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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:04:02 UTC

Update Date

2022-03-07 02:54:02 UTC

HMDB ID

HMDB0034263

Secondary Accession Numbers

HMDB34263

Metabolite Identification

Common Name

Triethyl citrate

Description

Triethyl citrate belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. Triethyl citrate is a mild, fruity, and odorless tasting compound. Based on a literature review a significant number of articles have been published on Triethyl citrate.

Structure

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

HMDB0034263
     RDKit          3D
Triethyl citrate
 39 38  0  0  0  0  0  0  0  0999 V2000
    4.6227   -2.3660    0.5977 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7893   -1.3739   -0.4995 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8798   -0.3004   -0.4532 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5148   -0.5341   -0.5254 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1458   -1.7300   -0.6316 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6001    0.6190   -0.4733 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1559    0.2706   -0.5607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0812   -0.3868   -1.7714 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3292   -0.5466    0.6144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7739   -0.8590    0.4700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5975    0.0338    0.7930 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2636   -2.0613    0.0062 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6544   -2.2721   -0.0998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3910   -2.1533    1.1930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6227    1.5366   -0.5770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3346    1.8539   -1.5634 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5993    2.4210    0.4915 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3284    3.6264    0.5033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9197    4.5542   -0.6413 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5757   -2.5207    1.1799 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3772   -3.3871    0.2048 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8518   -2.0832    1.3527 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8194   -0.9402   -0.4323 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7550   -1.9183   -1.4664 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8304    1.2849   -1.3497 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7621    1.2597    0.4379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0194   -1.3780   -1.6792 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2297   -1.4792    0.7631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2007    0.0605    1.5358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0931   -1.5280   -0.8105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8620   -3.2821   -0.5284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8346   -1.1315    1.2924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8085   -2.4524    2.0794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2817   -2.8465    1.1706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1087    4.1524    1.4554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4307    3.4396    0.4705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3407    5.5566   -0.3844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2325    4.1885   -1.6179 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1986    4.6732   -0.5464 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
  7 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  6 25  1  0
  6 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
 18 35  1  0
 18 36  1  0
 19 37  1  0
 19 38  1  0
 19 39  1  0
M  END


  Mrv1652305271900312D          

 19 18  0  0  0  0            999 V2000
    0.8250    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3184    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    0.4125    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  3  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 12  7  1  0  0  0  0
 12  8  1  0  0  0  0
 12 11  1  0  0  0  0
 13  9  2  0  0  0  0
 14 10  2  0  0  0  0
 15 11  2  0  0  0  0
 16 12  1  0  0  0  0
 17  4  1  0  0  0  0
 17  9  1  0  0  0  0
 18  5  1  0  0  0  0
 18 10  1  0  0  0  0
 19  6  1  0  0  0  0
 19 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034263

> <DATABASE_NAME>
hmdb

> <SMILES>
CCOC(=O)CC(O)(CC(=O)OCC)C(=O)OCC

> <INCHI_IDENTIFIER>
InChI=1S/C12H20O7/c1-4-17-9(13)7-12(16,11(15)19-6-3)8-10(14)18-5-2/h16H,4-8H2,1-3H3

> <INCHI_KEY>
DOOTYTYQINUNNV-UHFFFAOYSA-N

> <FORMULA>
C12H20O7

> <MOLECULAR_WEIGHT>
276.283

> <EXACT_MASS>
276.120902994

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
27.830255089552697

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,2,3-triethyl 2-hydroxypropane-1,2,3-tricarboxylate

> <ALOGPS_LOGP>
1.17

> <JCHEM_LOGP>
0.18541857999999972

> <ALOGPS_LOGS>
-1.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.68953824530732

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.818970937517243

> <JCHEM_PKA_STRONGEST_BASIC>
-4.190181588347824

> <JCHEM_POLAR_SURFACE_AREA>
99.13000000000001

> <JCHEM_REFRACTIVITY>
64.177

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.07e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
triethyl citrate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034263
     RDKit          3D
Triethyl citrate
 39 38  0  0  0  0  0  0  0  0999 V2000
    4.6227   -2.3660    0.5977 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7893   -1.3739   -0.4995 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8798   -0.3004   -0.4532 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5148   -0.5341   -0.5254 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1458   -1.7300   -0.6316 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6001    0.6190   -0.4733 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1559    0.2706   -0.5607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0812   -0.3868   -1.7714 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3292   -0.5466    0.6144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7739   -0.8590    0.4700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5975    0.0338    0.7930 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2636   -2.0613    0.0062 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6544   -2.2721   -0.0998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3910   -2.1533    1.1930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6227    1.5366   -0.5770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3346    1.8539   -1.5634 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5993    2.4210    0.4915 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3284    3.6264    0.5033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9197    4.5542   -0.6413 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5757   -2.5207    1.1799 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3772   -3.3871    0.2048 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8518   -2.0832    1.3527 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8194   -0.9402   -0.4323 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7550   -1.9183   -1.4664 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8304    1.2849   -1.3497 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7621    1.2597    0.4379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0194   -1.3780   -1.6792 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2297   -1.4792    0.7631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2007    0.0605    1.5358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0931   -1.5280   -0.8105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8620   -3.2821   -0.5284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8346   -1.1315    1.2924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8085   -2.4524    2.0794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2817   -2.8465    1.1706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1087    4.1524    1.4554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4307    3.4396    0.4705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3407    5.5566   -0.3844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2325    4.1885   -1.6179 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1986    4.6732   -0.5464 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
  7 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  6 25  1  0
  6 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
 18 35  1  0
 18 36  1  0
 19 37  1  0
 19 38  1  0
 19 39  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0       1.540   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.264   2.104   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.461   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.874   5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.127   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.207   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.644  -0.564   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.207   3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.541   3.850   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       5.954  -1.897   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       1.540  -1.540   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       2.104   2.104   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.874   3.850   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       5.954   0.770   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.206   0.770   0.000  0.00  0.00           O+0
CONECT    1    4                                                            
CONECT    2    5                                                            
CONECT    3    6                                                            
CONECT    4    1   17                                                       
CONECT    5    2   18                                                       
CONECT    6    3   19                                                       
CONECT    7    9   12                                                       
CONECT    8   10   12                                                       
CONECT    9    7   13   17                                                  
CONECT   10    8   14   18                                                  
CONECT   11   12   15   19                                                  
CONECT   12    7    8   11   16                                             
CONECT   13    9                                                            
CONECT   14   10                                                            
CONECT   15   11                                                            
CONECT   16   12                                                            
CONECT   17    4    9                                                       
CONECT   18    5   10                                                       
CONECT   19    6   11                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   36    0
END

COMPND    HMDB0034263
HETATM    1  C1  UNL     1       4.623  -2.366   0.598  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.789  -1.374  -0.499  1.00  0.00           C  
HETATM    3  O1  UNL     1       3.880  -0.300  -0.453  1.00  0.00           O  
HETATM    4  C3  UNL     1       2.515  -0.534  -0.525  1.00  0.00           C  
HETATM    5  O2  UNL     1       2.146  -1.730  -0.632  1.00  0.00           O  
HETATM    6  C4  UNL     1       1.600   0.619  -0.473  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.156   0.271  -0.561  1.00  0.00           C  
HETATM    8  O3  UNL     1      -0.081  -0.387  -1.771  1.00  0.00           O  
HETATM    9  C6  UNL     1      -0.329  -0.547   0.614  1.00  0.00           C  
HETATM   10  C7  UNL     1      -1.774  -0.859   0.470  1.00  0.00           C  
HETATM   11  O4  UNL     1      -2.597   0.034   0.793  1.00  0.00           O  
HETATM   12  O5  UNL     1      -2.264  -2.061   0.006  1.00  0.00           O  
HETATM   13  C8  UNL     1      -3.654  -2.272  -0.100  1.00  0.00           C  
HETATM   14  C9  UNL     1      -4.391  -2.153   1.193  1.00  0.00           C  
HETATM   15  C10 UNL     1      -0.623   1.537  -0.577  1.00  0.00           C  
HETATM   16  O6  UNL     1      -1.335   1.854  -1.563  1.00  0.00           O  
HETATM   17  O7  UNL     1      -0.599   2.421   0.491  1.00  0.00           O  
HETATM   18  C11 UNL     1      -1.328   3.626   0.503  1.00  0.00           C  
HETATM   19  C12 UNL     1      -0.920   4.554  -0.641  1.00  0.00           C  
HETATM   20  H1  UNL     1       5.576  -2.521   1.180  1.00  0.00           H  
HETATM   21  H2  UNL     1       4.377  -3.387   0.205  1.00  0.00           H  
HETATM   22  H3  UNL     1       3.852  -2.083   1.353  1.00  0.00           H  
HETATM   23  H4  UNL     1       5.819  -0.940  -0.432  1.00  0.00           H  
HETATM   24  H5  UNL     1       4.755  -1.918  -1.466  1.00  0.00           H  
HETATM   25  H6  UNL     1       1.830   1.285  -1.350  1.00  0.00           H  
HETATM   26  H7  UNL     1       1.762   1.260   0.438  1.00  0.00           H  
HETATM   27  H8  UNL     1      -0.019  -1.378  -1.679  1.00  0.00           H  
HETATM   28  H9  UNL     1       0.230  -1.479   0.763  1.00  0.00           H  
HETATM   29  H10 UNL     1      -0.201   0.061   1.536  1.00  0.00           H  
HETATM   30  H11 UNL     1      -4.093  -1.528  -0.810  1.00  0.00           H  
HETATM   31  H12 UNL     1      -3.862  -3.282  -0.528  1.00  0.00           H  
HETATM   32  H13 UNL     1      -4.835  -1.132   1.292  1.00  0.00           H  
HETATM   33  H14 UNL     1      -3.809  -2.452   2.079  1.00  0.00           H  
HETATM   34  H15 UNL     1      -5.282  -2.846   1.171  1.00  0.00           H  
HETATM   35  H16 UNL     1      -1.109   4.152   1.455  1.00  0.00           H  
HETATM   36  H17 UNL     1      -2.431   3.440   0.470  1.00  0.00           H  
HETATM   37  H18 UNL     1      -1.341   5.557  -0.384  1.00  0.00           H  
HETATM   38  H19 UNL     1      -1.233   4.188  -1.618  1.00  0.00           H  
HETATM   39  H20 UNL     1       0.199   4.673  -0.546  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3   23   24
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7   25   26
CONECT    7    8    9   15
CONECT    8   27
CONECT    9   10   28   29
CONECT   10   11   11   12
CONECT   12   13
CONECT   13   14   30   31
CONECT   14   32   33   34
CONECT   15   16   16   17
CONECT   17   18
CONECT   18   19   35   36
CONECT   19   37   38   39
END

HMDB0034263
     RDKit          3D
Triethyl citrate
 39 38  0  0  0  0  0  0  0  0999 V2000
    4.6227   -2.3660    0.5977 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7893   -1.3739   -0.4995 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8798   -0.3004   -0.4532 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5148   -0.5341   -0.5254 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1458   -1.7300   -0.6316 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6001    0.6190   -0.4733 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1559    0.2706   -0.5607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0812   -0.3868   -1.7714 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3292   -0.5466    0.6144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7739   -0.8590    0.4700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5975    0.0338    0.7930 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2636   -2.0613    0.0062 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6544   -2.2721   -0.0998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3910   -2.1533    1.1930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6227    1.5366   -0.5770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3346    1.8539   -1.5634 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5993    2.4210    0.4915 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3284    3.6264    0.5033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9197    4.5542   -0.6413 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5757   -2.5207    1.1799 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3772   -3.3871    0.2048 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8518   -2.0832    1.3527 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8194   -0.9402   -0.4323 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7550   -1.9183   -1.4664 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8304    1.2849   -1.3497 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7621    1.2597    0.4379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0194   -1.3780   -1.6792 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2297   -1.4792    0.7631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2007    0.0605    1.5358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0931   -1.5280   -0.8105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8620   -3.2821   -0.5284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8346   -1.1315    1.2924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8085   -2.4524    2.0794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2817   -2.8465    1.1706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1087    4.1524    1.4554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4307    3.4396    0.4705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3407    5.5566   -0.3844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2325    4.1885   -1.6179 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1986    4.6732   -0.5464 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
  7 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  6 25  1  0
  6 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
 18 35  1  0
 18 36  1  0
 19 37  1  0
 19 38  1  0
 19 39  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Triethyl citric acid	Generator
e1505	ChEMBL, HMDB
1,2,3-Propanetricarboxylic acid, 2-hydroxy-, triethyl ester	HMDB
2-Hydroxy-1,2,3-propanetricarboxylic acid, triethyl ester	HMDB
Citric acid, triethyl ester	HMDB
Citroflex 2	HMDB
Crodamol TC	HMDB
Ethyl citrate	HMDB, MeSH
Ethyl citrate, citric acid triethyl ester	HMDB
Eudraflex	HMDB
FEMA 3083	HMDB
Hydagen c.a.t	HMDB
Hydragen cat	HMDB
TEC	HMDB
Triaethylcitrat	HMDB
Triethyl 2-hydroxy-1,2,3-propanetricarboxylate	HMDB
Triethyl citrate (NF)	HMDB
Triethylester kyseliny citronove	HMDB
Uniflex tec	HMDB
Uniplex 80	HMDB

Chemical Formula

C₁₂H₂₀O₇

Average Molecular Weight

276.283

Monoisotopic Molecular Weight

276.120902994

IUPAC Name

1,2,3-triethyl 2-hydroxypropane-1,2,3-tricarboxylate

Traditional Name

triethyl citrate

CAS Registry Number

77-93-0

SMILES

CCOC(=O)CC(O)(CC(=O)OCC)C(=O)OCC

InChI Identifier

InChI=1S/C12H20O7/c1-4-17-9(13)7-12(16,11(15)19-6-3)8-10(14)18-5-2/h16H,4-8H2,1-3H3

InChI Key

DOOTYTYQINUNNV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tricarboxylic acids and derivatives

Direct Parent

Tricarboxylic acids and derivatives

Alternative Parents

Substituents

Tricarboxylic acid or derivatives
Fatty acid ester
Fatty acyl
Tertiary alcohol
Carboxylic acid ester
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

Cellular substructure

Extracellular (HMDB: HMDB0034263)
Cytoplasm (HMDB: HMDB0034263)

Source

Exogenous

Food

Food (HMDB: HMDB0034263)

Not Available

Nutrient (HMDB: HMDB0034263)

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring agent (HMDB: HMDB0034263)

Manufacturing industry

Laboratory chemical

Laboratory chemical (HMDB: HMDB0034263)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	< 25 °C	Not Available
Boiling Point	127.00 °C. @ 1.00 mm Hg	The Good Scents Company Information System
Water Solubility	65 mg/mL	Not Available
LogP	1.267 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	10.7 g/L	ALOGPS
logP	1.17	ALOGPS
logP	0.19	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	11.82	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	99.13 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	64.18 m³·mol⁻¹	ChemAxon
Polarizability	27.83 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]+	165.666	31661259
DarkChem	[M-H]-	161.787	31661259
DeepCCS	[M+H]+	160.089	30932474
DeepCCS	[M-H]-	157.731	30932474
DeepCCS	[M-2H]-	190.823	30932474
DeepCCS	[M+Na]+	166.182	30932474
AllCCS	[M+H]+	164.9	32859911
AllCCS	[M+H-H2O]+	161.8	32859911
AllCCS	[M+NH4]+	167.8	32859911
AllCCS	[M+Na]+	168.6	32859911
AllCCS	[M-H]-	163.5	32859911
AllCCS	[M+Na-2H]-	164.3	32859911
AllCCS	[M+HCOO]-	165.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Triethyl citrate	CCOC(=O)CC(O)(CC(=O)OCC)C(=O)OCC	2955.4	Standard polar	33892256
Triethyl citrate	CCOC(=O)CC(O)(CC(=O)OCC)C(=O)OCC	1542.4	Standard non polar	33892256
Triethyl citrate	CCOC(=O)CC(O)(CC(=O)OCC)C(=O)OCC	1779.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Triethyl citrate,1TMS,isomer #1	CCOC(=O)CC(CC(=O)OCC)(O[Si](C)(C)C)C(=O)OCC	1786.1	Semi standard non polar	33892256
Triethyl citrate,1TBDMS,isomer #1	CCOC(=O)CC(CC(=O)OCC)(O[Si](C)(C)C(C)(C)C)C(=O)OCC	2006.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Triethyl citrate EI-B (Non-derivatized)	splash10-0a4i-1920000000-f7c884b67f54e12797d9	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Triethyl citrate EI-B (Non-derivatized)	splash10-0a4i-0910000000-9ead4713599bcc551b12	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Triethyl citrate CI-B (Non-derivatized)	splash10-004i-0190000000-7b8558c43641df82df60	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Triethyl citrate EI-B (Non-derivatized)	splash10-0a4i-1920000000-f7c884b67f54e12797d9	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Triethyl citrate EI-B (Non-derivatized)	splash10-0a4i-0910000000-9ead4713599bcc551b12	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Triethyl citrate CI-B (Non-derivatized)	splash10-004i-0190000000-7b8558c43641df82df60	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Triethyl citrate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ufr-5890000000-e53cab1b65097a22eedf	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Triethyl citrate GC-MS (1 TMS) - 70eV, Positive	splash10-004i-5092000000-6e3fc95af9f04950f62f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Triethyl citrate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a6r-7910000000-e1114c0c65a16dd49eeb	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 - Triethyl citrate LC-ESI-ITFT , positive-QTOF	splash10-05o9-0900000000-abe5dcdf0bae8dc9ed54	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Triethyl citrate LC-ESI-ITFT , positive-QTOF	splash10-03dr-1900000000-9aa32164a05037b21622	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Triethyl citrate LC-ESI-ITFT , positive-QTOF	splash10-0zfr-0790000000-eaf06e927ea1ee1440b8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Triethyl citrate LC-ESI-ITFT , positive-QTOF	splash10-0zfr-0890000000-babd242488f267e29817	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Triethyl citrate LC-ESI-QFT , positive-QTOF	splash10-0a4i-0900000000-550d7ef825027f130a1e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Triethyl citrate 35V, Positive-QTOF	splash10-0a4i-0900000000-bcaf65f04f030fc362db	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Triethyl citrate 30V, Positive-QTOF	splash10-0a4i-0900000000-09a16a64d8b6a8409c0d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Triethyl citrate 40V, Positive-QTOF	splash10-052r-0900000000-f5da78fc91309994cf25	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Triethyl citrate 20V, Positive-QTOF	splash10-0a4i-0900000000-fed064182d82b13afe81	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Triethyl citrate 10V, Positive-QTOF	splash10-0pb9-0960000000-ecc9db61ae907f31c6d8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Triethyl citrate 50V, Positive-QTOF	splash10-000i-0900000000-595e183f161fb191ea18	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Triethyl citrate 10V, Positive-QTOF	splash10-004r-0790000000-8052cd9aa829d3b3770a	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Triethyl citrate 20V, Positive-QTOF	splash10-000i-9610000000-9ac2305d61fe7cc529e8	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Triethyl citrate 40V, Positive-QTOF	splash10-069a-3910000000-5dd15a26bff8e43df3ef	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Triethyl citrate 10V, Negative-QTOF	splash10-004r-1960000000-62c3e6b4cc939bf1a284	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Triethyl citrate 20V, Negative-QTOF	splash10-002u-6950000000-29afe05fe47ce4f75024	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Triethyl citrate 40V, Negative-QTOF	splash10-0a6s-8910000000-6dde72620e6bfe59a9e2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Triethyl citrate 10V, Positive-QTOF	splash10-004i-0090000000-f2deb2e421d123b4795f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Triethyl citrate 20V, Positive-QTOF	splash10-0a59-2390000000-8b8d674209f59fa49d88	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Triethyl citrate 40V, Positive-QTOF	splash10-0005-9400000000-aa1936e1a6ab993057a4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Triethyl citrate 10V, Negative-QTOF	splash10-002r-5590000000-470583cc7469f45edd1a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Triethyl citrate 20V, Negative-QTOF	splash10-002r-0930000000-90a982ba5053949631d1	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Triethyl citrate 40V, Negative-QTOF	splash10-0a59-5900000000-a44b708dde613f909556	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	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

FDB012587

KNApSAcK ID

Not Available

Chemspider ID

13850879

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Triethyl citrate

METLIN ID

Not Available

PubChem Compound

6506

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1012772

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 Triethyl citrate (HMDB0034263)

MOL for HMDB0034263 (Triethyl citrate)

3D MOL for HMDB0034263 (Triethyl citrate)

3D SDF for HMDB0034263 (Triethyl citrate)

3D-SDF for HMDB0034263 (Triethyl citrate)

PDB for HMDB0034263 (Triethyl citrate)

3D PDB for HMDB0034263 (Triethyl citrate)

SMILES for HMDB0034263 (Triethyl citrate)

INCHI for HMDB0034263 (Triethyl citrate)

Structure for HMDB0034263 (Triethyl citrate)

3D Structure for HMDB0034263 (Triethyl citrate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra