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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 03:59:00 UTC

Update Date

2021-09-26 23:00:23 UTC

HMDB ID

HMDB0249470

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Butralin

Description

Butralin belongs to the class of organic compounds known as dinitroanilines. These are organic compounds containing an aniline moiety, which is substituted at 2 positions by a nitro group. Based on a literature review a significant number of articles have been published on Butralin. This compound has been identified in human blood as reported by (PMID: 31557052 ). Butralin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Butralin 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

HMDB0249470
     RDKit          3D
Butralin
 42 42  0  0  0  0  0  0  0  0999 V2000
    4.4363    1.0252   -1.3700 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1115    0.9984   -0.5747 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1263   -0.3517    0.1140 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3938   -0.3003    1.0017 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0160   -0.6390    0.9501 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6438   -0.5456    0.6420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1022   -1.5542    0.0994 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4319   -2.8337   -0.0884 N   0  0  0  0  0  4  0  0  0  0  0  0
   -0.3636   -3.8171   -0.0276 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7233   -3.1010   -0.3254 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.4623   -1.3393   -0.2351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0738   -0.1362   -0.0291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5216    0.0808   -0.3773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6807    0.5869   -1.7772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0839    1.1188    0.6073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3417   -1.1721   -0.1914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3235    0.8796    0.5219 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0052    0.6834    0.8532 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7664    1.7196    1.4656 N   0  0  0  0  0  4  0  0  0  0  0  0
    0.4955    2.8927    1.2202 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7840    1.3310    2.3186 O   0  0  0  0  0  1  0  0  0  0  0  0
    4.5450    1.9639   -1.9199 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2769    0.9768   -0.6412 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4841    0.1376   -2.0206 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2862    1.1292   -1.2727 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2406    1.8074    0.1689 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3325   -1.1280   -0.6288 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2423   -0.7876    0.5103 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1992   -0.8199    1.9750 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6266    0.7463    1.2864 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2140   -0.9724    1.9468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0243   -2.1672   -0.6693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7409    0.9112   -1.9049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4733   -0.2198   -2.5022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0064    1.4326   -1.9772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4921    0.9898    1.5516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9675    2.1380    0.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1501    0.8924    0.7564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4088   -0.8450   -0.0271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3237   -1.8225   -1.0752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0617   -1.7167    0.7339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7792    1.8278    0.6933 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
  3  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  7 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 13 16  1  0
 12 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 18  6  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
 11 32  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 15 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  0
M  CHG  4   8   1  10  -1  19   1  21  -1
M  END


  Mrv0541 08291403382D          

 21 21  0  0  0  0            999 V2000
    2.1434   -2.8875    0.0000 C   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
    0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6283   -1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  9  2  1  0  0  0  0
  9  6  1  0  0  0  0
 10  7  2  0  0  0  0
 10  8  1  0  0  0  0
 11  7  1  0  0  0  0
 12  8  2  0  0  0  0
 13 11  2  0  0  0  0
 13 12  1  0  0  0  0
 14  3  1  0  0  0  0
 14  4  1  0  0  0  0
 14  5  1  0  0  0  0
 14 10  1  0  0  0  0
 15  9  1  0  0  0  0
 15 13  1  0  0  0  0
 16 11  1  0  0  0  0
 17 12  1  0  0  0  0
 18 16  2  0  0  0  0
 19 16  2  0  0  0  0
 20 17  2  0  0  0  0
 21 17  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0249470

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC(C)NC1=C(C=C(C=C1N(=O)=O)C(C)(C)C)N(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H21N3O4/c1-6-9(2)15-13-11(16(18)19)7-10(14(3,4)5)8-12(13)17(20)21/h7-9,15H,6H2,1-5H3

> <INCHI_KEY>
SPNQRCTZKIBOAX-UHFFFAOYSA-N

> <FORMULA>
C14H21N3O4

> <MOLECULAR_WEIGHT>
295.3342

> <EXACT_MASS>
295.153206175

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
30.43177268392437

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-(butan-2-yl)-4-tert-butyl-2,6-dinitroaniline

> <ALOGPS_LOGP>
5.24

> <JCHEM_LOGP>
4.816953967

> <ALOGPS_LOGS>
-4.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.865657219468677

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3254509707824722

> <JCHEM_POLAR_SURFACE_AREA>
103.66999999999999

> <JCHEM_REFRACTIVITY>
83.25849999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.07e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
butralin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0249470
     RDKit          3D
Butralin
 42 42  0  0  0  0  0  0  0  0999 V2000
    4.4363    1.0252   -1.3700 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1115    0.9984   -0.5747 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1263   -0.3517    0.1140 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3938   -0.3003    1.0017 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0160   -0.6390    0.9501 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6438   -0.5456    0.6420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1022   -1.5542    0.0994 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4319   -2.8337   -0.0884 N   0  0  0  0  0  4  0  0  0  0  0  0
   -0.3636   -3.8171   -0.0276 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7233   -3.1010   -0.3254 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.4623   -1.3393   -0.2351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0738   -0.1362   -0.0291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5216    0.0808   -0.3773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6807    0.5869   -1.7772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0839    1.1188    0.6073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3417   -1.1721   -0.1914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3235    0.8796    0.5219 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0052    0.6834    0.8532 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7664    1.7196    1.4656 N   0  0  0  0  0  4  0  0  0  0  0  0
    0.4955    2.8927    1.2202 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7840    1.3310    2.3186 O   0  0  0  0  0  1  0  0  0  0  0  0
    4.5450    1.9639   -1.9199 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2769    0.9768   -0.6412 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4841    0.1376   -2.0206 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2862    1.1292   -1.2727 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2406    1.8074    0.1689 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3325   -1.1280   -0.6288 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2423   -0.7876    0.5103 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1992   -0.8199    1.9750 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6266    0.7463    1.2864 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2140   -0.9724    1.9468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0243   -2.1672   -0.6693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7409    0.9112   -1.9049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4733   -0.2198   -2.5022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0064    1.4326   -1.9772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4921    0.9898    1.5516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9675    2.1380    0.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1501    0.8924    0.7564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4088   -0.8450   -0.0271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3237   -1.8225   -1.0752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0617   -1.7167    0.7339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7792    1.8278    0.6933 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
  3  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  7 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 13 16  1  0
 12 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 18  6  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
 11 32  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 15 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  0
M  CHG  4   8   1  10  -1  19   1  21  -1
M  END

HEADER    PROTEIN                                 29-AUG-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-AUG-14         0                                  
HETATM    1  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.874   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.206   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       1.334  -2.310   0.000  0.00  0.00           N+0
HETATM   16  N   UNK     0       4.001  -0.770   0.000  0.00  0.00           N+0
HETATM   17  N   UNK     0      -1.334  -0.770   0.000  0.00  0.00           N+0
HETATM   18  O   UNK     0       4.906  -2.016   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.335  -0.000   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2    9                                                            
CONECT    3   14                                                            
CONECT    4   14                                                            
CONECT    5   14                                                            
CONECT    6    1    9                                                       
CONECT    7   10   11                                                       
CONECT    8   10   12                                                       
CONECT    9    2    6   15                                                  
CONECT   10    7    8   14                                                  
CONECT   11    7   13   16                                                  
CONECT   12    8   13   17                                                  
CONECT   13   11   12   15                                                  
CONECT   14    3    4    5   10                                             
CONECT   15    9   13                                                       
CONECT   16   11   18   19                                                  
CONECT   17   12   20   21                                                  
CONECT   18   16                                                            
CONECT   19   16                                                            
CONECT   20   17                                                            
CONECT   21   17                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

COMPND    HMDB0249470
HETATM    1  C1  UNL     1       4.436   1.025  -1.370  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.111   0.998  -0.575  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.126  -0.352   0.114  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.394  -0.300   1.002  1.00  0.00           C  
HETATM    5  N1  UNL     1       2.016  -0.639   0.950  1.00  0.00           N  
HETATM    6  C5  UNL     1       0.644  -0.546   0.642  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.102  -1.554   0.099  1.00  0.00           C  
HETATM    8  N2  UNL     1       0.432  -2.834  -0.088  1.00  0.00           N1+
HETATM    9  O1  UNL     1      -0.364  -3.817  -0.028  1.00  0.00           O  
HETATM   10  O2  UNL     1       1.723  -3.101  -0.325  1.00  0.00           O1-
HETATM   11  C7  UNL     1      -1.462  -1.339  -0.235  1.00  0.00           C  
HETATM   12  C8  UNL     1      -2.074  -0.136  -0.029  1.00  0.00           C  
HETATM   13  C9  UNL     1      -3.522   0.081  -0.377  1.00  0.00           C  
HETATM   14  C10 UNL     1      -3.681   0.587  -1.777  1.00  0.00           C  
HETATM   15  C11 UNL     1      -4.084   1.119   0.607  1.00  0.00           C  
HETATM   16  C12 UNL     1      -4.342  -1.172  -0.191  1.00  0.00           C  
HETATM   17  C13 UNL     1      -1.323   0.880   0.522  1.00  0.00           C  
HETATM   18  C14 UNL     1       0.005   0.683   0.853  1.00  0.00           C  
HETATM   19  N3  UNL     1       0.766   1.720   1.466  1.00  0.00           N1+
HETATM   20  O3  UNL     1       0.495   2.893   1.220  1.00  0.00           O  
HETATM   21  O4  UNL     1       1.784   1.331   2.319  1.00  0.00           O1-
HETATM   22  H1  UNL     1       4.545   1.964  -1.920  1.00  0.00           H  
HETATM   23  H2  UNL     1       5.277   0.977  -0.641  1.00  0.00           H  
HETATM   24  H3  UNL     1       4.484   0.138  -2.021  1.00  0.00           H  
HETATM   25  H4  UNL     1       2.286   1.129  -1.273  1.00  0.00           H  
HETATM   26  H5  UNL     1       3.241   1.807   0.169  1.00  0.00           H  
HETATM   27  H6  UNL     1       3.333  -1.128  -0.629  1.00  0.00           H  
HETATM   28  H7  UNL     1       5.242  -0.788   0.510  1.00  0.00           H  
HETATM   29  H8  UNL     1       4.199  -0.820   1.975  1.00  0.00           H  
HETATM   30  H9  UNL     1       4.627   0.746   1.286  1.00  0.00           H  
HETATM   31  H10 UNL     1       2.214  -0.972   1.947  1.00  0.00           H  
HETATM   32  H11 UNL     1      -2.024  -2.167  -0.669  1.00  0.00           H  
HETATM   33  H12 UNL     1      -4.741   0.911  -1.905  1.00  0.00           H  
HETATM   34  H13 UNL     1      -3.473  -0.220  -2.502  1.00  0.00           H  
HETATM   35  H14 UNL     1      -3.006   1.433  -1.977  1.00  0.00           H  
HETATM   36  H15 UNL     1      -3.492   0.990   1.552  1.00  0.00           H  
HETATM   37  H16 UNL     1      -3.968   2.138   0.219  1.00  0.00           H  
HETATM   38  H17 UNL     1      -5.150   0.892   0.756  1.00  0.00           H  
HETATM   39  H18 UNL     1      -5.409  -0.845  -0.027  1.00  0.00           H  
HETATM   40  H19 UNL     1      -4.324  -1.823  -1.075  1.00  0.00           H  
HETATM   41  H20 UNL     1      -4.062  -1.717   0.734  1.00  0.00           H  
HETATM   42  H21 UNL     1      -1.779   1.828   0.693  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   25   26
CONECT    3    4    5   27
CONECT    4   28   29   30
CONECT    5    6   31
CONECT    6    7    7   18
CONECT    7    8   11
CONECT    8    9    9   10
CONECT   11   12   12   32
CONECT   12   13   17
CONECT   13   14   15   16
CONECT   14   33   34   35
CONECT   15   36   37   38
CONECT   16   39   40   41
CONECT   17   18   18   42
CONECT   18   19
CONECT   19   20   20   21
END

HMDB0249470
     RDKit          3D
Butralin
 42 42  0  0  0  0  0  0  0  0999 V2000
    4.4363    1.0252   -1.3700 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1115    0.9984   -0.5747 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1263   -0.3517    0.1140 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3938   -0.3003    1.0017 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0160   -0.6390    0.9501 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6438   -0.5456    0.6420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1022   -1.5542    0.0994 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4319   -2.8337   -0.0884 N   0  0  0  0  0  4  0  0  0  0  0  0
   -0.3636   -3.8171   -0.0276 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7233   -3.1010   -0.3254 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.4623   -1.3393   -0.2351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0738   -0.1362   -0.0291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5216    0.0808   -0.3773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6807    0.5869   -1.7772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0839    1.1188    0.6073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3417   -1.1721   -0.1914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3235    0.8796    0.5219 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0052    0.6834    0.8532 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7664    1.7196    1.4656 N   0  0  0  0  0  4  0  0  0  0  0  0
    0.4955    2.8927    1.2202 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7840    1.3310    2.3186 O   0  0  0  0  0  1  0  0  0  0  0  0
    4.5450    1.9639   -1.9199 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2769    0.9768   -0.6412 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4841    0.1376   -2.0206 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2862    1.1292   -1.2727 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2406    1.8074    0.1689 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3325   -1.1280   -0.6288 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2423   -0.7876    0.5103 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1992   -0.8199    1.9750 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6266    0.7463    1.2864 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2140   -0.9724    1.9468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0243   -2.1672   -0.6693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7409    0.9112   -1.9049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4733   -0.2198   -2.5022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0064    1.4326   -1.9772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4921    0.9898    1.5516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9675    2.1380    0.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1501    0.8924    0.7564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4088   -0.8450   -0.0271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3237   -1.8225   -1.0752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0617   -1.7167    0.7339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7792    1.8278    0.6933 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
  3  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  7 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 13 16  1  0
 12 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 18  6  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
 11 32  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 15 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  0
M  CHG  4   8   1  10  -1  19   1  21  -1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
N-Sec-butyl-4-tert-butyl-2,6-dinitroaniline	MeSH

Chemical Formula

C₁₄H₂₁N₃O₄

Average Molecular Weight

295.3342

Monoisotopic Molecular Weight

295.153206175

IUPAC Name

N-(butan-2-yl)-4-tert-butyl-2,6-dinitroaniline

Traditional Name

butralin

CAS Registry Number

Not Available

SMILES

CCC(C)NC1=C(C=C(C=C1N(=O)=O)C(C)(C)C)N(=O)=O

InChI Identifier

InChI=1S/C14H21N3O4/c1-6-9(2)15-13-11(16(18)19)7-10(14(3,4)5)8-12(13)17(20)21/h7-9,15H,6H2,1-5H3

InChI Key

SPNQRCTZKIBOAX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dinitroanilines. These are organic compounds containing an aniline moiety, which is substituted at 2 positions by a nitro group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Aniline and substituted anilines

Direct Parent

Dinitroanilines

Alternative Parents

Substituents

Dinitroaniline
Nitrobenzene
Phenylpropane
Nitroaromatic compound
Phenylalkylamine
Secondary aliphatic/aromatic amine
C-nitro compound
Organic nitro compound
Organic oxoazanium
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Allyl-type 1,3-dipolar organic compound
Secondary amine
Amine
Organic zwitterion
Hydrocarbon derivative
Organic oxide
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

C-nitro compound (CHEBI:81847 )
Pesticides (C18582 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Cellular substructure

Membrane (HMDB: HMDB0249470)

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	5.24	ALOGPS
logP	4.82	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	10.87	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	103.67 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	83.26 m³·mol⁻¹	ChemAxon
Polarizability	30.43 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]+	178.35	30932474
DeepCCS	[M-H]-	175.992	30932474
DeepCCS	[M-2H]-	208.878	30932474
DeepCCS	[M+Na]+	184.444	30932474
AllCCS	[M+H]+	167.2	32859911
AllCCS	[M+H-H2O]+	164.1	32859911
AllCCS	[M+NH4]+	170.1	32859911
AllCCS	[M+Na]+	171.0	32859911
AllCCS	[M-H]-	171.5	32859911
AllCCS	[M+Na-2H]-	171.5	32859911
AllCCS	[M+HCOO]-	171.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	19.777 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.03 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2600.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	611.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	202.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	318.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	114.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	736.8 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	992.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	111.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1499.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	641.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1537.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	520.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	408.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	453.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	470.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Butralin	CCC(C)NC1=C(C=C(C=C1N(=O)=O)C(C)(C)C)N(=O)=O	2739.1	Standard polar	33892256
Butralin	CCC(C)NC1=C(C=C(C=C1N(=O)=O)C(C)(C)C)N(=O)=O	2046.7	Standard non polar	33892256
Butralin	CCC(C)NC1=C(C=C(C=C1N(=O)=O)C(C)(C)C)N(=O)=O	2087.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Butralin,1TMS,isomer #1	CCC(C)N(C1=C([N+](=O)[O-])C=C(C(C)(C)C)C=C1[N+](=O)[O-])[Si](C)(C)C	2107.5	Semi standard non polar	33892256
Butralin,1TMS,isomer #1	CCC(C)N(C1=C([N+](=O)[O-])C=C(C(C)(C)C)C=C1[N+](=O)[O-])[Si](C)(C)C	2238.7	Standard non polar	33892256
Butralin,1TMS,isomer #1	CCC(C)N(C1=C([N+](=O)[O-])C=C(C(C)(C)C)C=C1[N+](=O)[O-])[Si](C)(C)C	2461.8	Standard polar	33892256
Butralin,1TBDMS,isomer #1	CCC(C)N(C1=C([N+](=O)[O-])C=C(C(C)(C)C)C=C1[N+](=O)[O-])[Si](C)(C)C(C)(C)C	2392.0	Semi standard non polar	33892256
Butralin,1TBDMS,isomer #1	CCC(C)N(C1=C([N+](=O)[O-])C=C(C(C)(C)C)C=C1[N+](=O)[O-])[Si](C)(C)C(C)(C)C	2445.4	Standard non polar	33892256
Butralin,1TBDMS,isomer #1	CCC(C)N(C1=C([N+](=O)[O-])C=C(C(C)(C)C)C=C1[N+](=O)[O-])[Si](C)(C)C(C)(C)C	2582.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Butralin GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-2190000000-c3d57ded44d5013715af	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Butralin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-014i-2690000000-e6993b6864e221f568b7	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Butralin 90V, Positive-QTOF	splash10-014l-4900000000-d8f299e40a5b32f143fb	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Butralin 75V, Positive-QTOF	splash10-05mn-3900000000-5679cb2991663b5d040e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Butralin 60V, Positive-QTOF	splash10-0002-1910000000-3d3933acc44468ff5c53	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Butralin 45V, Positive-QTOF	splash10-006t-1970000000-faa3ff61ae39de0e2787	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Butralin 15V, Positive-QTOF	splash10-0006-0090000000-71359f10f6a1a49714f0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Butralin 30V, Positive-QTOF	splash10-0006-0090000000-971c741df80d5cb241dc	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butralin 10V, Positive-QTOF	splash10-0002-0090000000-76a3795243def56139d0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butralin 20V, Positive-QTOF	splash10-059i-2090000000-e6bf38c6e1bf4f125878	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butralin 40V, Positive-QTOF	splash10-0a4i-9020000000-0f09645d24ee1fad6967	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butralin 10V, Negative-QTOF	splash10-0006-0090000000-43a0b48f6ed2f6d8fede	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butralin 20V, Negative-QTOF	splash10-0006-1090000000-43c179392c86a19ec07f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butralin 40V, Negative-QTOF	splash10-0a4i-9060000000-febb4d4acf803459b354	2016-08-03	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

33600

KEGG Compound ID

C18582

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

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 Butralin (HMDB0249470)

MOL for HMDB0249470 (Butralin)

3D MOL for HMDB0249470 (Butralin)

3D SDF for HMDB0249470 (Butralin)

3D-SDF for HMDB0249470 (Butralin)

PDB for HMDB0249470 (Butralin)

3D PDB for HMDB0249470 (Butralin)

SMILES for HMDB0249470 (Butralin)

INCHI for HMDB0249470 (Butralin)

Structure for HMDB0249470 (Butralin)

3D Structure for HMDB0249470 (Butralin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra