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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:36:33 UTC

Update Date

2022-03-07 02:52:32 UTC

HMDB ID

HMDB0030398

Secondary Accession Numbers

HMDB30398

Metabolite Identification

Common Name

N-(Carbomethoxyacetyl)-4-S-chlorotryptophan

Description

N-(Carbomethoxyacetyl)-4-S-chlorotryptophan belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. N-(Carbomethoxyacetyl)-4-S-chlorotryptophan has been detected, but not quantified in, common peas (Pisum sativum) and pulses. This could make N-(carbomethoxyacetyl)-4-S-chlorotryptophan a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on N-(Carbomethoxyacetyl)-4-S-chlorotryptophan.

Structure

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

HMDB0030398
     RDKit          3D
N-(Carbomethoxyacetyl)-4-S-chlorotryptophan
 38 39  0  0  0  0  0  0  0  0999 V2000
    6.1109    1.2001    0.1013 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7454    1.4503    0.3009 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8562    0.3765    0.5022 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2381   -0.8166    0.5110 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4336    0.7815    0.7018 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6549   -0.4841    0.8665 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9902   -1.3655    1.8754 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6696   -0.8094    0.1114 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1332   -1.9652    0.1669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5456   -1.8260    0.6775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4029   -0.9181   -0.0536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1393   -1.3229   -1.1796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7781   -0.2834   -1.7189 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4833    0.8034   -0.9747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8684    2.1319   -1.0530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4163    3.0330   -0.1240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5831    2.6518    0.8938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1903    1.3330    0.9850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1840    0.8017    2.3083 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.6259    0.4098    0.0667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1352   -2.6223   -1.1981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8149   -3.6614   -1.4308 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6097   -2.1047   -2.2395 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5159    1.9832   -0.5687 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6464    1.1461    1.0627 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2336    0.2366   -0.4540 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0866    1.3940   -0.1291 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4287    1.3771    1.6463 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0966   -1.0107    2.8246 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3227   -2.7825    0.8208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9856   -2.8681    0.5712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5482   -1.6967    1.7791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2059   -2.3223   -1.5836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3994   -0.2400   -2.5508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5289    2.4532   -1.8513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7066    4.0743   -0.1669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1976    3.3217    1.6530 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2334   -1.8597   -3.1501 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
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
  9 21  1  0
 21 22  2  0
 21 23  1  0
 20 11  1  0
 20 14  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  5 27  1  0
  5 28  1  0
  7 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
 12 33  1  0
 13 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
 23 38  1  0
M  END


  Mrv0541 05061305122D          

 23 24  0  0  0  0            999 V2000
   -4.0002    1.8218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    2.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8342    2.0919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768    3.1465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2822    2.7050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6412    2.2634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781    3.9312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4752    2.5334    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5371    3.4896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8961    3.0480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9851    4.1027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3739    4.5442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1932    1.6503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  8  5  1  0  0  0  0
  8  7  2  0  0  0  0
  9  3  1  0  0  0  0
 10  4  2  0  0  0  0
 11  5  1  0  0  0  0
 12  6  1  0  0  0  0
 13  6  1  0  0  0  0
 14  8  1  0  0  0  0
 14  9  2  0  0  0  0
 14 10  1  0  0  0  0
 15 11  1  0  0  0  0
 16  9  1  0  0  0  0
 17  7  1  0  0  0  0
 17 10  1  0  0  0  0
 18 11  1  0  0  0  0
 18 12  2  0  0  0  0
 19 12  1  0  0  0  0
 20 13  2  0  0  0  0
 21 15  2  0  0  0  0
 22 15  1  0  0  0  0
 23  1  1  0  0  0  0
 23 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030398

> <DATABASE_NAME>
hmdb

> <SMILES>
COC(=O)C\C(O)=N\C(CC1=CNC2=CC=CC(Cl)=C12)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H15ClN2O5/c1-23-13(20)6-12(19)18-11(15(21)22)5-8-7-17-10-4-2-3-9(16)14(8)10/h2-4,7,11,17H,5-6H2,1H3,(H,18,19)(H,21,22)

> <INCHI_KEY>
ITVFBZXHWIFZDX-UHFFFAOYSA-N

> <FORMULA>
C15H15ClN2O5

> <MOLECULAR_WEIGHT>
338.743

> <EXACT_MASS>
338.066949307

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
32.10399899668519

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(4-chloro-1H-indol-3-yl)-2-[(Z)-(1-hydroxy-3-methoxy-3-oxopropylidene)amino]propanoic acid

> <ALOGPS_LOGP>
1.83

> <JCHEM_LOGP>
2.456994954333333

> <ALOGPS_LOGS>
-3.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.602244627834041

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8224499772474907

> <JCHEM_PKA_STRONGEST_BASIC>
0.44870690739580577

> <JCHEM_POLAR_SURFACE_AREA>
111.97999999999999

> <JCHEM_REFRACTIVITY>
82.08630000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.87e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(4-chloro-1H-indol-3-yl)-2-[(Z)-(1-hydroxy-3-methoxy-3-oxopropylidene)amino]propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030398
     RDKit          3D
N-(Carbomethoxyacetyl)-4-S-chlorotryptophan
 38 39  0  0  0  0  0  0  0  0999 V2000
    6.1109    1.2001    0.1013 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7454    1.4503    0.3009 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8562    0.3765    0.5022 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2381   -0.8166    0.5110 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4336    0.7815    0.7018 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6549   -0.4841    0.8665 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9902   -1.3655    1.8754 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6696   -0.8094    0.1114 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1332   -1.9652    0.1669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5456   -1.8260    0.6775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4029   -0.9181   -0.0536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1393   -1.3229   -1.1796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7781   -0.2834   -1.7189 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4833    0.8034   -0.9747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8684    2.1319   -1.0530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4163    3.0330   -0.1240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5831    2.6518    0.8938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1903    1.3330    0.9850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1840    0.8017    2.3083 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.6259    0.4098    0.0667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1352   -2.6223   -1.1981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8149   -3.6614   -1.4308 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6097   -2.1047   -2.2395 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5159    1.9832   -0.5687 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6464    1.1461    1.0627 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2336    0.2366   -0.4540 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0866    1.3940   -0.1291 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4287    1.3771    1.6463 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0966   -1.0107    2.8246 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3227   -2.7825    0.8208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9856   -2.8681    0.5712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5482   -1.6967    1.7791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2059   -2.3223   -1.5836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3994   -0.2400   -2.5508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5289    2.4532   -1.8513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7066    4.0743   -0.1669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1976    3.3217    1.6530 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2334   -1.8597   -3.1501 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
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
  9 21  1  0
 21 22  2  0
 21 23  1  0
 20 11  1  0
 20 14  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  5 27  1  0
  5 28  1  0
  7 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
 12 33  1  0
 13 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
 23 38  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -7.467   3.401   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.650   5.553   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.424   3.905   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.126   4.089   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.143   5.873   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.393   5.049   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.930   4.225   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.332   7.338   0.000  0.00  0.00           C+0
HETATM   16 Cl   UNK     0       4.924   5.923   0.000  0.00  0.00          Cl+0
HETATM   17  N   UNK     0       2.126   1.597   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0      -0.887   4.729   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0      -2.869   6.514   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -5.406   5.690   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -1.839   7.658   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.698   8.483   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -5.961   3.081   0.000  0.00  0.00           O+0
CONECT    1   23                                                            
CONECT    2    3    4                                                       
CONECT    3    2    9                                                       
CONECT    4    2   10                                                       
CONECT    5    8   11                                                       
CONECT    6   12   13                                                       
CONECT    7    8   17                                                       
CONECT    8    5    7   14                                                  
CONECT    9    3   14   16                                                  
CONECT   10    4   14   17                                                  
CONECT   11    5   15   18                                                  
CONECT   12    6   18   19                                                  
CONECT   13    6   20   23                                                  
CONECT   14    8    9   10                                                  
CONECT   15   11   21   22                                                  
CONECT   16    9                                                            
CONECT   17    7   10                                                       
CONECT   18   11   12                                                       
CONECT   19   12                                                            
CONECT   20   13                                                            
CONECT   21   15                                                            
CONECT   22   15                                                            
CONECT   23    1   13                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

COMPND    HMDB0030398
HETATM    1  C1  UNL     1       6.111   1.200   0.101  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.745   1.450   0.301  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.856   0.376   0.502  1.00  0.00           C  
HETATM    4  O2  UNL     1       4.238  -0.817   0.511  1.00  0.00           O  
HETATM    5  C3  UNL     1       2.434   0.782   0.702  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.655  -0.484   0.867  1.00  0.00           C  
HETATM    7  O3  UNL     1       1.990  -1.366   1.875  1.00  0.00           O  
HETATM    8  N1  UNL     1       0.670  -0.809   0.111  1.00  0.00           N  
HETATM    9  C5  UNL     1      -0.133  -1.965   0.167  1.00  0.00           C  
HETATM   10  C6  UNL     1      -1.546  -1.826   0.678  1.00  0.00           C  
HETATM   11  C7  UNL     1      -2.403  -0.918  -0.054  1.00  0.00           C  
HETATM   12  C8  UNL     1      -3.139  -1.323  -1.180  1.00  0.00           C  
HETATM   13  N2  UNL     1      -3.778  -0.283  -1.719  1.00  0.00           N  
HETATM   14  C9  UNL     1      -3.483   0.803  -0.975  1.00  0.00           C  
HETATM   15  C10 UNL     1      -3.868   2.132  -1.053  1.00  0.00           C  
HETATM   16  C11 UNL     1      -3.416   3.033  -0.124  1.00  0.00           C  
HETATM   17  C12 UNL     1      -2.583   2.652   0.894  1.00  0.00           C  
HETATM   18  C13 UNL     1      -2.190   1.333   0.985  1.00  0.00           C  
HETATM   19 CL1  UNL     1      -1.184   0.802   2.308  1.00  0.00          CL  
HETATM   20  C14 UNL     1      -2.626   0.410   0.067  1.00  0.00           C  
HETATM   21  C15 UNL     1      -0.135  -2.622  -1.198  1.00  0.00           C  
HETATM   22  O4  UNL     1      -0.815  -3.661  -1.431  1.00  0.00           O  
HETATM   23  O5  UNL     1       0.610  -2.105  -2.239  1.00  0.00           O  
HETATM   24  H1  UNL     1       6.516   1.983  -0.569  1.00  0.00           H  
HETATM   25  H2  UNL     1       6.646   1.146   1.063  1.00  0.00           H  
HETATM   26  H3  UNL     1       6.234   0.237  -0.454  1.00  0.00           H  
HETATM   27  H4  UNL     1       2.087   1.394  -0.129  1.00  0.00           H  
HETATM   28  H5  UNL     1       2.429   1.377   1.646  1.00  0.00           H  
HETATM   29  H6  UNL     1       2.097  -1.011   2.825  1.00  0.00           H  
HETATM   30  H7  UNL     1       0.323  -2.782   0.821  1.00  0.00           H  
HETATM   31  H8  UNL     1      -1.986  -2.868   0.571  1.00  0.00           H  
HETATM   32  H9  UNL     1      -1.548  -1.697   1.779  1.00  0.00           H  
HETATM   33  H10 UNL     1      -3.206  -2.322  -1.584  1.00  0.00           H  
HETATM   34  H11 UNL     1      -4.399  -0.240  -2.551  1.00  0.00           H  
HETATM   35  H12 UNL     1      -4.529   2.453  -1.851  1.00  0.00           H  
HETATM   36  H13 UNL     1      -3.707   4.074  -0.167  1.00  0.00           H  
HETATM   37  H14 UNL     1      -2.198   3.322   1.653  1.00  0.00           H  
HETATM   38  H15 UNL     1       0.233  -1.860  -3.150  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3
CONECT    3    4    4    5
CONECT    5    6   27   28
CONECT    6    7    8    8
CONECT    7   29
CONECT    8    9
CONECT    9   10   21   30
CONECT   10   11   31   32
CONECT   11   12   12   20
CONECT   12   13   33
CONECT   13   14   34
CONECT   14   15   15   20
CONECT   15   16   35
CONECT   16   17   17   36
CONECT   17   18   37
CONECT   18   19   20   20
CONECT   21   22   22   23
CONECT   23   38
END

HMDB0030398
     RDKit          3D
N-(Carbomethoxyacetyl)-4-S-chlorotryptophan
 38 39  0  0  0  0  0  0  0  0999 V2000
    6.1109    1.2001    0.1013 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7454    1.4503    0.3009 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8562    0.3765    0.5022 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2381   -0.8166    0.5110 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4336    0.7815    0.7018 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6549   -0.4841    0.8665 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9902   -1.3655    1.8754 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6696   -0.8094    0.1114 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1332   -1.9652    0.1669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5456   -1.8260    0.6775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4029   -0.9181   -0.0536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1393   -1.3229   -1.1796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7781   -0.2834   -1.7189 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4833    0.8034   -0.9747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8684    2.1319   -1.0530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4163    3.0330   -0.1240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5831    2.6518    0.8938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1903    1.3330    0.9850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1840    0.8017    2.3083 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.6259    0.4098    0.0667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1352   -2.6223   -1.1981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8149   -3.6614   -1.4308 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6097   -2.1047   -2.2395 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5159    1.9832   -0.5687 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6464    1.1461    1.0627 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2336    0.2366   -0.4540 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0866    1.3940   -0.1291 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4287    1.3771    1.6463 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0966   -1.0107    2.8246 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3227   -2.7825    0.8208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9856   -2.8681    0.5712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5482   -1.6967    1.7791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2059   -2.3223   -1.5836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3994   -0.2400   -2.5508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5289    2.4532   -1.8513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7066    4.0743   -0.1669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1976    3.3217    1.6530 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2334   -1.8597   -3.1501 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
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
  9 21  1  0
 21 22  2  0
 21 23  1  0
 20 11  1  0
 20 14  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  5 27  1  0
  5 28  1  0
  7 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
 12 33  1  0
 13 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
 23 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-(4-Chloro-1H-indol-3-yl)-2-[(1-hydroxy-3-methoxy-3-oxopropylidene)amino]propanoate	HMDB

Chemical Formula

C₁₅H₁₅ClN₂O₅

Average Molecular Weight

338.743

Monoisotopic Molecular Weight

338.066949307

IUPAC Name

3-(4-chloro-1H-indol-3-yl)-2-[(Z)-(1-hydroxy-3-methoxy-3-oxopropylidene)amino]propanoic acid

Traditional Name

3-(4-chloro-1H-indol-3-yl)-2-[(Z)-(1-hydroxy-3-methoxy-3-oxopropylidene)amino]propanoic acid

CAS Registry Number

Not Available

SMILES

COC(=O)C\C(O)=N\C(CC1=CNC2=CC=CC(Cl)=C12)C(O)=O

InChI Identifier

InChI=1S/C15H15ClN2O5/c1-23-13(20)6-12(19)18-11(15(21)22)5-8-7-17-10-4-2-3-9(16)14(8)10/h2-4,7,11,17H,5-6H2,1H3,(H,18,19)(H,21,22)

InChI Key

ITVFBZXHWIFZDX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-alpha amino acids

Alternative Parents

Substituents

N-acyl-alpha-amino acid
3-alkylindole
Indole
Indole or derivatives
Aryl chloride
Aryl halide
Dicarboxylic acid or derivatives
Substituted pyrrole
Benzenoid
Heteroaromatic compound
Pyrrole
Methyl ester
Carboxylic acid ester
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organohalogen compound
Organochloride
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0030398)
Cytoplasm (HMDB: HMDB0030398)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030398)

Source

Endogenous

Endogenous (HMDB: HMDB0030398)

Plant

Fabaceae (HMDB: HMDB0030398)

Exogenous

Food

Food (HMDB: HMDB0030398)

Pulse

Pea

Common pea (FooDB: FOOD00141)

Pulses (FooDB: FOOD00867)

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
Water Solubility	0.049 g/L	ALOGPS
logP	1.83	ALOGPS
logP	2.46	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	3.82	ChemAxon
pKa (Strongest Basic)	0.45	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	111.98 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	82.09 m³·mol⁻¹	ChemAxon
Polarizability	32.1 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	205.065	30932474
DeepCCS	[M+Na]+	180.295	30932474
AllCCS	[M+H]+	174.2	32859911
AllCCS	[M+H-H2O]+	171.3	32859911
AllCCS	[M+NH4]+	177.0	32859911
AllCCS	[M+Na]+	177.7	32859911
AllCCS	[M-H]-	175.4	32859911
AllCCS	[M+Na-2H]-	175.4	32859911
AllCCS	[M+HCOO]-	175.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-(Carbomethoxyacetyl)-4-S-chlorotryptophan	COC(=O)C\C(O)=N\C(CC1=CNC2=CC=CC(Cl)=C12)C(O)=O	4107.4	Standard polar	33892256
N-(Carbomethoxyacetyl)-4-S-chlorotryptophan	COC(=O)C\C(O)=N\C(CC1=CNC2=CC=CC(Cl)=C12)C(O)=O	2258.0	Standard non polar	33892256
N-(Carbomethoxyacetyl)-4-S-chlorotryptophan	COC(=O)C\C(O)=N\C(CC1=CNC2=CC=CC(Cl)=C12)C(O)=O	2991.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-(Carbomethoxyacetyl)-4-S-chlorotryptophan,1TMS,isomer #1	COC(=O)C/C(=N/C(CC1=C[NH]C2=CC=CC(Cl)=C12)C(=O)O)O[Si](C)(C)C	2856.7	Semi standard non polar	33892256
N-(Carbomethoxyacetyl)-4-S-chlorotryptophan,1TMS,isomer #2	COC(=O)C/C(O)=N/C(CC1=C[NH]C2=CC=CC(Cl)=C12)C(=O)O[Si](C)(C)C	2827.5	Semi standard non polar	33892256
N-(Carbomethoxyacetyl)-4-S-chlorotryptophan,1TMS,isomer #3	COC(=O)C/C(O)=N/C(CC1=CN([Si](C)(C)C)C2=CC=CC(Cl)=C12)C(=O)O	2817.6	Semi standard non polar	33892256
N-(Carbomethoxyacetyl)-4-S-chlorotryptophan,2TMS,isomer #1	COC(=O)C/C(=N/C(CC1=C[NH]C2=CC=CC(Cl)=C12)C(=O)O[Si](C)(C)C)O[Si](C)(C)C	2857.3	Semi standard non polar	33892256
N-(Carbomethoxyacetyl)-4-S-chlorotryptophan,2TMS,isomer #2	COC(=O)C/C(=N/C(CC1=CN([Si](C)(C)C)C2=CC=CC(Cl)=C12)C(=O)O)O[Si](C)(C)C	2845.3	Semi standard non polar	33892256
N-(Carbomethoxyacetyl)-4-S-chlorotryptophan,2TMS,isomer #3	COC(=O)C/C(O)=N/C(CC1=CN([Si](C)(C)C)C2=CC=CC(Cl)=C12)C(=O)O[Si](C)(C)C	2806.0	Semi standard non polar	33892256
N-(Carbomethoxyacetyl)-4-S-chlorotryptophan,3TMS,isomer #1	COC(=O)C/C(=N/C(CC1=CN([Si](C)(C)C)C2=CC=CC(Cl)=C12)C(=O)O[Si](C)(C)C)O[Si](C)(C)C	2823.6	Semi standard non polar	33892256
N-(Carbomethoxyacetyl)-4-S-chlorotryptophan,3TMS,isomer #1	COC(=O)C/C(=N/C(CC1=CN([Si](C)(C)C)C2=CC=CC(Cl)=C12)C(=O)O[Si](C)(C)C)O[Si](C)(C)C	2672.0	Standard non polar	33892256
N-(Carbomethoxyacetyl)-4-S-chlorotryptophan,1TBDMS,isomer #1	COC(=O)C/C(=N/C(CC1=C[NH]C2=CC=CC(Cl)=C12)C(=O)O)O[Si](C)(C)C(C)(C)C	3080.4	Semi standard non polar	33892256
N-(Carbomethoxyacetyl)-4-S-chlorotryptophan,1TBDMS,isomer #2	COC(=O)C/C(O)=N/C(CC1=C[NH]C2=CC=CC(Cl)=C12)C(=O)O[Si](C)(C)C(C)(C)C	3063.1	Semi standard non polar	33892256
N-(Carbomethoxyacetyl)-4-S-chlorotryptophan,1TBDMS,isomer #3	COC(=O)C/C(O)=N/C(CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC(Cl)=C12)C(=O)O	3038.0	Semi standard non polar	33892256
N-(Carbomethoxyacetyl)-4-S-chlorotryptophan,2TBDMS,isomer #1	COC(=O)C/C(=N/C(CC1=C[NH]C2=CC=CC(Cl)=C12)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3270.2	Semi standard non polar	33892256
N-(Carbomethoxyacetyl)-4-S-chlorotryptophan,2TBDMS,isomer #2	COC(=O)C/C(=N/C(CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC(Cl)=C12)C(=O)O)O[Si](C)(C)C(C)(C)C	3248.1	Semi standard non polar	33892256
N-(Carbomethoxyacetyl)-4-S-chlorotryptophan,2TBDMS,isomer #3	COC(=O)C/C(O)=N/C(CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC(Cl)=C12)C(=O)O[Si](C)(C)C(C)(C)C	3236.4	Semi standard non polar	33892256
N-(Carbomethoxyacetyl)-4-S-chlorotryptophan,3TBDMS,isomer #1	COC(=O)C/C(=N/C(CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC(Cl)=C12)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3375.0	Semi standard non polar	33892256
N-(Carbomethoxyacetyl)-4-S-chlorotryptophan,3TBDMS,isomer #1	COC(=O)C/C(=N/C(CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC(Cl)=C12)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3176.8	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-(Carbomethoxyacetyl)-4-S-chlorotryptophan GC-MS (Non-derivatized) - 70eV, Positive	splash10-0296-5941000000-b3b9a36d190570d0e56a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-(Carbomethoxyacetyl)-4-S-chlorotryptophan GC-MS (2 TMS) - 70eV, Positive	splash10-01b9-9502400000-1048b4b363bbc018aef8	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-(Carbomethoxyacetyl)-4-S-chlorotryptophan GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-(Carbomethoxyacetyl)-4-S-chlorotryptophan GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(Carbomethoxyacetyl)-4-S-chlorotryptophan 10V, Positive-QTOF	splash10-000i-0398000000-c60a58d2c9a75fc7b2e4	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(Carbomethoxyacetyl)-4-S-chlorotryptophan 20V, Positive-QTOF	splash10-000f-1981000000-cedba87eabf6d3748ee1	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(Carbomethoxyacetyl)-4-S-chlorotryptophan 40V, Positive-QTOF	splash10-03di-1910000000-e0eb137203f374e5679e	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(Carbomethoxyacetyl)-4-S-chlorotryptophan 10V, Negative-QTOF	splash10-000i-1239000000-7361d9419aea6c347098	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(Carbomethoxyacetyl)-4-S-chlorotryptophan 20V, Negative-QTOF	splash10-00du-6694000000-2aec1fba015f94828d55	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(Carbomethoxyacetyl)-4-S-chlorotryptophan 40V, Negative-QTOF	splash10-0fyo-9330000000-3b36d7da113952b65318	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(Carbomethoxyacetyl)-4-S-chlorotryptophan 10V, Positive-QTOF	splash10-0079-0090000000-dca537ec6e8fb58a9728	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(Carbomethoxyacetyl)-4-S-chlorotryptophan 20V, Positive-QTOF	splash10-000l-0590000000-768d9bea9222a4934d2f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(Carbomethoxyacetyl)-4-S-chlorotryptophan 40V, Positive-QTOF	splash10-0006-2900000000-95bb7310822ec3a61969	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(Carbomethoxyacetyl)-4-S-chlorotryptophan 10V, Negative-QTOF	splash10-001r-1092000000-51b7947caa982a214b48	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(Carbomethoxyacetyl)-4-S-chlorotryptophan 20V, Negative-QTOF	splash10-001i-9530000000-01eea324a4541a6d79a6	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(Carbomethoxyacetyl)-4-S-chlorotryptophan 40V, Negative-QTOF	splash10-03dl-4920000000-71519297016a3ad2b9ed	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB002254

KNApSAcK ID

Not Available

Chemspider ID

35013188

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751010

PDB ID

Not Available

ChEBI ID

140762

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for N-(Carbomethoxyacetyl)-4-S-chlorotryptophan (HMDB0030398)

MOL for HMDB0030398 (N-(Carbomethoxyacetyl)-4-S-chlorotryptophan)

3D MOL for HMDB0030398 (N-(Carbomethoxyacetyl)-4-S-chlorotryptophan)

3D SDF for HMDB0030398 (N-(Carbomethoxyacetyl)-4-S-chlorotryptophan)

3D-SDF for HMDB0030398 (N-(Carbomethoxyacetyl)-4-S-chlorotryptophan)

PDB for HMDB0030398 (N-(Carbomethoxyacetyl)-4-S-chlorotryptophan)

3D PDB for HMDB0030398 (N-(Carbomethoxyacetyl)-4-S-chlorotryptophan)

SMILES for HMDB0030398 (N-(Carbomethoxyacetyl)-4-S-chlorotryptophan)

INCHI for HMDB0030398 (N-(Carbomethoxyacetyl)-4-S-chlorotryptophan)

Structure for HMDB0030398 (N-(Carbomethoxyacetyl)-4-S-chlorotryptophan)

3D Structure for HMDB0030398 (N-(Carbomethoxyacetyl)-4-S-chlorotryptophan)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra