ACCESSION: MSBNK-Eawag-EQ367852
RECORD_TITLE: Doxycycline; LC-ESI-QFT; MS2; CE: 30; 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 30 (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: splash10-0a4i-0589100000-4e4c770555258e2ec680
PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm)
84.0089 C3H2NO2- 1 84.0091 -2.28
85.0294 C4H5O2- 1 85.0295 -1.09
93.0346 C6H5O- 1 93.0346 0.02
95.0138 C5H3O2- 1 95.0139 -0.14
96.0091 C4H2NO2- 1 96.0091 -0.44
97.0295 C5H5O2- 1 97.0295 -0.13
99.0087 C4H3O3- 1 99.0088 -0.88
100.0768 C5H10NO- 1 100.0768 0.22
108.0215 C6H4O2- 1 108.0217 -1.46
109.0294 C6H5O2- 1 109.0295 -0.49
111.0087 C5H3O3- 1 111.0088 -0.97
119.0138 C7H3O2- 1 119.0139 -0.36
119.0499 C8H7O- 1 119.0502 -3.09
123.0088 C6H3O3- 1 123.0088 -0.14
124.0165 C6H4O3- 1 124.0166 -1.07
124.0766 C7H10NO- 1 124.0768 -1.51
124.988 C5HO4- 1 124.988 -0.18
125.0243 C6H5O3- 1 125.0244 -0.86
125.072 C6H9N2O- 1 125.072 -0.21
126.056 C6H8NO2- 1 126.0561 -0.1
128.0353 C5H6NO3- 1 128.0353 -0.44
134.0247 C7H4NO2- 1 134.0248 -0.46
135.0088 C7H3O3- 1 135.0088 0.54
136.0401 C7H6NO2- 1 136.0404 -2.37
136.0766 C8H10NO- 1 136.0768 -1.3
136.988 C6HO4- 1 136.988 -0.09
137.0243 C7H5O3- 1 137.0244 -0.49
138.032 C7H6O3- 1 138.0322 -1.61
138.0558 C7H8NO2- 1 138.0561 -1.54
138.0924 C8H12NO- 1 138.0924 -0.63
140.0353 C6H6NO3- 1 140.0353 -0.19
140.0716 C7H10NO2- 1 140.0717 -1.09
141.0191 C6H5O4- 1 141.0193 -1.29
142.0145 C5H4NO4- 1 142.0146 -0.64
142.9985 C5H3O5- 1 142.9986 -0.4
143.0824 C6H11N2O2- 1 143.0826 -1.06
147.0451 C9H7O2- 1 147.0452 -0.16
149.0608 C9H9O2- 1 149.0608 -0.09
150.0196 C7H4NO3- 1 150.0197 -0.44
151.0038 C7H3O4- 1 151.0037 0.85
151.0275 C7H5NO3- 1 151.0275 0.19
152.0353 C7H6NO3- 1 152.0353 -0.11
152.0717 C8H10NO2- 1 152.0717 -0.15
153.0191 C7H5O4- 1 153.0193 -1.58
154.0384 C6H6N2O3- 1 154.0384 0
154.0874 C8H12NO2- 1 154.0874 0.18
159.0448 C10H7O2- 1 159.0452 -2.28
159.0815 C11H11O- 1 159.0815 -0.31
161.061 C10H9O2- 1 161.0608 1.1
162.02 C8H4NO3- 1 162.0197 1.93
163.0037 C8H3O4- 1 163.0037 0.23
164.0117 C8H4O4- 1 164.0115 1.36
164.0716 C9H10NO2- 1 164.0717 -0.74
166.0145 C7H4NO4- 1 166.0146 -0.49
166.0513 C8H8NO3- 1 166.051 1.77
167.0223 C7H5NO4- 1 167.0224 -0.7
168.0302 C7H6NO4- 1 168.0302 -0.19
168.0666 C8H10NO3- 1 168.0666 -0.22
169.0255 C6H5N2O4- 1 169.0255 -0.06
169.0619 C7H9N2O3- 1 169.0619 0.2
171.0817 C12H11O- 1 171.0815 1.12
172.0532 C11H8O2- 1 172.053 1.12
173.0607 C11H9O2- 1 173.0608 -0.83
178.0145 C8H4NO4- 1 178.0146 -0.74
178.9986 C8H3O5- 1 178.9986 0.07
179.0825 C9H11N2O2- 1 179.0826 -0.34
180.0303 C8H6NO4- 1 180.0302 0.16
180.0666 C9H10NO3- 1 180.0666 -0.04
181.0381 C8H7NO4- 1 181.0381 0.35
181.0618 C8H9N2O3- 1 181.0619 -0.42
182.082 C9H12NO3- 1 182.0823 -1.3
186.0688 C12H10O2- 1 186.0686 1.03
187.0764 C12H11O2- 1 187.0765 -0.39
189.0559 C11H9O3- 1 189.0557 0.96
189.0668 C10H9N2O2- 1 189.067 -0.91
192.0539 C9H8N2O3- 1 192.054 -0.94
195.0773 C9H11N2O3- 1 195.0775 -1.26
196.025 C8H6NO5- 1 196.0251 -0.59
196.061 C9H10NO4- 1 196.0615 -2.66
197.0931 C9H13N2O3- 1 197.0932 -0.44
198.0771 C9H12NO4- 1 198.0772 -0.31
199.0397 C12H7O3- 1 199.0401 -1.65
199.0764 C13H11O2- 1 199.0765 -0.37
201.0557 C12H9O3- 1 201.0557 -0.14
203.0714 C12H11O3- 1 203.0714 0.31
207.0775 C10H11N2O3- 1 207.0775 -0.17
208.0615 C10H10NO4- 1 208.0615 -0.25
211.04 C13H7O3- 1 211.0401 -0.46
211.0768 C14H11O2- 1 211.0765 1.64
213.0554 C13H9O3- 1 213.0557 -1.3
213.0919 C14H13O2- 1 213.0921 -1.14
215.0712 C13H11O3- 1 215.0714 -0.97
217.0506 C12H9O4- 1 217.0506 -0.06
221.097 C16H13O- 1 221.0972 -0.67
223.0773 C15H11O2- 1 223.0765 3.98
225.0881 C10H13N2O4- 1 225.0881 0
226.0724 C10H12NO5- 1 226.0721 1.3
227.0352 C13H7O4- 1 227.035 0.91
227.0714 C14H11O3- 1 227.0714 0.23
229.0505 C13H9O4- 1 229.0506 -0.4
229.0871 C14H13O3- 1 229.087 0.23
231.0666 C13H11O4- 1 231.0663 1.5
234.0685 C16H10O2- 1 234.0686 -0.33
237.092 C16H13O2- 1 237.0921 -0.52
238.0638 C15H10O3- 1 238.0635 1.16
239.0714 C15H11O3- 1 239.0714 0.09
240.0427 C14H8O4- 1 240.0428 -0.66
241.0507 C14H9O4- 1 241.0506 0.11
241.0871 C15H13O3- 1 241.087 0.22
243.0665 C14H11O4- 1 243.0663 0.94
247.0755 C17H11O2- 1 247.0765 -3.66
249.0556 C16H9O3- 1 249.0557 -0.55
249.0918 C17H13O2- 1 249.0921 -1.1
250.0632 C16H10O3- 1 250.0635 -1.21
251.0712 C16H11O3- 1 251.0714 -0.67
252.0788 C16H12O3- 1 252.0792 -1.6
253.0507 C15H9O4- 1 253.0506 0.27
253.0869 C16H13O3- 1 253.087 -0.39
254.0823 C15H12NO3- 1 254.0823 0.17
255.0663 C15H11O4- 1 255.0663 -0.01
256.0976 C15H14NO3- 1 256.0979 -1.04
256.1347 C16H18NO2- 1 256.1343 1.67
257.0456 C14H9O5- 1 257.0455 0.28
257.0817 C15H13O4- 1 257.0819 -0.83
258.1135 C15H16NO3- 1 258.1136 -0.18
260.0471 C17H8O3- 1 260.0479 -2.86
261.0554 C17H9O3- 1 261.0557 -1.37
263.0708 C17H11O3- 1 263.0714 -2.16
265.0869 C17H13O3- 1 265.087 -0.41
266.0949 C17H14O3- 1 266.0948 0.25
267.0662 C16H11O4- 1 267.0663 -0.23
267.1023 C17H15O3- 1 267.1027 -1.53
268.0974 C16H14NO3- 1 268.0979 -2
268.1341 C17H18NO2- 1 268.1343 -0.68
269.0819 C16H13O4- 1 269.0819 0.03
270.1136 C16H16NO3- 1 270.1136 -0.03
271.0979 C16H15O4- 1 271.0976 1.28
273.0768 C15H13O5- 1 273.0768 -0.25
275.0714 C18H11O3- 1 275.0714 0.04
276.0797 C18H12O3- 1 276.0792 1.76
277.0502 C17H9O4- 1 277.0506 -1.56
277.0869 C18H13O3- 1 277.087 -0.5
278.0585 C17H10O4- 1 278.0585 0.26
278.0815 C17H12NO3- 1 278.0823 -2.61
278.1186 C18H16NO2- 1 278.1187 -0.22
279.066 C17H11O4- 1 279.0663 -1.08
280.0747 C17H12O4- 1 280.0741 2.26
280.0973 C17H14NO3- 1 280.0979 -2.13
281.0818 C17H13O4- 1 281.0819 -0.29
281.1053 C17H15NO3- 1 281.1057 -1.64
282.1132 C17H16NO3- 1 282.1136 -1.44
283.0975 C17H15O4- 1 283.0976 -0.4
284.129 C17H18NO3- 1 284.1292 -0.69
285.0765 C16H13O5- 1 285.0768 -1.22
290.0822 C18H12NO3- 1 290.0823 -0.09
291.0663 C18H11O4- 1 291.0663 -0.01
292.0739 C18H12O4- 1 292.0741 -0.57
292.0975 C18H14NO3- 1 292.0979 -1.43
292.1346 C19H18NO2- 1 292.1343 1.16
293.082 C18H13O4- 1 293.0819 0.3
294.0901 C18H14O4- 1 294.0898 1.1
294.1136 C18H16NO3- 1 294.1136 0.04
294.1499 C19H20NO2- 1 294.15 -0.11
295.0612 C17H11O5- 1 295.0612 0.15
295.0974 C18H15O4- 1 295.0976 -0.52
296.0921 C17H14NO4- 1 296.0928 -2.61
296.1292 C18H18NO3- 1 296.1292 -0.06
297.0768 C17H13O5- 1 297.0768 -0.16
300.1244 C17H18NO4- 1 300.1241 1.03
304.0619 C18H10NO4- 1 304.0615 1.25
305.0456 C18H9O5- 1 305.0455 0.21
305.1059 C19H15NO3- 1 305.1057 0.65
305.1301 C19H17N2O2- 1 305.1296 1.83
308.0928 C18H14NO4- 1 308.0928 -0.04
308.129 C19H18NO3- 1 308.1292 -0.67
309.0769 C18H13O5- 1 309.0768 0.04
310.145 C19H20NO3- 1 310.1449 0.43
311.0927 C18H15O5- 1 311.0925 0.75
312.1244 C18H18NO4- 1 312.1241 0.86
312.1605 C19H22NO3- 1 312.1605 0.07
313.0716 C17H13O6- 1 313.0718 -0.39
314.14 C18H20NO4- 1 314.1398 0.79
318.0771 C19H12NO4- 1 318.0772 -0.26
318.1135 C20H16NO3- 1 318.1136 -0.37
319.0614 C19H11O5- 1 319.0612 0.48
320.0695 C19H12O5- 1 320.069 1.59
320.1289 C20H18NO3- 1 320.1292 -0.93
321.0639 C18H11NO5- 1 321.0643 -1.28
321.101 C19H15NO4- 1 321.1007 0.95
322.0479 C18H10O6- 1 322.0483 -1.32
323.1161 C19H17NO4- 1 323.1163 -0.55
323.1396 C19H19N2O3- 1 323.1401 -1.6
326.1037 C18H16NO5- 1 326.1034 0.78
326.1396 C19H20NO4- 1 326.1398 -0.65
327.0882 C18H15O6- 1 327.0874 2.44
328.1554 C19H22NO4- 1 328.1554 -0.16
334.0709 C19H12NO5- 2 334.0721 -3.67
335.0564 C19H11O6- 1 335.0561 0.71
335.1404 C20H19N2O3- 1 335.1401 0.82
336.089 C19H14NO5- 2 336.0877 3.64
336.1242 C20H18NO4- 1 336.1241 0.17
337.0721 C19H13O6- 1 337.0718 0.97
337.0951 C19H15NO5- 1 337.0956 -1.49
338.0807 C19H14O6- 2 338.0796 3.2
338.1398 C20H20NO4- 1 338.1398 0.17
340.1189 C19H18NO5- 1 340.119 -0.58
349.0958 C20H15NO5- 1 349.0956 0.66
353.1507 C20H21N2O4- 1 353.1507 0.05
354.1346 C20H20NO5- 1 354.1347 -0.38
356.1503 C20H22NO5- 1 356.1503 -0.19
358.1297 C19H20NO6- 1 358.1296 0.36
359.132 C14H21N3O8- 1 359.1334 -4.05
362.0668 C20H12NO6- 1 362.067 -0.55
363.0506 C20H11O7- 1 363.051 -1.17
363.1342 C21H19N2O4- 1 363.135 -2.23
364.1191 C21H18NO5- 1 364.119 0.01
371.161 C20H23N2O5- 1 371.1612 -0.55
380.077 C20H14NO7- 1 380.0776 -1.54
381.0613 C20H13O8- 1 381.0616 -0.76
381.1456 C21H21N2O5- 1 381.1456 -0.09
382.1295 C21H20NO6- 1 382.1296 -0.34
399.1559 C21H23N2O6- 1 399.1562 -0.58
400.1399 C21H22NO7- 1 400.1402 -0.59
408.1088 C22H18NO7- 1 408.1089 -0.26
425.135 C22H21N2O7- 1 425.1354 -1
426.1193 C22H20NO8- 1 426.1194 -0.21
443.1458 C22H23N2O8- 1 443.146 -0.45
444.1295 C22H22NO9- 2 444.13 -1.09
PK$NUM_PEAK: 228
PK$PEAK: m/z int. rel.int.
84.0089 10965 5
85.0294 2102 1
93.0346 6053.3 2
95.0138 77250.2 36
96.0091 2628.1 1
97.0295 6104.8 2
99.0087 16017.2 7
100.0768 6725.2 3
108.0215 2950.4 1
109.0294 100099.4 47
111.0087 7060.6 3
119.0138 35673.1 16
119.0499 2290.6 1
123.0088 16896.9 8
124.0165 13440.5 6
124.0766 2529.3 1
124.988 11767.3 5
125.0243 16871.5 8
125.072 41305.9 19
126.056 23406.3 11
128.0353 5708.8 2
134.0247 14050.5 6
135.0088 42209.4 20
136.0401 5017.1 2
136.0766 12646.4 6
136.988 8281.6 3
137.0243 38950.7 18
138.032 2553.4 1
138.0558 12923.7 6
138.0924 2377.5 1
140.0353 20202.5 9
140.0716 9750.3 4
141.0191 3152.2 1
142.0145 280629.6 133
142.9985 30065.6 14
143.0824 22967.8 10
147.0451 38549.1 18
149.0608 12113.8 5
150.0196 9320.7 4
151.0038 10335.5 4
151.0275 2584.8 1
152.0353 123030.4 58
152.0717 30850.6 14
153.0191 9800.6 4
154.0384 8180.6 3
154.0874 18277.7 8
159.0448 5401.2 2
159.0815 5176.2 2
161.061 9788.6 4
162.02 9578.3 4
163.0037 123917.5 58
164.0117 13004.1 6
164.0716 43680.1 20
166.0145 5655 2
166.0513 2361.4 1
167.0223 26650 12
168.0302 144515.2 68
168.0666 75294 35
169.0255 11777.1 5
169.0619 95128 45
171.0817 6541.9 3
172.0532 6117.2 2
173.0607 322196.1 153
178.0145 7679.3 3
178.9986 9202.8 4
179.0825 16213.5 7
180.0303 82976.3 39
180.0666 34906.4 16
181.0381 18575 8
181.0618 14991.1 7
182.082 52314 24
186.0688 3109.9 1
187.0764 164572.7 78
189.0559 2586.1 1
189.0668 9112.2 4
192.0539 4843.7 2
195.0773 23366.9 11
196.025 39389.7 18
196.061 9675.6 4
197.0931 107109.4 50
198.0771 5597 2
199.0397 2185.4 1
199.0764 7837.2 3
201.0557 23901.2 11
203.0714 42497.8 20
207.0775 221912.5 105
208.0615 55051.4 26
211.04 6196.7 2
211.0768 39038.5 18
213.0554 16461.5 7
213.0919 7362.6 3
215.0712 7615.1 3
217.0506 579943 275
221.097 5075.6 2
223.0773 9100.5 4
225.0881 259913.1 123
226.0724 36122.4 17
227.0352 4907.9 2
227.0714 24937.9 11
229.0505 27681.8 13
229.0871 32990.2 15
231.0666 15362.8 7
234.0685 6505.8 3
237.092 7059.7 3
238.0638 5593.9 2
239.0714 40722 19
240.0427 103962.7 49
241.0507 10061.9 4
241.0871 28378.4 13
243.0665 2651.3 1
247.0755 5065.7 2
249.0556 3190.2 1
249.0918 23495 11
250.0632 5251.8 2
251.0712 26462 12
252.0788 2569 1
253.0507 5128.2 2
253.0869 24225.6 11
254.0823 5598 2
255.0663 620636.4 295
256.0976 7738.3 3
256.1347 5357.5 2
257.0456 54919.5 26
257.0817 14586.1 6
258.1135 2920.5 1
260.0471 2514.2 1
261.0554 5885 2
263.0708 2774.7 1
265.0869 68882.6 32
266.0949 2590.4 1
267.0662 22937.8 10
267.1023 15201.6 7
268.0974 6213.2 2
268.1341 8634.1 4
269.0819 137589.8 65
270.1136 6291.6 2
271.0979 2781 1
273.0768 352648.1 167
275.0714 75546.1 35
276.0797 6538.7 3
277.0502 11073.4 5
277.0869 2395.5 1
278.0585 18946.8 9
278.0815 2374.1 1
278.1186 7220.9 3
279.066 15338.6 7
280.0747 2726.5 1
280.0973 5479.8 2
281.0818 43111.3 20
281.1053 2282.7 1
282.1132 12568.5 5
283.0975 31826.4 15
284.129 12379.1 5
285.0765 18512.2 8
290.0822 2494.9 1
291.0663 29570.4 14
292.0739 7540.4 3
292.0975 2704.4 1
292.1346 13999.8 6
293.082 205673.1 97
294.0901 23938.3 11
294.1136 8782.9 4
294.1499 40522.2 19
295.0612 15351.7 7
295.0974 7233.7 3
296.0921 3072.3 1
296.1292 41591.4 19
297.0768 135785 64
300.1244 11514.7 5
304.0619 7670.6 3
305.0456 26963.8 12
305.1059 8545.8 4
305.1301 2365.8 1
308.0928 21795.2 10
308.129 3048.6 1
309.0769 138955.8 66
310.145 50601.3 24
311.0927 40941.4 19
312.1244 38615.6 18
312.1605 18646 8
313.0716 2433.1 1
314.14 27397.7 13
318.0771 8454.7 4
318.1135 10494.1 4
319.0614 27603.5 13
320.0695 9825.1 4
320.1289 50575.3 24
321.0639 2628.1 1
321.101 4660.8 2
322.0479 6056.9 2
323.1161 10924.8 5
323.1396 4735.7 2
326.1037 31283.6 14
326.1396 51311.9 24
327.0882 13580.3 6
328.1554 59393.5 28
334.0709 6793.3 3
335.0564 8502.8 4
335.1404 5158.5 2
336.089 24324.5 11
336.1242 129148.7 61
337.0721 96980.6 46
337.0951 17176.8 8
338.0807 18081.7 8
338.1398 210976.8 100
340.1189 31098.6 14
349.0958 5416.5 2
353.1507 36996.2 17
354.1346 92163.8 43
356.1503 70451.5 33
358.1297 2099432 999
359.132 2547.6 1
362.0668 5360.8 2
363.0506 11914.8 5
363.1342 11467 5
364.1191 70083.2 33
371.161 259946 123
380.077 15124.8 7
381.0613 6328.8 3
381.1456 28362.8 13
382.1295 135286.2 64
399.1559 174434.6 83
400.1399 282968 134
408.1088 67335.5 32
425.135 8937 4
426.1193 169496.4 80
443.1458 37723.6 17
444.1295 41196.4 19
//
