ACCESSION: MSBNK-Eawag-EQ367803
RECORD_TITLE: Doxycycline; LC-ESI-QFT; MS2; CE: 45; R=35000; [M+H]+
DATE: 2015.08.25
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$MASS_SPECTROMETRY: ION_MODE POSITIVE
AC$MASS_SPECTROMETRY: IONIZATION ESI
AC$MASS_SPECTROMETRY: FRAGMENTATION_MODE HCD
AC$MASS_SPECTROMETRY: COLLISION_ENERGY 45 (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$CHROMATOGRAPHY: RETENTION_TIME 6.4 min
AC$CHROMATOGRAPHY: SOLVENT A water with 0.1% formic acid
AC$CHROMATOGRAPHY: SOLVENT B methanol with 0.1% formic acid
MS$FOCUSED_ION: BASE_PEAK 445.1595
MS$FOCUSED_ION: PRECURSOR_M/Z 445.1605
MS$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: splash10-0v6r-2495100000-3d3d0ec5d3eecb31f5d1
PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm)
55.0178 C3H3O+ 1 55.0178 -0.38
56.0495 C3H6N+ 1 56.0495 0.44
58.0651 C3H8N+ 1 58.0651 0.07
68.0494 C4H6N+ 1 68.0495 -0.96
68.997 C3HO2+ 1 68.9971 -0.95
70.0651 C4H8N+ 1 70.0651 -0.22
72.0444 C3H6NO+ 1 72.0444 -0.42
72.0807 C4H10N+ 1 72.0808 -0.63
74.0599 C3H8NO+ 1 74.06 -1.35
81.0335 C5H5O+ 1 81.0335 -0.51
82.0651 C5H8N+ 1 82.0651 -0.56
83.0127 C4H3O2+ 1 83.0128 -0.67
84.0444 C4H6NO+ 1 84.0444 0
84.0807 C5H10N+ 1 84.0808 -0.78
85.0283 C4H5O2+ 1 85.0284 -0.89
85.0521 C4H7NO+ 1 85.0522 -1.83
86.06 C4H8NO+ 1 86.06 -0.93
94.065 C6H8N+ 1 94.0651 -1.55
95.0128 C5H3O2+ 1 95.0128 0.36
97.0285 C5H5O2+ 1 97.0284 0.76
98.0601 C5H8NO+ 1 98.06 0.2
99.0077 C4H3O3+ 1 99.0077 0.2
100.0757 C5H10NO+ 1 100.0757 0
108.0443 C6H6NO+ 1 108.0444 -0.56
109.0285 C6H5O2+ 1 109.0284 0.86
110.0602 C6H8NO+ 1 110.06 1.18
111.0076 C5H3O3+ 1 111.0077 -0.27
111.044 C6H7O2+ 1 111.0441 -0.86
112.0756 C6H10NO+ 1 112.0757 -0.81
114.055 C5H8NO2+ 1 114.055 0.22
115.054 C9H7+ 1 115.0542 -2.4
121.0285 C7H5O2+ 1 121.0284 0.94
121.0648 C8H9O+ 1 121.0648 0.07
123.0076 C6H3O3+ 1 123.0077 -0.25
123.0443 C7H7O2+ 1 123.0441 1.58
124.0394 C6H6NO2+ 1 124.0393 0.44
124.0758 C7H10NO+ 1 124.0757 0.88
125.0233 C6H5O3+ 1 125.0233 0.24
126.055 C6H8NO2+ 1 126.055 0.2
127.0026 C5H3O4+ 1 127.0026 0.43
128.0707 C6H10NO2+ 1 128.0706 0.51
131.0491 C9H7O+ 1 131.0491 -0.09
135.0074 C7H3O3+ 1 135.0077 -2.37
136.0757 C8H10NO+ 1 136.0757 -0.22
137.0233 C7H5O3+ 1 137.0233 0.14
139.0266 C6H5NO3+ 1 139.0264 1.26
139.0391 C7H7O3+ 1 139.039 1.22
140.0704 C7H10NO2+ 1 140.0706 -1.39
142.0499 C6H8NO3+ 1 142.0499 0.07
144.0655 C6H10NO3+ 1 144.0655 0.14
145.065 C10H9O+ 1 145.0648 1.09
147.044 C9H7O2+ 1 147.0441 -0.04
147.0805 C10H11O+ 1 147.0804 0.19
149.0234 C8H5O3+ 1 149.0233 0.6
149.0445 C5H9O5+ 1 149.0444 0.2
149.0602 C9H9O2+ 1 149.0597 3.18
152.0343 C7H6NO3+ 1 152.0342 0.73
152.0709 C8H10NO2+ 1 152.0706 1.74
153.0182 C7H5O4+ 1 153.0182 -0.43
154.0499 C7H8NO3+ 1 154.0499 0.26
155.0341 C7H7O4+ 1 155.0339 1.45
157.0369 C6H7NO4+ 1 157.037 -0.06
157.065 C11H9O+ 1 157.0648 1.14
158.0729 C11H10O+ 1 158.0726 1.54
159.0441 C10H7O2+ 1 159.0441 0.47
159.0807 C11H11O+ 1 159.0804 1.44
160.052 C10H8O2+ 1 160.0519 0.68
161.0597 C10H9O2+ 1 161.0597 -0.04
163.0026 C8H3O4+ 1 163.0026 0.15
163.0391 C9H7O3+ 1 163.039 1.04
163.0628 C9H9NO2+ 1 163.0628 0
164.0706 C9H10NO2+ 1 164.0706 -0.27
165.0183 C8H5O4+ 1 165.0182 0.39
166.0498 C8H8NO3+ 1 166.0499 -0.42
166.0865 C9H12NO2+ 1 166.0863 1.54
167.034 C8H7O4+ 1 167.0339 0.75
167.0557 C5H11O6+ 1 167.055 3.98
168.0655 C8H10NO3+ 1 168.0655 0.06
170.0448 C7H8NO4+ 1 170.0448 -0.08
170.081 C8H12NO3+ 1 170.0812 -0.88
171.0806 C12H11O+ 1 171.0804 1.16
172.0603 C7H10NO4+ 1 172.0604 -0.9
173.0598 C11H9O2+ 1 173.0597 0.6
174.0675 C11H10O2+ 1 174.0675 -0.01
175.0754 C11H11O2+ 1 175.0754 0.48
177.0185 C9H5O4+ 1 177.0182 1.33
178.05 C9H8NO3+ 1 178.0499 0.96
178.9974 C8H3O5+ 1 178.9975 -0.33
179.0338 C9H7O4+ 1 179.0339 -0.64
179.0852 C14H11+ 1 179.0855 -1.82
180.0656 C9H10NO3+ 1 180.0655 0.34
181.0132 C8H5O5+ 1 181.0131 0.44
181.0365 C8H7NO4+ 1 181.037 -2.43
182.0448 C8H8NO4+ 1 182.0448 -0.13
182.0813 C9H12NO3+ 1 182.0812 0.5
183.0288 C8H7O5+ 1 183.0288 0.22
183.0805 C13H11O+ 1 183.0804 0.48
184.0511 C12H8O2+ 1 184.0519 -4.46
185.0599 C12H9O2+ 1 185.0597 0.78
185.0962 C13H13O+ 1 185.0961 0.53
187.0392 C11H7O3+ 1 187.039 1.33
187.0754 C12H11O2+ 1 187.0754 0.18
190.0498 C10H8NO3+ 1 190.0499 -0.26
190.9976 C9H3O5+ 1 190.9975 0.58
191.0343 C10H7O4+ 1 191.0339 2.43
192.0656 C10H10NO3+ 1 192.0655 0.31
193.0133 C9H5O5+ 1 193.0131 0.93
194.0448 C9H8NO4+ 1 194.0448 0.08
195.0805 C14H11O+ 1 195.0804 0.25
196.0606 C9H10NO4+ 1 196.0604 0.85
197.0599 C13H9O2+ 1 197.0597 1.24
197.096 C14H13O+ 1 197.0961 -0.21
198.0673 C13H10O2+ 1 198.0675 -1.32
198.0756 C9H12NO4+ 1 198.0761 -2.34
199.0754 C13H11O2+ 1 199.0754 0.32
201.0547 C12H9O3+ 1 201.0546 0.3
203.0337 C11H7O4+ 1 203.0339 -0.76
203.0703 C12H11O3+ 1 203.0703 -0.05
204.0662 C11H10NO3+ 1 204.0655 3.58
205.0496 C11H9O4+ 1 205.0495 0.07
206.0449 C10H8NO4+ 1 206.0448 0.42
207.0805 C15H11O+ 1 207.0804 0.52
208.0606 C10H10NO4+ 1 208.0604 0.84
209.0082 C9H5O6+ 1 209.0081 0.79
209.0965 C15H13O+ 1 209.0961 1.71
210.0676 C14H10O2+ 1 210.0675 0.28
210.0762 C10H12NO4+ 1 210.0761 0.6
211.0754 C14H11O2+ 1 211.0754 0.45
212.0833 C14H12O2+ 1 212.0832 0.56
213.0548 C13H9O3+ 1 213.0546 0.89
213.0911 C14H13O2+ 1 213.091 0.35
214.0617 C13H10O3+ 1 214.0624 -3.62
215.0704 C13H11O3+ 1 215.0703 0.46
217.0129 C11H5O5+ 1 217.0131 -1.2
219.0293 C11H7O5+ 1 219.0288 2.1
219.0653 C12H11O4+ 1 219.0652 0.62
219.0809 C16H11O+ 1 219.0804 1.91
221.0601 C15H9O2+ 1 221.0597 2.01
221.071 C14H9N2O+ 1 221.0709 0.41
221.0959 C16H13O+ 1 221.0961 -1.05
222.0767 C11H12NO4+ 1 222.0761 2.55
223.0755 C15H11O2+ 1 223.0754 0.47
224.0834 C15H12O2+ 1 224.0832 0.98
225.0912 C15H13O2+ 1 225.091 0.73
226.0622 C14H10O3+ 1 226.0624 -0.95
227.0704 C14H11O3+ 1 227.0703 0.48
229.0497 C13H9O4+ 1 229.0495 0.85
229.0859 C14H13O3+ 1 229.0859 0.08
231.0652 C13H11O4+ 1 231.0652 -0.02
231.0809 C17H11O+ 1 231.0804 1.9
232.0608 C12H10NO4+ 1 232.0604 1.58
233.0804 C13H13O4+ 1 233.0808 -2.08
235.0755 C16H11O2+ 1 235.0754 0.57
236.0557 C11H10NO5+ 1 236.0553 1.49
237.0543 C15H9O3+ 1 237.0546 -1.39
237.0912 C16H13O2+ 1 237.091 0.86
238.0623 C15H10O3+ 1 238.0624 -0.49
239.0703 C15H11O3+ 1 239.0703 0.33
240.0783 C15H12O3+ 1 240.0781 0.68
241.086 C15H13O3+ 1 241.0859 0.37
242.0572 C14H10O4+ 1 242.0574 -0.79
243.0652 C14H11O4+ 1 243.0652 -0.1
243.1016 C15H15O3+ 1 243.1016 0.04
247.0753 C17H11O2+ 1 247.0754 -0.39
249.0543 C16H9O3+ 1 249.0546 -1.17
249.091 C17H13O2+ 1 249.091 0.02
251.0705 C16H11O3+ 1 251.0703 0.75
252.0418 C15H8O4+ 1 252.0417 0.2
253.086 C16H13O3+ 1 253.0859 0.19
254.0571 C15H10O4+ 1 254.0574 -1.06
255.0652 C15H11O4+ 1 255.0652 0.18
257.0809 C15H13O4+ 1 257.0808 0.13
259.0754 C18H11O2+ 1 259.0754 0.36
259.0966 C15H15O4+ 1 259.0965 0.4
261.0549 C17H9O3+ 1 261.0546 0.99
263.0704 C17H11O3+ 1 263.0703 0.34
264.0783 C17H12O3+ 1 264.0781 0.89
265.0497 C16H9O4+ 1 265.0495 0.66
265.086 C17H13O3+ 1 265.0859 0.26
266.0577 C16H10O4+ 1 266.0574 1.28
267.0653 C16H11O4+ 1 267.0652 0.35
268.0368 C15H8O5+ 1 268.0366 0.8
268.0696 C11H12N2O6+ 1 268.069 2.32
268.1336 C17H18NO2+ 1 268.1332 1.62
269.0809 C16H13O4+ 1 269.0808 0.28
271.0605 C15H11O5+ 1 271.0601 1.33
273.0547 C18H9O3+ 1 273.0546 0.4
275.0703 C18H11O3+ 1 275.0703 0.22
277.086 C18H13O3+ 1 277.0859 0.14
278.0575 C17H10O4+ 1 278.0574 0.47
279.0652 C17H11O4+ 1 279.0652 0.2
280.0731 C17H12O4+ 1 280.073 0.5
281.081 C17H13O4+ 1 281.0808 0.48
281.104 C17H15NO3+ 1 281.1046 -2.26
282.0523 C16H10O5+ 1 282.0523 0.02
282.1126 C17H16NO3+ 1 282.1125 0.53
283.0602 C16H11O5+ 1 283.0601 0.32
283.096 C17H15O4+ 1 283.0965 -1.75
285.0759 C16H13O5+ 1 285.0757 0.35
286.1439 C17H20NO3+ 1 286.1438 0.45
287.0915 C16H15O5+ 1 287.0914 0.49
289.0501 C18H9O4+ 1 289.0495 2.06
290.0578 C18H10O4+ 1 290.0574 1.69
291.0652 C18H11O4+ 1 291.0652 -0.12
292.0734 C18H12O4+ 1 292.073 1.2
293.0809 C18H13O4+ 1 293.0808 0.12
294.052 C17H10O5+ 1 294.0523 -0.93
294.1127 C18H16NO3+ 1 294.1125 0.78
295.0608 C17H11O5+ 1 295.0601 2.47
295.0964 C18H15O4+ 1 295.0965 -0.15
296.1282 C18H18NO3+ 1 296.1281 0.1
297.0757 C17H13O5+ 1 297.0757 -0.3
298.1064 C17H16NO4+ 1 298.1074 -3.44
299.0917 C17H15O5+ 1 299.0914 0.87
301.0493 C19H9O4+ 1 301.0495 -0.88
303.0653 C19H11O4+ 1 303.0652 0.28
305.0806 C19H13O4+ 1 305.0808 -0.9
305.1044 C19H15NO3+ 1 305.1046 -0.7
306.0523 C18H10O5+ 1 306.0523 0.18
307.06 C18H11O5+ 1 307.0601 -0.23
307.0974 C19H15O4+ 1 307.0965 2.82
308.0681 C18H12O5+ 1 308.0679 0.63
308.1283 C19H18NO3+ 1 308.1281 0.68
309.0759 C18H13O5+ 1 309.0757 0.58
311.0914 C18H15O5+ 1 311.0914 -0.06
314.1388 C18H20NO4+ 1 314.1387 0.3
315.0868 C17H15O6+ 1 315.0863 1.67
318.1123 C20H16NO3+ 1 318.1125 -0.44
319.0602 C19H11O5+ 1 319.0601 0.44
320.1288 C20H18NO3+ 1 320.1281 2.25
321.0758 C19H13O5+ 1 321.0757 0.25
322.0476 C18H10O6+ 1 322.0472 1.21
323.0921 C19H15O5+ 1 323.0914 2.07
324.0634 C18H12O6+ 1 324.0628 1.7
324.1228 C19H18NO4+ 1 324.123 -0.6
331.0604 C20H11O5+ 1 331.0601 0.76
332.1494 C18H22NO5+ 1 332.1492 0.57
334.0471 C19H10O6+ 1 334.0472 -0.15
336.123 C20H18NO4+ 1 336.123 -0.16
337.0707 C19H13O6+ 1 337.0707 0.13
338.1384 C20H20NO4+ 1 338.1387 -0.93
339.0864 C19H15O6+ 1 339.0863 0.25
347.0551 C20H11O6+ 1 347.055 0.16
348.1234 C21H18NO4+ 1 348.123 0.96
349.0709 C20H13O6+ 1 349.0707 0.82
349.0942 C20H15NO5+ 1 349.0945 -0.7
350.0423 C19H10O7+ 1 350.0421 0.7
352.0584 C19H12O7+ 1 352.0578 1.69
354.1332 C20H20NO5+ 1 354.1336 -1.18
355.0816 C19H15O7+ 1 355.0812 1.16
364.1178 C21H18NO5+ 1 364.1179 -0.35
365.0658 C20H13O7+ 1 365.0656 0.5
366.1338 C21H20NO5+ 1 366.1336 0.49
367.0814 C20H15O7+ 1 367.0812 0.36
374.1019 C22H16NO5+ 1 374.1023 -1.04
377.0894 C21H15NO6+ 1 377.0894 -0.05
382.1286 C21H20NO6+ 1 382.1285 0.12
383.0758 C20H15O8+ 1 383.0761 -0.98
384.1438 C21H22NO6+ 1 384.1442 -0.9
392.1129 C22H18NO6+ 1 392.1129 0.14
400.1398 C21H22NO7+ 1 400.1391 1.85
410.1235 C22H20NO7+ 1 410.1234 0.13
428.134 C22H22NO8+ 1 428.134 0.02
PK$NUM_PEAK: 263
PK$PEAK: m/z int. rel.int.
55.0178 140043.1 26
56.0495 83862.1 15
58.0651 1171098.6 222
68.0494 8372.1 1
68.997 25728.2 4
70.0651 88095.7 16
72.0444 257500.9 48
72.0807 36701.3 6
74.0599 30848.4 5
81.0335 13144.8 2
82.0651 27599.5 5
83.0127 28649.6 5
84.0444 531510.6 100
84.0807 27787.6 5
85.0283 13849.2 2
85.0521 8154.7 1
86.06 80782.5 15
94.065 8303.3 1
95.0128 75633.4 14
97.0285 7240.7 1
98.0601 2985678.2 567
99.0077 30102.2 5
100.0757 321546.1 61
108.0443 26368.7 5
109.0285 30651 5
110.0602 32316.2 6
111.0076 39973.8 7
111.044 9787 1
112.0756 8700.3 1
114.055 102124.8 19
115.054 8903.6 1
121.0285 40079.8 7
121.0648 56956.3 10
123.0076 33729.3 6
123.0443 7022.2 1
124.0394 159463.6 30
124.0758 8079.5 1
125.0233 7931.1 1
126.055 1790935.8 340
127.0026 32470.7 6
128.0707 46111.6 8
131.0491 24081.1 4
135.0074 6709.3 1
136.0757 36439.3 6
137.0233 152833.9 29
139.0266 54560.5 10
139.0391 39020.8 7
140.0704 13653.6 2
142.0499 40811.9 7
144.0655 116769 22
145.065 90395.4 17
147.044 43786.4 8
147.0805 100560.4 19
149.0234 47417.9 9
149.0445 8142.9 1
149.0602 44593.5 8
152.0343 118792.9 22
152.0709 50955.2 9
153.0182 75340.6 14
154.0499 4267560 810
155.0341 11669.8 2
157.0369 11460.1 2
157.065 14814.2 2
158.0729 33390.4 6
159.0441 41570.6 7
159.0807 49502.4 9
160.052 9791.6 1
161.0597 64907.1 12
163.0026 34294.7 6
163.0391 7570.5 1
163.0628 11492.6 2
164.0706 100413.4 19
165.0183 310433.2 58
166.0498 10523.2 1
166.0865 30725.2 5
167.034 79871.9 15
167.0557 13710.4 2
168.0655 25612.9 4
170.0448 75650.4 14
170.081 14778.8 2
171.0806 25420.3 4
172.0603 89697.4 17
173.0598 210969.9 40
174.0675 155977.2 29
175.0754 775488.3 147
177.0185 8098.8 1
178.05 77754.5 14
178.9974 13421.9 2
179.0338 14706.6 2
179.0852 9557.4 1
180.0656 109097.7 20
181.0132 41980.6 7
181.0365 6618.9 1
182.0448 103480.4 19
182.0813 265744.8 50
183.0288 29628.4 5
183.0805 11872.1 2
184.0511 6359.7 1
185.0599 49190.1 9
185.0962 11741 2
187.0392 57303.8 10
187.0754 459398.3 87
190.0498 26047.4 4
190.9976 23666.5 4
191.0343 12731.2 2
192.0656 269019.1 51
193.0133 40985.3 7
194.0448 13384.9 2
195.0805 154776 29
196.0606 77794.8 14
197.0599 31494.9 5
197.096 70037.3 13
198.0673 27988.3 5
198.0756 16634.6 3
199.0754 153505.1 29
201.0547 2179866.8 414
203.0337 7482 1
203.0703 101792.1 19
204.0662 10870.4 2
205.0496 35894.7 6
206.0449 10521.9 1
207.0805 36735.4 6
208.0606 111127 21
209.0082 35018.2 6
209.0965 25766.4 4
210.0676 26506 5
210.0762 335145.2 63
211.0754 192117 36
212.0833 12198.6 2
213.0548 138791.9 26
213.0911 443260.5 84
214.0617 6684.4 1
215.0704 72424.2 13
217.0129 11409.6 2
219.0293 28480.7 5
219.0653 436724.9 82
219.0809 27088 5
221.0601 8549.6 1
221.071 8397.8 1
221.0959 22389.6 4
222.0767 11423.4 2
223.0755 307162.9 58
224.0834 7292.3 1
225.0912 315337 59
226.0622 180534.7 34
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//
