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. 2018 Feb 23;410(9):2343–2361. doi: 10.1007/s00216-018-0889-x

Table 1.

Metabolites of compound 5 detected by EC/MS

Modification Sum formula Detected m/z Theoretical m/z Rel. deviation [ppm] Metabolic reaction
[M + H]+ C11H18N5S 252.12747 252.12774 1.08 –
[M–N–2xCH3]+ C9H11N4S 207.06998 207.06989 0.42
[M–2H + H]+ C11H16N5S 250.11211 250.11209 0.07 Dehydrogenation
[M–4H + H]+ C11H14N5S 248.09650 248.09644 0.23 Dehydrogenation
[M + O + H]+ C11H18N5SO 268.12256 268.12266 0.36 Hydroxylation
[M + O–2H + H]+ C11H16N5SO 266.10681 266.10701 0.74 Hydroxylation/
Dehydrogenation
[M + O–4H + H]+ C11H14N5SO 264.09116 264.09136 0.75 Hydroxylation/
Dehydrogenation
[M–S + O + H]+ C11H18N5O 236.15062 236.15059 0.14 Desulfuration
[M–S + O–2H + H]+ C11H16N5O 234.13492 234.13494 0.07 Desulfuration/
Dehydrogenation
[M–S + H]+ C11H18N5 220.15564 220.15567 0.15 Desulfuration
[M–S–2H + H]+ C11H16N5 218.14020 218.14002 0.82 Desulfuration/
Dehydrogenation
[M–CH2 + H]+ C10H16N5S 238.11206 238.11209 0.14 Demethylation
[M–CH2–2H + H]+ C10H14N5S 236.09641 236.09644 0.14 Demethylation/
Dehydrogenation
[M–2xCH2 + H]+ C9H14N5S 224.09621 224.09644 1.04 Demethylation*
[M–2xCH2–2H + H]+ C9H12N5S 222.08055 222.08079 1.09 Demethylation/
Dehydrogenation*
[M–3xCH2–2H + H]+ C8H10N5S 208.06487 208.06514 1.31 Demethylation/
Dehydrogenation*
[2M–2H + H]+ C22H33N10S2 501.23254 501.23256 0.04 Disulfide formation
[2M–4H + H]+ C22H31N10S2 499.21692 499.21691 0.02 Disulfide formation/
Dehydrogenation

*Observed after electrochemical oxidation only via LC-HRMS, but not via EC-HRMS