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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2020-02-04 19:35:57 UTC

Update Date

2022-03-07 03:18:20 UTC

HMDB ID

HMDB0240628

Secondary Accession Numbers

None

Metabolite Identification

Common Name

1-Carboxyethylphenylalanine

Description

1-Carboxyethylphenylalanine belongs to the class of organic compounds known as phenylalanine and derivatives. These are compounds containing phenylalanine or a derivative thereof resulting from a reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. 1-Carboxyethylphenylalanine was identified as one of forty plasma metabolites that could be used to predict gut microbiome Shannon diversity (PMID: 31477923 ). Shannon diversity is a metric that summarizes both species abundance and evenness, and it has been suggested as a marker for microbiome health.

Structure

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

HMDB0240628
     RDKit          3D
1-Carboxyethylphenylalanine
 32 32  0  0  0  0  0  0  0  0999 V2000
   -3.0315    1.5149    1.0546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5067    0.6387   -0.1893 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9488   -0.5290    0.4278 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5741   -0.8340    0.0059 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3137    0.2897    0.2174 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7487    0.1949   -0.0784 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3451    0.2491   -1.3113 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7023    0.3215   -1.4826 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6145    0.3415   -0.4043 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0082    0.2889    0.8498 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6555    0.2187    1.0102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2773   -2.1751    0.4531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0618   -3.1441    0.2044 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8869   -2.4917    1.1851 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6855    0.4684   -1.0335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7795    1.0434   -0.7758 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6290   -0.3487   -2.1640 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1630    2.5145    0.6706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9344    1.0161    1.4257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2074    1.4412    1.7543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8086    1.3042   -0.6430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5528   -1.3408    0.4693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7339   -0.8869   -1.1489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0606    1.1639   -0.4640 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1365    0.7135    1.2465 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6878    0.2373   -2.2039 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1857    0.3718   -2.4805 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6969    0.4164   -0.5347 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6905    0.3047    1.6909 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1828    0.1845    2.0121 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9299   -2.1608    2.1662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8302   -1.3267   -1.9298 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  4 12  1  0
 12 13  2  0
 12 14  1  0
  2 15  1  0
 15 16  2  0
 15 17  1  0
 11  6  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  6
  3 22  1  0
  4 23  1  6
  5 24  1  0
  5 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 14 31  1  0
 17 32  1  0
M  END


  Mrv1652302042020262D          

 17 17  0  0  0  0            999 V2000
 9999.988110001.0357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.702410000.6229    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.7024 9999.7977    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10001.4249 9999.3981    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.4249 9998.5723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7085 9998.1584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.1391 9998.1584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.1391 9999.8099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.418710001.0357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.132910000.6229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.418710001.8615    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.271010000.6227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.556610001.0351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.842110000.6226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8420 9999.7976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5565 9999.3851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2711 9999.7977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  1  0  0  0
  2  9  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  4  8  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 12  1  0  0  0  0
  1 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0240628

> <DATABASE_NAME>
hmdb

> <SMILES>
C[C@@H](N[C@@H](CC1=CC=CC=C1)C(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H15NO4/c1-8(11(14)15)13-10(12(16)17)7-9-5-3-2-4-6-9/h2-6,8,10,13H,7H2,1H3,(H,14,15)(H,16,17)/t8-,10+/m1/s1

> <INCHI_KEY>
MSBSJGQKNVMMQB-SCZZXKLOSA-N

> <FORMULA>
C12H15NO4

> <MOLECULAR_WEIGHT>
237.255

> <EXACT_MASS>
237.100107967

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
24.058531467113

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-{[(1R)-1-carboxyethyl]amino}-3-phenylpropanoic acid

> <ALOGPS_LOGP>
-0.60

> <JCHEM_LOGP>
-1.135644549049044

> <ALOGPS_LOGS>
-1.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.503708537944158

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.7995246971365098

> <JCHEM_PKA_STRONGEST_BASIC>
8.578392714793198

> <JCHEM_POLAR_SURFACE_AREA>
86.63

> <JCHEM_REFRACTIVITY>
60.46940000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.77e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-{[(1R)-1-carboxyethyl]amino}-3-phenylpropanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0240628
     RDKit          3D
1-Carboxyethylphenylalanine
 32 32  0  0  0  0  0  0  0  0999 V2000
   -3.0315    1.5149    1.0546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5067    0.6387   -0.1893 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9488   -0.5290    0.4278 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5741   -0.8340    0.0059 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3137    0.2897    0.2174 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7487    0.1949   -0.0784 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3451    0.2491   -1.3113 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7023    0.3215   -1.4826 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6145    0.3415   -0.4043 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0082    0.2889    0.8498 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6555    0.2187    1.0102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2773   -2.1751    0.4531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0618   -3.1441    0.2044 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8869   -2.4917    1.1851 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6855    0.4684   -1.0335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7795    1.0434   -0.7758 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6290   -0.3487   -2.1640 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1630    2.5145    0.6706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9344    1.0161    1.4257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2074    1.4412    1.7543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8086    1.3042   -0.6430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5528   -1.3408    0.4693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7339   -0.8869   -1.1489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0606    1.1639   -0.4640 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1365    0.7135    1.2465 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6878    0.2373   -2.2039 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1857    0.3718   -2.4805 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6969    0.4164   -0.5347 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6905    0.3047    1.6909 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1828    0.1845    2.0121 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9299   -2.1608    2.1662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8302   -1.3267   -1.9298 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  4 12  1  0
 12 13  2  0
 12 14  1  0
  2 15  1  0
 15 16  2  0
 15 17  1  0
 11  6  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  6
  3 22  1  0
  4 23  1  6
  5 24  1  0
  5 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 14 31  1  0
 17 32  1  0
M  END

HEADER    PROTEIN                                 04-FEB-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-FEB-20         0                                  
HETATM    1  C   UNK     0    8666.6448668.600   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8667.9788667.829   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0    8667.9788666.289   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0    8669.3268665.543   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8669.3268664.002   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0    8667.9898663.229   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    8670.6608663.229   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0    8670.6608666.312   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8669.3158668.600   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0    8670.6488667.829   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0    8669.3158670.141   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0    8665.3068667.829   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8663.9728668.599   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8662.6398667.829   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8662.6388666.289   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8663.9728665.519   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8665.3068666.289   0.000  0.00  0.00           C+0
CONECT    1    2   12                                                       
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    8                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    4                                                            
CONECT    9    2   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12   13   17    1                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

COMPND    HMDB0240628
HETATM    1  C1  UNL     1      -3.031   1.515   1.055  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.507   0.639  -0.189  1.00  0.00           C  
HETATM    3  N1  UNL     1      -1.949  -0.529   0.428  1.00  0.00           N  
HETATM    4  C3  UNL     1      -0.574  -0.834   0.006  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.314   0.290   0.217  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.749   0.195  -0.078  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.345   0.249  -1.311  1.00  0.00           C  
HETATM    8  C7  UNL     1       3.702   0.321  -1.483  1.00  0.00           C  
HETATM    9  C8  UNL     1       4.615   0.341  -0.404  1.00  0.00           C  
HETATM   10  C9  UNL     1       4.008   0.289   0.850  1.00  0.00           C  
HETATM   11  C10 UNL     1       2.655   0.219   1.010  1.00  0.00           C  
HETATM   12  C11 UNL     1      -0.277  -2.175   0.453  1.00  0.00           C  
HETATM   13  O1  UNL     1      -1.062  -3.144   0.204  1.00  0.00           O  
HETATM   14  O2  UNL     1       0.887  -2.492   1.185  1.00  0.00           O  
HETATM   15  C12 UNL     1      -3.686   0.468  -1.034  1.00  0.00           C  
HETATM   16  O3  UNL     1      -4.779   1.043  -0.776  1.00  0.00           O  
HETATM   17  O4  UNL     1      -3.629  -0.349  -2.164  1.00  0.00           O  
HETATM   18  H1  UNL     1      -3.163   2.515   0.671  1.00  0.00           H  
HETATM   19  H2  UNL     1      -3.934   1.016   1.426  1.00  0.00           H  
HETATM   20  H3  UNL     1      -2.207   1.441   1.754  1.00  0.00           H  
HETATM   21  H4  UNL     1      -1.809   1.304  -0.643  1.00  0.00           H  
HETATM   22  H5  UNL     1      -2.553  -1.341   0.469  1.00  0.00           H  
HETATM   23  H6  UNL     1      -0.734  -0.887  -1.149  1.00  0.00           H  
HETATM   24  H7  UNL     1      -0.061   1.164  -0.464  1.00  0.00           H  
HETATM   25  H8  UNL     1       0.136   0.713   1.246  1.00  0.00           H  
HETATM   26  H9  UNL     1       1.688   0.237  -2.204  1.00  0.00           H  
HETATM   27  H10 UNL     1       4.186   0.372  -2.480  1.00  0.00           H  
HETATM   28  H11 UNL     1       5.697   0.416  -0.535  1.00  0.00           H  
HETATM   29  H12 UNL     1       4.691   0.305   1.691  1.00  0.00           H  
HETATM   30  H13 UNL     1       2.183   0.184   2.012  1.00  0.00           H  
HETATM   31  H14 UNL     1       0.930  -2.161   2.166  1.00  0.00           H  
HETATM   32  H15 UNL     1      -3.830  -1.327  -1.930  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3   15   21
CONECT    3    4   22
CONECT    4    5   12   23
CONECT    5    6   24   25
CONECT    6    7    7   11
CONECT    7    8   26
CONECT    8    9    9   27
CONECT    9   10   28
CONECT   10   11   11   29
CONECT   11   30
CONECT   12   13   13   14
CONECT   14   31
CONECT   15   16   16   17
CONECT   17   32
END

HMDB0240628
     RDKit          3D
1-Carboxyethylphenylalanine
 32 32  0  0  0  0  0  0  0  0999 V2000
   -3.0315    1.5149    1.0546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5067    0.6387   -0.1893 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9488   -0.5290    0.4278 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5741   -0.8340    0.0059 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3137    0.2897    0.2174 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7487    0.1949   -0.0784 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3451    0.2491   -1.3113 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7023    0.3215   -1.4826 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6145    0.3415   -0.4043 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0082    0.2889    0.8498 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6555    0.2187    1.0102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2773   -2.1751    0.4531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0618   -3.1441    0.2044 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8869   -2.4917    1.1851 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6855    0.4684   -1.0335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7795    1.0434   -0.7758 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6290   -0.3487   -2.1640 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1630    2.5145    0.6706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9344    1.0161    1.4257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2074    1.4412    1.7543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8086    1.3042   -0.6430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5528   -1.3408    0.4693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7339   -0.8869   -1.1489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0606    1.1639   -0.4640 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1365    0.7135    1.2465 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6878    0.2373   -2.2039 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1857    0.3718   -2.4805 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6969    0.4164   -0.5347 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6905    0.3047    1.6909 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1828    0.1845    2.0121 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9299   -2.1608    2.1662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8302   -1.3267   -1.9298 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  4 12  1  0
 12 13  2  0
 12 14  1  0
  2 15  1  0
 15 16  2  0
 15 17  1  0
 11  6  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  6
  3 22  1  0
  4 23  1  6
  5 24  1  0
  5 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 14 31  1  0
 17 32  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(2S)-2-{[(1R)-1-carboxyethyl]amino}-3-phenylpropanoate	HMDB
(R)-N-(1-Carboxyethyl)-L-phenylalanine	HMDB
N-(1-Carboxyethyl)-L-phenylalanine	HMDB
N-[(1R)-1-Carboxyethyl]-L-phenylalanine	HMDB
1-Carboxyethylphenylalanine	HMDB

Chemical Formula

C₁₂H₁₅NO₄

Average Molecular Weight

237.255

Monoisotopic Molecular Weight

237.100107967

IUPAC Name

(2S)-2-{[(1R)-1-carboxyethyl]amino}-3-phenylpropanoic acid

Traditional Name

(2S)-2-{[(1R)-1-carboxyethyl]amino}-3-phenylpropanoic acid

CAS Registry Number

123300-05-0

SMILES

C[C@@H](N[C@@H](CC1=CC=CC=C1)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C12H15NO4/c1-8(11(14)15)13-10(12(16)17)7-9-5-3-2-4-6-9/h2-6,8,10,13H,7H2,1H3,(H,14,15)(H,16,17)/t8-,10+/m1/s1

InChI Key

MSBSJGQKNVMMQB-SCZZXKLOSA-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
Alanine or derivatives
3-phenylpropanoic-acid
L-alpha-amino acid
D-alpha-amino acid
Amphetamine or derivatives
Alpha-amino acid
Aralkylamine
Benzenoid
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Amino acid
Secondary amine
Secondary aliphatic amine
Carboxylic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

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	-0.6	ALOGPS
logP	-1.1	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	2.8	ChemAxon
pKa (Strongest Basic)	8.58	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.63 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	60.47 m³·mol⁻¹	ChemAxon
Polarizability	24.06 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
DeepCCS	[M+H]+	154.686	30932474
DeepCCS	[M-H]-	152.291	30932474
DeepCCS	[M-2H]-	185.314	30932474
DeepCCS	[M+Na]+	160.668	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1-Carboxyethylphenylalanine	C[C@@H](N[C@@H](CC1=CC=CC=C1)C(O)=O)C(O)=O	3409.2	Standard polar	33892256
1-Carboxyethylphenylalanine	C[C@@H](N[C@@H](CC1=CC=CC=C1)C(O)=O)C(O)=O	1877.9	Standard non polar	33892256
1-Carboxyethylphenylalanine	C[C@@H](N[C@@H](CC1=CC=CC=C1)C(O)=O)C(O)=O	2009.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
1-Carboxyethylphenylalanine,1TMS,isomer #1	C[C@@H](N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)C(=O)O	2014.0	Semi standard non polar	33892256
1-Carboxyethylphenylalanine,1TMS,isomer #2	C[C@@H](N[C@@H](CC1=CC=CC=C1)C(=O)O)C(=O)O[Si](C)(C)C	2001.8	Semi standard non polar	33892256
1-Carboxyethylphenylalanine,1TMS,isomer #3	C[C@H](C(=O)O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C	2065.0	Semi standard non polar	33892256
1-Carboxyethylphenylalanine,2TMS,isomer #1	C[C@@H](N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1988.2	Semi standard non polar	33892256
1-Carboxyethylphenylalanine,2TMS,isomer #2	C[C@H](C(=O)O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2060.8	Semi standard non polar	33892256
1-Carboxyethylphenylalanine,2TMS,isomer #3	C[C@H](C(=O)O[Si](C)(C)C)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C	2043.4	Semi standard non polar	33892256
1-Carboxyethylphenylalanine,3TMS,isomer #1	C[C@H](C(=O)O[Si](C)(C)C)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2059.8	Semi standard non polar	33892256
1-Carboxyethylphenylalanine,3TMS,isomer #1	C[C@H](C(=O)O[Si](C)(C)C)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2087.9	Standard non polar	33892256
1-Carboxyethylphenylalanine,3TMS,isomer #1	C[C@H](C(=O)O[Si](C)(C)C)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2329.0	Standard polar	33892256
1-Carboxyethylphenylalanine,1TBDMS,isomer #1	C[C@@H](N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O	2264.4	Semi standard non polar	33892256
1-Carboxyethylphenylalanine,1TBDMS,isomer #2	C[C@@H](N[C@@H](CC1=CC=CC=C1)C(=O)O)C(=O)O[Si](C)(C)C(C)(C)C	2253.6	Semi standard non polar	33892256
1-Carboxyethylphenylalanine,1TBDMS,isomer #3	C[C@H](C(=O)O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C	2307.5	Semi standard non polar	33892256
1-Carboxyethylphenylalanine,2TBDMS,isomer #1	C[C@@H](N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2464.9	Semi standard non polar	33892256
1-Carboxyethylphenylalanine,2TBDMS,isomer #2	C[C@H](C(=O)O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2558.2	Semi standard non polar	33892256
1-Carboxyethylphenylalanine,2TBDMS,isomer #3	C[C@H](C(=O)O[Si](C)(C)C(C)(C)C)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C	2542.5	Semi standard non polar	33892256
1-Carboxyethylphenylalanine,3TBDMS,isomer #1	C[C@H](C(=O)O[Si](C)(C)C(C)(C)C)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2762.5	Semi standard non polar	33892256
1-Carboxyethylphenylalanine,3TBDMS,isomer #1	C[C@H](C(=O)O[Si](C)(C)C(C)(C)C)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2700.4	Standard non polar	33892256
1-Carboxyethylphenylalanine,3TBDMS,isomer #1	C[C@H](C(=O)O[Si](C)(C)C(C)(C)C)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2689.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Carboxyethylphenylalanine 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 - 1-Carboxyethylphenylalanine 10V, Negative-QTOF	splash10-000i-4970000000-8a0243a1731af3f3dd55	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Carboxyethylphenylalanine 20V, Negative-QTOF	splash10-0w2a-2900000000-9e453638563bd181a033	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Carboxyethylphenylalanine 40V, Negative-QTOF	splash10-0v6u-9700000000-12f88d0448991565da38	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Carboxyethylphenylalanine 10V, Positive-QTOF	splash10-006w-0920000000-650ef8c19153badf621c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Carboxyethylphenylalanine 20V, Positive-QTOF	splash10-006t-1900000000-89e232f273025161f881	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Carboxyethylphenylalanine 40V, Positive-QTOF	splash10-0fdo-6900000000-fcddcd70806d687b633b	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

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

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	31477923	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

58808957

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

127261991

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

Wilmanski T, Rappaport N, Earls JC, Magis AT, Manor O, Lovejoy J, Omenn GS, Hood L, Gibbons SM, Price ND: Blood metabolome predicts gut microbiome alpha-diversity in humans. Nat Biotechnol. 2019 Oct;37(10):1217-1228. doi: 10.1038/s41587-019-0233-9. Epub 2019 Sep 2. [PubMed:31477923 ]

Showing metabocard for 1-Carboxyethylphenylalanine (HMDB0240628)

MOL for HMDB0240628 (1-Carboxyethylphenylalanine)

3D MOL for HMDB0240628 (1-Carboxyethylphenylalanine)

3D SDF for HMDB0240628 (1-Carboxyethylphenylalanine)

3D-SDF for HMDB0240628 (1-Carboxyethylphenylalanine)

PDB for HMDB0240628 (1-Carboxyethylphenylalanine)

3D PDB for HMDB0240628 (1-Carboxyethylphenylalanine)

SMILES for HMDB0240628 (1-Carboxyethylphenylalanine)

INCHI for HMDB0240628 (1-Carboxyethylphenylalanine)

Structure for HMDB0240628 (1-Carboxyethylphenylalanine)

3D Structure for HMDB0240628 (1-Carboxyethylphenylalanine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra