ACCESSION: MSBNK-Eawag-EQ367854
RECORD_TITLE: Doxycycline; LC-ESI-QFT; MS2; CE: 60; R=35000; [M-H]-
DATE: 2015.08.26
AUTHORS: Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag and Thomaidis N, University of Athens
LICENSE: CC BY
COPYRIGHT: Copyright (C) 2015 Eawag, Duebendorf, Switzerland
COMMENT: CONFIDENCE standard compound
COMMENT: EAWAG_UCHEM_ID 3678
CH$NAME: Doxycycline
CH$NAME: 8-carbamoyl-10-(dimethylazaniumyl)-4,6a,7,11-tetrahydroxy-12-methyl-6,9-dioxo-10a,11,11a,12-tetrahydro-10H-tetracen-5-olate
CH$COMPOUND_CLASS: N/A; Environmental Standard
CH$FORMULA: C22H24N2O8
CH$EXACT_MASS: 444.15327
CH$SMILES: CC1C2C(C3C(C(=O)C(=C(C3(C(=O)C2=C(C4=C1C=CC=C4O)O)O)O)C(=O)N)N(C)C)O
CH$IUPAC: InChI=1S/C22H24N2O8/c1-7-8-5-4-6-9(25)11(8)16(26)12-10(7)17(27)14-15(24(2)3)18(28)13(21(23)31)20(30)22(14,32)19(12)29/h4-7,10,14-15,17,25-27,30,32H,1-3H3,(H2,23,31)
CH$LINK: CAS
564-25-0
CH$LINK: PUBCHEM
CID:54681536
CH$LINK: INCHIKEY
SGKRLCUYIXIAHR-UHFFFAOYSA-N
CH$LINK: CHEMSPIDER
10482106
AC$INSTRUMENT: Q Exactive Plus Orbitrap Thermo Scientific
AC$INSTRUMENT_TYPE: LC-ESI-QFT
AC$MASS_SPECTROMETRY: MS_TYPE MS2
AC$MASS_SPECTROMETRY: ION_MODE NEGATIVE
AC$MASS_SPECTROMETRY: IONIZATION ESI
AC$MASS_SPECTROMETRY: FRAGMENTATION_MODE HCD
AC$MASS_SPECTROMETRY: COLLISION_ENERGY 60 (nominal)
AC$MASS_SPECTROMETRY: RESOLUTION 35000
AC$CHROMATOGRAPHY: COLUMN_NAME XBridge C18 3.5um, 2.1x50mm, Waters
AC$CHROMATOGRAPHY: FLOW_GRADIENT 90/10 at 0 min, 50/50 at 4 min, 5/95 at 17 min, 5/95 at 25 min, 90/10 at 25.1 min, 90/10 at 30 min
AC$CHROMATOGRAPHY: FLOW_RATE 200 ul/min
AC$CHROMATOGRAPHY: RETENTION_TIME 6.3 min
AC$CHROMATOGRAPHY: SOLVENT A water with 0.1% formic acid
AC$CHROMATOGRAPHY: SOLVENT B methanol with 0.1% formic acid
MS$FOCUSED_ION: BASE_PEAK 443.1457
MS$FOCUSED_ION: PRECURSOR_M/Z 443.146
MS$FOCUSED_ION: PRECURSOR_TYPE [M-H]-
MS$DATA_PROCESSING: RECALIBRATE loess on assigned fragments and MS1
MS$DATA_PROCESSING: REANALYZE Peaks with additional N2/O included
MS$DATA_PROCESSING: WHOLE RMassBank 1.9.6
PK$SPLASH: splash10-0006-1590000000-cd470825386f8ba028c9
PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm)
57.0346 C3H5O- 1 57.0346 -0.5
63.024 C5H3- 1 63.024 0.1
65.0033 C4HO- 1 65.0033 0.33
65.0397 C5H5- 1 65.0397 0.56
65.9985 C3NO- 1 65.9985 0.04
67.019 C4H3O- 1 67.0189 0.32
68.9982 C3HO2- 1 68.9982 0.25
69.0346 C4H5O- 1 69.0346 0.6
71.0139 C3H3O2- 1 71.0139 0.66
79.0189 C5H3O- 1 79.0189 -0.36
80.0268 C5H4O- 1 80.0268 0.21
81.022 C4H3NO- 1 81.022 -0.4
81.0345 C5H5O- 1 81.0346 -1.21
83.0139 C4H3O2- 1 83.0139 0.33
84.0091 C3H2NO2- 1 84.0091 -0.62
85.0294 C4H5O2- 1 85.0295 -0.62
91.019 C6H3O- 1 91.0189 0.13
93.0345 C6H5O- 1 93.0346 -1.06
95.0138 C5H3O2- 1 95.0139 -0.24
96.0091 C4H2NO2- 1 96.0091 0.08
96.0454 C5H6NO- 1 96.0455 -0.49
96.993 C4HO3- 1 96.9931 -0.8
97.0295 C5H5O2- 1 97.0295 -0.24
99.0088 C4H3O3- 1 99.0088 -0.08
100.0768 C5H10NO- 1 100.0768 -0.08
107.0138 C6H3O2- 1 107.0139 -0.4
107.0504 C7H7O- 1 107.0502 1.14
107.0615 C6H7N2- 1 107.0615 0.64
108.0217 C6H4O2- 1 108.0217 -0.07
109.0295 C6H5O2- 1 109.0295 -0.3
110.0611 C6H8NO- 1 110.0611 -0.16
111.0088 C5H3O3- 1 111.0088 0.65
112.0404 C5H6NO2- 1 112.0404 -0.37
112.0769 C6H10NO- 1 112.0768 0.91
117.0345 C8H5O- 1 117.0346 -0.41
119.0138 C7H3O2- 1 119.0139 -0.28
119.0502 C8H7O- 1 119.0502 -0.15
120.0217 C7H4O2- 1 120.0217 0.1
121.0295 C7H5O2- 1 121.0295 0.06
121.0533 C7H7NO- 1 121.0533 -0.19
121.0659 C8H9O- 1 121.0659 -0.24
122.0248 C6H4NO2- 1 122.0248 0.39
123.0088 C6H3O3- 1 123.0088 0.1
123.0327 C6H5NO2- 1 123.0326 1.16
124.0165 C6H4O3- 1 124.0166 -0.59
124.0767 C7H10NO- 1 124.0768 -0.79
124.988 C5HO4- 1 124.988 -0.5
125.0244 C6H5O3- 1 125.0244 -0.38
125.072 C6H9N2O- 1 125.072 -0.37
126.0196 C5H4NO3- 1 126.0197 -0.85
126.056 C6H8NO2- 1 126.0561 -0.25
131.0503 C9H7O- 1 131.0502 0.47
134.0247 C7H4NO2- 1 134.0248 -0.31
135.0088 C7H3O3- 1 135.0088 0.09
135.0451 C8H7O2- 1 135.0452 -0.39
136.0166 C7H4O3- 1 136.0166 0.13
136.0403 C7H6NO2- 1 136.0404 -0.68
136.0767 C8H10NO- 1 136.0768 -0.94
137.0243 C7H5O3- 1 137.0244 -0.79
137.048 C7H7NO2- 1 137.0482 -1.73
138.0195 C6H4NO3- 1 138.0197 -0.92
138.0322 C7H6O3- 1 138.0322 -0.38
138.056 C7H8NO2- 1 138.0561 -0.45
139.0149 C5H3N2O3- 1 139.0149 -0.18
139.0273 C6H5NO3- 1 139.0275 -1.67
140.0354 C6H6NO3- 1 140.0353 0.81
140.0718 C7H10NO2- 1 140.0717 0.77
141.0194 C6H5O4- 1 141.0193 0.41
141.067 C6H9N2O2- 1 141.067 0.56
142.0146 C5H4NO4- 1 142.0146 0.06
142.9986 C5H3O5- 1 142.9986 -0.26
143.0504 C10H7O- 1 143.0502 1.27
143.0826 C6H11N2O2- 1 143.0826 -0.08
144.058 C10H8O- 1 144.0581 -0.72
145.0295 C9H5O2- 1 145.0295 0.26
145.066 C10H9O- 1 145.0659 1.04
146.0372 C9H6O2- 1 146.0373 -1.08
147.0451 C9H7O2- 1 147.0452 -0.56
148.0167 C8H4O3- 1 148.0166 0.66
148.0402 C8H6NO2- 1 148.0404 -1.43
149.0117 C7H3NO3- 1 149.0118 -1.15
149.0482 C8H7NO2- 1 149.0482 -0.45
149.0608 C9H9O2- 1 149.0608 0.25
149.9957 C7H2O4- 1 149.9959 -0.85
150.0196 C7H4NO3- 1 150.0197 -0.24
151.0037 C7H3O4- 1 151.0037 0.12
151.0275 C7H5NO3- 1 151.0275 -0.01
152.0114 C7H4O4- 1 152.0115 -0.57
152.0353 C7H6NO3- 1 152.0353 0.22
152.0716 C8H10NO2- 1 152.0717 -0.93
153.0194 C7H5O4- 1 153.0193 0.38
154.0386 C6H6N2O3- 1 154.0384 1.29
154.0876 C8H12NO2- 1 154.0874 1.41
157.066 C11H9O- 1 157.0659 0.65
158.0373 C10H6O2- 1 158.0373 -0.49
159.0452 C10H7O2- 1 159.0452 0.3
159.0815 C11H11O- 1 159.0815 -0.12
161.0246 C9H5O3- 1 161.0244 1.19
161.0609 C10H9O2- 1 161.0608 0.6
162.0198 C8H4NO3- 1 162.0197 0.64
162.0561 C9H8NO2- 1 162.0561 0.54
163.0038 C8H3O4- 1 163.0037 0.6
163.0274 C8H5NO3- 1 163.0275 -0.38
163.0766 C10H11O2- 1 163.0765 0.66
164.0116 C8H4O4- 1 164.0115 0.81
164.0358 C8H6NO3- 1 164.0353 3.19
164.0597 C8H8N2O2- 1 164.0591 3.25
164.0719 C9H10NO2- 1 164.0717 1.02
165.043 C8H7NO3- 1 165.0431 -0.68
166.0509 C8H8NO3- 1 166.051 -0.34
167.0223 C7H5NO4- 1 167.0224 -0.34
167.0462 C7H7N2O3- 1 167.0462 -0.09
168.0303 C7H6NO4- 1 168.0302 0.17
168.0665 C8H10NO3- 1 168.0666 -0.64
169.0141 C7H5O5- 1 169.0142 -0.75
169.0254 C6H5N2O4- 1 169.0255 -0.3
169.0667 C12H9O- 1 169.0659 4.98
171.045 C11H7O2- 1 171.0452 -0.72
171.0818 C12H11O- 1 171.0815 1.29
172.0531 C11H8O2- 1 172.053 0.48
173.0607 C11H9O2- 1 173.0608 -0.36
174.0321 C10H6O3- 1 174.0322 -0.99
175.0763 C11H11O2- 1 175.0765 -0.99
177.0307 C8H5N2O3- 1 177.0306 0.99
178.0146 C8H4NO4- 1 178.0146 0.27
178.0511 C9H8NO3- 1 178.051 0.92
178.9984 C8H3O5- 1 178.9986 -1.21
179.0825 C9H11N2O2- 1 179.0826 -0.34
180.0303 C8H6NO4- 1 180.0302 0.66
180.0581 C13H8O- 1 180.0581 0.37
180.0667 C9H10NO3- 1 180.0666 0.41
181.0661 C13H9O- 1 181.0659 1.22
182.0822 C9H12NO3- 1 182.0823 -0.42
183.0449 C12H7O2- 1 183.0452 -1.38
183.0816 C13H11O- 1 183.0815 0.28
185.0608 C12H9O2- 1 185.0608 -0.12
186.0319 C11H6O3- 1 186.0322 -1.68
186.0687 C12H10O2- 1 186.0686 0.28
187.0401 C11H7O3- 1 187.0401 0.23
187.0764 C12H11O2- 1 187.0765 -0.18
188.0479 C11H8O3- 1 188.0479 -0.01
189.0667 C10H9N2O2- 1 189.067 -1.59
189.0919 C12H13O2- 1 189.0921 -1.18
194.0738 C14H10O- 1 194.0737 0.5
195.0818 C14H11O- 1 195.0815 1.24
196.0249 C8H6NO5- 1 196.0251 -1.2
196.0529 C13H8O2- 1 196.053 -0.3
197.0608 C13H9O2- 1 197.0608 0.03
198.0321 C12H6O3- 1 198.0322 -0.67
198.0689 C13H10O2- 1 198.0686 1.27
199.0395 C12H7O3- 1 199.0401 -2.65
199.0764 C13H11O2- 1 199.0765 -0.47
200.0483 C12H8O3- 1 200.0479 2.04
201.0193 C11H5O4- 1 201.0193 -0.21
201.0557 C12H9O3- 1 201.0557 0.06
201.0921 C13H13O2- 1 201.0921 -0.26
203.0715 C12H11O3- 1 203.0714 0.45
204.0428 C11H8O4- 1 204.0428 0.01
206.0737 C15H10O- 1 206.0737 -0.26
207.082 C15H11O- 1 207.0815 2.04
208.0529 C14H8O2- 1 208.053 -0.33
209.0607 C14H9O2- 1 209.0608 -0.45
210.0686 C14H10O2- 1 210.0686 0.06
211.0401 C13H7O3- 1 211.0401 0.34
211.0765 C14H11O2- 1 211.0765 0.08
212.0481 C13H8O3- 1 212.0479 1.21
213.0557 C13H9O3- 1 213.0557 0.01
213.0921 C14H13O2- 1 213.0921 -0.25
214.0273 C12H6O4- 1 214.0272 0.53
215.0714 C13H11O3- 1 215.0714 0.15
217.0506 C12H9O4- 1 217.0506 0.08
218.0579 C12H10O4- 1 218.0585 -2.37
219.0812 C16H11O- 1 219.0815 -1.64
220.0534 C15H8O2- 1 220.053 1.96
221.0608 C15H9O2- 1 221.0608 0.17
221.0973 C16H13O- 1 221.0972 0.5
222.0686 C15H10O2- 1 222.0686 -0.31
223.0403 C14H7O3- 1 223.0401 0.91
223.0765 C15H11O2- 1 223.0765 0.21
224.0478 C14H8O3- 1 224.0479 -0.24
224.0844 C15H12O2- 1 224.0843 0.5
225.0557 C14H9O3- 1 225.0557 0.14
225.0922 C15H13O2- 1 225.0921 0.3
226.0636 C14H10O3- 1 226.0635 0.12
226.0872 C14H12NO2- 1 226.0874 -0.54
227.0714 C14H11O3- 1 227.0714 0.1
229.0506 C13H9O4- 1 229.0506 -0.18
229.0869 C14H13O3- 1 229.087 -0.43
231.0666 C13H11O4- 1 231.0663 1.29
232.0532 C16H8O2- 1 232.053 1.04
233.0607 C16H9O2- 1 233.0608 -0.66
234.0687 C16H10O2- 1 234.0686 0.22
235.0404 C15H7O3- 1 235.0401 1.29
235.0764 C16H11O2- 1 235.0765 -0.31
236.0481 C15H8O3- 1 236.0479 1.05
236.0845 C16H12O2- 1 236.0843 0.98
237.0558 C15H9O3- 1 237.0557 0.35
237.0806 C15H11NO2- 1 237.0795 4.74
237.092 C16H13O2- 1 237.0921 -0.27
238.0635 C15H10O3- 1 238.0635 -0.01
238.0873 C15H12NO2- 1 238.0874 -0.14
239.0352 C14H7O4- 1 239.035 1.12
239.0714 C15H11O3- 1 239.0714 0.22
240.043 C14H8O4- 1 240.0428 0.72
241.051 C14H9O4- 1 241.0506 1.57
241.0869 C15H13O3- 1 241.087 -0.57
243.1028 C15H15O3- 1 243.1027 0.67
244.0377 C13H8O5- 1 244.0377 0.07
247.0638 C16H9NO2- 1 247.0639 -0.19
247.0761 C17H11O2- 1 247.0765 -1.31
248.048 C16H8O3- 1 248.0479 0.63
248.0715 C16H10NO2- 1 248.0717 -0.77
248.0836 C17H12O2- 1 248.0843 -2.69
249.0555 C16H9O3- 1 249.0557 -0.87
249.0919 C17H13O2- 1 249.0921 -0.62
250.0501 C15H8NO3- 1 250.051 -3.35
250.0633 C16H10O3- 1 250.0635 -0.93
251.0714 C16H11O3- 1 251.0714 -0.03
252.0428 C15H8O4- 1 252.0428 -0.19
252.0667 C15H10NO3- 1 252.0666 0.29
252.0789 C16H12O3- 1 252.0792 -1.12
252.1028 C16H14NO2- 1 252.103 -0.76
253.051 C15H9O4- 1 253.0506 1.29
253.0872 C16H13O3- 1 253.087 0.6
254.0585 C15H10O4- 1 254.0585 0.09
254.0822 C15H12NO3- 1 254.0823 -0.42
255.0663 C15H11O4- 1 255.0663 0.15
257.0822 C15H13O4- 1 257.0819 0.85
258.1498 C16H20NO2- 1 258.15 -0.67
260.048 C17H8O3- 1 260.0479 0.41
261.0558 C17H9O3- 1 261.0557 0.35
262.0635 C17H10O3- 1 262.0635 -0.28
262.0868 C17H12NO2- 1 262.0874 -2.26
263.0713 C17H11O3- 1 263.0714 -0.3
264.0431 C16H8O4- 1 264.0428 1.07
264.0664 C16H10NO3- 1 264.0666 -0.82
264.079 C17H12O3- 1 264.0792 -0.81
264.1036 C17H14NO2- 1 264.103 2.41
265.0499 C16H9O4- 1 265.0506 -2.65
265.0742 C16H11NO3- 1 265.0744 -1.06
265.0871 C17H13O3- 1 265.087 0.31
266.0582 C16H10O4- 1 266.0585 -0.97
266.0822 C16H12NO3- 1 266.0823 -0.1
266.095 C17H14O3- 1 266.0948 0.7
267.0662 C16H11O4- 1 267.0663 -0.35
268.1348 C17H18NO2- 1 268.1343 1.71
269.0818 C16H13O4- 1 269.0819 -0.53
273.0767 C15H13O5- 1 273.0768 -0.69
275.0714 C18H11O3- 1 275.0714 0.04
276.0432 C17H8O4- 1 276.0428 1.24
277.0506 C17H9O4- 1 277.0506 -0.23
278.0582 C17H10O4- 1 278.0585 -1.03
278.0818 C17H12NO3- 1 278.0823 -1.61
278.1186 C18H16NO2- 1 278.1187 -0.12
279.0663 C17H11O4- 1 279.0663 -0.12
280.038 C16H8O5- 1 280.0377 1.06
280.0981 C17H14NO3- 1 280.0979 0.48
281.0817 C17H13O4- 1 281.0819 -0.86
281.106 C17H15NO3- 1 281.1057 0.74
282.0529 C16H10O5- 1 282.0534 -1.64
282.0775 C16H12NO4- 1 282.0772 1.06
282.1132 C17H16NO3- 1 282.1136 -1.34
288.0665 C18H10NO3- 1 288.0666 -0.34
290.0222 C17H6O5- 1 290.0221 0.48
290.0825 C18H12NO3- 1 290.0823 0.73
291.0533 C17H9NO4- 1 291.0537 -1.36
291.0665 C18H11O4- 1 291.0663 0.71
292.0749 C18H12O4- 1 292.0741 2.54
293.0458 C17H9O5- 1 293.0455 0.76
293.0829 C18H13O4- 1 293.0819 3.13
293.1055 C18H15NO3- 1 293.1057 -0.76
294.0536 C17H10O5- 1 294.0534 0.71
294.1136 C18H16NO3- 1 294.1136 0.15
295.0615 C17H11O5- 1 295.0612 0.96
296.1293 C18H18NO3- 1 296.1292 0.25
297.076 C17H13O5- 1 297.0768 -2.92
304.0376 C18H8O5- 1 304.0377 -0.37
304.0622 C18H10NO4- 1 304.0615 2.33
305.0456 C18H9O5- 1 305.0455 0.21
306.0766 C18H12NO4- 1 306.0772 -1.97
308.0929 C18H14NO4- 1 308.0928 0.16
309.077 C18H13O5- 1 309.0768 0.62
319.0611 C19H11O5- 1 319.0612 -0.37
322.0485 C18H10O6- 1 322.0483 0.57
358.1302 C19H20NO6- 1 358.1296 1.53
PK$NUM_PEAK: 285
PK$PEAK: m/z int. rel.int.
57.0346 2513 1
63.024 35344.9 16
65.0033 12586.7 5
65.0397 7670.7 3
65.9985 33719.9 15
67.019 7038.2 3
68.9982 38643.6 17
69.0346 25875.7 11
71.0139 11113 5
79.0189 12721 5
80.0268 11408.6 5
81.022 4842.9 2
81.0345 13039.9 6
83.0139 10519.1 4
84.0091 93070 42
85.0294 12692.8 5
91.019 14011.1 6
93.0345 25379.3 11
95.0138 133962.4 61
96.0091 15383.2 7
96.0454 2832.6 1
96.993 57140.4 26
97.0295 30761.6 14
99.0088 13413.6 6
100.0768 13886.2 6
107.0138 17399 8
107.0504 2456.5 1
107.0615 2632.5 1
108.0217 54111.6 24
109.0295 103907.9 47
110.0611 9785.5 4
111.0088 9924.4 4
112.0404 5408.9 2
112.0769 2917.4 1
117.0345 15758.7 7
119.0138 54069.4 24
119.0502 87195.6 40
120.0217 2398 1
121.0295 13100.5 6
121.0533 8284 3
121.0659 35356.8 16
122.0248 7859 3
123.0088 71964.2 33
123.0327 10451.8 4
124.0165 37670 17
124.0767 3097.5 1
124.988 20211.8 9
125.0244 28769.3 13
125.072 40420.9 18
126.0196 11479.7 5
126.056 80295 37
131.0503 2333.3 1
134.0247 46321.8 21
135.0088 122085.9 56
135.0451 9199.3 4
136.0166 7597 3
136.0403 5823.4 2
136.0767 13683.9 6
137.0243 40113.2 18
137.048 9921.6 4
138.0195 17851.9 8
138.0322 6191.3 2
138.056 19662.5 9
139.0149 50640.6 23
139.0273 2563.4 1
140.0354 2937.8 1
140.0718 6904.1 3
141.0194 11940.5 5
141.067 6165 2
142.0146 21506 9
142.9986 65216.4 30
143.0504 10139.8 4
143.0826 8600.1 3
144.058 2778.3 1
145.0295 3112.4 1
145.066 2299.7 1
146.0372 9380.5 4
147.0451 22265.5 10
148.0167 5891.3 2
148.0402 2268.4 1
149.0117 11880.8 5
149.0482 10580.8 4
149.0608 19309 8
149.9957 10861.2 5
150.0196 77844.8 35
151.0037 21065.8 9
151.0275 11091.1 5
152.0114 5123.1 2
152.0353 32061.8 14
152.0716 16539.7 7
153.0194 5839.8 2
154.0386 10405.4 4
154.0876 7956.7 3
157.066 22896.5 10
158.0373 38692.5 17
159.0452 49892.1 22
159.0815 30824 14
161.0246 18675 8
161.0609 16799.7 7
162.0198 22666.9 10
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//
