ACCESSION: MSBNK-Eawag-EQ367805
RECORD_TITLE: Doxycycline; LC-ESI-QFT; MS2; CE: 75; 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 75 (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: splash10-0f6t-4890000000-caa6a03b4b07eec38ef7
PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm)
50.0151 C4H2+ 1 50.0151 -0.23
51.0229 C4H3+ 1 51.0229 -0.52
53.0022 C3HO+ 1 53.0022 0.55
53.0386 C4H5+ 1 53.0386 0.44
54.0339 C3H4N+ 1 54.0338 1.75
55.0179 C3H3O+ 1 55.0178 0.16
55.0417 C3H5N+ 1 55.0417 1.44
56.0495 C3H6N+ 1 56.0495 0.08
57.0336 C3H5O+ 1 57.0335 2.26
57.0574 C3H7N+ 1 57.0573 1.22
58.0651 C3H8N+ 1 58.0651 0.07
63.0228 C5H3+ 1 63.0229 -1.21
65.0385 C5H5+ 1 65.0386 -1.02
67.0178 C4H3O+ 1 67.0178 -0.46
67.0542 C5H7+ 1 67.0542 -0.4
68.0495 C4H6N+ 1 68.0495 0.06
68.9971 C3HO2+ 1 68.9971 -0.52
69.0335 C4H5O+ 1 69.0335 -0.31
70.0651 C4H8N+ 1 70.0651 -0.37
71.0365 C3H5NO+ 1 71.0366 -0.78
71.0728 C4H9N+ 1 71.073 -1.84
72.0444 C3H6NO+ 1 72.0444 -0.42
72.0808 C4H10N+ 1 72.0808 -0.22
74.06 C3H8NO+ 1 74.06 -0.81
75.0228 C6H3+ 1 75.0229 -1.69
77.0384 C6H5+ 1 77.0386 -2.81
79.0178 C5H3O+ 1 79.0178 -0.14
79.0542 C6H7+ 1 79.0542 -0.72
80.0494 C5H6N+ 1 80.0495 -0.32
81.0335 C5H5O+ 1 81.0335 0.23
81.0571 C5H7N+ 1 81.0573 -2.48
82.0651 C5H8N+ 1 82.0651 -0.56
83.0127 C4H3O2+ 1 83.0128 -0.55
83.0366 C4H5NO+ 1 83.0366 -0.06
84.0444 C4H6NO+ 1 84.0444 0.12
84.0808 C5H10N+ 1 84.0808 -0.19
85.0284 C4H5O2+ 1 85.0284 -0.3
86.06 C4H8NO+ 1 86.06 -0.58
89.0386 C7H5+ 1 89.0386 -0.07
91.0543 C7H7+ 1 91.0542 0.92
93.0336 C6H5O+ 1 93.0335 1.49
93.0576 C6H7N+ 1 93.0573 2.79
93.0699 C7H9+ 1 93.0699 0.25
94.0652 C6H8N+ 1 94.0651 0.79
95.0127 C5H3O2+ 1 95.0128 -0.06
95.0491 C6H7O+ 1 95.0491 0.09
96.0444 C5H6NO+ 1 96.0444 0
96.0808 C6H10N+ 1 96.0808 0.67
97.0284 C5H5O2+ 1 97.0284 0.15
97.0524 C5H7NO+ 1 97.0522 1.59
98.0601 C5H8NO+ 1 98.06 0.2
99.0076 C4H3O3+ 1 99.0077 -0.41
100.0757 C5H10NO+ 1 100.0757 -0.1
103.0542 C8H7+ 1 103.0542 -0.45
105.0336 C7H5O+ 1 105.0335 0.56
105.0447 C6H5N2+ 1 105.0447 -0.52
105.07 C8H9+ 1 105.0699 1.55
106.0651 C7H8N+ 1 106.0651 -0.43
107.0127 C6H3O2+ 1 107.0128 -0.52
107.0491 C7H7O+ 1 107.0491 0.08
108.0444 C6H6NO+ 1 108.0444 0.28
108.0807 C7H10N+ 1 108.0808 -0.79
109.0285 C6H5O2+ 1 109.0284 0.5
110.06 C6H8NO+ 1 110.06 -0.09
111.0076 C5H3O3+ 1 111.0077 -0.27
111.0441 C6H7O2+ 1 111.0441 0.13
112.0757 C6H10NO+ 1 112.0757 -0.18
114.0551 C5H8NO2+ 1 114.055 1.36
115.0542 C9H7+ 1 115.0542 0.12
116.062 C9H8+ 1 116.0621 -0.62
117.0699 C9H9+ 1 117.0699 -0.14
118.0651 C8H8N+ 1 118.0651 -0.22
119.0128 C7H3O2+ 1 119.0128 0.71
119.0492 C8H7O+ 1 119.0491 0.49
119.0855 C9H11+ 1 119.0855 -0.48
121.0284 C7H5O2+ 1 121.0284 -0.13
121.0648 C8H9O+ 1 121.0648 0.24
122.0601 C7H8NO+ 1 122.06 0.08
123.0077 C6H3O3+ 1 123.0077 0.24
123.044 C7H7O2+ 1 123.0441 -0.13
124.0156 C6H4O3+ 1 124.0155 0.44
124.0394 C6H6NO2+ 1 124.0393 0.93
124.0758 C7H10NO+ 1 124.0757 0.64
125.0235 C6H5O3+ 1 125.0233 1.28
125.0469 C6H7NO2+ 1 125.0471 -1.76
126.0549 C6H8NO2+ 1 126.055 -0.44
127.0027 C5H3O4+ 1 127.0026 0.59
127.0543 C10H7+ 1 127.0542 0.34
128.062 C10H8+ 1 128.0621 -0.4
128.0708 C6H10NO2+ 1 128.0706 1.6
129.0699 C10H9+ 1 129.0699 -0.05
131.0492 C9H7O+ 1 131.0491 0.14
131.0855 C10H11+ 1 131.0855 0.02
132.057 C9H8O+ 1 132.057 0.56
133.0285 C8H5O2+ 1 133.0284 0.63
133.0648 C9H9O+ 1 133.0648 0.14
134.0599 C8H8NO+ 1 134.06 -0.75
135.0076 C7H3O3+ 1 135.0077 -0.37
135.0442 C8H7O2+ 1 135.0441 1.14
136.0758 C8H10NO+ 1 136.0757 1.03
137.0233 C7H5O3+ 1 137.0233 0.14
138.055 C7H8NO2+ 1 138.055 0.18
139.0265 C6H5NO3+ 1 139.0264 1.12
139.039 C7H7O3+ 1 139.039 0
139.0539 C11H7+ 1 139.0542 -2.06
140.0619 C11H8+ 1 140.0621 -1.01
140.0709 C7H10NO2+ 1 140.0706 1.75
141.0699 C11H9+ 1 141.0699 -0.19
142.0498 C6H8NO3+ 1 142.0499 -0.56
142.0776 C11H10+ 1 142.0777 -0.5
143.0493 C10H7O+ 1 143.0491 1.18
143.0855 C11H11+ 1 143.0855 -0.26
144.0571 C10H8O+ 1 144.057 0.79
145.0648 C10H9O+ 1 145.0648 0.2
147.0441 C9H7O2+ 1 147.0441 0.57
147.0805 C10H11O+ 1 147.0804 0.26
148.0521 C9H8O2+ 1 148.0519 1.41
149.0234 C8H5O3+ 1 149.0233 0.67
149.0598 C9H9O2+ 1 149.0597 0.63
150.0549 C8H8NO2+ 1 150.055 -0.63
151.0026 C7H3O4+ 1 151.0026 -0.03
151.039 C8H7O3+ 1 151.039 0.26
151.0541 C12H7+ 1 151.0542 -0.84
152.0342 C7H6NO3+ 1 152.0342 -0.19
152.062 C12H8+ 1 152.0621 -0.08
152.0709 C8H10NO2+ 1 152.0706 1.87
153.0181 C7H5O4+ 1 153.0182 -1.01
153.0698 C12H9+ 1 153.0699 -0.37
154.0498 C7H8NO3+ 1 154.0499 -0.32
154.0777 C12H10+ 1 154.0777 0.18
155.0604 C10H7N2+ 1 155.0604 0.03
155.0855 C12H11+ 1 155.0855 -0.37
156.0569 C11H8O+ 1 156.057 -0.68
157.037 C6H7NO4+ 1 157.037 0.52
157.0648 C11H9O+ 1 157.0648 0.25
157.1014 C12H13+ 1 157.1012 1.23
158.0727 C11H10O+ 1 158.0726 0.4
159.044 C10H7O2+ 1 159.0441 -0.23
159.0805 C11H11O+ 1 159.0804 0.24
160.0519 C10H8O2+ 1 160.0519 -0.19
161.0231 C9H5O3+ 1 161.0233 -1.18
161.0599 C10H9O2+ 1 161.0597 1.02
162.0548 C9H8NO2+ 1 162.055 -1.02
163.0025 C8H3O4+ 1 163.0026 -0.77
163.0389 C9H7O3+ 1 163.039 -0.56
163.055 C13H7+ 1 163.0542 4.68
163.0624 C9H9NO2+ 1 163.0628 -2.58
164.0617 C13H8+ 1 164.0621 -2.14
164.0706 C9H10NO2+ 1 164.0706 -0.27
165.0183 C8H5O4+ 1 165.0182 0.58
165.0699 C13H9+ 1 165.0699 0.38
166.0499 C8H8NO3+ 1 166.0499 0.24
166.0778 C13H10+ 1 166.0777 0.35
167.0855 C13H11+ 1 167.0855 0.08
168.057 C12H8O+ 1 168.057 0.2
169.0649 C12H9O+ 1 169.0648 0.58
169.0763 C11H9N2+ 1 169.076 1.75
169.1013 C13H13+ 1 169.1012 0.91
170.0728 C12H10O+ 1 170.0726 1.31
171.0439 C11H7O2+ 1 171.0441 -0.97
171.0804 C12H11O+ 1 171.0804 -0.07
172.0521 C11H8O2+ 1 172.0519 1.16
173.0236 C10H5O3+ 1 173.0233 1.67
173.0598 C11H9O2+ 1 173.0597 0.43
174.0676 C11H10O2+ 1 174.0675 0.34
175.0754 C11H11O2+ 1 175.0754 0.31
176.0622 C14H8+ 1 176.0621 1.07
177.0699 C14H9+ 1 177.0699 0.02
178.0778 C14H10+ 1 178.0777 0.44
179.0855 C14H11+ 1 179.0855 -0.09
180.0572 C13H8O+ 1 180.057 1.24
180.0649 C9H10NO3+ 1 180.0655 -3.22
181.0131 C8H5O5+ 1 181.0131 -0.44
181.0648 C13H9O+ 1 181.0648 -0.23
181.1014 C14H13+ 1 181.1012 1.34
182.0728 C13H10O+ 1 182.0726 0.73
182.0807 C9H12NO3+ 1 182.0812 -2.41
183.0289 C8H7O5+ 1 183.0288 0.6
183.0554 C11H7N2O+ 1 183.0553 0.39
183.0805 C13H11O+ 1 183.0804 0.43
184.0517 C12H8O2+ 1 184.0519 -0.82
185.0598 C12H9O2+ 1 185.0597 0.29
185.0711 C11H9N2O+ 1 185.0709 0.65
185.0962 C13H13O+ 1 185.0961 0.37
186.0311 C11H6O3+ 1 186.0311 -0.14
186.0676 C12H10O2+ 1 186.0675 0.32
187.0389 C11H7O3+ 1 187.039 -0.54
187.0754 C12H11O2+ 1 187.0754 0.18
189.0182 C10H5O4+ 1 189.0182 -0.19
189.0549 C11H9O3+ 1 189.0546 1.48
189.0699 C15H9+ 1 189.0699 0.02
190.0776 C15H10+ 1 190.0777 -0.43
191.0341 C10H7O4+ 1 191.0339 1.33
191.0855 C15H11+ 1 191.0855 -0.19
192.0569 C14H8O+ 1 192.057 -0.24
193.0136 C9H5O5+ 1 193.0131 2.44
193.065 C14H9O+ 1 193.0648 0.93
193.0759 C13H9N2+ 1 193.076 -0.44
193.1013 C15H13+ 1 193.1012 0.48
194.0727 C14H10O+ 1 194.0726 0.17
195.0805 C14H11O+ 1 195.0804 0.35
196.052 C13H8O2+ 1 196.0519 0.35
197.0598 C13H9O2+ 1 197.0597 0.27
197.0961 C14H13O+ 1 197.0961 -0.06
198.0675 C13H10O2+ 1 198.0675 0
199.0385 C12H7O3+ 1 199.039 -2.16
199.0754 C13H11O2+ 1 199.0754 0.02
200.0464 C12H8O3+ 1 200.0468 -1.73
201.0547 C12H9O3+ 1 201.0546 0.15
202.0776 C16H10+ 1 202.0777 -0.55
203.0708 C12H11O3+ 1 203.0703 2.66
203.0857 C16H11+ 1 203.0855 1.1
204.0571 C15H8O+ 1 204.057 0.66
205.0498 C11H9O4+ 1 205.0495 1.24
205.0649 C15H9O+ 1 205.0648 0.68
206.0729 C15H10O+ 1 206.0726 1.23
207.0806 C15H11O+ 1 207.0804 0.67
208.0522 C14H8O2+ 1 208.0519 1.58
208.0883 C15H12O+ 1 208.0883 0.31
209.0597 C14H9O2+ 1 209.0597 -0.12
209.0963 C15H13O+ 1 209.0961 0.85
210.0676 C14H10O2+ 1 210.0675 0.42
211.0391 C13H7O3+ 1 211.039 0.61
211.0754 C14H11O2+ 1 211.0754 0.35
212.0468 C13H8O3+ 1 212.0468 0.16
212.0834 C14H12O2+ 1 212.0832 0.89
213.0546 C13H9O3+ 1 213.0546 -0.33
213.091 C14H13O2+ 1 213.091 0.21
214.0626 C13H10O3+ 1 214.0624 0.86
215.0701 C13H11O3+ 1 215.0703 -0.84
217.0496 C12H9O4+ 1 217.0495 0.21
217.065 C16H9O+ 1 217.0648 0.78
218.0727 C16H10O+ 1 218.0726 0.29
219.0289 C11H7O5+ 1 219.0288 0.23
219.0651 C12H11O4+ 1 219.0652 -0.3
219.0805 C16H11O+ 1 219.0804 0.4
220.0522 C15H8O2+ 1 220.0519 1.36
221.0599 C15H9O2+ 1 221.0597 0.65
221.0956 C16H13O+ 1 221.0961 -2.04
222.0675 C15H10O2+ 1 222.0675 -0.23
223.0755 C15H11O2+ 1 223.0754 0.56
224.0469 C14H8O3+ 1 224.0468 0.42
224.0829 C15H12O2+ 1 224.0832 -1.21
225.0546 C14H9O3+ 1 225.0546 0.04
225.0911 C15H13O2+ 1 225.091 0.37
226.0625 C14H10O3+ 1 226.0624 0.24
227.0704 C14H11O3+ 1 227.0703 0.44
229.0501 C13H9O4+ 1 229.0495 2.29
229.0654 C17H9O+ 1 229.0648 2.57
229.0759 C16H9N2+ 1 229.076 -0.68
229.0858 C14H13O3+ 1 229.0859 -0.31
231.0654 C13H11O4+ 1 231.0652 0.97
231.0806 C17H11O+ 1 231.0804 0.9
232.0519 C16H8O2+ 1 232.0519 0.25
233.06 C16H9O2+ 1 233.0597 1.13
234.0677 C16H10O2+ 1 234.0675 0.94
234.0909 C16H12NO+ 1 234.0913 -1.71
235.0753 C16H11O2+ 1 235.0754 -0.03
236.0468 C15H8O3+ 1 236.0468 -0.02
236.0829 C16H12O2+ 1 236.0832 -1.28
237.0546 C15H9O3+ 1 237.0546 -0.04
237.091 C16H13O2+ 1 237.091 -0.19
238.0625 C15H10O3+ 1 238.0624 0.06
239.0703 C15H11O3+ 1 239.0703 0.12
240.0418 C14H8O4+ 1 240.0417 0.21
240.0781 C15H12O3+ 1 240.0781 0.23
241.086 C15H13O3+ 1 241.0859 0.25
242.0573 C14H10O4+ 1 242.0574 -0.08
243.0654 C14H11O4+ 1 243.0652 0.88
243.1016 C15H15O3+ 1 243.1016 0
245.0601 C17H9O2+ 1 245.0597 1.73
246.068 C17H10O2+ 1 246.0675 2.11
247.0753 C17H11O2+ 1 247.0754 -0.02
248.0468 C16H8O3+ 1 248.0468 0.02
248.0825 C17H12O2+ 1 248.0832 -2.79
249.0546 C16H9O3+ 1 249.0546 -0.2
249.0907 C17H13O2+ 1 249.091 -1.19
250.0625 C16H10O3+ 1 250.0624 0.26
251.0704 C16H11O3+ 1 251.0703 0.36
252.0418 C15H8O4+ 1 252.0417 0.28
253.049 C15H9O4+ 1 253.0495 -2
253.0858 C16H13O3+ 1 253.0859 -0.52
254.0573 C15H10O4+ 1 254.0574 -0.24
255.065 C15H11O4+ 1 255.0652 -0.61
257.0595 C18H9O2+ 1 257.0597 -0.88
257.0807 C15H13O4+ 1 257.0808 -0.68
259.0752 C18H11O2+ 1 259.0754 -0.72
260.0467 C17H8O3+ 1 260.0468 -0.25
261.0542 C17H9O3+ 1 261.0546 -1.69
262.0622 C17H10O3+ 1 262.0624 -1.01
262.0861 C17H12NO2+ 1 262.0863 -0.71
263.0705 C17H11O3+ 1 263.0703 0.8
263.0933 C17H13NO2+ 1 263.0941 -3.04
264.042 C16H8O4+ 1 264.0417 1.14
264.0779 C17H12O3+ 1 264.0781 -0.63
265.0493 C16H9O4+ 1 265.0495 -0.96
265.086 C17H13O3+ 1 265.0859 0.37
266.0577 C16H10O4+ 1 266.0574 1.16
267.0652 C16H11O4+ 1 267.0652 0.09
268.0365 C15H8O5+ 1 268.0366 -0.47
268.0732 C16H12O4+ 1 268.073 0.75
269.0811 C16H13O4+ 1 269.0808 1.06
270.0524 C15H10O5+ 1 270.0523 0.61
271.0602 C15H11O5+ 1 271.0601 0.44
273.0537 C18H9O3+ 1 273.0546 -3.3
275.0704 C18H11O3+ 1 275.0703 0.54
276.0417 C17H8O4+ 1 276.0417 0
277.0496 C17H9O4+ 1 277.0495 0.41
277.0858 C18H13O3+ 1 277.0859 -0.51
278.0575 C17H10O4+ 1 278.0574 0.36
279.0652 C17H11O4+ 1 279.0652 0.09
279.0886 C17H13NO3+ 1 279.089 -1.24
280.0725 C17H12O4+ 1 280.073 -1.79
280.097 C17H14NO3+ 1 280.0968 0.72
281.0807 C17H13O4+ 1 281.0808 -0.52
281.1044 C17H15NO3+ 1 281.1046 -0.76
282.0519 C16H10O5+ 1 282.0523 -1.51
283.0612 C16H11O5+ 1 283.0601 3.89
284.0679 C16H12O5+ 1 284.0679 -0.26
285.0757 C16H13O5+ 1 285.0757 -0.07
288.0651 C18H10NO3+ 1 288.0655 -1.53
289.0509 C18H9O4+ 2 289.0495 4.79
290.0565 C18H10O4+ 1 290.0574 -2.93
291.0652 C18H11O4+ 1 291.0652 0.09
292.0725 C18H12O4+ 1 292.073 -1.61
292.0965 C18H14NO3+ 1 292.0968 -1.03
293.0808 C18H13O4+ 1 293.0808 -0.19
294.052 C17H10O5+ 1 294.0523 -1.04
294.112 C18H16NO3+ 1 294.1125 -1.6
295.0597 C17H11O5+ 1 295.0601 -1.36
298.1078 C17H16NO4+ 1 298.1074 1.29
303.065 C19H11O4+ 1 303.0652 -0.55
304.0366 C18H8O5+ 1 304.0366 -0.05
305.0436 C18H9O5+ 1 305.0444 -2.88
306.0523 C18H10O5+ 1 306.0523 0.18
308.0682 C18H12O5+ 1 308.0679 0.73
319.0604 C19H11O5+ 1 319.0601 0.91
321.0754 C19H13O5+ 1 321.0757 -1.06
321.0999 C19H15NO4+ 1 321.0996 1.09
322.047 C18H10O6+ 1 322.0472 -0.59
334.0471 C19H10O6+ 1 334.0472 -0.24
PK$NUM_PEAK: 341
PK$PEAK: m/z int. rel.int.
50.0151 7702.9 2
51.0229 10727.7 2
53.0022 33505.2 8
53.0386 51430.6 13
54.0339 6815.9 1
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//
