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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 23:55:38 UTC

Update Date

2021-09-26 22:56:15 UTC

HMDB ID

HMDB0246904

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Ethyl butylacetylaminopropionate

Description

Ethyl butylacetylaminopropionate, also known as insect repellent m 3535 or EBAAP, belongs to the class of organic compounds known as tertiary carboxylic acid amides. Tertiary carboxylic acid amides are compounds containing an amide derivative of carboxylic acid, with the general structure RN(R1)C(R2)=O (R1-R2 any atom but H). Based on a literature review a significant number of articles have been published on Ethyl butylacetylaminopropionate. This compound has been identified in human blood as reported by (PMID: 31557052 ). Ethyl butylacetylaminopropionate is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Ethyl butylacetylaminopropionate 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

HMDB0246904
     RDKit          3D
Ethyl butylacetylaminopropionate
 36 35  0  0  0  0  0  0  0  0999 V2000
   -4.4568    2.2071    0.5205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4910    1.2042    1.0724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5922    0.6552   -0.0079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6593   -0.3344    0.6120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7395   -0.9367   -0.3285 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5598   -0.3581   -0.6190 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6305   -0.8906    0.3098 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9075   -0.2455   -0.0641 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9882    0.5957   -1.0142 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1101   -0.5105    0.5936 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3134    0.1274    0.2065 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2514    1.6205    0.3184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1336   -2.1328   -0.9813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4355   -2.7539   -0.7149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3413   -2.6762   -1.8135 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4622    1.7360    0.4926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1328    2.4817   -0.5028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5616    3.1103    1.1757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8652    1.6835    1.8692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0170    0.3568    1.5716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1970    0.2101   -0.8087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0142    1.5301   -0.4034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0840    0.2248    1.4085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2340   -1.1158    1.1149 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5436    0.7466   -0.6027 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8218   -0.6603   -1.6526 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6594   -1.9953    0.2054 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3560   -0.6668    1.3757 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1367   -0.2749    0.8236 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5864   -0.1116   -0.8536 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3179    1.9875    0.2688 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8643    1.9793    1.2823 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7509    2.0766   -0.5550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6288   -2.9583    0.3596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4623   -3.7549   -1.2149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2899   -2.1568   -1.1365 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  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
  5 13  1  0
 13 14  1  0
 13 15  2  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
M  END


  Mrv1572004221603592D          

 15 14  0  0  0  0            999 V2000
    3.8230   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9677   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3954   -0.4934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2533   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1099   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9664   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3954   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6809   -0.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8243   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6809   -1.7309    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9664   -0.4934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8243   -2.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5388   -1.7309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  2  1  0  0  0  0
  6  4  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  1  0  0  0  0
 10  3  1  0  0  0  0
 11  7  1  0  0  0  0
 12  8  1  0  0  0  0
 12  9  1  0  0  0  0
 12 10  1  0  0  0  0
 13 10  2  0  0  0  0
 14 11  2  0  0  0  0
 15  5  1  0  0  0  0
 15 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0246904

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCN(CCC(=O)OCC)C(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H21NO3/c1-4-6-8-12(10(3)13)9-7-11(14)15-5-2/h4-9H2,1-3H3

> <INCHI_KEY>
VZRKEAFHFMSHCD-UHFFFAOYSA-N

> <FORMULA>
C11H21NO3

> <MOLECULAR_WEIGHT>
215.293

> <EXACT_MASS>
215.15214354

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
24.468422075117715

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
ethyl 3-(N-butylacetamido)propanoate

> <ALOGPS_LOGP>
1.68

> <JCHEM_LOGP>
0.9586608733333335

> <ALOGPS_LOGS>
-1.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-1.291331618833405

> <JCHEM_POLAR_SURFACE_AREA>
46.61

> <JCHEM_REFRACTIVITY>
58.43460000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.65e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ethyl 3-(N-butylacetamido)propanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0246904
     RDKit          3D
Ethyl butylacetylaminopropionate
 36 35  0  0  0  0  0  0  0  0999 V2000
   -4.4568    2.2071    0.5205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4910    1.2042    1.0724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5922    0.6552   -0.0079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6593   -0.3344    0.6120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7395   -0.9367   -0.3285 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5598   -0.3581   -0.6190 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6305   -0.8906    0.3098 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9075   -0.2455   -0.0641 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9882    0.5957   -1.0142 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1101   -0.5105    0.5936 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3134    0.1274    0.2065 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2514    1.6205    0.3184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1336   -2.1328   -0.9813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4355   -2.7539   -0.7149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3413   -2.6762   -1.8135 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4622    1.7360    0.4926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1328    2.4817   -0.5028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5616    3.1103    1.1757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8652    1.6835    1.8692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0170    0.3568    1.5716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1970    0.2101   -0.8087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0142    1.5301   -0.4034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0840    0.2248    1.4085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2340   -1.1158    1.1149 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5436    0.7466   -0.6027 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8218   -0.6603   -1.6526 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6594   -1.9953    0.2054 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3560   -0.6668    1.3757 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1367   -0.2749    0.8236 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5864   -0.1116   -0.8536 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3179    1.9875    0.2688 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8643    1.9793    1.2823 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7509    2.0766   -0.5550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6288   -2.9583    0.3596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4623   -3.7549   -1.2149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2899   -2.1568   -1.1365 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  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
  5 13  1  0
 13 14  1  0
 13 15  2  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
M  END

HEADER    PROTEIN                                 22-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-16         0                                  
HETATM    1  C   UNK     0       7.136  -3.231   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      20.473  -3.231   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.805  -0.921   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.470  -4.001   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      19.139  -4.001   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.804  -3.231   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      15.138  -3.231   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.137  -4.001   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.805  -4.001   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.471  -1.691   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      16.472  -4.001   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      12.471  -3.231   0.000  0.00  0.00           N+0
HETATM   13  O   UNK     0      11.137  -0.921   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      16.472  -5.541   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      17.806  -3.231   0.000  0.00  0.00           O+0
CONECT    1    4                                                            
CONECT    2    5                                                            
CONECT    3   10                                                            
CONECT    4    1    6                                                       
CONECT    5    2   15                                                       
CONECT    6    4    8                                                       
CONECT    7    9   11                                                       
CONECT    8    6   12                                                       
CONECT    9    7   12                                                       
CONECT   10    3   12   13                                                  
CONECT   11    7   14   15                                                  
CONECT   12    8    9   10                                                  
CONECT   13   10                                                            
CONECT   14   11                                                            
CONECT   15    5   11                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   28    0
END

COMPND    HMDB0246904
HETATM    1  C1  UNL     1      -4.457   2.207   0.520  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.491   1.204   1.072  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.592   0.655  -0.008  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.659  -0.334   0.612  1.00  0.00           C  
HETATM    5  N1  UNL     1      -0.739  -0.937  -0.328  1.00  0.00           N  
HETATM    6  C5  UNL     1       0.560  -0.358  -0.619  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.631  -0.891   0.310  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.908  -0.246  -0.064  1.00  0.00           C  
HETATM    9  O1  UNL     1       2.988   0.596  -1.014  1.00  0.00           O  
HETATM   10  O2  UNL     1       4.110  -0.510   0.594  1.00  0.00           O  
HETATM   11  C8  UNL     1       5.313   0.127   0.207  1.00  0.00           C  
HETATM   12  C9  UNL     1       5.251   1.621   0.318  1.00  0.00           C  
HETATM   13  C10 UNL     1      -1.134  -2.133  -0.981  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.435  -2.754  -0.715  1.00  0.00           C  
HETATM   15  O3  UNL     1      -0.341  -2.676  -1.813  1.00  0.00           O  
HETATM   16  H1  UNL     1      -5.462   1.736   0.493  1.00  0.00           H  
HETATM   17  H2  UNL     1      -4.133   2.482  -0.503  1.00  0.00           H  
HETATM   18  H3  UNL     1      -4.562   3.110   1.176  1.00  0.00           H  
HETATM   19  H4  UNL     1      -2.865   1.683   1.869  1.00  0.00           H  
HETATM   20  H5  UNL     1      -4.017   0.357   1.572  1.00  0.00           H  
HETATM   21  H6  UNL     1      -3.197   0.210  -0.809  1.00  0.00           H  
HETATM   22  H7  UNL     1      -2.014   1.530  -0.403  1.00  0.00           H  
HETATM   23  H8  UNL     1      -1.084   0.225   1.408  1.00  0.00           H  
HETATM   24  H9  UNL     1      -2.234  -1.116   1.115  1.00  0.00           H  
HETATM   25  H10 UNL     1       0.544   0.747  -0.603  1.00  0.00           H  
HETATM   26  H11 UNL     1       0.822  -0.660  -1.653  1.00  0.00           H  
HETATM   27  H12 UNL     1       1.659  -1.995   0.205  1.00  0.00           H  
HETATM   28  H13 UNL     1       1.356  -0.667   1.376  1.00  0.00           H  
HETATM   29  H14 UNL     1       6.137  -0.275   0.824  1.00  0.00           H  
HETATM   30  H15 UNL     1       5.586  -0.112  -0.854  1.00  0.00           H  
HETATM   31  H16 UNL     1       6.318   1.988   0.269  1.00  0.00           H  
HETATM   32  H17 UNL     1       4.864   1.979   1.282  1.00  0.00           H  
HETATM   33  H18 UNL     1       4.751   2.077  -0.555  1.00  0.00           H  
HETATM   34  H19 UNL     1      -2.629  -2.958   0.360  1.00  0.00           H  
HETATM   35  H20 UNL     1      -2.462  -3.755  -1.215  1.00  0.00           H  
HETATM   36  H21 UNL     1      -3.290  -2.157  -1.136  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3   19   20
CONECT    3    4   21   22
CONECT    4    5   23   24
CONECT    5    6   13
CONECT    6    7   25   26
CONECT    7    8   27   28
CONECT    8    9    9   10
CONECT   10   11
CONECT   11   12   29   30
CONECT   12   31   32   33
CONECT   13   14   15   15
CONECT   14   34   35   36
END

HMDB0246904
     RDKit          3D
Ethyl butylacetylaminopropionate
 36 35  0  0  0  0  0  0  0  0999 V2000
   -4.4568    2.2071    0.5205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4910    1.2042    1.0724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5922    0.6552   -0.0079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6593   -0.3344    0.6120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7395   -0.9367   -0.3285 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5598   -0.3581   -0.6190 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6305   -0.8906    0.3098 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9075   -0.2455   -0.0641 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9882    0.5957   -1.0142 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1101   -0.5105    0.5936 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3134    0.1274    0.2065 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2514    1.6205    0.3184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1336   -2.1328   -0.9813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4355   -2.7539   -0.7149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3413   -2.6762   -1.8135 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4622    1.7360    0.4926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1328    2.4817   -0.5028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5616    3.1103    1.1757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8652    1.6835    1.8692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0170    0.3568    1.5716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1970    0.2101   -0.8087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0142    1.5301   -0.4034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0840    0.2248    1.4085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2340   -1.1158    1.1149 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5436    0.7466   -0.6027 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8218   -0.6603   -1.6526 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6594   -1.9953    0.2054 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3560   -0.6668    1.3757 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1367   -0.2749    0.8236 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5864   -0.1116   -0.8536 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3179    1.9875    0.2688 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8643    1.9793    1.2823 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7509    2.0766   -0.5550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6288   -2.9583    0.3596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4623   -3.7549   -1.2149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2899   -2.1568   -1.1365 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  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
  5 13  1  0
 13 14  1  0
 13 15  2  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Ethyl butylacetylaminopropionic acid	Generator
3-(N-N-Butyl)-N-acetylaminopropionic acid ethyl ester	HMDB
Ethyl-3-(N-N-butyl-N-acetyl)aminopropionate	HMDB
Insect repellent m 3535	HMDB
Repellent 3535	HMDB
EBAAP	HMDB
Insect repellent merck 3535	HMDB
Ethyl 3-[acetyl(butyl)amino]propanoic acid	HMDB
Ethyl 3-(N-butylacetamido)propanoic acid	HMDB
Ethyl butylacetylaminopropionate	KEGG

Chemical Formula

C₁₁H₂₁NO₃

Average Molecular Weight

215.293

Monoisotopic Molecular Weight

215.15214354

IUPAC Name

ethyl 3-(N-butylacetamido)propanoate

Traditional Name

ethyl 3-(N-butylacetamido)propanoate

CAS Registry Number

Not Available

SMILES

CCCCN(CCC(=O)OCC)C(C)=O

InChI Identifier

InChI=1S/C11H21NO3/c1-4-6-8-12(10(3)13)9-7-11(14)15-5-2/h4-9H2,1-3H3

InChI Key

VZRKEAFHFMSHCD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tertiary carboxylic acid amides. Tertiary carboxylic acid amides are compounds containing an amide derivative of carboxylic acid, with the general structure RN(R1)C(R2)=O (R1-R2 any atom but H).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Carboxylic acid derivatives

Direct Parent

Tertiary carboxylic acid amides

Alternative Parents

Substituents

Acetamide
Tertiary carboxylic acid amide
Carboxylic acid ester
Monocarboxylic acid or derivatives
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

carboxamide (CHEBI:81991 )
Insect repellents (C18830 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	1.68	ALOGPS
logP	0.96	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	46.61 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	58.43 m³·mol⁻¹	ChemAxon
Polarizability	24.47 Å³	ChemAxon
Number of Rings	0	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]+	154.294	30932474
DeepCCS	[M-H]-	150.4	30932474
DeepCCS	[M-2H]-	187.6	30932474
DeepCCS	[M+Na]+	163.253	30932474
AllCCS	[M+H]+	154.0	32859911
AllCCS	[M+H-H2O]+	150.6	32859911
AllCCS	[M+NH4]+	157.2	32859911
AllCCS	[M+Na]+	158.1	32859911
AllCCS	[M-H]-	153.1	32859911
AllCCS	[M+Na-2H]-	154.5	32859911
AllCCS	[M+HCOO]-	156.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ethyl butylacetylaminopropionate	CCCCN(CCC(=O)OCC)C(C)=O	2361.2	Standard polar	33892256
Ethyl butylacetylaminopropionate	CCCCN(CCC(=O)OCC)C(C)=O	1541.1	Standard non polar	33892256
Ethyl butylacetylaminopropionate	CCCCN(CCC(=O)OCC)C(C)=O	1636.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyl butylacetylaminopropionate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0kp3-9800000000-468a32b8cb03acd08429	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyl butylacetylaminopropionate 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ethyl butylacetylaminopropionate 60V, Positive-QTOF	splash10-000i-9000000000-fa9084489b5df2aa115b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ethyl butylacetylaminopropionate 45V, Positive-QTOF	splash10-000i-9400000000-9f7585ffeab56c92c4f7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ethyl butylacetylaminopropionate 15V, Positive-QTOF	splash10-00di-0900000000-d14f3acd8a1f1f6127bd	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ethyl butylacetylaminopropionate 30V, Positive-QTOF	splash10-00fr-2900000000-9e78a71320a1bd168fb1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ethyl butylacetylaminopropionate 90V, Positive-QTOF	splash10-052r-9000000000-a4927a065ab5dbdd96c6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ethyl butylacetylaminopropionate 75V, Positive-QTOF	splash10-000i-9000000000-d9597b303fc7d0c934b2	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl butylacetylaminopropionate 10V, Positive-QTOF	splash10-01b9-3960000000-9c639471090ff4379712	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl butylacetylaminopropionate 20V, Positive-QTOF	splash10-0kos-6910000000-6fd65c2ffa0f333cd1d0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl butylacetylaminopropionate 40V, Positive-QTOF	splash10-0a4i-9100000000-82a2364c485d3e7a5f36	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl butylacetylaminopropionate 10V, Negative-QTOF	splash10-03xr-2970000000-b2bfc118015cab15f66d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl butylacetylaminopropionate 20V, Negative-QTOF	splash10-03xs-3910000000-f9f80c57c2183cda3739	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl butylacetylaminopropionate 40V, Negative-QTOF	splash10-03dj-9800000000-dfbcdcd5a2c5055ee70b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl butylacetylaminopropionate 10V, Positive-QTOF	splash10-0170-5940000000-14138c78c956f565d692	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl butylacetylaminopropionate 20V, Positive-QTOF	splash10-0kmj-9400000000-7ae8835162fb3f002d70	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl butylacetylaminopropionate 40V, Positive-QTOF	splash10-0a4i-9000000000-a6066883a51ef0891c96	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl butylacetylaminopropionate 10V, Negative-QTOF	splash10-03di-1940000000-999ee7ba5af1e301c72a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl butylacetylaminopropionate 20V, Negative-QTOF	splash10-004i-1900000000-09b036f90e4b00bc1030	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl butylacetylaminopropionate 40V, Negative-QTOF	splash10-056u-9500000000-3a6f3d1ed99d2df01029	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	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

C00053100

Chemspider ID

94028

KEGG Compound ID

C18830

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ethyl butylacetylaminopropionate

METLIN ID

Not Available

PubChem Compound

104150

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1362771

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 Ethyl butylacetylaminopropionate (HMDB0246904)

MOL for HMDB0246904 (Ethyl butylacetylaminopropionate)

3D MOL for HMDB0246904 (Ethyl butylacetylaminopropionate)

3D SDF for HMDB0246904 (Ethyl butylacetylaminopropionate)

3D-SDF for HMDB0246904 (Ethyl butylacetylaminopropionate)

PDB for HMDB0246904 (Ethyl butylacetylaminopropionate)

3D PDB for HMDB0246904 (Ethyl butylacetylaminopropionate)

SMILES for HMDB0246904 (Ethyl butylacetylaminopropionate)

INCHI for HMDB0246904 (Ethyl butylacetylaminopropionate)

Structure for HMDB0246904 (Ethyl butylacetylaminopropionate)

3D Structure for HMDB0246904 (Ethyl butylacetylaminopropionate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra