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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 21:35:52 UTC

Update Date

2022-11-23 22:29:20 UTC

HMDB ID

HMDB0259135

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Tri-O-cresyl phosphate

Description

tris(2-methylphenyl) phosphate belongs to the class of organic compounds known as aryl phosphotriesters. These are aryl phosphates in which the phosphate is esterified at exactly three positions. Based on a literature review very few articles have been published on tris(2-methylphenyl) phosphate. This compound has been identified in human blood as reported by (PMID: 31557052 ). Tri-o-cresyl phosphate is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Tri-O-cresyl 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


  Mrv1572004221603512D          

 26 28  0  0  0  0            999 V2000
    2.3645    1.4586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    3.9336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414    3.4105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934   -0.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    5.5836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1914    1.9816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    0.2211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    5.1711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6039    1.2671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    0.2211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    5.1711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6039    2.6961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    1.0461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    4.3461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.2671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    1.0461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    4.3461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.6961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    1.4586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    3.9336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414    1.9816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914    3.4105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    2.2836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    3.1086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    1.9816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    2.6961    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
  7  4  2  0  0  0  0
  8  5  2  0  0  0  0
  9  6  2  0  0  0  0
 10  4  1  0  0  0  0
 11  5  1  0  0  0  0
 12  6  1  0  0  0  0
 13  7  1  0  0  0  0
 14  8  1  0  0  0  0
 15  9  1  0  0  0  0
 16  1  1  0  0  0  0
 16 10  2  0  0  0  0
 17  2  1  0  0  0  0
 17 11  2  0  0  0  0
 18  3  1  0  0  0  0
 18 12  2  0  0  0  0
 19 13  2  0  0  0  0
 19 16  1  0  0  0  0
 20 14  2  0  0  0  0
 20 17  1  0  0  0  0
 21 15  2  0  0  0  0
 21 18  1  0  0  0  0
 23 19  1  0  0  0  0
 24 20  1  0  0  0  0
 25 21  1  0  0  0  0
 26 22  2  0  0  0  0
 26 23  1  0  0  0  0
 26 24  1  0  0  0  0
 26 25  1  0  0  0  0
M  END

HMDB0259135
     RDKit          3D
TRI-O-CRESYL PHOSPHATE
 47 49  0  0  0  0  0  0  0  0999 V2000
    2.8609    3.1709    0.0870 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4034    1.7787    0.1388 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7411    1.6060    0.5007 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2043    0.3130    0.5374 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3946   -0.7611    0.2337 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0930   -0.5632   -0.1163 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5838    0.7117   -0.1672 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2776    0.9944   -0.5125 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1271   -0.2019   -0.9204 P   0  0  0  0  0  5  0  0  0  0  0  0
    0.8194   -1.0176   -2.0467 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1985    0.5121   -1.6052 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0578    1.4962   -1.3817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0531    1.6702   -2.3671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0217    2.6244   -2.3156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0129    3.4650   -1.2226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0583    3.3185   -0.2512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0702    2.3424   -0.3070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0791    2.2703    0.8061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2225   -1.2451    0.3859 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7315   -2.5027    0.2663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0465   -3.1372   -0.9108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5608   -4.4183   -0.9544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7790   -5.1173    0.2187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4702   -4.5018    1.4220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9567   -3.2186    1.4337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6375   -2.5927    2.7555 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4128    3.4748    1.0601 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1071    3.1802   -0.7317 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6668    3.8711   -0.2231 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3714    2.4600    0.7385 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2398    0.1742    0.8173 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8098   -1.7729    0.2772 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4153   -1.3737   -0.3642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0807    1.0135   -3.2462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7876    2.7468   -3.0887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7666    4.2482   -1.1304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0566    3.9925    0.6186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8792    1.2367    1.1229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5965    2.7249    1.7150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2063    2.9157    0.6592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8822   -2.6047   -1.8377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7803   -4.8395   -1.9325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1845   -6.1258    0.1717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6409   -5.0513    2.3578 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4599   -2.5480    2.9295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0859   -1.5618    2.8043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0845   -3.1573    3.5753 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
  9 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
  7  2  1  0
 17 12  1  0
 25 20  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  4 31  1  0
  5 32  1  0
  6 33  1  0
 13 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
 18 38  1  0
 18 39  1  0
 18 40  1  0
 21 41  1  0
 22 42  1  0
 23 43  1  0
 24 44  1  0
 26 45  1  0
 26 46  1  0
 26 47  1  0
M  END


