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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 21:38:20 UTC

Update Date

2022-11-23 22:29:20 UTC

HMDB ID

HMDB0259164

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Tributyl Phosphate

Description

tributyl phosphate, also known as TBP or butyl phosphoric acid, belongs to the class of organic compounds known as trialkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly three alkyl chains. Based on a literature review very few articles have been published on tributyl phosphate. This compound has been identified in human blood as reported by (PMID: 31557052 ). Tributyl phosphate is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Tributyl Phosphate 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

HMDB0259164
     RDKit          3D
TRIBUTYL PHOSPHATE
 44 43  0  0  0  0  0  0  0  0999 V2000
   -0.4780    4.6677    0.6872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5278    4.6340   -0.7902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3695    3.5704   -1.3948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9837    2.1772   -1.0605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0226    1.8940    0.2979 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5979    0.3521    0.6951 P   0  0  0  0  0  5  0  0  0  0  0  0
   -0.4438    0.2844    2.2181 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9286   -0.0809    0.0692 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9034    0.5943    0.8176 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2434    0.1900    0.2390 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4635   -1.3051    0.3320 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8425   -1.5671   -0.2837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7033   -0.8191    0.2601 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0186   -1.9961   -0.0324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9696   -3.1064   -0.4369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9517   -3.4149    0.6676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8496   -4.5291    0.1664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4621    4.3739    1.1486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2605    5.7043    1.0511 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2743    4.0184    1.1571 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5274    4.5660   -1.1883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8985    5.6163   -1.1556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3309    3.6842   -2.4984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4278    3.7213   -1.1016 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0844    1.9912   -1.3778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5855    1.4673   -1.6640 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8296    0.3500    1.8891 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7891    1.6806    0.6290 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0604    0.6768    0.8120 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3055    0.4668   -0.8326 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4577   -1.6300    1.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6784   -1.8784   -0.1768 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7159   -1.3425   -1.3792 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1988   -2.5804   -0.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5013   -0.7647    0.1098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4592   -2.3870    0.8651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2502   -1.8656   -0.8213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5716   -2.7984   -1.3230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3663   -4.0184   -0.6236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5992   -2.5641    0.9118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4389   -3.7470    1.5994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2526   -5.2488   -0.4278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6598   -4.0615   -0.4300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3251   -4.9756    1.0569 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
 10 11  1  0
 11 12  1  0
  6 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
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 12 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  0
 17 43  1  0
 17 44  1  0
M  END


  Mrv1572004191602102D          

 17 16  0  0  0  0            999 V2000
    1.9520   -3.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -0.3020    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
    0.8250    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 P   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
  7  4  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  7  1  0  0  0  0
 11  8  1  0  0  0  0
 12  9  1  0  0  0  0
 14 10  1  0  0  0  0
 15 11  1  0  0  0  0
 16 12  1  0  0  0  0
 17 13  2  0  0  0  0
 17 14  1  0  0  0  0
 17 15  1  0  0  0  0
 17 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0259164

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCOP(=O)(OCCCC)OCCCC

> <INCHI_IDENTIFIER>
InChI=1S/C12H27O4P/c1-4-7-10-14-17(13,15-11-8-5-2)16-12-9-6-3/h4-12H2,1-3H3

> <INCHI_KEY>
STCOOQWBFONSKY-UHFFFAOYSA-N

> <FORMULA>
C12H27O4P

> <MOLECULAR_WEIGHT>
266.318

> <EXACT_MASS>
266.164696347

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
30.225853903375224

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
tributyl phosphate

> <ALOGPS_LOGP>
3.65

> <JCHEM_LOGP>
4.085475389333332

> <ALOGPS_LOGS>
-2.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-9.056953586735924

> <JCHEM_POLAR_SURFACE_AREA>
44.760000000000005

> <JCHEM_REFRACTIVITY>
69.71960000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.91e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tributyl phosphate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0259164
     RDKit          3D
TRIBUTYL PHOSPHATE
 44 43  0  0  0  0  0  0  0  0999 V2000
   -0.4780    4.6677    0.6872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5278    4.6340   -0.7902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3695    3.5704   -1.3948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9837    2.1772   -1.0605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0226    1.8940    0.2979 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5979    0.3521    0.6951 P   0  0  0  0  0  5  0  0  0  0  0  0
   -0.4438    0.2844    2.2181 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9286   -0.0809    0.0692 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9034    0.5943    0.8176 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2434    0.1900    0.2390 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4635   -1.3051    0.3320 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8425   -1.5671   -0.2837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7033   -0.8191    0.2601 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0186   -1.9961   -0.0324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9696   -3.1064   -0.4369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9517   -3.4149    0.6676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8496   -4.5291    0.1664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4621    4.3739    1.1486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2605    5.7043    1.0511 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2743    4.0184    1.1571 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5274    4.5660   -1.1883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8985    5.6163   -1.1556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3309    3.6842   -2.4984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4278    3.7213   -1.1016 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0844    1.9912   -1.3778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5855    1.4673   -1.6640 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8296    0.3500    1.8891 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7891    1.6806    0.6290 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0604    0.6768    0.8120 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3055    0.4668   -0.8326 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4577   -1.6300    1.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6784   -1.8784   -0.1768 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7159   -1.3425   -1.3792 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1988   -2.5804   -0.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5013   -0.7647    0.1098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4592   -2.3870    0.8651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2502   -1.8656   -0.8213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5716   -2.7984   -1.3230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3663   -4.0184   -0.6236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5992   -2.5641    0.9118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4389   -3.7470    1.5994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2526   -5.2488   -0.4278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6598   -4.0615   -0.4300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3251   -4.9756    1.0569 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
 10 11  1  0
 11 12  1  0
  6 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
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 12 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  0
 17 43  1  0
 17 44  1  0
M  END

HEADER    PROTEIN                                 19-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-16         0                                  
HETATM    1  C   UNK     0       3.644  -5.898   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.104   7.438   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.127   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.874  -4.565   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.874   6.105   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.127   3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.644  -3.231   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.104   4.771   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.206   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.874  -1.897   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.874   3.437   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.206   0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.207   1.540   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       3.644  -0.564   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       2.104   2.104   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       1.540   0.000   0.000  0.00  0.00           O+0
HETATM   17  P   UNK     0       2.874   0.770   0.000  0.00  0.00           P+0
CONECT    1    4                                                            
CONECT    2    5                                                            
CONECT    3    6                                                            
CONECT    4    1    7                                                       
CONECT    5    2    8                                                       
CONECT    6    3    9                                                       
CONECT    7    4   10                                                       
CONECT    8    5   11                                                       
CONECT    9    6   12                                                       
CONECT   10    7   14                                                       
CONECT   11    8   15                                                       
CONECT   12    9   16                                                       
CONECT   13   17                                                            
CONECT   14   10   17                                                       
CONECT   15   11   17                                                       
CONECT   16   12   17                                                       
CONECT   17   13   14   15   16                                             
MASTER        0    0    0    0    0    0    0    0   17    0   32    0
END

COMPND    HMDB0259164
HETATM    1  C1  UNL     1      -0.478   4.668   0.687  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.528   4.634  -0.790  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.369   3.570  -1.395  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.984   2.177  -1.061  1.00  0.00           C  
HETATM    5  O1  UNL     1      -1.023   1.894   0.298  1.00  0.00           O  
HETATM    6  P1  UNL     1      -0.598   0.352   0.695  1.00  0.00           P  
HETATM    7  O2  UNL     1      -0.444   0.284   2.218  1.00  0.00           O  
HETATM    8  O3  UNL     1       0.929  -0.081   0.069  1.00  0.00           O  
HETATM    9  C5  UNL     1       1.903   0.594   0.818  1.00  0.00           C  
HETATM   10  C6  UNL     1       3.243   0.190   0.239  1.00  0.00           C  
HETATM   11  C7  UNL     1       3.464  -1.305   0.332  1.00  0.00           C  
HETATM   12  C8  UNL     1       4.843  -1.567  -0.284  1.00  0.00           C  
HETATM   13  O4  UNL     1      -1.703  -0.819   0.260  1.00  0.00           O  
HETATM   14  C9  UNL     1      -1.019  -1.996  -0.032  1.00  0.00           C  
HETATM   15  C10 UNL     1      -1.970  -3.106  -0.437  1.00  0.00           C  
HETATM   16  C11 UNL     1      -2.952  -3.415   0.668  1.00  0.00           C  
HETATM   17  C12 UNL     1      -3.850  -4.529   0.166  1.00  0.00           C  
HETATM   18  H1  UNL     1      -1.462   4.374   1.149  1.00  0.00           H  
HETATM   19  H2  UNL     1      -0.261   5.704   1.051  1.00  0.00           H  
HETATM   20  H3  UNL     1       0.274   4.018   1.157  1.00  0.00           H  
HETATM   21  H4  UNL     1       0.527   4.566  -1.188  1.00  0.00           H  
HETATM   22  H5  UNL     1      -0.899   5.616  -1.156  1.00  0.00           H  
HETATM   23  H6  UNL     1      -1.331   3.684  -2.498  1.00  0.00           H  
HETATM   24  H7  UNL     1      -2.428   3.721  -1.102  1.00  0.00           H  
HETATM   25  H8  UNL     1       0.084   1.991  -1.378  1.00  0.00           H  
HETATM   26  H9  UNL     1      -1.585   1.467  -1.664  1.00  0.00           H  
HETATM   27  H10 UNL     1       1.830   0.350   1.889  1.00  0.00           H  
HETATM   28  H11 UNL     1       1.789   1.681   0.629  1.00  0.00           H  
HETATM   29  H12 UNL     1       4.060   0.677   0.812  1.00  0.00           H  
HETATM   30  H13 UNL     1       3.306   0.467  -0.833  1.00  0.00           H  
HETATM   31  H14 UNL     1       3.458  -1.630   1.409  1.00  0.00           H  
HETATM   32  H15 UNL     1       2.678  -1.878  -0.177  1.00  0.00           H  
HETATM   33  H16 UNL     1       4.716  -1.342  -1.379  1.00  0.00           H  
HETATM   34  H17 UNL     1       5.199  -2.580  -0.091  1.00  0.00           H  
HETATM   35  H18 UNL     1       5.501  -0.765   0.110  1.00  0.00           H  
HETATM   36  H19 UNL     1      -0.459  -2.387   0.865  1.00  0.00           H  
HETATM   37  H20 UNL     1      -0.250  -1.866  -0.821  1.00  0.00           H  
HETATM   38  H21 UNL     1      -2.572  -2.798  -1.323  1.00  0.00           H  
HETATM   39  H22 UNL     1      -1.366  -4.018  -0.624  1.00  0.00           H  
HETATM   40  H23 UNL     1      -3.599  -2.564   0.912  1.00  0.00           H  
HETATM   41  H24 UNL     1      -2.439  -3.747   1.599  1.00  0.00           H  
HETATM   42  H25 UNL     1      -3.253  -5.249  -0.428  1.00  0.00           H  
HETATM   43  H26 UNL     1      -4.660  -4.062  -0.430  1.00  0.00           H  
HETATM   44  H27 UNL     1      -4.325  -4.976   1.057  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   13
CONECT    8    9
CONECT    9   10   27   28
CONECT   10   11   29   30
CONECT   11   12   31   32
CONECT   12   33   34   35
CONECT   13   14
CONECT   14   15   36   37
CONECT   15   16   38   39
CONECT   16   17   40   41
CONECT   17   42   43   44
END

HMDB0259164
     RDKit          3D
TRIBUTYL PHOSPHATE
 44 43  0  0  0  0  0  0  0  0999 V2000
   -0.4780    4.6677    0.6872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5278    4.6340   -0.7902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3695    3.5704   -1.3948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9837    2.1772   -1.0605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0226    1.8940    0.2979 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5979    0.3521    0.6951 P   0  0  0  0  0  5  0  0  0  0  0  0
   -0.4438    0.2844    2.2181 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9286   -0.0809    0.0692 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9034    0.5943    0.8176 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2434    0.1900    0.2390 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4635   -1.3051    0.3320 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8425   -1.5671   -0.2837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7033   -0.8191    0.2601 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0186   -1.9961   -0.0324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9696   -3.1064   -0.4369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9517   -3.4149    0.6676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8496   -4.5291    0.1664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4621    4.3739    1.1486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2605    5.7043    1.0511 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2743    4.0184    1.1571 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5274    4.5660   -1.1883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8985    5.6163   -1.1556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3309    3.6842   -2.4984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4278    3.7213   -1.1016 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0844    1.9912   -1.3778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5855    1.4673   -1.6640 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8296    0.3500    1.8891 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7891    1.6806    0.6290 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0604    0.6768    0.8120 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3055    0.4668   -0.8326 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4577   -1.6300    1.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6784   -1.8784   -0.1768 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7159   -1.3425   -1.3792 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1988   -2.5804   -0.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5013   -0.7647    0.1098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4592   -2.3870    0.8651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2502   -1.8656   -0.8213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5716   -2.7984   -1.3230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3663   -4.0184   -0.6236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5992   -2.5641    0.9118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4389   -3.7470    1.5994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2526   -5.2488   -0.4278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6598   -4.0615   -0.4300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3251   -4.9756    1.0569 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
 10 11  1  0
 11 12  1  0
  6 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
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 12 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  0
 17 43  1  0
 17 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Butyl phosphate	ChEBI
Phosphoric acid tri-N-butyl ester	ChEBI
Phosphoric acid, tributyl ester	ChEBI
TBP	ChEBI
Tri-N-butyl phosphate	ChEBI
Tributyle (phosphate de)	ChEBI
Tributylphosphat	ChEBI
Tributylphosphate	ChEBI
Butyl phosphoric acid	Generator
Phosphate tri-N-butyl ester	Generator
Phosphate, tributyl ester	Generator
Tri-N-butyl phosphoric acid	Generator
Tributyle (phosphoric acid de)	Generator
Tributylphosphoric acid	Generator
Tributyl phosphoric acid	Generator
Tri-N-butylphosphate	MeSH
Tri-(N-butyl )-phosphate	MeSH

Chemical Formula

C₁₂H₂₇O₄P

Average Molecular Weight

266.318

Monoisotopic Molecular Weight

266.164696347

IUPAC Name

tributyl phosphate

Traditional Name

tributyl phosphate

CAS Registry Number

Not Available

SMILES

CCCCOP(=O)(OCCCC)OCCCC

InChI Identifier

InChI=1S/C12H27O4P/c1-4-7-10-14-17(13,15-11-8-5-2)16-12-9-6-3/h4-12H2,1-3H3

InChI Key

STCOOQWBFONSKY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as trialkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly three alkyl chains.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic phosphoric acids and derivatives

Sub Class

Phosphate esters

Direct Parent

Trialkyl phosphates

Alternative Parents

Substituents

Trialkyl phosphate
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

trialkyl phosphate (CHEBI:35019 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	3.65	ALOGPS
logP	4.09	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Basic)	-9.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	44.76 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	69.72 m³·mol⁻¹	ChemAxon
Polarizability	30.23 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]+	162.51	30932474
DeepCCS	[M-H]-	160.03	30932474
DeepCCS	[M-2H]-	195.097	30932474
DeepCCS	[M+Na]+	170.429	30932474
AllCCS	[M+H]+	168.8	32859911
AllCCS	[M+H-H2O]+	165.8	32859911
AllCCS	[M+NH4]+	171.5	32859911
AllCCS	[M+Na]+	172.3	32859911
AllCCS	[M-H]-	162.2	32859911
AllCCS	[M+Na-2H]-	163.5	32859911
AllCCS	[M+HCOO]-	165.0	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.	8.64 minutes	32390414
Predicted by Siyang on May 30, 2022	18.5077 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.27 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2732.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	549.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	208.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	297.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	435.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	991.4 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	843.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	81.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1580.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	562.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1712.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	617.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	422.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	323.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	407.4 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	7.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
TRIBUTYL PHOSPHATE	CCCCOP(=O)(OCCCC)OCCCC	2118.6	Standard polar	33892256
TRIBUTYL PHOSPHATE	CCCCOP(=O)(OCCCC)OCCCC	1635.9	Standard non polar	33892256
TRIBUTYL PHOSPHATE	CCCCOP(=O)(OCCCC)OCCCC	1649.1	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 - Tributyl Phosphate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-8790000000-831440b51604430b1a7c	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tributyl Phosphate 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 - Tributyl Phosphate 10V, Positive-QTOF	splash10-0aor-9080000000-49ef595a896037bc6cc7	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tributyl Phosphate 20V, Positive-QTOF	splash10-0a4i-9000000000-f0a399edfbcd80d58978	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tributyl Phosphate 40V, Positive-QTOF	splash10-0a4i-9000000000-b8fac79a00c57f9a5f7d	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tributyl Phosphate 10V, Negative-QTOF	splash10-014i-0290000000-dcd0fcf3e61a9e9adc6b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tributyl Phosphate 20V, Negative-QTOF	splash10-0a4i-1890000000-4b27f7db1013bac5f4dd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tributyl Phosphate 40V, Negative-QTOF	splash10-0udi-0900000000-c9688697e51b91c39262	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

29090

KEGG Compound ID

C14439

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Tributyl_phosphate

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

35019

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1291841

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 Tributyl Phosphate (HMDB0259164)

MOL for HMDB0259164 (Tributyl Phosphate)

3D MOL for HMDB0259164 (Tributyl Phosphate)

3D SDF for HMDB0259164 (Tributyl Phosphate)

3D-SDF for HMDB0259164 (Tributyl Phosphate)

PDB for HMDB0259164 (Tributyl Phosphate)

3D PDB for HMDB0259164 (Tributyl Phosphate)

SMILES for HMDB0259164 (Tributyl Phosphate)

INCHI for HMDB0259164 (Tributyl Phosphate)

Structure for HMDB0259164 (Tributyl Phosphate)

3D Structure for HMDB0259164 (Tributyl Phosphate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra