Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-22 21:04:17 UTC

Update Date

2021-09-22 21:04:18 UTC

HMDB ID

HMDB0301783

Secondary Accession Numbers

None

Metabolite Identification

Common Name

alpha-N-Carbomethoxyacetyl-4-chloro-D-tryptophan

Description

Alpha-n-carbomethoxyacetyl-4-chloro-d-tryptophan is a member of the class of 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. Alpha-n-carbomethoxyacetyl-4-chloro-d-tryptophan is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Alpha-n-carbomethoxyacetyl-4-chloro-d-tryptophan can be found in common pea, which makes alpha-n-carbomethoxyacetyl-4-chloro-d-tryptophan a potential biomarker for the consumption of this food product.

Structure

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

HMDB0301783
     RDKit          3D
alpha-N-Carbomethoxyacetyl-4-chloro-D-tryptophan
 38 39  0  0  0  0  0  0  0  0999 V2000
    5.1440   -4.6453    0.6556 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9863   -3.2432    0.8913 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7182   -2.6993    0.7896 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7645   -3.4396    0.4990 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5280   -1.2624    1.0267 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1067   -0.9169    0.8661 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2932   -1.8460    0.5769 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6397    0.4162    1.0266 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2161    0.6939    0.8541 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0187    1.7792   -0.1802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4043    2.0477   -0.3695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1446    3.0690    0.2286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4173    2.9987   -0.1388 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5620    1.9588   -0.9710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6876    1.4767   -1.6281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5366    0.3840   -2.4408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3228   -0.2393   -2.6230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1934    0.2375   -1.9689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6334   -0.4941   -2.2066 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.3198    1.3326   -1.1451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3703    1.1778    2.1343 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4318    1.3122    3.1058 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6779    1.4849    2.3574 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1936   -5.0806    0.2666 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4337   -5.1479    1.6007 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9484   -4.7733   -0.0766 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0912   -0.6967    0.2302 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9230   -1.0022    2.0317 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3456    1.1399    1.2627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3203   -0.2322    0.6219 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5342    1.4318   -1.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5343    2.7281    0.1641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7122    3.7956    0.8883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1877    3.6281    0.1538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6441    1.9802   -1.4751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4252    0.0174   -2.9481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2126   -1.1088   -3.2725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0790    1.7378    3.2328 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  2  0
  6  8  1  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
  8 29  1  0
  9 30  1  6
 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 02241212172D          

 23 24  0  0  0  0            999 V2000
   -4.4491   -0.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1636   -0.4714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1636   -1.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4491   -1.7089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7346   -1.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7346   -0.4714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9500   -0.2165    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9500   -1.5514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4651   -0.8840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6951   -2.3360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4491   -2.5339    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.8881   -2.5075    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3361   -1.8944    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6332   -3.2922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8262   -3.4637    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1852   -3.9052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5291   -2.0660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0229   -1.4529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8299   -1.6244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3819   -1.0113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2742   -2.8506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0848   -2.4090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1889   -1.1828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  8  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  7  9  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  4 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 13 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 17 21  2  0  0  0  0
 19 22  2  0  0  0  0
 20 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0301783

> <DATABASE_NAME>
hmdb

> <SMILES>
COC(=O)CC(=O)N[C@H](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)/t11-/m1/s1

> <INCHI_KEY>
ITVFBZXHWIFZDX-LLVKDONJSA-N

> <FORMULA>
C15H15ClN2O5

> <MOLECULAR_WEIGHT>
338.743

> <EXACT_MASS>
338.066949307

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
31.6345609172209

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R)-3-(4-chloro-1H-indol-3-yl)-2-(3-methoxy-3-oxopropanamido)propanoic acid

> <ALOGPS_LOGP>
1.87

> <JCHEM_LOGP>
1.6373908273333333

> <ALOGPS_LOGS>
-3.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.749138090574704

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7664580476686065

> <JCHEM_PKA_STRONGEST_BASIC>
-5.743747891235015

> <JCHEM_POLAR_SURFACE_AREA>
108.49000000000001

> <JCHEM_REFRACTIVITY>
81.56460000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.67e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-3-(4-chloro-1H-indol-3-yl)-2-(3-methoxy-3-oxopropanamido)propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0301783
     RDKit          3D
alpha-N-Carbomethoxyacetyl-4-chloro-D-tryptophan
 38 39  0  0  0  0  0  0  0  0999 V2000
    5.1440   -4.6453    0.6556 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9863   -3.2432    0.8913 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7182   -2.6993    0.7896 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7645   -3.4396    0.4990 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5280   -1.2624    1.0267 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1067   -0.9169    0.8661 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2932   -1.8460    0.5769 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6397    0.4162    1.0266 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2161    0.6939    0.8541 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0187    1.7792   -0.1802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4043    2.0477   -0.3695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1446    3.0690    0.2286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4173    2.9987   -0.1388 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5620    1.9588   -0.9710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6876    1.4767   -1.6281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5366    0.3840   -2.4408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3228   -0.2393   -2.6230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1934    0.2375   -1.9689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6334   -0.4941   -2.2066 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.3198    1.3326   -1.1451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3703    1.1778    2.1343 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4318    1.3122    3.1058 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6779    1.4849    2.3574 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1936   -5.0806    0.2666 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4337   -5.1479    1.6007 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9484   -4.7733   -0.0766 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0912   -0.6967    0.2302 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9230   -1.0022    2.0317 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3456    1.1399    1.2627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3203   -0.2322    0.6219 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5342    1.4318   -1.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5343    2.7281    0.1641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7122    3.7956    0.8883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1877    3.6281    0.1538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6441    1.9802   -1.4751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4252    0.0174   -2.9481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2126   -1.1088   -3.2725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0790    1.7378    3.2328 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  2  0
  6  8  1  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
  8 29  1  0
  9 30  1  6
 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                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -8.305  -0.110   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -9.639  -0.880   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -9.639  -2.420   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.305  -3.190   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.971  -2.420   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.971  -0.880   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -5.507  -0.404   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -5.507  -2.896   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.602  -1.650   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.031  -4.361   0.000  0.00  0.00           C+0
HETATM   11 Cl   UNK     0      -8.305  -4.730   0.000  0.00  0.00          Cl+0
HETATM   12  C   UNK     0      -3.524  -4.681   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      -2.494  -3.536   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      -3.049  -6.145   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.542  -6.466   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -4.079  -7.290   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -0.988  -3.857   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.043  -2.712   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.549  -3.032   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.580  -1.888   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -0.512  -5.321   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       2.025  -4.497   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.086  -2.208   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    8    6                                                  
CONECT    6    1    5    7                                                  
CONECT    7    6    9                                                       
CONECT    8    5    9   10                                                  
CONECT    9    7    8                                                       
CONECT   10    8   12                                                       
CONECT   11    4                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12   17                                                       
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   13   18   21                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   22                                                  
CONECT   20   19   23                                                       
CONECT   21   17                                                            
CONECT   22   19                                                            
CONECT   23   20                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

COMPND    HMDB0301783
HETATM    1  C1  UNL     1       5.144  -4.645   0.656  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.986  -3.243   0.891  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.718  -2.699   0.790  1.00  0.00           C  
HETATM    4  O2  UNL     1       2.764  -3.440   0.499  1.00  0.00           O  
HETATM    5  C3  UNL     1       3.528  -1.262   1.027  1.00  0.00           C  
HETATM    6  C4  UNL     1       2.107  -0.917   0.866  1.00  0.00           C  
HETATM    7  O3  UNL     1       1.293  -1.846   0.577  1.00  0.00           O  
HETATM    8  N1  UNL     1       1.640   0.416   1.027  1.00  0.00           N  
HETATM    9  C5  UNL     1       0.216   0.694   0.854  1.00  0.00           C  
HETATM   10  C6  UNL     1       0.019   1.779  -0.180  1.00  0.00           C  
HETATM   11  C7  UNL     1      -1.404   2.048  -0.369  1.00  0.00           C  
HETATM   12  C8  UNL     1      -2.145   3.069   0.229  1.00  0.00           C  
HETATM   13  N2  UNL     1      -3.417   2.999  -0.139  1.00  0.00           N  
HETATM   14  C9  UNL     1      -3.562   1.959  -0.971  1.00  0.00           C  
HETATM   15  C10 UNL     1      -4.688   1.477  -1.628  1.00  0.00           C  
HETATM   16  C11 UNL     1      -4.537   0.384  -2.441  1.00  0.00           C  
HETATM   17  C12 UNL     1      -3.323  -0.239  -2.623  1.00  0.00           C  
HETATM   18  C13 UNL     1      -2.193   0.237  -1.969  1.00  0.00           C  
HETATM   19 CL1  UNL     1      -0.633  -0.494  -2.207  1.00  0.00          CL  
HETATM   20  C14 UNL     1      -2.320   1.333  -1.145  1.00  0.00           C  
HETATM   21  C15 UNL     1      -0.370   1.178   2.134  1.00  0.00           C  
HETATM   22  O4  UNL     1       0.432   1.312   3.106  1.00  0.00           O  
HETATM   23  O5  UNL     1      -1.678   1.485   2.357  1.00  0.00           O  
HETATM   24  H1  UNL     1       4.194  -5.081   0.267  1.00  0.00           H  
HETATM   25  H2  UNL     1       5.434  -5.148   1.601  1.00  0.00           H  
HETATM   26  H3  UNL     1       5.948  -4.773  -0.077  1.00  0.00           H  
HETATM   27  H4  UNL     1       4.091  -0.697   0.230  1.00  0.00           H  
HETATM   28  H5  UNL     1       3.923  -1.002   2.032  1.00  0.00           H  
HETATM   29  H6  UNL     1       2.346   1.140   1.263  1.00  0.00           H  
HETATM   30  H7  UNL     1      -0.320  -0.232   0.622  1.00  0.00           H  
HETATM   31  H8  UNL     1       0.534   1.432  -1.101  1.00  0.00           H  
HETATM   32  H9  UNL     1       0.534   2.728   0.164  1.00  0.00           H  
HETATM   33  H10 UNL     1      -1.712   3.796   0.888  1.00  0.00           H  
HETATM   34  H11 UNL     1      -4.188   3.628   0.154  1.00  0.00           H  
HETATM   35  H12 UNL     1      -5.644   1.980  -1.475  1.00  0.00           H  
HETATM   36  H13 UNL     1      -5.425   0.017  -2.948  1.00  0.00           H  
HETATM   37  H14 UNL     1      -3.213  -1.109  -3.273  1.00  0.00           H  
HETATM   38  H15 UNL     1      -2.079   1.738   3.233  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    7    8
CONECT    8    9   29
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

HMDB0301783
     RDKit          3D
alpha-N-Carbomethoxyacetyl-4-chloro-D-tryptophan
 38 39  0  0  0  0  0  0  0  0999 V2000
    5.1440   -4.6453    0.6556 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9863   -3.2432    0.8913 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7182   -2.6993    0.7896 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7645   -3.4396    0.4990 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5280   -1.2624    1.0267 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1067   -0.9169    0.8661 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2932   -1.8460    0.5769 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6397    0.4162    1.0266 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2161    0.6939    0.8541 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0187    1.7792   -0.1802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4043    2.0477   -0.3695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1446    3.0690    0.2286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4173    2.9987   -0.1388 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5620    1.9588   -0.9710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6876    1.4767   -1.6281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5366    0.3840   -2.4408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3228   -0.2393   -2.6230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1934    0.2375   -1.9689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6334   -0.4941   -2.2066 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.3198    1.3326   -1.1451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3703    1.1778    2.1343 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4318    1.3122    3.1058 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6779    1.4849    2.3574 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1936   -5.0806    0.2666 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4337   -5.1479    1.6007 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9484   -4.7733   -0.0766 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0912   -0.6967    0.2302 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9230   -1.0022    2.0317 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3456    1.1399    1.2627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3203   -0.2322    0.6219 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5342    1.4318   -1.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5343    2.7281    0.1641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7122    3.7956    0.8883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1877    3.6281    0.1538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6441    1.9802   -1.4751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4252    0.0174   -2.9481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2126   -1.1088   -3.2725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0790    1.7378    3.2328 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  2  0
  6  8  1  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
  8 29  1  0
  9 30  1  6
 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
a-N-Carbomethoxyacetyl-4-chloro-D-tryptophan	Generator
Α-N-carbomethoxyacetyl-4-chloro-D-tryptophan	Generator

Chemical Formula

C₁₅H₁₅ClN₂O₅

Average Molecular Weight

338.743

Monoisotopic Molecular Weight

338.066949307

IUPAC Name

(2R)-3-(4-chloro-1H-indol-3-yl)-2-(3-methoxy-3-oxopropanamido)propanoic acid

Traditional Name

(2R)-3-(4-chloro-1H-indol-3-yl)-2-(3-methoxy-3-oxopropanamido)propanoic acid

CAS Registry Number

27542-40-1

SMILES

COC(=O)CC(=O)N[C@H](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)/t11-/m1/s1

InChI Key

ITVFBZXHWIFZDX-LLVKDONJSA-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
1,3-dicarbonyl compound
Benzenoid
Heteroaromatic compound
Pyrrole
Methyl ester
Secondary carboxylic acid amide
Carboxamide group
Carboxylic acid ester
Organoheterocyclic compound
Azacycle
Carboxylic acid
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organohalogen compound
Organochloride
Organonitrogen compound
Carbonyl group
Organooxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Common pea (FooDB: FOOD00141)

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	1.87	ALOGPS
logP	1.64	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	3.77	ChemAxon
pKa (Strongest Basic)	-5.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	108.49 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	81.56 m³·mol⁻¹	ChemAxon
Polarizability	31.63 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
AllCCS	[M+H]+	174.188	32859911
AllCCS	[M+H-H2O]+	171.234	32859911
AllCCS	[M+Na]+	177.7	32859911
AllCCS	[M+NH4]+	176.917	32859911
AllCCS	[M-H]-	175.56	32859911
AllCCS	[M+Na-2H]-	175.535	32859911
AllCCS	[M+HCOO]-	175.64	32859911
DeepCCS	[M-2H]-	206.932	30932474
DeepCCS	[M+Na]+	182.159	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
alpha-N-Carbomethoxyacetyl-4-chloro-D-tryptophan,2TMS,isomer #1	COC(=O)CC(=O)N([C@H](CC1=C[NH]C2=CC=CC(Cl)=C12)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2833.6	Semi standard non polar	33892256
alpha-N-Carbomethoxyacetyl-4-chloro-D-tryptophan,2TMS,isomer #1	COC(=O)CC(=O)N([C@H](CC1=C[NH]C2=CC=CC(Cl)=C12)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2751.7	Standard non polar	33892256
alpha-N-Carbomethoxyacetyl-4-chloro-D-tryptophan,2TMS,isomer #1	COC(=O)CC(=O)N([C@H](CC1=C[NH]C2=CC=CC(Cl)=C12)C(=O)O[Si](C)(C)C)[Si](C)(C)C	3631.3	Standard polar	33892256
alpha-N-Carbomethoxyacetyl-4-chloro-D-tryptophan,2TMS,isomer #2	COC(=O)CC(=O)N[C@H](CC1=CN([Si](C)(C)C)C2=CC=CC(Cl)=C12)C(=O)O[Si](C)(C)C	2823.9	Semi standard non polar	33892256
alpha-N-Carbomethoxyacetyl-4-chloro-D-tryptophan,2TMS,isomer #2	COC(=O)CC(=O)N[C@H](CC1=CN([Si](C)(C)C)C2=CC=CC(Cl)=C12)C(=O)O[Si](C)(C)C	2707.0	Standard non polar	33892256
alpha-N-Carbomethoxyacetyl-4-chloro-D-tryptophan,2TMS,isomer #2	COC(=O)CC(=O)N[C@H](CC1=CN([Si](C)(C)C)C2=CC=CC(Cl)=C12)C(=O)O[Si](C)(C)C	3642.9	Standard polar	33892256
alpha-N-Carbomethoxyacetyl-4-chloro-D-tryptophan,2TMS,isomer #3	COC(=O)CC(=O)N([C@H](CC1=CN([Si](C)(C)C)C2=CC=CC(Cl)=C12)C(=O)O)[Si](C)(C)C	2802.2	Semi standard non polar	33892256
alpha-N-Carbomethoxyacetyl-4-chloro-D-tryptophan,2TMS,isomer #3	COC(=O)CC(=O)N([C@H](CC1=CN([Si](C)(C)C)C2=CC=CC(Cl)=C12)C(=O)O)[Si](C)(C)C	2769.2	Standard non polar	33892256
alpha-N-Carbomethoxyacetyl-4-chloro-D-tryptophan,2TMS,isomer #3	COC(=O)CC(=O)N([C@H](CC1=CN([Si](C)(C)C)C2=CC=CC(Cl)=C12)C(=O)O)[Si](C)(C)C	3760.6	Standard polar	33892256
alpha-N-Carbomethoxyacetyl-4-chloro-D-tryptophan,3TMS,isomer #1	COC(=O)CC(=O)N([C@H](CC1=CN([Si](C)(C)C)C2=CC=CC(Cl)=C12)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2825.4	Semi standard non polar	33892256
alpha-N-Carbomethoxyacetyl-4-chloro-D-tryptophan,3TMS,isomer #1	COC(=O)CC(=O)N([C@H](CC1=CN([Si](C)(C)C)C2=CC=CC(Cl)=C12)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2780.4	Standard non polar	33892256
alpha-N-Carbomethoxyacetyl-4-chloro-D-tryptophan,3TMS,isomer #1	COC(=O)CC(=O)N([C@H](CC1=CN([Si](C)(C)C)C2=CC=CC(Cl)=C12)C(=O)O[Si](C)(C)C)[Si](C)(C)C	3349.2	Standard polar	33892256
alpha-N-Carbomethoxyacetyl-4-chloro-D-tryptophan,2TBDMS,isomer #1	COC(=O)CC(=O)N([C@H](CC1=C[NH]C2=CC=CC(Cl)=C12)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3309.5	Semi standard non polar	33892256
alpha-N-Carbomethoxyacetyl-4-chloro-D-tryptophan,2TBDMS,isomer #1	COC(=O)CC(=O)N([C@H](CC1=C[NH]C2=CC=CC(Cl)=C12)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3182.4	Standard non polar	33892256
alpha-N-Carbomethoxyacetyl-4-chloro-D-tryptophan,2TBDMS,isomer #1	COC(=O)CC(=O)N([C@H](CC1=C[NH]C2=CC=CC(Cl)=C12)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3692.8	Standard polar	33892256
alpha-N-Carbomethoxyacetyl-4-chloro-D-tryptophan,2TBDMS,isomer #2	COC(=O)CC(=O)N[C@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC(Cl)=C12)C(=O)O[Si](C)(C)C(C)(C)C	3254.3	Semi standard non polar	33892256
alpha-N-Carbomethoxyacetyl-4-chloro-D-tryptophan,2TBDMS,isomer #2	COC(=O)CC(=O)N[C@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC(Cl)=C12)C(=O)O[Si](C)(C)C(C)(C)C	3101.1	Standard non polar	33892256
alpha-N-Carbomethoxyacetyl-4-chloro-D-tryptophan,2TBDMS,isomer #2	COC(=O)CC(=O)N[C@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC(Cl)=C12)C(=O)O[Si](C)(C)C(C)(C)C	3694.3	Standard polar	33892256
alpha-N-Carbomethoxyacetyl-4-chloro-D-tryptophan,2TBDMS,isomer #3	COC(=O)CC(=O)N([C@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC(Cl)=C12)C(=O)O)[Si](C)(C)C(C)(C)C	3262.4	Semi standard non polar	33892256
alpha-N-Carbomethoxyacetyl-4-chloro-D-tryptophan,2TBDMS,isomer #3	COC(=O)CC(=O)N([C@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC(Cl)=C12)C(=O)O)[Si](C)(C)C(C)(C)C	3132.2	Standard non polar	33892256
alpha-N-Carbomethoxyacetyl-4-chloro-D-tryptophan,2TBDMS,isomer #3	COC(=O)CC(=O)N([C@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC(Cl)=C12)C(=O)O)[Si](C)(C)C(C)(C)C	3761.7	Standard polar	33892256
alpha-N-Carbomethoxyacetyl-4-chloro-D-tryptophan,3TBDMS,isomer #1	COC(=O)CC(=O)N([C@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC(Cl)=C12)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3432.7	Semi standard non polar	33892256
alpha-N-Carbomethoxyacetyl-4-chloro-D-tryptophan,3TBDMS,isomer #1	COC(=O)CC(=O)N([C@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC(Cl)=C12)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3305.7	Standard non polar	33892256
alpha-N-Carbomethoxyacetyl-4-chloro-D-tryptophan,3TBDMS,isomer #1	COC(=O)CC(=O)N([C@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC(Cl)=C12)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3538.9	Standard polar	33892256

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-N-Carbomethoxyacetyl-4-chloro-D-tryptophan 10V, Positive-QTOF	splash10-000i-0398000000-c60a58d2c9a75fc7b2e4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-N-Carbomethoxyacetyl-4-chloro-D-tryptophan 20V, Positive-QTOF	splash10-000f-1981000000-cedba87eabf6d3748ee1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-N-Carbomethoxyacetyl-4-chloro-D-tryptophan 40V, Positive-QTOF	splash10-03di-1910000000-e0eb137203f374e5679e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-N-Carbomethoxyacetyl-4-chloro-D-tryptophan 10V, Negative-QTOF	splash10-000i-1239000000-7361d9419aea6c347098	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-N-Carbomethoxyacetyl-4-chloro-D-tryptophan 20V, Negative-QTOF	splash10-00du-6694000000-2aec1fba015f94828d55	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-N-Carbomethoxyacetyl-4-chloro-D-tryptophan 40V, Negative-QTOF	splash10-0fyo-9330000000-3b36d7da113952b65318	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-N-Carbomethoxyacetyl-4-chloro-D-tryptophan 10V, Positive-QTOF	splash10-0079-0093000000-354457ed25ac1deff136	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-N-Carbomethoxyacetyl-4-chloro-D-tryptophan 20V, Positive-QTOF	splash10-00di-0590000000-2b9fabc2c4df833b5650	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-N-Carbomethoxyacetyl-4-chloro-D-tryptophan 40V, Positive-QTOF	splash10-0006-4910000000-ca82afc6904328feb94b	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-N-Carbomethoxyacetyl-4-chloro-D-tryptophan 10V, Negative-QTOF	splash10-000i-2359000000-11ba54c2f5acf1aa77ea	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-N-Carbomethoxyacetyl-4-chloro-D-tryptophan 20V, Negative-QTOF	splash10-001i-9420000000-ef0d671ba1b44fe2ab69	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-N-Carbomethoxyacetyl-4-chloro-D-tryptophan 40V, Negative-QTOF	splash10-0imi-4920000000-7f25f75333332fd6e4ed	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

FDB001405

KNApSAcK ID

Not Available

Chemspider ID

59696181

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

154326943

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

Not Available

Showing metabocard for alpha-N-Carbomethoxyacetyl-4-chloro-D-tryptophan (HMDB0301783)

MOL for HMDB0301783 (alpha-N-Carbomethoxyacetyl-4-chloro-D-tryptophan)

3D MOL for HMDB0301783 (alpha-N-Carbomethoxyacetyl-4-chloro-D-tryptophan)

3D SDF for HMDB0301783 (alpha-N-Carbomethoxyacetyl-4-chloro-D-tryptophan)

3D-SDF for HMDB0301783 (alpha-N-Carbomethoxyacetyl-4-chloro-D-tryptophan)

PDB for HMDB0301783 (alpha-N-Carbomethoxyacetyl-4-chloro-D-tryptophan)

3D PDB for HMDB0301783 (alpha-N-Carbomethoxyacetyl-4-chloro-D-tryptophan)

SMILES for HMDB0301783 (alpha-N-Carbomethoxyacetyl-4-chloro-D-tryptophan)

INCHI for HMDB0301783 (alpha-N-Carbomethoxyacetyl-4-chloro-D-tryptophan)

Structure for HMDB0301783 (alpha-N-Carbomethoxyacetyl-4-chloro-D-tryptophan)

3D Structure for HMDB0301783 (alpha-N-Carbomethoxyacetyl-4-chloro-D-tryptophan)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

MS/MS Spectra