ACCESSION: MSBNK-Eawag-EQ367807
RECORD_TITLE: Doxycycline; LC-ESI-QFT; MS2; CE: 120; 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 120 (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: splash10-014i-2900000000-e5ffc3e6114b39eecd3f
PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm)
50.0151 C4H2+ 1 50.0151 0.17
51.0229 C4H3+ 1 51.0229 -0.13
53.0022 C3HO+ 1 53.0022 0.73
53.0386 C4H5+ 1 53.0386 0.44
54.0338 C3H4N+ 1 54.0338 0.27
55.0179 C3H3O+ 1 55.0178 0.34
55.0417 C3H5N+ 1 55.0417 0.72
56.0495 C3H6N+ 1 56.0495 0.44
57.0335 C3H5O+ 1 57.0335 0.5
57.0573 C3H7N+ 1 57.0573 0.51
58.0651 C3H8N+ 1 58.0651 0.07
62.015 C5H2+ 1 62.0151 -1.31
63.0228 C5H3+ 1 63.0229 -1.21
65.0386 C5H5+ 1 65.0386 -0.1
66.0338 C4H4N+ 1 66.0338 -0.54
66.0464 C5H6+ 1 66.0464 -0.33
67.0178 C4H3O+ 1 67.0178 -0.32
67.0417 C4H5N+ 1 67.0417 0.44
67.0542 C5H7+ 1 67.0542 -0.55
68.0257 C4H4O+ 1 68.0257 -0.09
68.0495 C4H6N+ 1 68.0495 -0.23
68.9971 C3HO2+ 1 68.9971 -0.08
69.0334 C4H5O+ 1 69.0335 -1.03
70.0651 C4H8N+ 1 70.0651 -0.08
71.0365 C3H5NO+ 1 71.0366 -0.64
71.0729 C4H9N+ 1 71.073 -0.71
72.0444 C3H6NO+ 1 72.0444 0
72.0808 C4H10N+ 1 72.0808 0.06
75.0228 C6H3+ 1 75.0229 -1.69
76.0307 C6H4+ 1 76.0308 -1.07
77.0021 C5HO+ 1 77.0022 -0.92
77.0385 C6H5+ 1 77.0386 -0.86
78.0464 C6H6+ 1 78.0464 0.24
79.0178 C5H3O+ 1 79.0178 -0.27
79.0542 C6H7+ 1 79.0542 0.04
80.0494 C5H6N+ 1 80.0495 -0.44
81.0335 C5H5O+ 1 81.0335 0.11
81.0573 C5H7N+ 1 81.0573 -0.13
82.0651 C5H8N+ 1 82.0651 -0.68
83.0127 C4H3O2+ 1 83.0128 -0.55
83.0366 C4H5NO+ 1 83.0366 -0.06
84.0444 C4H6NO+ 1 84.0444 -0.36
84.0807 C5H10N+ 1 84.0808 -0.31
85.0285 C4H5O2+ 1 85.0284 1.58
86.0148 C7H2+ 1 86.0151 -3.51
86.06 C4H8NO+ 1 86.06 -0.93
87.0227 C7H3+ 1 87.0229 -2.37
88.0306 C7H4+ 1 88.0308 -2.18
89.0385 C7H5+ 1 89.0386 -0.41
90.0464 C7H6+ 1 90.0464 0.43
91.0542 C7H7+ 1 91.0542 0.26
92.0256 C6H4O+ 1 92.0257 -0.28
92.0494 C6H6N+ 1 92.0495 -1.26
93.0335 C6H5O+ 1 93.0335 0.2
93.0573 C6H7N+ 1 93.0573 0.32
93.0698 C7H9+ 1 93.0699 -1.15
94.0414 C6H6O+ 1 94.0413 1.42
94.0652 C6H8N+ 1 94.0651 0.26
95.0127 C5H3O2+ 1 95.0128 -0.27
95.0492 C6H7O+ 1 95.0491 0.2
96.0443 C5H6NO+ 1 96.0444 -0.42
96.0807 C6H10N+ 1 96.0808 -0.79
97.0285 C5H5O2+ 1 97.0284 0.76
97.0523 C5H7NO+ 1 97.0522 0.77
98.0601 C5H8NO+ 1 98.06 0.3
101.0387 C8H5+ 1 101.0386 1.42
102.0464 C8H6+ 1 102.0464 0.18
103.0542 C8H7+ 1 103.0542 0.03
104.062 C8H8+ 1 104.0621 -0.78
105.0336 C7H5O+ 1 105.0335 0.75
105.0448 C6H5N2+ 1 105.0447 0.34
105.0699 C8H9+ 1 105.0699 0.32
106.0652 C7H8N+ 1 106.0651 0.98
107.0129 C6H3O2+ 1 107.0128 1.63
107.0491 C7H7O+ 1 107.0491 -0.01
108.0443 C6H6NO+ 1 108.0444 -0.93
109.0285 C6H5O2+ 1 109.0284 0.86
110.06 C6H8NO+ 1 110.06 -0.82
111.0077 C5H3O3+ 1 111.0077 0.54
111.044 C6H7O2+ 1 111.0441 -0.05
113.0386 C9H5+ 1 113.0386 0.03
114.0464 C9H6+ 1 114.0464 -0.1
115.0543 C9H7+ 1 115.0542 0.38
116.0621 C9H8+ 1 116.0621 0.07
117.0699 C9H9+ 1 117.0699 0.03
118.0413 C8H6O+ 1 118.0413 -0.22
118.0653 C8H8N+ 1 118.0651 1.22
119.0128 C7H3O2+ 1 119.0128 0.71
119.0493 C8H7O+ 1 119.0491 1.33
119.0855 C9H11+ 1 119.0855 -0.56
121.0283 C7H5O2+ 1 121.0284 -0.79
121.0397 C6H5N2O+ 1 121.0396 0.92
121.0643 C8H9O+ 1 121.0648 -3.89
123.0078 C6H3O3+ 1 123.0077 1.22
124.0155 C6H4O3+ 1 124.0155 -0.12
125.0231 C6H5O3+ 1 125.0233 -1.92
125.0387 C10H5+ 1 125.0386 0.59
126.0464 C10H6+ 1 126.0464 0.3
127.0542 C10H7+ 1 127.0542 0.18
128.0621 C10H8+ 1 128.0621 0.22
129.0447 C8H5N2+ 1 129.0447 -0.04
129.0699 C10H9+ 1 129.0699 0.18
130.0416 C9H6O+ 1 130.0413 2.49
131.0492 C9H7O+ 1 131.0491 0.52
131.0856 C10H11+ 1 131.0855 0.48
132.0571 C9H8O+ 1 132.057 0.86
134.0601 C8H8NO+ 1 134.06 0.45
135.0077 C7H3O3+ 1 135.0077 0.44
137.0233 C7H5O3+ 1 137.0233 0.07
137.0385 C11H5+ 1 137.0386 -0.27
138.0462 C11H6+ 1 138.0464 -1.1
139.0543 C11H7+ 1 139.0542 0.24
140.0621 C11H8+ 1 140.0621 0.2
141.0699 C11H9+ 1 141.0699 0.09
142.0414 C10H6O+ 1 142.0413 0.45
142.0778 C11H10+ 1 142.0777 0.83
143.0491 C10H7O+ 1 143.0491 0.06
143.0853 C11H11+ 1 143.0855 -1.31
144.057 C10H8O+ 1 144.057 0.37
145.0649 C10H9O+ 1 145.0648 0.4
147.0439 C9H7O2+ 1 147.0441 -1.13
147.0804 C10H11O+ 1 147.0804 -0.21
150.0463 C12H6+ 1 150.0464 -0.48
151.0543 C12H7+ 1 151.0542 0.49
152.0621 C12H8+ 1 152.0621 0.38
153.0699 C12H9+ 1 153.0699 0.35
154.0777 C12H10+ 1 154.0777 0.25
155.0493 C11H7O+ 1 155.0491 0.77
155.0604 C10H7N2+ 1 155.0604 0.16
155.0855 C12H11+ 1 155.0855 0.09
156.0571 C11H8O+ 1 156.057 1.11
157.0649 C11H9O+ 1 157.0648 0.44
158.0726 C11H10O+ 1 158.0726 -0.23
159.0442 C10H7O2+ 1 159.0441 0.84
159.0807 C11H11O+ 1 159.0804 1.88
160.0519 C10H8O2+ 1 160.0519 0.31
163.0542 C13H7+ 1 163.0542 0.02
164.0621 C13H8+ 1 164.0621 0.05
165.07 C13H9+ 1 165.0699 0.57
166.0778 C13H10+ 1 166.0777 0.59
167.0491 C12H7O+ 1 167.0491 0.05
167.0856 C13H11+ 1 167.0855 0.74
168.057 C12H8O+ 1 168.057 0.38
169.0648 C12H9O+ 1 169.0648 0.29
170.0726 C12H10O+ 1 170.0726 -0.39
171.0441 C11H7O2+ 1 171.0441 0.32
171.0804 C12H11O+ 1 171.0804 -0.07
172.0517 C11H8O2+ 1 172.0519 -0.88
173.0598 C11H9O2+ 1 173.0597 0.31
174.0675 C11H10O2+ 1 174.0675 -0.24
175.0546 C14H7+ 1 175.0542 2.13
176.0621 C14H8+ 1 176.0621 0.39
177.07 C14H9+ 1 177.0699 0.58
178.0778 C14H10+ 1 178.0777 0.55
179.0491 C13H7O+ 1 179.0491 0.05
179.0603 C12H7N2+ 1 179.0604 -0.14
179.0854 C14H11+ 1 179.0855 -0.54
180.057 C13H8O+ 1 180.057 0.13
181.0648 C13H9O+ 1 181.0648 0.1
182.0726 C13H10O+ 1 182.0726 -0.03
183.0549 C11H7N2O+ 1 183.0553 -2.29
183.0804 C13H11O+ 1 183.0804 -0.23
184.0519 C12H8O2+ 1 184.0519 -0.17
185.0597 C12H9O2+ 1 185.0597 -0.3
185.0712 C11H9N2O+ 1 185.0709 1.3
186.0675 C12H10O2+ 1 186.0675 -0.17
187.039 C11H7O3+ 1 187.039 0.21
187.0546 C15H7+ 1 187.0542 1.94
187.0754 C12H11O2+ 1 187.0754 0.4
188.0623 C15H8+ 1 188.0621 1.32
189.0699 C15H9+ 1 189.0699 0.12
190.0653 C14H8N+ 1 190.0651 0.97
190.0779 C15H10+ 1 190.0777 0.94
191.0735 C14H9N+ 1 191.073 2.77
191.0853 C15H11+ 1 191.0855 -1.24
192.057 C14H8O+ 1 192.057 0.02
193.0649 C14H9O+ 1 193.0648 0.61
194.0727 C14H10O+ 1 194.0726 0.48
195.0442 C13H7O2+ 1 195.0441 0.64
195.0805 C14H11O+ 1 195.0804 0.51
196.052 C13H8O2+ 1 196.0519 0.35
197.0598 C13H9O2+ 1 197.0597 0.27
198.0674 C13H10O2+ 1 198.0675 -0.46
200.0467 C12H8O3+ 1 200.0468 -0.43
200.0621 C16H8+ 1 200.0621 0.29
201.0548 C12H9O3+ 1 201.0546 1.04
201.0698 C16H9+ 1 201.0699 -0.53
202.0778 C16H10+ 1 202.0777 0.54
203.0597 C14H7N2+ 1 203.0604 -3.22
203.0728 C15H9N+ 1 203.073 -0.84
204.057 C15H8O+ 1 204.057 -0.08
205.065 C15H9O+ 1 205.0648 0.97
206.073 C15H10O+ 1 206.0726 1.96
207.0441 C14H7O2+ 1 207.0441 0.41
207.0805 C15H11O+ 1 207.0804 0.38
208.0518 C14H8O2+ 1 208.0519 -0.39
208.0876 C15H12O+ 1 208.0883 -3.11
209.0595 C14H9O2+ 1 209.0597 -0.94
210.0675 C14H10O2+ 1 210.0675 0
211.0392 C13H7O3+ 1 211.039 0.99
211.0753 C14H11O2+ 1 211.0754 -0.27
212.0471 C13H8O3+ 1 212.0468 1.39
213.055 C13H9O3+ 1 213.0546 1.59
217.0646 C16H9O+ 1 217.0648 -1.07
218.0727 C16H10O+ 1 218.0726 0.25
219.0807 C16H11O+ 1 219.0804 1.32
220.052 C15H8O2+ 1 220.0519 0.68
221.0599 C15H9O2+ 1 221.0597 0.79
222.0685 C15H10O2+ 1 222.0675 4.32
223.0391 C14H7O3+ 1 223.039 0.45
223.0754 C15H11O2+ 1 223.0754 0.2
224.0465 C14H8O3+ 1 224.0468 -1.36
225.0546 C14H9O3+ 1 225.0546 -0.31
226.0628 C14H10O3+ 1 226.0624 1.74
229.0645 C17H9O+ 1 229.0648 -1.23
233.0598 C16H9O2+ 1 233.0597 0.53
234.0673 C16H10O2+ 1 234.0675 -1.07
234.0908 C16H12NO+ 1 234.0913 -2.52
236.0472 C15H8O3+ 1 236.0468 1.54
237.0545 C15H9O3+ 1 237.0546 -0.64
238.0629 C15H10O3+ 1 238.0624 1.78
241.0495 C14H9O4+ 1 241.0495 0.02
249.0553 C16H9O3+ 1 249.0546 2.57
250.0626 C16H10O3+ 1 250.0624 0.58
PK$NUM_PEAK: 224
PK$PEAK: m/z int. rel.int.
50.0151 88775.2 29
51.0229 63054.8 20
53.0022 99642.2 33
53.0386 231770.8 77
54.0338 47967.7 15
55.0179 411633.8 137
55.0417 140660.5 46
56.0495 129155 42
57.0335 9130.9 3
57.0573 10870.8 3
58.0651 886765.2 295
62.015 13351.7 4
63.0228 114611 38
65.0386 346905.2 115
66.0338 7069.3 2
66.0464 11562.4 3
67.0178 97898.8 32
67.0417 44284.5 14
67.0542 23761 7
68.0257 22656.3 7
68.0495 165095.8 54
68.9971 492354.3 163
69.0334 40635.6 13
70.0651 441138.2 146
71.0365 30833.5 10
71.0729 25130.1 8
72.0444 86053 28
72.0808 13666.4 4
75.0228 56887.2 18
76.0307 5943.6 1
77.0021 8329.4 2
77.0385 125142.9 41
78.0464 44764.4 14
79.0178 152624.5 50
79.0542 104901.4 34
80.0494 75297.3 25
81.0335 166527.7 55
81.0573 27569.6 9
82.0651 89178.9 29
83.0127 90496.8 30
83.0366 58795 19
84.0444 11047.4 3
84.0807 53377.3 17
85.0285 5451.6 1
86.0148 7659.7 2
86.06 8479 2
87.0227 7929.5 2
88.0306 5883.8 1
89.0385 132315.3 44
90.0464 30602.1 10
91.0542 1233133.6 410
92.0256 7073.8 2
92.0494 8058 2
93.0335 11247.7 3
93.0573 25484.2 8
93.0698 8321.8 2
94.0414 11465.9 3
94.0652 52650 17
95.0127 81516 27
95.0492 386131.4 128
96.0443 34111.8 11
96.0807 7075.9 2
97.0285 39664.2 13
97.0523 8084.6 2
98.0601 378477.4 125
101.0387 29683.4 9
102.0464 182720.2 60
103.0542 370054.6 123
104.062 40695.4 13
105.0336 76935.2 25
105.0448 292463.6 97
105.0699 59035.5 19
106.0652 10430.2 3
107.0129 41488.4 13
107.0491 174728.4 58
108.0443 12106.7 4
109.0285 22200.4 7
110.06 10847.7 3
111.0077 23530.6 7
111.044 9089.4 3
113.0386 50755.9 16
114.0464 65363 21
115.0543 3000936.5 999
116.0621 388763.3 129
117.0699 394947.6 131
118.0413 47882.8 15
118.0653 6526.9 2
119.0128 33179.7 11
119.0493 42110 14
119.0855 32177.8 10
121.0283 48418.4 16
121.0397 11618.1 3
121.0643 6614.7 2
123.0078 9937 3
124.0155 6242.6 2
125.0231 7026.2 2
125.0387 24084.3 8
126.0464 280831.7 93
127.0542 1627985.4 541
128.0621 1616458.1 538
129.0447 70825.9 23
129.0699 387936.8 129
130.0416 7733.9 2
131.0492 403516.3 134
131.0856 36844.5 12
132.0571 164558 54
134.0601 7831 2
135.0077 6691.4 2
137.0233 23000.3 7
137.0385 6115 2
138.0462 13342.9 4
139.0543 1658095.8 551
140.0621 1380183.4 459
141.0699 694056.1 231
142.0414 30438 10
142.0778 81461.1 27
143.0491 24274.7 8
143.0853 45392.2 15
144.057 469161.5 156
145.0649 748250.1 249
147.0439 6798.8 2
147.0804 13469 4
150.0463 95086.7 31
151.0543 119743.6 39
152.0621 2631343.8 875
153.0699 718712.6 239
154.0777 109373.4 36
155.0493 159886.9 53
155.0604 1228891.4 409
155.0855 90463.2 30
156.0571 73630.3 24
157.0649 207611 69
158.0726 26363.5 8
159.0442 10069.2 3
159.0807 41937.9 13
160.0519 235100.6 78
163.0542 346550.3 115
164.0621 357237.5 118
165.07 2773931.2 923
166.0778 198937.2 66
167.0491 40875.5 13
167.0856 99499.8 33
168.057 2634022.5 876
169.0648 665028.2 221
170.0726 80027.4 26
171.0441 20010.7 6
171.0804 40126.5 13
172.0517 51367.3 17
173.0598 113549.2 37
174.0675 12922.6 4
175.0546 24638.1 8
176.0621 818366.7 272
177.07 209715.8 69
178.0778 685334.2 228
179.0491 84933.7 28
179.0603 143862.6 47
179.0854 68325.5 22
180.057 220795.9 73
181.0648 651462.5 216
182.0726 120471.4 40
183.0549 10552.5 3
183.0804 48054.2 15
184.0519 123839.8 41
185.0597 32900.3 10
185.0712 6056.3 2
186.0675 6013.7 2
187.039 34756.4 11
187.0546 47413.4 15
187.0754 24296.4 8
188.0623 52761.4 17
189.0699 628356.6 209
190.0653 6704.4 2
190.0779 65711.5 21
191.0735 8452.4 2
191.0853 51755.5 17
192.057 140062.5 46
193.0649 144975.3 48
194.0727 202214.9 67
195.0442 41371.9 13
195.0805 69928.1 23
196.052 311866.8 103
197.0598 560789.4 186
198.0674 114824.2 38
200.0467 27880.9 9
200.0621 75592.5 25
201.0548 22089.1 7
201.0698 23627.1 7
202.0778 82663.6 27
203.0597 8564 2
203.0728 8948.2 2
204.057 67151.9 22
205.065 190729.5 63
206.073 13580.4 4
207.0441 12332.5 4
207.0805 39270 13
208.0518 59694.8 19
208.0876 6255.3 2
209.0595 48280.2 16
210.0675 64414.5 21
211.0392 24852.1 8
211.0753 88112.5 29
212.0471 23770.6 7
213.055 13135.8 4
217.0646 11618.5 3
218.0727 48383.5 16
219.0807 25875.3 8
220.052 24272.1 8
221.0599 197820.8 65
222.0685 19709.4 6
223.0391 11406.4 3
223.0754 12323.3 4
224.0465 29938.8 9
225.0546 44180.3 14
226.0628 48989.3 16
229.0645 8108.7 2
233.0598 12135.9 4
234.0673 20937.3 6
234.0908 6502.2 2
236.0472 13330.3 4
237.0545 8192.5 2
238.0629 8690.2 2
241.0495 7238.9 2
249.0553 12554.1 4
250.0626 10981.6 3
//
