Table 1 Identified TPHP metabolites in earthworms from LC-QTOF spectra after 28 days of TPHP exposure in soil.

From: Untargeted metabolomics reveals transformation pathways and metabolic response of the earthworm Perionyx excavatus after exposure to triphenyl phosphate

Type

Metabolites

Adducts

Formula

Theoretical m/z

Experimental m/z

Mass error (ppm)

Theoretical isotope ratio (%)

Experimental isotope ratio (%)

Retention time (min)

Characteristic product ions

phase I metabolites

DPHP

[M + H]+

C12H12O4P1

251.0468

251.0458

3.7

13.6

13.5

10.52

152.0608, 175.0128, 215.0245, 233.0353

OH-TPHP (3 isomers)

[M + H]+

C18H16O5P1

343.0730

343.0726

1.2

20.4

19.5

12.27, 13.95, 16.72

152.0608, 215.0245, 233.0353, 357.0335

[M-H]−

C18H14O5P1

341.0584

341.0596

3.3

20.4

20.6

13.49, 16.71, 17.10

93.0345, 185.0614, 233.0383, 249.0347

di-OH-TPHP (4 isomers)

[M + H]+

C18H16O6P1

359.0679

359.0680

0.2

20.4

19.5

12.85, 13.07, 13.43, 16.22

153.0709, 215.0245, 233.0353, 251.0456

thiol conjugates

mercaptolactic acid-TPHP (3 isomers)

[M + H]+

C21H20O7S1P1

447.0662

447.0656

1.3

24.6

22.6

13.14, 13.94, 16.24

152.0608, 215.0245, 233.0353, 357.0335

[M + NH4]+

C21H23O7N1S1P1

464.0927

464.0925

0.5

25.0

30.0

12.08, 13.91, 16.25

152.0608, 215.0245, 233.0353, 357.0335

[M-H]−

C21H18O7S1P1

445.0516

445.0518

0.4

24.6

24.6

13.38,15.64

177.0355, 249.0347, 267.1975, 357.0363

cysteine-TPHP (2 isomers)

[M + H]+

C21H21O6N1S1P1

446.0822

446.0813

2.0

25.0

23.8

12.05, 13.15

152.0608, 215.0245, 233.0353, 357.0335

cysteinylglycine-TPHP (2 isomers)

[M + H]+

C23H24O7N2S1P1

503.1036

503.1028

1.7

27.6

30.5

11.85, 12.80

152.0608, 215.0245, 233.0353, 357.0335

mercaptoethanol-TPHP (2 isomers)

[M + H]+

C20H20O5S1P1

403.0764

403.0762

0.1

23.4

25.1

14.69, 17.45

152.0608, 215.0245, 233.0353, 357.0335

glutathione-TPHP

[M+H]+

C28H31O10N3P1S1

632.1462

632.1444

2.9

33.7

30.5

13.06

—

glucoside conjugates

glucoside-TPHP

[M+NH4]+

C24H29O10N1P1

522.1524

522.1511

2.4

27.8

24.4

13.55

343.0732

[M+COOH]−

C25H26O12P1

549.1167

549.1186

3.4

28.5

27.6

13.57

233.0366, 249.0330, 341.0598, 503.1092

phosphate-glucoside-TPHP

[M+H]+

C24H27O13P2

585.0921

585.0911

1.8

27.5

23.7

13.11

343.0732

[M-H]−

C24H25O13P2

583.0776

583.0786

1.7

27.5

27.5

12.66

78.9586, 241.0018, 291.0917, 537.3042

C14H19O10P-TPHP (3 isomers)

[M+H]+

C32H33O14P2

703.1340

703.1327

1.9

36.5

34.8

15.67, 16.31

91.0534, 127.0385, 263.0913, 343.0732

[M-H]−

C32H31O14 P2

701.1195

701.1221

3.8

36.5

35.0

14.66, 15.16

78.9586, 223.0013, 359.0560, 583.0755

[M+NH4]+

C32H36O14N1P2

720.1606

720.1578

3.9

36.9

39.2

14.72, 14.95, 16.30

127.0385, 263.0913, 343.0732, 703.1316

C14H19O10P-TPHP-OH (3 isomers)

[M+H]+

C32H33O15P2

719.1289

719.1271

2.6

36.5

38.1

14.13, 14.72, 16.24

107.0478, 279.0848, 343.0732, 469.1023

[M-H]−

C32H31O15P2

717.1144

717.1175

4.3

36.5

37.0

13.46, 13.98, 15.13

78.9586, 359.0560

  1. The structure of C14H19O10P could not be unambiguously identified by MS/MS spectra, and are tentatively proposed in Supplementary Fig. S2.
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