  Mrv1572004221603512D          

 26 28  0  0  0  0            999 V2000
    2.3645    1.4586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    3.9336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414    3.4105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934   -0.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    5.5836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1914    1.9816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    0.2211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    5.1711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6039    1.2671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    0.2211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    5.1711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6039    2.6961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    1.0461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    4.3461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.2671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    1.0461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    4.3461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.6961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    1.4586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    3.9336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414    1.9816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914    3.4105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    2.2836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    3.1086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    1.9816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    2.6961    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
  7  4  2  0  0  0  0
  8  5  2  0  0  0  0
  9  6  2  0  0  0  0
 10  4  1  0  0  0  0
 11  5  1  0  0  0  0
 12  6  1  0  0  0  0
 13  7  1  0  0  0  0
 14  8  1  0  0  0  0
 15  9  1  0  0  0  0
 16  1  1  0  0  0  0
 16 10  2  0  0  0  0
 17  2  1  0  0  0  0
 17 11  2  0  0  0  0
 18  3  1  0  0  0  0
 18 12  2  0  0  0  0
 19 13  2  0  0  0  0
 19 16  1  0  0  0  0
 20 14  2  0  0  0  0
 20 17  1  0  0  0  0
 21 15  2  0  0  0  0
 21 18  1  0  0  0  0
 23 19  1  0  0  0  0
 24 20  1  0  0  0  0
 25 21  1  0  0  0  0
 26 22  2  0  0  0  0
 26 23  1  0  0  0  0
 26 24  1  0  0  0  0
 26 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0259135

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC=CC=C1OP(=O)(OC1=CC=CC=C1C)OC1=CC=CC=C1C

> <INCHI_IDENTIFIER>
InChI=1S/C21H21O4P/c1-16-10-4-7-13-19(16)23-26(22,24-20-14-8-5-11-17(20)2)25-21-15-9-6-12-18(21)3/h4-15H,1-3H3

> <INCHI_KEY>
YSMRWXYRXBRSND-UHFFFAOYSA-N

> <FORMULA>
C21H21O4P

> <MOLECULAR_WEIGHT>
368.369

> <EXACT_MASS>
368.117746154

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
37.18888970645672

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
tris(2-methylphenyl) phosphate

> <ALOGPS_LOGP>
4.80

> <JCHEM_LOGP>
6.627917859333333

> <ALOGPS_LOGS>
-5.33

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-9.397251644461484

> <JCHEM_POLAR_SURFACE_AREA>
44.760000000000005

> <JCHEM_REFRACTIVITY>
102.55519999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.74e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tricresyl phosphate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0259135
     RDKit          3D
TRI-O-CRESYL PHOSPHATE
 47 49  0  0  0  0  0  0  0  0999 V2000
    2.8609    3.1709    0.0870 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4034    1.7787    0.1388 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7411    1.6060    0.5007 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2043    0.3130    0.5374 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3946   -0.7611    0.2337 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0930   -0.5632   -0.1163 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5838    0.7117   -0.1672 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2776    0.9944   -0.5125 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1271   -0.2019   -0.9204 P   0  0  0  0  0  5  0  0  0  0  0  0
    0.8194   -1.0176   -2.0467 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1985    0.5121   -1.6052 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0578    1.4962   -1.3817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0531    1.6702   -2.3671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0217    2.6244   -2.3156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0129    3.4650   -1.2226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0583    3.3185   -0.2512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0702    2.3424   -0.3070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0791    2.2703    0.8061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2225   -1.2451    0.3859 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7315   -2.5027    0.2663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0465   -3.1372   -0.9108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5608   -4.4183   -0.9544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7790   -5.1173    0.2187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4702   -4.5018    1.4220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9567   -3.2186    1.4337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6375   -2.5927    2.7555 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4128    3.4748    1.0601 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1071    3.1802   -0.7317 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6668    3.8711   -0.2231 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3714    2.4600    0.7385 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2398    0.1742    0.8173 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8098   -1.7729    0.2772 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4153   -1.3737   -0.3642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0807    1.0135   -3.2462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7876    2.7468   -3.0887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7666    4.2482   -1.1304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0566    3.9925    0.6186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8792    1.2367    1.1229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5965    2.7249    1.7150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2063    2.9157    0.6592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8822   -2.6047   -1.8377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7803   -4.8395   -1.9325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1845   -6.1258    0.1717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6409   -5.0513    2.3578 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4599   -2.5480    2.9295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0859   -1.5618    2.8043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0845   -3.1573    3.5753 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
  9 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
  7  2  1  0
 17 12  1  0
 25 20  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  4 31  1  0
  5 32  1  0
  6 33  1  0
 13 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
 18 38  1  0
 18 39  1  0
 18 40  1  0
 21 41  1  0
 22 42  1  0
 23 43  1  0
 24 44  1  0
 26 45  1  0
 26 46  1  0
 26 47  1  0
M  END

HEADER    PROTEIN                                 22-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-16         0                                  
HETATM    1  C   UNK     0       4.414   2.723   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.081   7.343   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.437   6.366   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.081  -0.357   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.414  10.423   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.357   3.699   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.415   0.413   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.080   9.653   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.127   2.365   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.747   0.413   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.747   9.653   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.127   5.033   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.415   1.953   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.080   8.113   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   2.365   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.747   1.953   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.747   8.113   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667   5.033   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.081   2.723   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.414   7.343   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.437   3.699   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.517   6.366   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       7.081   4.263   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       4.414   5.803   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       4.977   3.699   0.000  0.00  0.00           O+0
HETATM   26  P   UNK     0       5.747   5.033   0.000  0.00  0.00           P+0
CONECT    1   16                                                            
CONECT    2   17                                                            
CONECT    3   18                                                            
CONECT    4    7   10                                                       
CONECT    5    8   11                                                       
CONECT    6    9   12                                                       
CONECT    7    4   13                                                       
CONECT    8    5   14                                                       
CONECT    9    6   15                                                       
CONECT   10    4   16                                                       
CONECT   11    5   17                                                       
CONECT   12    6   18                                                       
CONECT   13    7   19                                                       
CONECT   14    8   20                                                       
CONECT   15    9   21                                                       
CONECT   16    1   10   19                                                  
CONECT   17    2   11   20                                                  
CONECT   18    3   12   21                                                  
CONECT   19   13   16   23                                                  
CONECT   20   14   17   24                                                  
CONECT   21   15   18   25                                                  
CONECT   22   26                                                            
CONECT   23   19   26                                                       
CONECT   24   20   26                                                       
CONECT   25   21   26                                                       
CONECT   26   22   23   24   25                                             
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

COMPND    HMDB0259135
HETATM    1  C1  UNL     1       2.861   3.171   0.087  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.403   1.779   0.139  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.741   1.606   0.501  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.204   0.313   0.537  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.395  -0.761   0.234  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.093  -0.563  -0.116  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.584   0.712  -0.167  1.00  0.00           C  
HETATM    8  O1  UNL     1       1.278   0.994  -0.512  1.00  0.00           O  
HETATM    9  P1  UNL     1       0.127  -0.202  -0.920  1.00  0.00           P  
HETATM   10  O2  UNL     1       0.819  -1.018  -2.047  1.00  0.00           O  
HETATM   11  O3  UNL     1      -1.198   0.512  -1.605  1.00  0.00           O  
HETATM   12  C8  UNL     1      -2.058   1.496  -1.382  1.00  0.00           C  
HETATM   13  C9  UNL     1      -3.053   1.670  -2.367  1.00  0.00           C  
HETATM   14  C10 UNL     1      -4.022   2.624  -2.316  1.00  0.00           C  
HETATM   15  C11 UNL     1      -4.013   3.465  -1.223  1.00  0.00           C  
HETATM   16  C12 UNL     1      -3.058   3.319  -0.251  1.00  0.00           C  
HETATM   17  C13 UNL     1      -2.070   2.342  -0.307  1.00  0.00           C  
HETATM   18  C14 UNL     1      -1.079   2.270   0.806  1.00  0.00           C  
HETATM   19  O4  UNL     1      -0.223  -1.245   0.386  1.00  0.00           O  
HETATM   20  C15 UNL     1      -0.731  -2.503   0.266  1.00  0.00           C  
HETATM   21  C16 UNL     1      -1.047  -3.137  -0.911  1.00  0.00           C  
HETATM   22  C17 UNL     1      -1.561  -4.418  -0.954  1.00  0.00           C  
HETATM   23  C18 UNL     1      -1.779  -5.117   0.219  1.00  0.00           C  
HETATM   24  C19 UNL     1      -1.470  -4.502   1.422  1.00  0.00           C  
HETATM   25  C20 UNL     1      -0.957  -3.219   1.434  1.00  0.00           C  
HETATM   26  C21 UNL     1      -0.637  -2.593   2.756  1.00  0.00           C  
HETATM   27  H1  UNL     1       2.413   3.475   1.060  1.00  0.00           H  
HETATM   28  H2  UNL     1       2.107   3.180  -0.732  1.00  0.00           H  
HETATM   29  H3  UNL     1       3.667   3.871  -0.223  1.00  0.00           H  
HETATM   30  H4  UNL     1       5.371   2.460   0.738  1.00  0.00           H  
HETATM   31  H5  UNL     1       6.240   0.174   0.817  1.00  0.00           H  
HETATM   32  H6  UNL     1       4.810  -1.773   0.277  1.00  0.00           H  
HETATM   33  H7  UNL     1       2.415  -1.374  -0.364  1.00  0.00           H  
HETATM   34  H8  UNL     1      -3.081   1.014  -3.246  1.00  0.00           H  
HETATM   35  H9  UNL     1      -4.788   2.747  -3.089  1.00  0.00           H  
HETATM   36  H10 UNL     1      -4.767   4.248  -1.130  1.00  0.00           H  
HETATM   37  H11 UNL     1      -3.057   3.993   0.619  1.00  0.00           H  
HETATM   38  H12 UNL     1      -0.879   1.237   1.123  1.00  0.00           H  
HETATM   39  H13 UNL     1      -1.596   2.725   1.715  1.00  0.00           H  
HETATM   40  H14 UNL     1      -0.206   2.916   0.659  1.00  0.00           H  
HETATM   41  H15 UNL     1      -0.882  -2.605  -1.838  1.00  0.00           H  
HETATM   42  H16 UNL     1      -1.780  -4.840  -1.932  1.00  0.00           H  
HETATM   43  H17 UNL     1      -2.185  -6.126   0.172  1.00  0.00           H  
HETATM   44  H18 UNL     1      -1.641  -5.051   2.358  1.00  0.00           H  
HETATM   45  H19 UNL     1       0.460  -2.548   2.930  1.00  0.00           H  
HETATM   46  H20 UNL     1      -1.086  -1.562   2.804  1.00  0.00           H  
HETATM   47  H21 UNL     1      -1.085  -3.157   3.575  1.00  0.00           H  
CONECT    1    2   27   28   29
CONECT    2    3    3    7
CONECT    3    4   30
CONECT    4    5    5   31
CONECT    5    6   32
CONECT    6    7    7   33
CONECT    7    8
CONECT    8    9
CONECT    9   10   10   11   19
CONECT   11   12
CONECT   12   13   13   17
CONECT   13   14   34
CONECT   14   15   15   35
CONECT   15   16   36
CONECT   16   17   17   37
CONECT   17   18
CONECT   18   38   39   40
CONECT   19   20
CONECT   20   21   21   25
CONECT   21   22   41
CONECT   22   23   23   42
CONECT   23   24   43
CONECT   24   25   25   44
CONECT   25   26
CONECT   26   45   46   47
END

HMDB0259135
     RDKit          3D
TRI-O-CRESYL PHOSPHATE
 47 49  0  0  0  0  0  0  0  0999 V2000
    2.8609    3.1709    0.0870 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4034    1.7787    0.1388 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7411    1.6060    0.5007 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2043    0.3130    0.5374 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3946   -0.7611    0.2337 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0930   -0.5632   -0.1163 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5838    0.7117   -0.1672 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2776    0.9944   -0.5125 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1271   -0.2019   -0.9204 P   0  0  0  0  0  5  0  0  0  0  0  0
    0.8194   -1.0176   -2.0467 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1985    0.5121   -1.6052 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0578    1.4962   -1.3817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0531    1.6702   -2.3671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0217    2.6244   -2.3156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0129    3.4650   -1.2226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0583    3.3185   -0.2512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0702    2.3424   -0.3070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0791    2.2703    0.8061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2225   -1.2451    0.3859 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7315   -2.5027    0.2663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0465   -3.1372   -0.9108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5608   -4.4183   -0.9544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7790   -5.1173    0.2187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4702   -4.5018    1.4220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9567   -3.2186    1.4337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6375   -2.5927    2.7555 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4128    3.4748    1.0601 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1071    3.1802   -0.7317 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6668    3.8711   -0.2231 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3714    2.4600    0.7385 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2398    0.1742    0.8173 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8098   -1.7729    0.2772 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4153   -1.3737   -0.3642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0807    1.0135   -3.2462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7876    2.7468   -3.0887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7666    4.2482   -1.1304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0566    3.9925    0.6186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8792    1.2367    1.1229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5965    2.7249    1.7150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2063    2.9157    0.6592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8822   -2.6047   -1.8377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7803   -4.8395   -1.9325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1845   -6.1258    0.1717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6409   -5.0513    2.3578 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4599   -2.5480    2.9295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0859   -1.5618    2.8043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0845   -3.1573    3.5753 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
  9 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
  7  2  1  0
 17 12  1  0
 25 20  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  4 31  1  0
  5 32  1  0
  6 33  1  0
 13 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
 18 38  1  0
 18 39  1  0
 18 40  1  0
 21 41  1  0
 22 42  1  0
 23 43  1  0
 24 44  1  0
 26 45  1  0
 26 46  1  0
 26 47  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Tris(2-methylphenyl) phosphoric acid	Generator
Tri-O-cresyl phosphate	MeSH
Triorthotolyl phosphate	MeSH
Tri-2-cresyl phosphate	MeSH
TOCP	MeSH
TOTP	MeSH
Tri-O-tolyl phosphate	MeSH
Triorthocresyl phosphate	MeSH
TRI-O-cresyl phosphoric acid	Generator
Phosphoric acid, tris(2-methylphenyl) ester	MeSH

Chemical Formula

C₂₁H₂₁O₄P

Average Molecular Weight

368.369

Monoisotopic Molecular Weight

368.117746154

IUPAC Name

tris(2-methylphenyl) phosphate

Traditional Name

tricresyl phosphate

CAS Registry Number

Not Available

SMILES

CC1=CC=CC=C1OP(=O)(OC1=CC=CC=C1C)OC1=CC=CC=C1C

InChI Identifier

InChI=1S/C21H21O4P/c1-16-10-4-7-13-19(16)23-26(22,24-20-14-8-5-11-17(20)2)25-21-15-9-6-12-18(21)3/h4-15H,1-3H3

InChI Key

YSMRWXYRXBRSND-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aryl phosphotriesters. These are aryl phosphates in which the phosphate is esterified at exactly three positions.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic phosphoric acids and derivatives

Sub Class

Phosphate esters

Direct Parent

Aryl phosphotriesters

Alternative Parents

Substituents

Aryl phosphotriester
Phenoxy compound
Toluene
Benzenoid
Monocyclic benzene moiety
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

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	4.8	ALOGPS
logP	6.63	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Basic)	-9.4	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	6	ChemAxon
Refractivity	102.56 m³·mol⁻¹	ChemAxon
Polarizability	37.19 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	173.858	30932474
DeepCCS	[M-H]-	171.5	30932474
DeepCCS	[M-2H]-	205.719	30932474
DeepCCS	[M+Na]+	180.946	30932474
AllCCS	[M+H]+	185.3	32859911
AllCCS	[M+H-H2O]+	182.2	32859911
AllCCS	[M+NH4]+	188.2	32859911
AllCCS	[M+Na]+	189.0	32859911
AllCCS	[M-H]-	174.9	32859911
AllCCS	[M+Na-2H]-	173.4	32859911
AllCCS	[M+HCOO]-	171.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
TRI-O-CRESYL PHOSPHATE	CC1=CC=CC=C1OP(=O)(OC1=CC=CC=C1C)OC1=CC=CC=C1C	3574.5	Standard polar	33892256
TRI-O-CRESYL PHOSPHATE	CC1=CC=CC=C1OP(=O)(OC1=CC=CC=C1C)OC1=CC=CC=C1C	2742.2	Standard non polar	33892256
TRI-O-CRESYL PHOSPHATE	CC1=CC=CC=C1OP(=O)(OC1=CC=CC=C1C)OC1=CC=CC=C1C	2534.8	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 - Tri-O-cresyl phosphate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0aor-4629000000-f51d2603ac015b405e9c	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tri-O-cresyl 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tri-O-cresyl phosphate 35V, Positive-QTOF	splash10-014i-1429000000-99becfe641eb9f64e4bf	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tri-O-cresyl phosphate 10V, Positive-QTOF	splash10-014i-0009000000-45a8c8b1941168405391	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tri-O-cresyl phosphate 20V, Positive-QTOF	splash10-014i-0009000000-9308a30e3c7e70dfc23a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tri-O-cresyl phosphate 40V, Positive-QTOF	splash10-1000-9301000000-eab25457801d024acc9c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tri-O-cresyl phosphate 10V, Negative-QTOF	splash10-014i-0009000000-09f41a7873b5f9dafd77	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tri-O-cresyl phosphate 20V, Negative-QTOF	splash10-014i-1009000000-675e9e59c324a190ac52	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tri-O-cresyl phosphate 40V, Negative-QTOF	splash10-014i-9314000000-b68f6ddb82344a1ac556	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

21106216

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Tri-O-cresyl phosphate (HMDB0259135)

MOL for HMDB0259135 (Tri-O-cresyl phosphate)

3D MOL for HMDB0259135 (Tri-O-cresyl phosphate)

3D SDF for HMDB0259135 (Tri-O-cresyl phosphate)

3D-SDF for HMDB0259135 (Tri-O-cresyl phosphate)

PDB for HMDB0259135 (Tri-O-cresyl phosphate)

3D PDB for HMDB0259135 (Tri-O-cresyl phosphate)

SMILES for HMDB0259135 (Tri-O-cresyl phosphate)

INCHI for HMDB0259135 (Tri-O-cresyl phosphate)

Structure for HMDB0259135 (Tri-O-cresyl phosphate)

3D Structure for HMDB0259135 (Tri-O-cresyl phosphate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra