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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2017-08-01 02:11:28 UTC

Update Date

2022-03-07 03:18:00 UTC

HMDB ID

HMDB0094646

Secondary Accession Numbers

HMDB94646

Metabolite Identification

Common Name

2-Pentanamido-3-phenylpropanoic acid

Description

2-pentanamido-3-phenylpropanoic acid is classified as a phenylalanine or a Phenylalanine derivative. Phenylalanines are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. 2-pentanamido-3-phenylpropanoic acid is considered to be a practically insoluble (in water) and a weak acidic compound. 2-pentanamido-3-phenylpropanoic acid can be found in feces.

Structure

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

HMDB0094646
     RDKit          3D
2-Pentanamido-3-phenylpropanoic acid
 37 37  0  0  0  0  0  0  0  0999 V2000
    4.9208    1.1691   -1.0789 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6532    1.0770   -0.2529 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2198   -0.3718   -0.0977 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9396   -0.3314    0.7485 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4303   -1.6838    0.9623 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2707   -2.5991    1.6224 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3033   -2.0725    0.5973 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6660   -1.2756   -0.0808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4032   -0.4355    0.9413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4379    0.4360    0.3703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1358    1.7084   -0.0835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0911    2.5464   -0.6145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4032    2.1222   -0.7069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7007    0.8528   -0.2532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7442    0.0200    0.2761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6270   -2.2097   -0.7642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4814   -3.4381   -0.5717 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6434   -1.7492   -1.5827 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6470    1.0630   -2.1541 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6667    0.4322   -0.7588 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3214    2.1867   -0.9312 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8208    1.5980   -0.7648 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7674    1.4928    0.7586 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9886   -0.9152    0.4529 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9824   -0.8205   -1.0686 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1906    0.2771    0.2160 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1770    0.1762    1.7287 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7899   -3.2936    1.0652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2013   -0.6074   -0.8420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7302    0.1347    1.5907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9384   -1.1877    1.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0947    2.0702   -0.0205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8572    3.5515   -0.9739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1538    2.7877   -1.1270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7474    0.5422   -0.3380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0205   -0.9458    0.6178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0126   -2.3075   -2.3206 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
  5  7  2  3
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  8 16  1  0
 16 17  2  0
 16 18  1  0
 15 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  6 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 11 32  1  0
 12 33  1  0
 13 34  1  0
 14 35  1  0
 15 36  1  0
 18 37  1  0
M  END


  Mrv1652308011703392D          

 18 18  0  0  0  0            999 V2000
    2.1434    6.1875    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
    1.4289    4.9500    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
    1.4289    0.0000    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
    1.4289    0.8250    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
    0.7145    4.5375    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
    0.7145    1.2375    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
    0.7145    3.7125    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
    0.0000    3.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    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
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  5  4  2  0  0  0  0
  6  4  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  7  2  0  0  0  0
 11  8  1  0  0  0  0
 11 10  1  0  0  0  0
 12 10  1  0  0  0  0
 13  9  1  0  0  0  0
 14 12  1  0  0  0  0
 15 12  1  4  0  0  0
 15 13  2  0  0  0  0
 16 13  1  0  0  0  0
 17 14  2  0  0  0  0
 18 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0094646

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC(O)=NC(CC1=CC=CC=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H19NO3/c1-2-3-9-13(16)15-12(14(17)18)10-11-7-5-4-6-8-11/h4-8,12H,2-3,9-10H2,1H3,(H,15,16)(H,17,18)

> <INCHI_KEY>
YXQLJEQFZUMUPB-UHFFFAOYSA-N

> <FORMULA>
C14H19NO3

> <MOLECULAR_WEIGHT>
249.31

> <EXACT_MASS>
249.136493476

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
26.737973366723356

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(1-hydroxypentylidene)amino]-3-phenylpropanoic acid

> <ALOGPS_LOGP>
2.25

> <JCHEM_LOGP>
3.3057389599999993

> <ALOGPS_LOGS>
-3.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
6.128210950436043

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.256523026735413

> <JCHEM_PKA_STRONGEST_BASIC>
1.5206466025585084

> <JCHEM_POLAR_SURFACE_AREA>
69.89

> <JCHEM_REFRACTIVITY>
68.9107

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.78e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(1-hydroxypentylidene)amino]-3-phenylpropanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0094646
     RDKit          3D
2-Pentanamido-3-phenylpropanoic acid
 37 37  0  0  0  0  0  0  0  0999 V2000
    4.9208    1.1691   -1.0789 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6532    1.0770   -0.2529 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2198   -0.3718   -0.0977 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9396   -0.3314    0.7485 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4303   -1.6838    0.9623 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2707   -2.5991    1.6224 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3033   -2.0725    0.5973 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6660   -1.2756   -0.0808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4032   -0.4355    0.9413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4379    0.4360    0.3703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1358    1.7084   -0.0835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0911    2.5464   -0.6145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4032    2.1222   -0.7069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7007    0.8528   -0.2532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7442    0.0200    0.2761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6270   -2.2097   -0.7642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4814   -3.4381   -0.5717 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6434   -1.7492   -1.5827 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6470    1.0630   -2.1541 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6667    0.4322   -0.7588 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3214    2.1867   -0.9312 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8208    1.5980   -0.7648 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7674    1.4928    0.7586 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9886   -0.9152    0.4529 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9824   -0.8205   -1.0686 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1906    0.2771    0.2160 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1770    0.1762    1.7287 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7899   -3.2936    1.0652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2013   -0.6074   -0.8420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7302    0.1347    1.5907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9384   -1.1877    1.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0947    2.0702   -0.0205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8572    3.5515   -0.9739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1538    2.7877   -1.1270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7474    0.5422   -0.3380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0205   -0.9458    0.6178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0126   -2.3075   -2.3206 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
  5  7  2  3
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  8 16  1  0
 16 17  2  0
 16 18  1  0
 15 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  6 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 11 32  1  0
 12 33  1  0
 13 34  1  0
 14 35  1  0
 15 36  1  0
 18 37  1  0
M  END

HEADER    PROTEIN                                 01-AUG-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   01-AUG-17         0                                  
HETATM    1  C   UNK     0       4.001  11.550   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  10.780   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       1.334  -0.770   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      -0.000   0.000   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   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       0.000   6.160   0.000  0.00  0.00           N+0
HETATM   16  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -2.667   4.620   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    9                                                       
CONECT    4    5    6                                                       
CONECT    5    4    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5   11                                                       
CONECT    8    6   11                                                       
CONECT    9    3   13                                                       
CONECT   10   11   12                                                       
CONECT   11    7    8   10                                                  
CONECT   12   10   14   15                                                  
CONECT   13    9   15   16                                                  
CONECT   14   12   17   18                                                  
CONECT   15   12   13                                                       
CONECT   16   13                                                            
CONECT   17   14                                                            
CONECT   18   14                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

COMPND    HMDB0094646
HETATM    1  C1  UNL     1       4.921   1.169  -1.079  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.653   1.077  -0.253  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.220  -0.372  -0.098  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.940  -0.331   0.748  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.430  -1.684   0.962  1.00  0.00           C  
HETATM    6  O1  UNL     1       2.271  -2.599   1.622  1.00  0.00           O  
HETATM    7  N1  UNL     1       0.303  -2.073   0.597  1.00  0.00           N  
HETATM    8  C6  UNL     1      -0.666  -1.276  -0.081  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.403  -0.435   0.941  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.438   0.436   0.370  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.136   1.708  -0.084  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.091   2.546  -0.615  1.00  0.00           C  
HETATM   13  C11 UNL     1      -4.403   2.122  -0.707  1.00  0.00           C  
HETATM   14  C12 UNL     1      -4.701   0.853  -0.253  1.00  0.00           C  
HETATM   15  C13 UNL     1      -3.744   0.020   0.276  1.00  0.00           C  
HETATM   16  C14 UNL     1      -1.627  -2.210  -0.764  1.00  0.00           C  
HETATM   17  O2  UNL     1      -1.481  -3.438  -0.572  1.00  0.00           O  
HETATM   18  O3  UNL     1      -2.643  -1.749  -1.583  1.00  0.00           O  
HETATM   19  H1  UNL     1       4.647   1.063  -2.154  1.00  0.00           H  
HETATM   20  H2  UNL     1       5.667   0.432  -0.759  1.00  0.00           H  
HETATM   21  H3  UNL     1       5.321   2.187  -0.931  1.00  0.00           H  
HETATM   22  H4  UNL     1       2.821   1.598  -0.765  1.00  0.00           H  
HETATM   23  H5  UNL     1       3.767   1.493   0.759  1.00  0.00           H  
HETATM   24  H6  UNL     1       3.989  -0.915   0.453  1.00  0.00           H  
HETATM   25  H7  UNL     1       2.982  -0.820  -1.069  1.00  0.00           H  
HETATM   26  H8  UNL     1       1.191   0.277   0.216  1.00  0.00           H  
HETATM   27  H9  UNL     1       2.177   0.176   1.729  1.00  0.00           H  
HETATM   28  H10 UNL     1       2.790  -3.294   1.065  1.00  0.00           H  
HETATM   29  H11 UNL     1      -0.201  -0.607  -0.842  1.00  0.00           H  
HETATM   30  H12 UNL     1      -0.730   0.135   1.591  1.00  0.00           H  
HETATM   31  H13 UNL     1      -1.938  -1.188   1.588  1.00  0.00           H  
HETATM   32  H14 UNL     1      -1.095   2.070  -0.020  1.00  0.00           H  
HETATM   33  H15 UNL     1      -2.857   3.551  -0.974  1.00  0.00           H  
HETATM   34  H16 UNL     1      -5.154   2.788  -1.127  1.00  0.00           H  
HETATM   35  H17 UNL     1      -5.747   0.542  -0.338  1.00  0.00           H  
HETATM   36  H18 UNL     1      -4.020  -0.946   0.618  1.00  0.00           H  
HETATM   37  H19 UNL     1      -3.013  -2.308  -2.321  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3   22   23
CONECT    3    4   24   25
CONECT    4    5   26   27
CONECT    5    6    7    7
CONECT    6   28
CONECT    7    8
CONECT    8    9   16   29
CONECT    9   10   30   31
CONECT   10   11   11   15
CONECT   11   12   32
CONECT   12   13   13   33
CONECT   13   14   34
CONECT   14   15   15   35
CONECT   15   36
CONECT   16   17   17   18
CONECT   18   37
END

HMDB0094646
     RDKit          3D
2-Pentanamido-3-phenylpropanoic acid
 37 37  0  0  0  0  0  0  0  0999 V2000
    4.9208    1.1691   -1.0789 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6532    1.0770   -0.2529 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2198   -0.3718   -0.0977 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9396   -0.3314    0.7485 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4303   -1.6838    0.9623 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2707   -2.5991    1.6224 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3033   -2.0725    0.5973 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6660   -1.2756   -0.0808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4032   -0.4355    0.9413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4379    0.4360    0.3703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1358    1.7084   -0.0835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0911    2.5464   -0.6145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4032    2.1222   -0.7069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7007    0.8528   -0.2532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7442    0.0200    0.2761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6270   -2.2097   -0.7642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4814   -3.4381   -0.5717 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6434   -1.7492   -1.5827 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6470    1.0630   -2.1541 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6667    0.4322   -0.7588 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3214    2.1867   -0.9312 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8208    1.5980   -0.7648 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7674    1.4928    0.7586 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9886   -0.9152    0.4529 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9824   -0.8205   -1.0686 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1906    0.2771    0.2160 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1770    0.1762    1.7287 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7899   -3.2936    1.0652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2013   -0.6074   -0.8420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7302    0.1347    1.5907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9384   -1.1877    1.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0947    2.0702   -0.0205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8572    3.5515   -0.9739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1538    2.7877   -1.1270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7474    0.5422   -0.3380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0205   -0.9458    0.6178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0126   -2.3075   -2.3206 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
  5  7  2  3
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  8 16  1  0
 16 17  2  0
 16 18  1  0
 15 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  6 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 11 32  1  0
 12 33  1  0
 13 34  1  0
 14 35  1  0
 15 36  1  0
 18 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Pentanamido-3-phenylpropanoate	Generator

Chemical Formula

C₁₄H₁₉NO₃

Average Molecular Weight

249.31

Monoisotopic Molecular Weight

249.136493476

IUPAC Name

2-[(1-hydroxypentylidene)amino]-3-phenylpropanoic acid

Traditional Name

2-[(1-hydroxypentylidene)amino]-3-phenylpropanoic acid

CAS Registry Number

Not Available

SMILES

CCCCC(O)=NC(CC1=CC=CC=C1)C(O)=O

InChI Identifier

InChI=1S/C14H19NO3/c1-2-3-9-13(16)15-12(14(17)18)10-11-7-5-4-6-8-11/h4-8,12H,2-3,9-10H2,1H3,(H,15,16)(H,17,18)

InChI Key

YXQLJEQFZUMUPB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Phenylalanine and derivatives

Alternative Parents

Substituents

Phenylalanine or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
3-phenylpropanoic-acid
Amphetamine or derivatives
Monocyclic benzene moiety
Fatty amide
Fatty acyl
Benzenoid
N-acyl-amine
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic nitrogen compound
Organic oxide
Carbonyl group
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Feces (PMID: 27275383)

Source

Exogenous

Exogenous (HMDB: HMDB0094646)

Process

Not Available

Role

Not Available

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
logP	2.25	ALOGPS
logP	3.31	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	4.26	ChemAxon
pKa (Strongest Basic)	1.52	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	69.89 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	68.91 m³·mol⁻¹	ChemAxon
Polarizability	26.74 Å³	ChemAxon
Number of Rings	1	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]+	159.684	31661259
DarkChem	[M-H]-	159.652	31661259
DeepCCS	[M+H]+	156.731	30932474
DeepCCS	[M-H]-	154.373	30932474
DeepCCS	[M-2H]-	188.481	30932474
DeepCCS	[M+Na]+	164.706	30932474
AllCCS	[M+H]+	159.7	32859911
AllCCS	[M+H-H2O]+	156.2	32859911
AllCCS	[M+NH4]+	162.9	32859911
AllCCS	[M+Na]+	163.8	32859911
AllCCS	[M-H]-	161.2	32859911
AllCCS	[M+Na-2H]-	161.7	32859911
AllCCS	[M+HCOO]-	162.3	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.	5.46 minutes	32390414
Predicted by Siyang on May 30, 2022	12.405 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.97 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1820.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	312.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	157.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	182.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	215.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	513.0 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	489.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	68.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1074.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	462.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1266.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	300.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	355.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	266.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	154.0 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	20.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Pentanamido-3-phenylpropanoic acid	CCCCC(O)=NC(CC1=CC=CC=C1)C(O)=O	3058.5	Standard polar	33892256
2-Pentanamido-3-phenylpropanoic acid	CCCCC(O)=NC(CC1=CC=CC=C1)C(O)=O	2017.5	Standard non polar	33892256
2-Pentanamido-3-phenylpropanoic acid	CCCCC(O)=NC(CC1=CC=CC=C1)C(O)=O	1961.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Pentanamido-3-phenylpropanoic acid,1TMS,isomer #1	CCCCC(=NC(CC1=CC=CC=C1)C(=O)O)O[Si](C)(C)C	2020.2	Semi standard non polar	33892256
2-Pentanamido-3-phenylpropanoic acid,1TMS,isomer #2	CCCCC(O)=NC(CC1=CC=CC=C1)C(=O)O[Si](C)(C)C	2042.9	Semi standard non polar	33892256
2-Pentanamido-3-phenylpropanoic acid,2TMS,isomer #1	CCCCC(=NC(CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)O[Si](C)(C)C	2032.5	Semi standard non polar	33892256
2-Pentanamido-3-phenylpropanoic acid,1TBDMS,isomer #1	CCCCC(=NC(CC1=CC=CC=C1)C(=O)O)O[Si](C)(C)C(C)(C)C	2252.3	Semi standard non polar	33892256
2-Pentanamido-3-phenylpropanoic acid,1TBDMS,isomer #2	CCCCC(O)=NC(CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C	2263.6	Semi standard non polar	33892256
2-Pentanamido-3-phenylpropanoic acid,2TBDMS,isomer #1	CCCCC(=NC(CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2483.5	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 - 2-Pentanamido-3-phenylpropanoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9120000000-de4bb28f0abbac258459	2017-09-14	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Pentanamido-3-phenylpropanoic acid GC-MS (2 TMS) - 70eV, Positive	splash10-002f-9213000000-43793fda5049bfa6f206	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Pentanamido-3-phenylpropanoic acid 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 - 2-Pentanamido-3-phenylpropanoic acid 10V, Negative-QTOF	splash10-0002-0090000000-7e014468ea363956075f	2017-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Pentanamido-3-phenylpropanoic acid 20V, Negative-QTOF	splash10-0uej-6890000000-64d1a22a4af666147c98	2017-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Pentanamido-3-phenylpropanoic acid 40V, Negative-QTOF	splash10-00kf-9400000000-3fd2712b94669b05a66c	2017-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Pentanamido-3-phenylpropanoic acid 10V, Positive-QTOF	splash10-0w30-2590000000-6a3356e9d89b2940ab8e	2017-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Pentanamido-3-phenylpropanoic acid 20V, Positive-QTOF	splash10-02t9-3920000000-bc5e839b023e53725ba7	2017-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Pentanamido-3-phenylpropanoic acid 40V, Positive-QTOF	splash10-0006-9200000000-93f27672c4b676e79f94	2017-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Pentanamido-3-phenylpropanoic acid 10V, Positive-QTOF	splash10-0gb9-0950000000-0a80dcfc16f081eba3d4	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Pentanamido-3-phenylpropanoic acid 20V, Positive-QTOF	splash10-066r-3900000000-6fab57d124367fc5435b	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Pentanamido-3-phenylpropanoic acid 40V, Positive-QTOF	splash10-006x-9700000000-2cfe4e4eb45e6468f559	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Pentanamido-3-phenylpropanoic acid 10V, Negative-QTOF	splash10-01ot-1980000000-18b161d3ea175e4935ff	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Pentanamido-3-phenylpropanoic acid 20V, Negative-QTOF	splash10-0w2a-2920000000-cbf20358ebdaa49d29c4	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Pentanamido-3-phenylpropanoic acid 40V, Negative-QTOF	splash10-00kf-9700000000-40ce01d211a26c035487	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

14753835

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13890535

PDB ID

Not Available

ChEBI ID

189895

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

Not Available

Showing metabocard for 2-Pentanamido-3-phenylpropanoic acid (HMDB0094646)

MOL for HMDB0094646 (2-Pentanamido-3-phenylpropanoic acid)

3D MOL for HMDB0094646 (2-Pentanamido-3-phenylpropanoic acid)

3D SDF for HMDB0094646 (2-Pentanamido-3-phenylpropanoic acid)

3D-SDF for HMDB0094646 (2-Pentanamido-3-phenylpropanoic acid)

PDB for HMDB0094646 (2-Pentanamido-3-phenylpropanoic acid)

3D PDB for HMDB0094646 (2-Pentanamido-3-phenylpropanoic acid)

SMILES for HMDB0094646 (2-Pentanamido-3-phenylpropanoic acid)

INCHI for HMDB0094646 (2-Pentanamido-3-phenylpropanoic acid)

Structure for HMDB0094646 (2-Pentanamido-3-phenylpropanoic acid)

3D Structure for HMDB0094646 (2-Pentanamido-3-phenylpropanoic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra