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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 07:01:55 UTC

Update Date

2021-09-26 23:01:16 UTC

HMDB ID

HMDB0250058

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(3s)-3-(Benzyloxy)-L-Aspartic Acid

Description

(3s)-3-(Benzyloxy)-L-Aspartic Acid, also known as DL-TBOA or benzyloxyaspartate, belongs to the class of organic compounds known as aspartic acid and derivatives. Aspartic acid and derivatives are compounds containing an aspartic acid or a derivative thereof resulting from reaction of aspartic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Based on a literature review a small amount of articles have been published on (3s)-3-(Benzyloxy)-L-Aspartic Acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). (3s)-3-(benzyloxy)-l-aspartic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (3s)-3-(Benzyloxy)-L-Aspartic Acid is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0250058
     RDKit          3D
(3s)-3-(Benzyloxy)-L-Aspartic Acid
 30 30  0  0  0  0  0  0  0  0999 V2000
    0.7035    0.4545   -1.5554 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6119    0.8577   -0.5252 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9058    0.0988   -0.6535 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8517    0.2889    0.1444 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0458   -0.8292   -1.6799 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1144    0.6454    0.8758 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8623   -0.6783    1.0813 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3965   -1.0466    1.4370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4756   -0.7245    0.4879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7307   -1.5367   -0.6140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7318   -1.2767   -1.5213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5019   -0.1529   -1.3040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2699    0.6673   -0.2210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2550    0.3918    0.6873 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1276    1.1978    1.8193 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4229    2.4137    1.7029 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7543    0.4662    2.8011 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2488   -0.0020   -2.3184 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2396    1.3059   -1.9447 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8778    1.9378   -0.6682 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6837   -1.6245   -1.5866 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1837    1.2557    1.0296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7201   -0.6698    2.4283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3747   -2.1696    1.5656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1343   -2.4328   -0.8079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9588   -1.8743   -2.3778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3179    0.1060   -1.9972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8822    1.5645   -0.0444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1337    1.0832    1.5208 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2493    0.2828    3.6595 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
  3  5  1  0
  2  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  6 15  1  0
 15 16  2  0
 15 17  1  0
 14  9  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  5 21  1  0
  6 22  1  0
  8 23  1  0
  8 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 17 30  1  0
M  END


  Mrv1652309112109022D          

 17 17  0  0  0  0            999 V2000
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    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    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   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
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 10 14  1  0  0  0  0
  9 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0250058

> <DATABASE_NAME>
hmdb

> <SMILES>
NC(C(OCC1=CC=CC=C1)C(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H13NO5/c12-8(10(13)14)9(11(15)16)17-6-7-4-2-1-3-5-7/h1-5,8-9H,6,12H2,(H,13,14)(H,15,16)

> <INCHI_KEY>
BYOBCYXURWDEDS-UHFFFAOYSA-N

> <FORMULA>
C11H13NO5

> <MOLECULAR_WEIGHT>
239.227

> <EXACT_MASS>
239.079372523

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
23.05704032350102

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-3-(benzyloxy)butanedioic acid

> <ALOGPS_LOGP>
-1.59

> <JCHEM_LOGP>
-2.0820696880629996

> <ALOGPS_LOGS>
-1.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.6956484284670794

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.9654906693288794

> <JCHEM_PKA_STRONGEST_BASIC>
8.96793354926045

> <JCHEM_POLAR_SURFACE_AREA>
109.85000000000001

> <JCHEM_REFRACTIVITY>
57.234700000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.18e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-3-(benzyloxy)butanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0250058
     RDKit          3D
(3s)-3-(Benzyloxy)-L-Aspartic Acid
 30 30  0  0  0  0  0  0  0  0999 V2000
    0.7035    0.4545   -1.5554 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6119    0.8577   -0.5252 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9058    0.0988   -0.6535 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8517    0.2889    0.1444 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0458   -0.8292   -1.6799 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1144    0.6454    0.8758 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8623   -0.6783    1.0813 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3965   -1.0466    1.4370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4756   -0.7245    0.4879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7307   -1.5367   -0.6140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7318   -1.2767   -1.5213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5019   -0.1529   -1.3040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2699    0.6673   -0.2210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2550    0.3918    0.6873 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1276    1.1978    1.8193 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4229    2.4137    1.7029 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7543    0.4662    2.8011 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2488   -0.0020   -2.3184 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2396    1.3059   -1.9447 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8778    1.9378   -0.6682 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6837   -1.6245   -1.5866 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1837    1.2557    1.0296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7201   -0.6698    2.4283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3747   -2.1696    1.5656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1343   -2.4328   -0.8079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9588   -1.8743   -2.3778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3179    0.1060   -1.9972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8822    1.5645   -0.0444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1337    1.0832    1.5208 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2493    0.2828    3.6595 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
  3  5  1  0
  2  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  6 15  1  0
 15 16  2  0
 15 17  1  0
 14  9  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  5 21  1  0
  6 22  1  0
  8 23  1  0
  8 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 17 30  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       8.002   4.620   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
HETATM   14  N   UNK     0       5.335   6.160   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   15                                                  
CONECT   10    9   11   14                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   10                                                            
CONECT   15    9   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

COMPND    HMDB0250058
HETATM    1  N1  UNL     1       0.703   0.454  -1.555  1.00  0.00           N  
HETATM    2  C1  UNL     1       1.612   0.858  -0.525  1.00  0.00           C  
HETATM    3  C2  UNL     1       2.906   0.099  -0.653  1.00  0.00           C  
HETATM    4  O1  UNL     1       3.852   0.289   0.144  1.00  0.00           O  
HETATM    5  O2  UNL     1       3.046  -0.829  -1.680  1.00  0.00           O  
HETATM    6  C3  UNL     1       1.114   0.645   0.876  1.00  0.00           C  
HETATM    7  O3  UNL     1       0.862  -0.678   1.081  1.00  0.00           O  
HETATM    8  C4  UNL     1      -0.397  -1.047   1.437  1.00  0.00           C  
HETATM    9  C5  UNL     1      -1.476  -0.724   0.488  1.00  0.00           C  
HETATM   10  C6  UNL     1      -1.731  -1.537  -0.614  1.00  0.00           C  
HETATM   11  C7  UNL     1      -2.732  -1.277  -1.521  1.00  0.00           C  
HETATM   12  C8  UNL     1      -3.502  -0.153  -1.304  1.00  0.00           C  
HETATM   13  C9  UNL     1      -3.270   0.667  -0.221  1.00  0.00           C  
HETATM   14  C10 UNL     1      -2.255   0.392   0.687  1.00  0.00           C  
HETATM   15  C11 UNL     1       2.128   1.198   1.819  1.00  0.00           C  
HETATM   16  O4  UNL     1       2.423   2.414   1.703  1.00  0.00           O  
HETATM   17  O5  UNL     1       2.754   0.466   2.801  1.00  0.00           O  
HETATM   18  H1  UNL     1       1.249  -0.002  -2.318  1.00  0.00           H  
HETATM   19  H2  UNL     1       0.240   1.306  -1.945  1.00  0.00           H  
HETATM   20  H3  UNL     1       1.878   1.938  -0.668  1.00  0.00           H  
HETATM   21  H4  UNL     1       3.684  -1.624  -1.587  1.00  0.00           H  
HETATM   22  H5  UNL     1       0.184   1.256   1.030  1.00  0.00           H  
HETATM   23  H6  UNL     1      -0.720  -0.670   2.428  1.00  0.00           H  
HETATM   24  H7  UNL     1      -0.375  -2.170   1.566  1.00  0.00           H  
HETATM   25  H8  UNL     1      -1.134  -2.433  -0.808  1.00  0.00           H  
HETATM   26  H9  UNL     1      -2.959  -1.874  -2.378  1.00  0.00           H  
HETATM   27  H10 UNL     1      -4.318   0.106  -1.997  1.00  0.00           H  
HETATM   28  H11 UNL     1      -3.882   1.564  -0.044  1.00  0.00           H  
HETATM   29  H12 UNL     1      -2.134   1.083   1.521  1.00  0.00           H  
HETATM   30  H13 UNL     1       2.249   0.283   3.660  1.00  0.00           H  
CONECT    1    2   18   19
CONECT    2    3    6   20
CONECT    3    4    4    5
CONECT    5   21
CONECT    6    7   15   22
CONECT    7    8
CONECT    8    9   23   24
CONECT    9   10   10   14
CONECT   10   11   25
CONECT   11   12   12   26
CONECT   12   13   27
CONECT   13   14   14   28
CONECT   14   29
CONECT   15   16   16   17
CONECT   17   30
END

HMDB0250058
     RDKit          3D
(3s)-3-(Benzyloxy)-L-Aspartic Acid
 30 30  0  0  0  0  0  0  0  0999 V2000
    0.7035    0.4545   -1.5554 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6119    0.8577   -0.5252 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9058    0.0988   -0.6535 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8517    0.2889    0.1444 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0458   -0.8292   -1.6799 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1144    0.6454    0.8758 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8623   -0.6783    1.0813 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3965   -1.0466    1.4370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4756   -0.7245    0.4879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7307   -1.5367   -0.6140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7318   -1.2767   -1.5213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5019   -0.1529   -1.3040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2699    0.6673   -0.2210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2550    0.3918    0.6873 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1276    1.1978    1.8193 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4229    2.4137    1.7029 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7543    0.4662    2.8011 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2488   -0.0020   -2.3184 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2396    1.3059   -1.9447 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8778    1.9378   -0.6682 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6837   -1.6245   -1.5866 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1837    1.2557    1.0296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7201   -0.6698    2.4283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3747   -2.1696    1.5656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1343   -2.4328   -0.8079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9588   -1.8743   -2.3778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3179    0.1060   -1.9972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8822    1.5645   -0.0444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1337    1.0832    1.5208 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2493    0.2828    3.6595 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
  3  5  1  0
  2  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  6 15  1  0
 15 16  2  0
 15 17  1  0
 14  9  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  5 21  1  0
  6 22  1  0
  8 23  1  0
  8 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 17 30  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(3S)-3-(Benzyloxy)-L-aspartate	Generator
2-Amino-3-(benzyloxy)butanedioate	HMDB
DL-TBOA	HMDB
TBOA	HMDB
Benzyloxyaspartate	HMDB
DL-Threo-beta-benzyloxyaspartate	HMDB

Chemical Formula

C₁₁H₁₃NO₅

Average Molecular Weight

239.227

Monoisotopic Molecular Weight

239.079372523

IUPAC Name

2-amino-3-(benzyloxy)butanedioic acid

Traditional Name

2-amino-3-(benzyloxy)butanedioic acid

CAS Registry Number

Not Available

SMILES

NC(C(OCC1=CC=CC=C1)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C11H13NO5/c12-8(10(13)14)9(11(15)16)17-6-7-4-2-1-3-5-7/h1-5,8-9H,6,12H2,(H,13,14)(H,15,16)

InChI Key

BYOBCYXURWDEDS-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aspartic acid and derivatives. Aspartic acid and derivatives are compounds containing an aspartic acid or a derivative thereof resulting from reaction of aspartic acid 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

Aspartic acid and derivatives

Alternative Parents

Substituents

Aspartic acid or derivatives
Alpha-amino acid
Benzylether
Monocyclic benzene moiety
Benzenoid
Dicarboxylic acid or derivatives
Monosaccharide
Amino acid
Carboxylic acid
Dialkyl ether
Ether
Organic nitrogen compound
Organonitrogen compound
Primary aliphatic amine
Organooxygen compound
Primary amine
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

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	-1.6	ALOGPS
logP	-2.1	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	2.97	ChemAxon
pKa (Strongest Basic)	8.97	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	109.85 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	57.23 m³·mol⁻¹	ChemAxon
Polarizability	23.06 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]+	145.89	30932474
DeepCCS	[M-H]-	143.532	30932474
DeepCCS	[M-2H]-	177.393	30932474
DeepCCS	[M+Na]+	152.606	30932474
AllCCS	[M+H]+	153.5	32859911
AllCCS	[M+H-H2O]+	149.9	32859911
AllCCS	[M+NH4]+	156.9	32859911
AllCCS	[M+Na]+	157.8	32859911
AllCCS	[M-H]-	151.9	32859911
AllCCS	[M+Na-2H]-	152.2	32859911
AllCCS	[M+HCOO]-	152.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	11.0085 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	7.84 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	910.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	286.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	79.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	176.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	87.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	294.6 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	293.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	682.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	699.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	201.0 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	917.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	199.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	251.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	459.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	330.3 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	317.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(3s)-3-(Benzyloxy)-L-Aspartic Acid	NC(C(OCC1=CC=CC=C1)C(O)=O)C(O)=O	3223.2	Standard polar	33892256
(3s)-3-(Benzyloxy)-L-Aspartic Acid	NC(C(OCC1=CC=CC=C1)C(O)=O)C(O)=O	1971.1	Standard non polar	33892256
(3s)-3-(Benzyloxy)-L-Aspartic Acid	NC(C(OCC1=CC=CC=C1)C(O)=O)C(O)=O	2342.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(3s)-3-(Benzyloxy)-L-Aspartic Acid,3TMS,isomer #1	C[Si](C)(C)NC(C(=O)O[Si](C)(C)C)C(OCC1=CC=CC=C1)C(=O)O[Si](C)(C)C	2062.6	Semi standard non polar	33892256
(3s)-3-(Benzyloxy)-L-Aspartic Acid,3TMS,isomer #1	C[Si](C)(C)NC(C(=O)O[Si](C)(C)C)C(OCC1=CC=CC=C1)C(=O)O[Si](C)(C)C	2108.8	Standard non polar	33892256
(3s)-3-(Benzyloxy)-L-Aspartic Acid,3TMS,isomer #1	C[Si](C)(C)NC(C(=O)O[Si](C)(C)C)C(OCC1=CC=CC=C1)C(=O)O[Si](C)(C)C	2479.1	Standard polar	33892256
(3s)-3-(Benzyloxy)-L-Aspartic Acid,3TMS,isomer #2	C[Si](C)(C)OC(=O)C(OCC1=CC=CC=C1)C(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2266.2	Semi standard non polar	33892256
(3s)-3-(Benzyloxy)-L-Aspartic Acid,3TMS,isomer #2	C[Si](C)(C)OC(=O)C(OCC1=CC=CC=C1)C(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2171.7	Standard non polar	33892256
(3s)-3-(Benzyloxy)-L-Aspartic Acid,3TMS,isomer #2	C[Si](C)(C)OC(=O)C(OCC1=CC=CC=C1)C(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2625.5	Standard polar	33892256
(3s)-3-(Benzyloxy)-L-Aspartic Acid,3TMS,isomer #3	C[Si](C)(C)OC(=O)C(C(OCC1=CC=CC=C1)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2237.7	Semi standard non polar	33892256
(3s)-3-(Benzyloxy)-L-Aspartic Acid,3TMS,isomer #3	C[Si](C)(C)OC(=O)C(C(OCC1=CC=CC=C1)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2188.3	Standard non polar	33892256
(3s)-3-(Benzyloxy)-L-Aspartic Acid,3TMS,isomer #3	C[Si](C)(C)OC(=O)C(C(OCC1=CC=CC=C1)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2617.4	Standard polar	33892256
(3s)-3-(Benzyloxy)-L-Aspartic Acid,4TMS,isomer #1	C[Si](C)(C)OC(=O)C(OCC1=CC=CC=C1)C(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2274.6	Semi standard non polar	33892256
(3s)-3-(Benzyloxy)-L-Aspartic Acid,4TMS,isomer #1	C[Si](C)(C)OC(=O)C(OCC1=CC=CC=C1)C(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2248.0	Standard non polar	33892256
(3s)-3-(Benzyloxy)-L-Aspartic Acid,4TMS,isomer #1	C[Si](C)(C)OC(=O)C(OCC1=CC=CC=C1)C(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2443.9	Standard polar	33892256
(3s)-3-(Benzyloxy)-L-Aspartic Acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(C(=O)O[Si](C)(C)C(C)(C)C)C(OCC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C	2722.9	Semi standard non polar	33892256
(3s)-3-(Benzyloxy)-L-Aspartic Acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(C(=O)O[Si](C)(C)C(C)(C)C)C(OCC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C	2693.4	Standard non polar	33892256
(3s)-3-(Benzyloxy)-L-Aspartic Acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(C(=O)O[Si](C)(C)C(C)(C)C)C(OCC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C	2843.1	Standard polar	33892256
(3s)-3-(Benzyloxy)-L-Aspartic Acid,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C(OCC1=CC=CC=C1)C(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2926.4	Semi standard non polar	33892256
(3s)-3-(Benzyloxy)-L-Aspartic Acid,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C(OCC1=CC=CC=C1)C(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2735.8	Standard non polar	33892256
(3s)-3-(Benzyloxy)-L-Aspartic Acid,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C(OCC1=CC=CC=C1)C(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2898.2	Standard polar	33892256
(3s)-3-(Benzyloxy)-L-Aspartic Acid,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C(C(OCC1=CC=CC=C1)C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2937.9	Semi standard non polar	33892256
(3s)-3-(Benzyloxy)-L-Aspartic Acid,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C(C(OCC1=CC=CC=C1)C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2740.7	Standard non polar	33892256
(3s)-3-(Benzyloxy)-L-Aspartic Acid,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C(C(OCC1=CC=CC=C1)C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2890.4	Standard polar	33892256
(3s)-3-(Benzyloxy)-L-Aspartic Acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(OCC1=CC=CC=C1)C(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3131.3	Semi standard non polar	33892256
(3s)-3-(Benzyloxy)-L-Aspartic Acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(OCC1=CC=CC=C1)C(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2980.6	Standard non polar	33892256
(3s)-3-(Benzyloxy)-L-Aspartic Acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(OCC1=CC=CC=C1)C(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2831.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (3s)-3-(Benzyloxy)-L-Aspartic Acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9200000000-3651d7b04e6e31aaf41a	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (3s)-3-(Benzyloxy)-L-Aspartic Acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (3s)-3-(Benzyloxy)-L-Aspartic Acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (3s)-3-(Benzyloxy)-L-Aspartic Acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (3s)-3-(Benzyloxy)-L-Aspartic Acid GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (3s)-3-(Benzyloxy)-L-Aspartic Acid GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (3s)-3-(Benzyloxy)-L-Aspartic Acid GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (3s)-3-(Benzyloxy)-L-Aspartic Acid GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (3s)-3-(Benzyloxy)-L-Aspartic Acid GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (3s)-3-(Benzyloxy)-L-Aspartic Acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (3s)-3-(Benzyloxy)-L-Aspartic Acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (3s)-3-(Benzyloxy)-L-Aspartic Acid GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (3s)-3-(Benzyloxy)-L-Aspartic Acid GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (3s)-3-(Benzyloxy)-L-Aspartic Acid GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (3s)-3-(Benzyloxy)-L-Aspartic Acid GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (3s)-3-(Benzyloxy)-L-Aspartic Acid GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	2021-11-03	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 - (3s)-3-(Benzyloxy)-L-Aspartic Acid 10V, Positive-QTOF	splash10-0006-9430000000-395e6cdb3c9d14bf92d3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3s)-3-(Benzyloxy)-L-Aspartic Acid 20V, Positive-QTOF	splash10-0006-9200000000-423da4f33f03b90aa45b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3s)-3-(Benzyloxy)-L-Aspartic Acid 40V, Positive-QTOF	splash10-0006-9000000000-26186aab5ab9dacdc971	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3s)-3-(Benzyloxy)-L-Aspartic Acid 10V, Negative-QTOF	splash10-000i-2390000000-fe68a6b3157f7132e1fa	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3s)-3-(Benzyloxy)-L-Aspartic Acid 20V, Negative-QTOF	splash10-01p9-9700000000-5d6ee23d24a22c9b1a64	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3s)-3-(Benzyloxy)-L-Aspartic Acid 40V, Negative-QTOF	splash10-002f-9100000000-2fcd5369a5f45b3c4c42	2021-10-12	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	Not Specified	Not Specified	Normal	31557052	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

3346208

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

4133412

PDB ID

Not Available

ChEBI ID

94964

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for (3s)-3-(Benzyloxy)-L-Aspartic Acid (HMDB0250058)

MOL for HMDB0250058 ((3s)-3-(Benzyloxy)-L-Aspartic Acid)

3D MOL for HMDB0250058 ((3s)-3-(Benzyloxy)-L-Aspartic Acid)

3D SDF for HMDB0250058 ((3s)-3-(Benzyloxy)-L-Aspartic Acid)

3D-SDF for HMDB0250058 ((3s)-3-(Benzyloxy)-L-Aspartic Acid)

PDB for HMDB0250058 ((3s)-3-(Benzyloxy)-L-Aspartic Acid)

3D PDB for HMDB0250058 ((3s)-3-(Benzyloxy)-L-Aspartic Acid)

SMILES for HMDB0250058 ((3s)-3-(Benzyloxy)-L-Aspartic Acid)

INCHI for HMDB0250058 ((3s)-3-(Benzyloxy)-L-Aspartic Acid)

Structure for HMDB0250058 ((3s)-3-(Benzyloxy)-L-Aspartic Acid)

3D Structure for HMDB0250058 ((3s)-3-(Benzyloxy)-L-Aspartic Acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra