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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 13:20:00 UTC

Update Date

2021-09-26 23:07:57 UTC

HMDB ID

HMDB0254147

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Lodoxamide ethyl

Description

Lodoxamide ethyl, also known as lodoxamide, belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. Based on a literature review a small amount of articles have been published on Lodoxamide ethyl. This compound has been identified in human blood as reported by (PMID: 31557052 ). Lodoxamide ethyl is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Lodoxamide ethyl 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

HMDB0254147
     RDKit          3D
Lodoxamide ethyl
 39 39  0  0  0  0  0  0  0  0999 V2000
   -8.4493    0.6911    0.2120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2310    0.6131    1.1050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1042    0.5015    0.2605 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8212    0.4085    0.7411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6350    0.4231    1.9981 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6897    0.2946   -0.1852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9539    0.2875   -1.3972 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3816    0.1999    0.3096 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1765    0.0848   -0.4165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1387    0.0495   -1.7851 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0556   -0.0642   -2.4905 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0980   -0.1013   -3.9218 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1361   -0.1508   -5.0754 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2402   -0.1434   -1.7568 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2170   -0.1092   -0.3853 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3661   -0.1840    0.4138 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6747   -0.3020   -0.0877 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9857   -0.3552   -1.2813 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7864   -0.3691    0.9135 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5493   -0.3211    2.1432 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1046   -0.4857    0.5078 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1231   -0.5459    1.4760 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4444   -0.6709    0.7207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0003    0.0058    0.2934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0208    0.0492    2.0679 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -8.3052    0.1275   -0.7232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5616    1.7741   -0.0780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3656    0.3091    0.7021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1487    1.5372    1.7185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2613   -0.2958    1.7368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2879    0.2175    1.3771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0192    0.1071   -2.3850 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1438   -0.2305   -2.3344 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2764   -0.1518    1.4784 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9968   -1.4406    2.1294 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1595    0.3986    2.0782 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3705    0.0212   -0.1478 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3043   -0.4510    1.3642 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5189   -1.7282    0.3987 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  3  0
 11 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 15 24  2  0
 24 25  1  0
 24  9  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  8 31  1  0
 10 32  1  0
 14 33  1  0
 16 34  1  0
 22 35  1  0
 22 36  1  0
 23 37  1  0
 23 38  1  0
 23 39  1  0
M  END

  Mrv1652309112115202D          

 25 25  0  0  0  0            999 V2000
   -4.2868    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    1.6500    0.0000 O   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
   -2.1434    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    1.6500    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
   -0.7145    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    1.6500    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    2.8875    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
    1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 11 24  1  0  0  0  0
 24 25  3  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0254147

> <DATABASE_NAME>
hmdb

> <SMILES>
CCOC(=O)C(=O)NC1=CC(=CC(NC(=O)C(=O)OCC)=C1Cl)C#N

> <INCHI_IDENTIFIER>
InChI=1S/C15H14ClN3O6/c1-3-24-14(22)12(20)18-9-5-8(7-17)6-10(11(9)16)19-13(21)15(23)25-4-2/h5-6H,3-4H2,1-2H3,(H,18,20)(H,19,21)

> <INCHI_KEY>
BNTAPIYHWPPFBW-UHFFFAOYSA-N

> <FORMULA>
C15H14ClN3O6

> <MOLECULAR_WEIGHT>
367.74

> <EXACT_MASS>
367.0571129

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
35.068438125843

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
ethyl ({2-chloro-5-cyano-3-[(ethyl carboxy)formamido]phenyl}carbamoyl)formate

> <ALOGPS_LOGP>
2.10

> <JCHEM_LOGP>
2.300066393333333

> <ALOGPS_LOGS>
-4.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.18899341204518

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.570119477418196

> <JCHEM_PKA_STRONGEST_BASIC>
-6.014779591745149

> <JCHEM_POLAR_SURFACE_AREA>
134.59

> <JCHEM_REFRACTIVITY>
88.9356

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.80e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ethyl ({2-chloro-5-cyano-3-[(ethyl carboxy)formamido]phenyl}carbamoyl)formate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0254147
     RDKit          3D
Lodoxamide ethyl
 39 39  0  0  0  0  0  0  0  0999 V2000
   -8.4493    0.6911    0.2120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2310    0.6131    1.1050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1042    0.5015    0.2605 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8212    0.4085    0.7411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6350    0.4231    1.9981 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6897    0.2946   -0.1852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9539    0.2875   -1.3972 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3816    0.1999    0.3096 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1765    0.0848   -0.4165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1387    0.0495   -1.7851 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0556   -0.0642   -2.4905 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0980   -0.1013   -3.9218 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1361   -0.1508   -5.0754 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2402   -0.1434   -1.7568 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2170   -0.1092   -0.3853 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3661   -0.1840    0.4138 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6747   -0.3020   -0.0877 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9857   -0.3552   -1.2813 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7864   -0.3691    0.9135 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5493   -0.3211    2.1432 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1046   -0.4857    0.5078 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1231   -0.5459    1.4760 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4444   -0.6709    0.7207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0003    0.0058    0.2934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0208    0.0492    2.0679 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -8.3052    0.1275   -0.7232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5616    1.7741   -0.0780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3656    0.3091    0.7021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1487    1.5372    1.7185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2613   -0.2958    1.7368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2879    0.2175    1.3771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0192    0.1071   -2.3850 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1438   -0.2305   -2.3344 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2764   -0.1518    1.4784 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9968   -1.4406    2.1294 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1595    0.3986    2.0782 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3705    0.0212   -0.1478 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3043   -0.4510    1.3642 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5189   -1.7282    0.3987 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  3  0
 11 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 15 24  2  0
 24 25  1  0
 24  9  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  8 31  1  0
 10 32  1  0
 14 33  1  0
 16 34  1  0
 22 35  1  0
 22 36  1  0
 23 37  1  0
 23 38  1  0
 23 39  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      -8.002   3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -5.335   3.080   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -4.001   0.770   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -2.667   3.080   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.667   4.620   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0      -1.334   2.310   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      -0.000   3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   5.390   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   15 Cl   UNK     0       1.334   0.770   0.000  0.00  0.00          Cl+0
HETATM   16  N   UNK     0       4.001   2.310   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.668   0.770   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       8.002   3.080   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.669   3.080   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0       1.334   8.470   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   24                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   16                                                  
CONECT   14   13    9   15                                                  
CONECT   15   14                                                            
CONECT   16   13   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   11   25                                                       
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   50    0
END

COMPND    HMDB0254147
HETATM    1  C1  UNL     1      -8.449   0.691   0.212  1.00  0.00           C  
HETATM    2  C2  UNL     1      -7.231   0.613   1.105  1.00  0.00           C  
HETATM    3  O1  UNL     1      -6.104   0.502   0.260  1.00  0.00           O  
HETATM    4  C3  UNL     1      -4.821   0.409   0.741  1.00  0.00           C  
HETATM    5  O2  UNL     1      -4.635   0.423   1.998  1.00  0.00           O  
HETATM    6  C4  UNL     1      -3.690   0.295  -0.185  1.00  0.00           C  
HETATM    7  O3  UNL     1      -3.954   0.287  -1.397  1.00  0.00           O  
HETATM    8  N1  UNL     1      -2.382   0.200   0.310  1.00  0.00           N  
HETATM    9  C5  UNL     1      -1.177   0.085  -0.417  1.00  0.00           C  
HETATM   10  C6  UNL     1      -1.139   0.050  -1.785  1.00  0.00           C  
HETATM   11  C7  UNL     1       0.056  -0.064  -2.491  1.00  0.00           C  
HETATM   12  C8  UNL     1       0.098  -0.101  -3.922  1.00  0.00           C  
HETATM   13  N2  UNL     1       0.136  -0.151  -5.075  1.00  0.00           N  
HETATM   14  C9  UNL     1       1.240  -0.143  -1.757  1.00  0.00           C  
HETATM   15  C10 UNL     1       1.217  -0.109  -0.385  1.00  0.00           C  
HETATM   16  N3  UNL     1       2.366  -0.184   0.414  1.00  0.00           N  
HETATM   17  C11 UNL     1       3.675  -0.302  -0.088  1.00  0.00           C  
HETATM   18  O4  UNL     1       3.986  -0.355  -1.281  1.00  0.00           O  
HETATM   19  C12 UNL     1       4.786  -0.369   0.913  1.00  0.00           C  
HETATM   20  O5  UNL     1       4.549  -0.321   2.143  1.00  0.00           O  
HETATM   21  O6  UNL     1       6.105  -0.486   0.508  1.00  0.00           O  
HETATM   22  C13 UNL     1       7.123  -0.546   1.476  1.00  0.00           C  
HETATM   23  C14 UNL     1       8.444  -0.671   0.721  1.00  0.00           C  
HETATM   24  C15 UNL     1      -0.000   0.006   0.293  1.00  0.00           C  
HETATM   25 CL1  UNL     1      -0.021   0.049   2.068  1.00  0.00          CL  
HETATM   26  H1  UNL     1      -8.305   0.128  -0.723  1.00  0.00           H  
HETATM   27  H2  UNL     1      -8.562   1.774  -0.078  1.00  0.00           H  
HETATM   28  H3  UNL     1      -9.366   0.309   0.702  1.00  0.00           H  
HETATM   29  H4  UNL     1      -7.149   1.537   1.718  1.00  0.00           H  
HETATM   30  H5  UNL     1      -7.261  -0.296   1.737  1.00  0.00           H  
HETATM   31  H6  UNL     1      -2.288   0.217   1.377  1.00  0.00           H  
HETATM   32  H7  UNL     1      -2.019   0.107  -2.385  1.00  0.00           H  
HETATM   33  H8  UNL     1       2.144  -0.230  -2.334  1.00  0.00           H  
HETATM   34  H9  UNL     1       2.276  -0.152   1.478  1.00  0.00           H  
HETATM   35  H10 UNL     1       6.997  -1.441   2.129  1.00  0.00           H  
HETATM   36  H11 UNL     1       7.160   0.399   2.078  1.00  0.00           H  
HETATM   37  H12 UNL     1       8.371   0.021  -0.148  1.00  0.00           H  
HETATM   38  H13 UNL     1       9.304  -0.451   1.364  1.00  0.00           H  
HETATM   39  H14 UNL     1       8.519  -1.728   0.399  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3   29   30
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7    7    8
CONECT    8    9   31
CONECT    9   10   10   24
CONECT   10   11   32
CONECT   11   12   14   14
CONECT   12   13   13   13
CONECT   14   15   33
CONECT   15   16   24   24
CONECT   16   17   34
CONECT   17   18   18   19
CONECT   19   20   20   21
CONECT   21   22
CONECT   22   23   35   36
CONECT   23   37   38   39
CONECT   24   25
END

HMDB0254147
     RDKit          3D
Lodoxamide ethyl
 39 39  0  0  0  0  0  0  0  0999 V2000
   -8.4493    0.6911    0.2120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2310    0.6131    1.1050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1042    0.5015    0.2605 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8212    0.4085    0.7411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6350    0.4231    1.9981 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6897    0.2946   -0.1852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9539    0.2875   -1.3972 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3816    0.1999    0.3096 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1765    0.0848   -0.4165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1387    0.0495   -1.7851 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0556   -0.0642   -2.4905 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0980   -0.1013   -3.9218 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1361   -0.1508   -5.0754 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2402   -0.1434   -1.7568 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2170   -0.1092   -0.3853 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3661   -0.1840    0.4138 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6747   -0.3020   -0.0877 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9857   -0.3552   -1.2813 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7864   -0.3691    0.9135 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5493   -0.3211    2.1432 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1046   -0.4857    0.5078 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1231   -0.5459    1.4760 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4444   -0.6709    0.7207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0003    0.0058    0.2934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0208    0.0492    2.0679 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -8.3052    0.1275   -0.7232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5616    1.7741   -0.0780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3656    0.3091    0.7021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1487    1.5372    1.7185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2613   -0.2958    1.7368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2879    0.2175    1.3771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0192    0.1071   -2.3850 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1438   -0.2305   -2.3344 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2764   -0.1518    1.4784 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9968   -1.4406    2.1294 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1595    0.3986    2.0782 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3705    0.0212   -0.1478 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3043   -0.4510    1.3642 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5189   -1.7282    0.3987 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  3  0
 11 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 15 24  2  0
 24 25  1  0
 24  9  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  8 31  1  0
 10 32  1  0
 14 33  1  0
 16 34  1  0
 22 35  1  0
 22 36  1  0
 23 37  1  0
 23 38  1  0
 23 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Diethyl N,n'-(2-chloro-5-cyano-m-phenylene)dioxamate	HMDB
Lodoxamide	HMDB

Chemical Formula

C₁₅H₁₄ClN₃O₆

Average Molecular Weight

367.74

Monoisotopic Molecular Weight

367.0571129

IUPAC Name

ethyl ({2-chloro-5-cyano-3-[(ethyl carboxy)formamido]phenyl}carbamoyl)formate

Traditional Name

ethyl ({2-chloro-5-cyano-3-[(ethyl carboxy)formamido]phenyl}carbamoyl)formate

CAS Registry Number

Not Available

SMILES

CCOC(=O)C(=O)NC1=CC(=CC(NC(=O)C(=O)OCC)=C1Cl)C#N

InChI Identifier

InChI=1S/C15H14ClN3O6/c1-3-24-14(22)12(20)18-9-5-8(7-17)6-10(11(9)16)19-13(21)15(23)25-4-2/h5-6H,3-4H2,1-2H3,(H,18,20)(H,19,21)

InChI Key

BNTAPIYHWPPFBW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids and derivatives

Alternative Parents

Substituents

Alpha-amino acid or derivatives
Anilide
Benzonitrile
N-arylamide
Chlorobenzene
Halobenzene
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Benzenoid
Dicarboxylic acid or derivatives
Secondary carboxylic acid amide
Carboxamide group
Carboxylic acid ester
Nitrile
Carbonitrile
Organohalogen compound
Organochloride
Organonitrogen compound
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
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	2.1	ALOGPS
logP	2.3	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	9.57	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	134.59 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	88.94 m³·mol⁻¹	ChemAxon
Polarizability	35.07 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	180.116	30932474
DeepCCS	[M-H]-	177.719	30932474
DeepCCS	[M-2H]-	212.051	30932474
DeepCCS	[M+Na]+	187.278	30932474
AllCCS	[M+H]+	178.4	32859911
AllCCS	[M+H-H2O]+	175.7	32859911
AllCCS	[M+NH4]+	180.8	32859911
AllCCS	[M+Na]+	181.5	32859911
AllCCS	[M-H]-	179.7	32859911
AllCCS	[M+Na-2H]-	179.9	32859911
AllCCS	[M+HCOO]-	180.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Lodoxamide ethyl	CCOC(=O)C(=O)NC1=CC(=CC(NC(=O)C(=O)OCC)=C1Cl)C#N	3822.4	Standard polar	33892256
Lodoxamide ethyl	CCOC(=O)C(=O)NC1=CC(=CC(NC(=O)C(=O)OCC)=C1Cl)C#N	2560.3	Standard non polar	33892256
Lodoxamide ethyl	CCOC(=O)C(=O)NC1=CC(=CC(NC(=O)C(=O)OCC)=C1Cl)C#N	2745.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Lodoxamide ethyl,1TMS,isomer #1	CCOC(=O)C(=O)NC1=CC(C#N)=CC(N(C(=O)C(=O)OCC)[Si](C)(C)C)=C1Cl	2880.0	Semi standard non polar	33892256
Lodoxamide ethyl,1TMS,isomer #1	CCOC(=O)C(=O)NC1=CC(C#N)=CC(N(C(=O)C(=O)OCC)[Si](C)(C)C)=C1Cl	2545.8	Standard non polar	33892256
Lodoxamide ethyl,1TMS,isomer #1	CCOC(=O)C(=O)NC1=CC(C#N)=CC(N(C(=O)C(=O)OCC)[Si](C)(C)C)=C1Cl	4558.8	Standard polar	33892256
Lodoxamide ethyl,2TMS,isomer #1	CCOC(=O)C(=O)N(C1=CC(C#N)=CC(N(C(=O)C(=O)OCC)[Si](C)(C)C)=C1Cl)[Si](C)(C)C	2700.5	Semi standard non polar	33892256
Lodoxamide ethyl,2TMS,isomer #1	CCOC(=O)C(=O)N(C1=CC(C#N)=CC(N(C(=O)C(=O)OCC)[Si](C)(C)C)=C1Cl)[Si](C)(C)C	2538.2	Standard non polar	33892256
Lodoxamide ethyl,2TMS,isomer #1	CCOC(=O)C(=O)N(C1=CC(C#N)=CC(N(C(=O)C(=O)OCC)[Si](C)(C)C)=C1Cl)[Si](C)(C)C	3840.2	Standard polar	33892256
Lodoxamide ethyl,1TBDMS,isomer #1	CCOC(=O)C(=O)NC1=CC(C#N)=CC(N(C(=O)C(=O)OCC)[Si](C)(C)C(C)(C)C)=C1Cl	3082.7	Semi standard non polar	33892256
Lodoxamide ethyl,1TBDMS,isomer #1	CCOC(=O)C(=O)NC1=CC(C#N)=CC(N(C(=O)C(=O)OCC)[Si](C)(C)C(C)(C)C)=C1Cl	2747.5	Standard non polar	33892256
Lodoxamide ethyl,1TBDMS,isomer #1	CCOC(=O)C(=O)NC1=CC(C#N)=CC(N(C(=O)C(=O)OCC)[Si](C)(C)C(C)(C)C)=C1Cl	4453.6	Standard polar	33892256
Lodoxamide ethyl,2TBDMS,isomer #1	CCOC(=O)C(=O)N(C1=CC(C#N)=CC(N(C(=O)C(=O)OCC)[Si](C)(C)C(C)(C)C)=C1Cl)[Si](C)(C)C(C)(C)C	3118.1	Semi standard non polar	33892256
Lodoxamide ethyl,2TBDMS,isomer #1	CCOC(=O)C(=O)N(C1=CC(C#N)=CC(N(C(=O)C(=O)OCC)[Si](C)(C)C(C)(C)C)=C1Cl)[Si](C)(C)C(C)(C)C	2934.5	Standard non polar	33892256
Lodoxamide ethyl,2TBDMS,isomer #1	CCOC(=O)C(=O)N(C1=CC(C#N)=CC(N(C(=O)C(=O)OCC)[Si](C)(C)C(C)(C)C)=C1Cl)[Si](C)(C)C(C)(C)C	3889.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Lodoxamide ethyl GC-MS (Non-derivatized) - 70eV, Positive	splash10-002f-5191000000-fecfa463148e6e55e97f	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lodoxamide ethyl 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 - Lodoxamide ethyl 10V, Positive-QTOF	splash10-014i-0019000000-a0d3a21474ba2eaf0e93	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lodoxamide ethyl 20V, Positive-QTOF	splash10-014i-0389000000-7e606f61ee8654c9ed5a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lodoxamide ethyl 40V, Positive-QTOF	splash10-0gbd-1941000000-b44ebde1d483834c4238	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lodoxamide ethyl 10V, Negative-QTOF	splash10-014i-0129000000-7b648a0335dfaf13c228	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lodoxamide ethyl 20V, Negative-QTOF	splash10-00r6-0390000000-b0d62ec1e669bf724674	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lodoxamide ethyl 40V, Negative-QTOF	splash10-0006-8190000000-f72ac5dc703f3601b6c6	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

37361

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

40915

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

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 Lodoxamide ethyl (HMDB0254147)

MOL for HMDB0254147 (Lodoxamide ethyl)

3D MOL for HMDB0254147 (Lodoxamide ethyl)

3D SDF for HMDB0254147 (Lodoxamide ethyl)

3D-SDF for HMDB0254147 (Lodoxamide ethyl)

PDB for HMDB0254147 (Lodoxamide ethyl)

3D PDB for HMDB0254147 (Lodoxamide ethyl)

SMILES for HMDB0254147 (Lodoxamide ethyl)

INCHI for HMDB0254147 (Lodoxamide ethyl)

Structure for HMDB0254147 (Lodoxamide ethyl)

3D Structure for HMDB0254147 (Lodoxamide ethyl)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra