT   19   36
CONECT   20   21   21   37
CONECT   21   38
END

HMDB0030191
     RDKit          3D
N-[2-Hydroxy-2-(4-hydroxyphenyl)ethyl]cinnamide
 38 39  0  0  0  0  0  0  0  0999 V2000
    1.6416    0.7686    0.7807 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8028   -0.0267    0.0484 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1013   -1.1387   -0.8140 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2621   -1.6442   -1.0120 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5000   -1.2406   -0.4132 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6095   -1.2883   -1.2855 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8509   -1.0456   -0.7756 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0808   -0.7549    0.5524 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9839   -0.7171    1.3781 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6879   -0.9581    0.9171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4767    0.3301    0.1947 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8588    1.4373    1.0428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0008    2.1625    0.3178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4352    3.2549    1.0720 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1223    1.2245    0.0536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3234    0.6905   -1.1989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3519   -0.1737   -1.4543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2244   -0.5392   -0.4597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2606   -1.4183   -0.7449 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0269   -0.0061    0.7990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9931    0.8595    1.0455 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5556    0.9897    1.7620 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2281   -1.6161   -1.3744 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2961   -2.5119   -1.7445 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4810   -1.5140   -2.3453 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7305   -1.0773   -1.4367 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0950   -0.5661    0.9139 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1082   -0.4927    2.4343 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8809   -0.9851    1.6678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3021    1.0928    2.0095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0454    2.1249    1.2854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6599    2.5588   -0.6587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9854    3.3130    1.9522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6554    0.9479   -2.0343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5214   -0.6064   -2.4530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0716   -2.4020   -0.6283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7119   -0.2864    1.6018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8687    1.2544    2.0330 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  2 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 10  5  1  0
 21 15  1  0
  1 22  1  0
  3 23  1  0
  4 24  1  0
  6 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 16 34  1  0
 17 35  1  0
 19 36  1  0
 20 37  1  0
 21 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
N-Cinnamoyl-2,4'-dihydroxyphenethylamine	HMDB
N-Cinnamoyloctopamine	HMDB
N-[2-Hydroxy-2-(4-hydroxyphenyl)ethyl]-3-phenyl-2-propenamide	HMDB
(2Z)-N-[2-Hydroxy-2-(4-hydroxyphenyl)ethyl]-3-phenylprop-2-enimidate	HMDB

Chemical Formula

C₁₇H₁₇NO₃

Average Molecular Weight

283.3218

Monoisotopic Molecular Weight

283.120843415

IUPAC Name

(Z,2Z)-N-[2-hydroxy-2-(4-hydroxyphenyl)ethyl]-3-phenylpropa-2-enimidic acid

Traditional Name

(Z,2Z)-N-[2-hydroxy-2-(4-hydroxyphenyl)ethyl]-3-phenylpropa-2-enimidic acid

CAS Registry Number

87596-52-9

SMILES

OC(C\N=C(/O)\C=C/C1=CC=CC=C1)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C17H17NO3/c19-15-9-7-14(8-10-15)16(20)12-18-17(21)11-6-13-4-2-1-3-5-13/h1-11,16,19-20H,12H2,(H,18,21)/b11-6-

InChI Key

CWMOJJSULWWJSO-WDZFZDKYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as styrenes. These are organic compounds containing an ethenylbenzene moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Styrenes

Direct Parent

Styrenes

Alternative Parents

Substituents

Styrene
1-hydroxy-2-unsubstituted benzenoid
Phenol
Secondary alcohol
Carboximidic acid
Carboximidic acid derivative
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Alcohol
Aromatic alcohol
Hydrocarbon derivative
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0030191)
Cytoplasm (HMDB: HMDB0030191)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030191)

Source

Endogenous

Endogenous (HMDB: HMDB0030191)

Plant

Plant (HMDB: HMDB0030191)

Exogenous

Food

Food (HMDB: HMDB0030191)

Fruit

Fruits (FooDB: FOOD00871)

Exogenous (HMDB: HMDB0030191)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	158 °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	0.045 g/L	ALOGPS
logP	2.39	ALOGPS
logP	3.16	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	7.78	ChemAxon
pKa (Strongest Basic)	4.23	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	73.05 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	82.86 m³·mol⁻¹	ChemAxon
Polarizability	30.53 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
DeepCCS	[M+H]+	167.471	30932474
DeepCCS	[M-H]-	165.113	30932474
DeepCCS	[M-2H]-	198.082	30932474
DeepCCS	[M+Na]+	173.565	30932474
AllCCS	[M+H]+	168.3	32859911
AllCCS	[M+H-H2O]+	164.7	32859911
AllCCS	[M+NH4]+	171.6	32859911
AllCCS	[M+Na]+	172.6	32859911
AllCCS	[M-H]-	170.4	32859911
AllCCS	[M+Na-2H]-	170.1	32859911
AllCCS	[M+HCOO]-	169.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-[2-Hydroxy-2-(4-hydroxyphenyl)ethyl]cinnamide	OC(C\N=C(/O)\C=C/C1=CC=CC=C1)C1=CC=C(O)C=C1	4386.6	Standard polar	33892256
N-[2-Hydroxy-2-(4-hydroxyphenyl)ethyl]cinnamide	OC(C\N=C(/O)\C=C/C1=CC=CC=C1)C1=CC=C(O)C=C1	2482.9	Standard non polar	33892256
N-[2-Hydroxy-2-(4-hydroxyphenyl)ethyl]cinnamide	OC(C\N=C(/O)\C=C/C1=CC=CC=C1)C1=CC=C(O)C=C1	2809.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-[2-Hydroxy-2-(4-hydroxyphenyl)ethyl]cinnamide,1TMS,isomer #1	C[Si](C)(C)OC(C/N=C(O)/C=C\C1=CC=CC=C1)C1=CC=C(O)C=C1	2856.5	Semi standard non polar	33892256
N-[2-Hydroxy-2-(4-hydroxyphenyl)ethyl]cinnamide,1TMS,isomer #2	C[Si](C)(C)OC(/C=C\C1=CC=CC=C1)=N\CC(O)C1=CC=C(O)C=C1	2852.7	Semi standard non polar	33892256
N-[2-Hydroxy-2-(4-hydroxyphenyl)ethyl]cinnamide,1TMS,isomer #3	C[Si](C)(C)OC1=CC=C(C(O)C/N=C(O)/C=C\C2=CC=CC=C2)C=C1	2839.9	Semi standard non polar	33892256
N-[2-Hydroxy-2-(4-hydroxyphenyl)ethyl]cinnamide,2TMS,isomer #1	C[Si](C)(C)OC(/C=C\C1=CC=CC=C1)=N\CC(O[Si](C)(C)C)C1=CC=C(O)C=C1	2807.8	Semi standard non polar	33892256
N-[2-Hydroxy-2-(4-hydroxyphenyl)ethyl]cinnamide,2TMS,isomer #2	C[Si](C)(C)OC1=CC=C(C(C/N=C(O)/C=C\C2=CC=CC=C2)O[Si](C)(C)C)C=C1	2760.1	Semi standard non polar	33892256
N-[2-Hydroxy-2-(4-hydroxyphenyl)ethyl]cinnamide,2TMS,isomer #3	C[Si](C)(C)OC(/C=C\C1=CC=CC=C1)=N\CC(O)C1=CC=C(O[Si](C)(C)C)C=C1	2774.0	Semi standard non polar	33892256
N-[2-Hydroxy-2-(4-hydroxyphenyl)ethyl]cinnamide,3TMS,isomer #1	C[Si](C)(C)OC(/C=C\C1=CC=CC=C1)=N\CC(O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C=C1	2717.8	Semi standard non polar	33892256
N-[2-Hydroxy-2-(4-hydroxyphenyl)ethyl]cinnamide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(C/N=C(O)/C=C\C1=CC=CC=C1)C1=CC=C(O)C=C1	3094.6	Semi standard non polar	33892256
N-[2-Hydroxy-2-(4-hydroxyphenyl)ethyl]cinnamide,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(/C=C\C1=CC=CC=C1)=N\CC(O)C1=CC=C(O)C=C1	3110.6	Semi standard non polar	33892256
N-[2-Hydroxy-2-(4-hydroxyphenyl)ethyl]cinnamide,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(C(O)C/N=C(O)/C=C\C2=CC=CC=C2)C=C1	3077.9	Semi standard non polar	33892256
N-[2-Hydroxy-2-(4-hydroxyphenyl)ethyl]cinnamide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(/C=C\C1=CC=CC=C1)=N\CC(O[Si](C)(C)C(C)(C)C)C1=CC=C(O)C=C1	3265.1	Semi standard non polar	33892256
N-[2-Hydroxy-2-(4-hydroxyphenyl)ethyl]cinnamide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(C(C/N=C(O)/C=C\C2=CC=CC=C2)O[Si](C)(C)C(C)(C)C)C=C1	3231.5	Semi standard non polar	33892256
N-[2-Hydroxy-2-(4-hydroxyphenyl)ethyl]cinnamide,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(/C=C\C1=CC=CC=C1)=N\CC(O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	3251.6	Semi standard non polar	33892256
N-[2-Hydroxy-2-(4-hydroxyphenyl)ethyl]cinnamide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(/C=C\C1=CC=CC=C1)=N\CC(O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	3405.4	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 - N-[2-Hydroxy-2-(4-hydroxyphenyl)ethyl]cinnamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-00si-2910000000-717ca9f9d77b19914f96	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-[2-Hydroxy-2-(4-hydroxyphenyl)ethyl]cinnamide GC-MS (3 TMS) - 70eV, Positive	splash10-0159-0090700000-3a3d02a5f1299f98becf	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-[2-Hydroxy-2-(4-hydroxyphenyl)ethyl]cinnamide 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 - N-[2-Hydroxy-2-(4-hydroxyphenyl)ethyl]cinnamide 10V, Positive-QTOF	splash10-0uyi-0970000000-fd9bbf1bd2a2480f23b3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-[2-Hydroxy-2-(4-hydroxyphenyl)ethyl]cinnamide 20V, Positive-QTOF	splash10-0f89-0900000000-b161965bc9dadbb6f856	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-[2-Hydroxy-2-(4-hydroxyphenyl)ethyl]cinnamide 40V, Positive-QTOF	splash10-0f89-1900000000-bc8cf09e39fc69bfd3e0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-[2-Hydroxy-2-(4-hydroxyphenyl)ethyl]cinnamide 10V, Negative-QTOF	splash10-001i-0390000000-02363d80604ea046442c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-[2-Hydroxy-2-(4-hydroxyphenyl)ethyl]cinnamide 20V, Negative-QTOF	splash10-01qa-1940000000-79f16a6b4c5c4badc7b5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-[2-Hydroxy-2-(4-hydroxyphenyl)ethyl]cinnamide 40V, Negative-QTOF	splash10-0006-9700000000-3c9cf02deda07b16f747	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-[2-Hydroxy-2-(4-hydroxyphenyl)ethyl]cinnamide 10V, Negative-QTOF	splash10-001i-0290000000-ed5d1079bc0ad20b67d2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-[2-Hydroxy-2-(4-hydroxyphenyl)ethyl]cinnamide 20V, Negative-QTOF	splash10-0gwf-5970000000-cbffd5d85f73fdcf5d7e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-[2-Hydroxy-2-(4-hydroxyphenyl)ethyl]cinnamide 40V, Negative-QTOF	splash10-0f9x-9640000000-2aaef57d8a1f1fad2e46	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-[2-Hydroxy-2-(4-hydroxyphenyl)ethyl]cinnamide 10V, Positive-QTOF	splash10-014i-0290000000-f7ae36f3b8127f7dcbfe	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-[2-Hydroxy-2-(4-hydroxyphenyl)ethyl]cinnamide 20V, Positive-QTOF	splash10-02u0-0920000000-efb3fadfda43a167aafd	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-[2-Hydroxy-2-(4-hydroxyphenyl)ethyl]cinnamide 40V, Positive-QTOF	splash10-0udi-2900000000-c4bcc6740933d341a426	2021-09-23	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

FDB002009

KNApSAcK ID

C00053996

Chemspider ID

35013157

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131750976

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 N-[2-Hydroxy-2-(4-hydroxyphenyl)ethyl]cinnamide (HMDB0030191)

MOL for HMDB0030191 (N-[2-Hydroxy-2-(4-hydroxyphenyl)ethyl]cinnamide)

3D MOL for HMDB0030191 (N-[2-Hydroxy-2-(4-hydroxyphenyl)ethyl]cinnamide)

3D SDF for HMDB0030191 (N-[2-Hydroxy-2-(4-hydroxyphenyl)ethyl]cinnamide)

3D-SDF for HMDB0030191 (N-[2-Hydroxy-2-(4-hydroxyphenyl)ethyl]cinnamide)

PDB for HMDB0030191 (N-[2-Hydroxy-2-(4-hydroxyphenyl)ethyl]cinnamide)

3D PDB for HMDB0030191 (N-[2-Hydroxy-2-(4-hydroxyphenyl)ethyl]cinnamide)

SMILES for HMDB0030191 (N-[2-Hydroxy-2-(4-hydroxyphenyl)ethyl]cinnamide)

INCHI for HMDB0030191 (N-[2-Hydroxy-2-(4-hydroxyphenyl)ethyl]cinnamide)

Structure for HMDB0030191 (N-[2-Hydroxy-2-(4-hydroxyphenyl)ethyl]cinnamide)

3D Structure for HMDB0030191 (N-[2-Hydroxy-2-(4-hydroxyphenyl)ethyl]cinnamide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra