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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:44:53 UTC

Update Date

2022-03-07 02:53:05 UTC

HMDB ID

HMDB0031696

Secondary Accession Numbers

HMDB31696

Metabolite Identification

Common Name

Dibutyl malate

Description

Dibutyl malate, also known as dibutyl tartrate, belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom. Based on a literature review very few articles have been published on Dibutyl malate.

Structure

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

HMDB0031696
     RDKit          3D
Dibutyl malate
 39 38  0  0  0  0  0  0  0  0999 V2000
   -5.6854   -1.4452    0.4774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7265   -0.8930   -0.5231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7183    0.6044   -0.5929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3468    1.2599    0.6972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0570    0.8550    1.0960 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9670    1.1249    0.2888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0313    1.7252   -0.8121 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6428    0.6718    0.7637 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4516    1.0403   -0.2287 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5120    2.3992   -0.4104 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7544    0.4765    0.2685 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8192   -0.7562    0.4714 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8503    1.2328    0.5048 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1139    0.9285    0.9331 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0398    0.1666    0.0632 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6052   -1.1808   -0.3924 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7658   -1.7813   -1.2148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3765   -2.4450    0.8614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9541   -0.7499    1.2929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6566   -1.6417   -0.0655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9708   -1.3109   -1.5209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7101   -1.2708   -0.2471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7562    0.9800   -0.8403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1048    0.9314   -1.4503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0274    1.0502    1.5222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2784    2.3814    0.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4014    1.2240    1.7046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6003   -0.3992    1.0072 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2058    0.5548   -1.1792 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7174    2.5914   -1.3491 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1019    0.3738    1.9413 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5824    1.9197    1.2599 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9737   -0.0198    0.6933 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4528    0.7878   -0.7786 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3532   -1.8110    0.4690 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7800   -1.1451   -1.1452 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4516   -2.8248   -1.4642 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8315   -1.1677   -2.1262 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6495   -1.7358   -0.5654 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  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  8 27  1  0
  8 28  1  0
  9 29  1  0
 10 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
 17 38  1  0
 17 39  1  0
M  END


  Mrv0541 05061306042D          

 17 16  0  0  0  0            999 V2000
    3.1086   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3967   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8230   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6822   -2.1434    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
   10.9677   -1.7309    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
   10.2533   -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
    8.1099   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6809   -1.7309    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
    8.1099   -0.9059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6809   -0.9059    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
    5.9664   -2.1434    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
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
 10  9  1  0  0  0  0
 11  9  1  0  0  0  0
 12 10  1  0  0  0  0
 13 10  1  0  0  0  0
 14 11  2  0  0  0  0
 15 12  2  0  0  0  0
 16  7  1  0  0  0  0
 16 11  1  0  0  0  0
 17  8  1  0  0  0  0
 17 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031696

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCOC(=O)CC(O)C(=O)OCCCC

> <INCHI_IDENTIFIER>
InChI=1S/C12H22O5/c1-3-5-7-16-11(14)9-10(13)12(15)17-8-6-4-2/h10,13H,3-9H2,1-2H3

> <INCHI_KEY>
PDSCSYLDRHAHOX-UHFFFAOYSA-N

> <FORMULA>
C12H22O5

> <MOLECULAR_WEIGHT>
246.3001

> <EXACT_MASS>
246.146723814

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
27.550966961934762

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,4-dibutyl 2-hydroxybutanedioate

> <ALOGPS_LOGP>
1.91

> <JCHEM_LOGP>
1.8259447133333335

> <ALOGPS_LOGS>
-1.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.442620271150748

> <JCHEM_PKA_STRONGEST_BASIC>
-3.917397893398662

> <JCHEM_POLAR_SURFACE_AREA>
72.83

> <JCHEM_REFRACTIVITY>
62.16060000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.17e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
malic acid dibutyl ester

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0031696
     RDKit          3D
Dibutyl malate
 39 38  0  0  0  0  0  0  0  0999 V2000
   -5.6854   -1.4452    0.4774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7265   -0.8930   -0.5231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7183    0.6044   -0.5929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3468    1.2599    0.6972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0570    0.8550    1.0960 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9670    1.1249    0.2888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0313    1.7252   -0.8121 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6428    0.6718    0.7637 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4516    1.0403   -0.2287 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5120    2.3992   -0.4104 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7544    0.4765    0.2685 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8192   -0.7562    0.4714 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8503    1.2328    0.5048 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1139    0.9285    0.9331 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0398    0.1666    0.0632 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6052   -1.1808   -0.3924 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7658   -1.7813   -1.2148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3765   -2.4450    0.8614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9541   -0.7499    1.2929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6566   -1.6417   -0.0655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9708   -1.3109   -1.5209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7101   -1.2708   -0.2471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7562    0.9800   -0.8403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1048    0.9314   -1.4503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0274    1.0502    1.5222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2784    2.3814    0.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4014    1.2240    1.7046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6003   -0.3992    1.0072 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2058    0.5548   -1.1792 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7174    2.5914   -1.3491 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1019    0.3738    1.9413 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5824    1.9197    1.2599 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9737   -0.0198    0.6933 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4528    0.7878   -0.7786 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3532   -1.8110    0.4690 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7800   -1.1451   -1.1452 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4516   -2.8248   -1.4642 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8315   -1.1677   -2.1262 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6495   -1.7358   -0.5654 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  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  8 27  1  0
  8 28  1  0
  9 29  1  0
 10 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
 17 38  1  0
 17 39  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       5.803  -4.001   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      23.141  -3.231   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.136  -3.231   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      21.807  -4.001   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.470  -4.001   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      20.473  -3.231   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.804  -3.231   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      19.139  -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      15.138  -3.231   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.471  -3.231   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      16.472  -4.001   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      15.138  -1.691   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      12.471  -1.691   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      16.472  -5.541   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      11.137  -4.001   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      17.806  -3.231   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2    4                                                            
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5   16                                                       
CONECT    8    6   17                                                       
CONECT    9   10   11                                                       
CONECT   10    9   12   13                                                  
CONECT   11    9   14   16                                                  
CONECT   12   10   15   17                                                  
CONECT   13   10                                                            
CONECT   14   11                                                            
CONECT   15   12                                                            
CONECT   16    7   11                                                       
CONECT   17    8   12                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   32    0
END

COMPND    HMDB0031696
HETATM    1  C1  UNL     1      -5.685  -1.445   0.477  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.727  -0.893  -0.523  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.718   0.604  -0.593  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.347   1.260   0.697  1.00  0.00           C  
HETATM    5  O1  UNL     1      -3.057   0.855   1.096  1.00  0.00           O  
HETATM    6  C5  UNL     1      -1.967   1.125   0.289  1.00  0.00           C  
HETATM    7  O2  UNL     1      -2.031   1.725  -0.812  1.00  0.00           O  
HETATM    8  C6  UNL     1      -0.643   0.672   0.764  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.452   1.040  -0.229  1.00  0.00           C  
HETATM   10  O3  UNL     1       0.512   2.399  -0.410  1.00  0.00           O  
HETATM   11  C8  UNL     1       1.754   0.477   0.269  1.00  0.00           C  
HETATM   12  O4  UNL     1       1.819  -0.756   0.471  1.00  0.00           O  
HETATM   13  O5  UNL     1       2.850   1.233   0.505  1.00  0.00           O  
HETATM   14  C9  UNL     1       4.114   0.928   0.933  1.00  0.00           C  
HETATM   15  C10 UNL     1       5.040   0.167   0.063  1.00  0.00           C  
HETATM   16  C11 UNL     1       4.605  -1.181  -0.392  1.00  0.00           C  
HETATM   17  C12 UNL     1       5.766  -1.781  -1.215  1.00  0.00           C  
HETATM   18  H1  UNL     1      -5.377  -2.445   0.861  1.00  0.00           H  
HETATM   19  H2  UNL     1      -5.954  -0.750   1.293  1.00  0.00           H  
HETATM   20  H3  UNL     1      -6.657  -1.642  -0.066  1.00  0.00           H  
HETATM   21  H4  UNL     1      -4.971  -1.311  -1.521  1.00  0.00           H  
HETATM   22  H5  UNL     1      -3.710  -1.271  -0.247  1.00  0.00           H  
HETATM   23  H6  UNL     1      -5.756   0.980  -0.840  1.00  0.00           H  
HETATM   24  H7  UNL     1      -4.105   0.931  -1.450  1.00  0.00           H  
HETATM   25  H8  UNL     1      -5.027   1.050   1.522  1.00  0.00           H  
HETATM   26  H9  UNL     1      -4.278   2.381   0.591  1.00  0.00           H  
HETATM   27  H10 UNL     1      -0.401   1.224   1.705  1.00  0.00           H  
HETATM   28  H11 UNL     1      -0.600  -0.399   1.007  1.00  0.00           H  
HETATM   29  H12 UNL     1       0.206   0.555  -1.179  1.00  0.00           H  
HETATM   30  H13 UNL     1       0.717   2.591  -1.349  1.00  0.00           H  
HETATM   31  H14 UNL     1       4.102   0.374   1.941  1.00  0.00           H  
HETATM   32  H15 UNL     1       4.582   1.920   1.260  1.00  0.00           H  
HETATM   33  H16 UNL     1       5.974  -0.020   0.693  1.00  0.00           H  
HETATM   34  H17 UNL     1       5.453   0.788  -0.779  1.00  0.00           H  
HETATM   35  H18 UNL     1       4.353  -1.811   0.469  1.00  0.00           H  
HETATM   36  H19 UNL     1       3.780  -1.145  -1.145  1.00  0.00           H  
HETATM   37  H20 UNL     1       5.452  -2.825  -1.464  1.00  0.00           H  
HETATM   38  H21 UNL     1       5.831  -1.168  -2.126  1.00  0.00           H  
HETATM   39  H22 UNL     1       6.649  -1.736  -0.565  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3   21   22
CONECT    3    4   23   24
CONECT    4    5   25   26
CONECT    5    6
CONECT    6    7    7    8
CONECT    8    9   27   28
CONECT    9   10   11   29
CONECT   10   30
CONECT   11   12   12   13
CONECT   13   14
CONECT   14   15   31   32
CONECT   15   16   33   34
CONECT   16   17   35   36
CONECT   17   37   38   39
END

HMDB0031696
     RDKit          3D
Dibutyl malate
 39 38  0  0  0  0  0  0  0  0999 V2000
   -5.6854   -1.4452    0.4774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7265   -0.8930   -0.5231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7183    0.6044   -0.5929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3468    1.2599    0.6972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0570    0.8550    1.0960 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9670    1.1249    0.2888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0313    1.7252   -0.8121 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6428    0.6718    0.7637 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4516    1.0403   -0.2287 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5120    2.3992   -0.4104 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7544    0.4765    0.2685 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8192   -0.7562    0.4714 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8503    1.2328    0.5048 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1139    0.9285    0.9331 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0398    0.1666    0.0632 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6052   -1.1808   -0.3924 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7658   -1.7813   -1.2148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3765   -2.4450    0.8614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9541   -0.7499    1.2929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6566   -1.6417   -0.0655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9708   -1.3109   -1.5209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7101   -1.2708   -0.2471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7562    0.9800   -0.8403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1048    0.9314   -1.4503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0274    1.0502    1.5222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2784    2.3814    0.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4014    1.2240    1.7046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6003   -0.3992    1.0072 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2058    0.5548   -1.1792 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7174    2.5914   -1.3491 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1019    0.3738    1.9413 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5824    1.9197    1.2599 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9737   -0.0198    0.6933 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4528    0.7878   -0.7786 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3532   -1.8110    0.4690 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7800   -1.1451   -1.1452 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4516   -2.8248   -1.4642 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8315   -1.1677   -2.1262 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6495   -1.7358   -0.5654 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  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  8 27  1  0
  8 28  1  0
  9 29  1  0
 10 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
 17 38  1  0
 17 39  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Dibutyl malic acid	Generator
Butanedioic acid, 2,3-dihydroxy- (2R,3R)-, dibutyl ester	HMDB
Butanedioic acid, 2,3-dihydroxy-, dibutyl ester	HMDB
Dibutyl ester(.+/-.)-malic acid	HMDB
Dibutyl tartrate	HMDB
Hydroxy-dibutyl ester(.+/-.)-butanedioic acid	HMDB
1,4-Dibutyl 2-hydroxybutanedioic acid	HMDB
Dibutyl L-malic acid	HMDB

Chemical Formula

C₁₂H₂₂O₅

Average Molecular Weight

246.3001

Monoisotopic Molecular Weight

246.146723814

IUPAC Name

1,4-dibutyl 2-hydroxybutanedioate

Traditional Name

malic acid dibutyl ester

CAS Registry Number

2385-79-7

SMILES

CCCCOC(=O)CC(O)C(=O)OCCCC

InChI Identifier

InChI=1S/C12H22O5/c1-3-5-7-16-11(14)9-10(13)12(15)17-8-6-4-2/h10,13H,3-9H2,1-2H3

InChI Key

PDSCSYLDRHAHOX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Hydroxy acids and derivatives

Sub Class

Beta hydroxy acids and derivatives

Direct Parent

Beta hydroxy acids and derivatives

Alternative Parents

Substituents

Fatty acid ester
Beta-hydroxy acid
Fatty acyl
Dicarboxylic acid or derivatives
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0031696)
Cytoplasm (HMDB: HMDB0031696)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031696)

Source

Endogenous

Endogenous (HMDB: HMDB0031696)

Plant

Plant (HMDB: HMDB0031696)

Exogenous

Food

Food (HMDB: HMDB0031696)

Fruit

Fruits (FooDB: FOOD00871)

Exogenous (HMDB: HMDB0031696)

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	2270 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	4.17 g/L	ALOGPS
logP	1.91	ALOGPS
logP	1.83	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	12.44	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	62.16 m³·mol⁻¹	ChemAxon
Polarizability	27.55 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
DarkChem	[M+H]+	159.126	31661259
DarkChem	[M-H]-	155.093	31661259
DeepCCS	[M+H]+	159.424	30932474
DeepCCS	[M-H]-	157.066	30932474
DeepCCS	[M-2H]-	190.987	30932474
DeepCCS	[M+Na]+	166.778	30932474
AllCCS	[M+H]+	160.9	32859911
AllCCS	[M+H-H2O]+	157.8	32859911
AllCCS	[M+NH4]+	163.7	32859911
AllCCS	[M+Na]+	164.5	32859911
AllCCS	[M-H]-	160.1	32859911
AllCCS	[M+Na-2H]-	161.1	32859911
AllCCS	[M+HCOO]-	162.3	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.32 minutes	32390414
Predicted by Siyang on May 30, 2022	13.6557 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.37 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	24.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2301.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	344.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	158.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	187.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	177.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	597.2 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	653.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	73.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1137.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	467.4 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	1455.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	366.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	376.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	307.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	257.2 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	21.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dibutyl malate	CCCCOC(=O)CC(O)C(=O)OCCCC	2822.8	Standard polar	33892256
Dibutyl malate	CCCCOC(=O)CC(O)C(=O)OCCCC	1529.5	Standard non polar	33892256
Dibutyl malate	CCCCOC(=O)CC(O)C(=O)OCCCC	1692.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dibutyl malate,1TMS,isomer #1	CCCCOC(=O)CC(O[Si](C)(C)C)C(=O)OCCCC	1733.9	Semi standard non polar	33892256
Dibutyl malate,1TBDMS,isomer #1	CCCCOC(=O)CC(O[Si](C)(C)C(C)(C)C)C(=O)OCCCC	1938.1	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 - Dibutyl malate GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-9400000000-0dd6ec6c9b562f70b042	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dibutyl malate GC-MS (1 TMS) - 70eV, Positive	splash10-06di-9360000000-5ed495f593ba32ad525d	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dibutyl malate 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 - Dibutyl malate 10V, Positive-QTOF	splash10-05bb-4890000000-7eb0bf0fc3333038c55c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dibutyl malate 20V, Positive-QTOF	splash10-0a4i-9610000000-f6d1cd5bb22663ef37e6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dibutyl malate 40V, Positive-QTOF	splash10-0a4i-9100000000-b251b5fe6a7b6a5c9706	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dibutyl malate 10V, Negative-QTOF	splash10-00dj-3940000000-e517d747e2a3a6492729	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dibutyl malate 20V, Negative-QTOF	splash10-00di-4900000000-fff6b869661f6349921b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dibutyl malate 40V, Negative-QTOF	splash10-05g0-9300000000-3d6ee48ac1920653cbf7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dibutyl malate 10V, Positive-QTOF	splash10-0002-1590000000-fd81109b7f6f551a65ff	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dibutyl malate 20V, Positive-QTOF	splash10-0a4i-7900000000-51d32d457ebcdc7bd816	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dibutyl malate 40V, Positive-QTOF	splash10-0a4i-9000000000-41a47cb8f5acc9857984	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dibutyl malate 10V, Negative-QTOF	splash10-0002-1390000000-38750c70f9b901c964df	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dibutyl malate 20V, Negative-QTOF	splash10-0101-9700000000-94e56408b85292bb134f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dibutyl malate 40V, Negative-QTOF	splash10-006w-9200000000-dccfba12038293436f5c	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB008359

KNApSAcK ID

C00054032

Chemspider ID

86081

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

95385

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1827491

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Showing metabocard for Dibutyl malate (HMDB0031696)

MOL for HMDB0031696 (Dibutyl malate)

3D MOL for HMDB0031696 (Dibutyl malate)

3D SDF for HMDB0031696 (Dibutyl malate)

3D-SDF for HMDB0031696 (Dibutyl malate)

PDB for HMDB0031696 (Dibutyl malate)

3D PDB for HMDB0031696 (Dibutyl malate)

SMILES for HMDB0031696 (Dibutyl malate)

INCHI for HMDB0031696 (Dibutyl malate)

Structure for HMDB0031696 (Dibutyl malate)

3D Structure for HMDB0031696 (Dibutyl malate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra