ACCESSION: MSBNK-Eawag-EQ367855
RECORD_TITLE: Doxycycline; LC-ESI-QFT; MS2; CE: 75; 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 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$CHROMATOGRAPHY: RETENTION_TIME 6.3 min
AC$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: splash10-0006-1690000000-b94e6217326b0ce00c62
PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm)
55.0189 C3H3O- 1 55.0189 -0.33
57.0345 C3H5O- 1 57.0346 -0.85
59.0138 C2H3O2- 1 59.0139 -0.05
63.024 C5H3- 1 63.024 -0.22
65.0033 C4HO- 1 65.0033 0.18
65.0396 C5H5- 1 65.0397 -0.52
65.9985 C3NO- 1 65.9985 -0.11
67.019 C4H3O- 1 67.0189 0.17
68.0142 C3H2NO- 1 68.0142 0.33
68.9982 C3HO2- 1 68.9982 0.54
69.0346 C4H5O- 1 69.0346 0.17
71.0139 C3H3O2- 1 71.0139 0.1
72.9933 C2HO3- 1 72.9931 2.5
78.0349 C5H4N- 1 78.0349 0.22
79.0189 C5H3O- 1 79.0189 -0.1
80.0268 C5H4O- 1 80.0268 0.08
81.022 C4H3NO- 1 81.022 -0.65
81.0346 C5H5O- 1 81.0346 -0.35
82.0299 C4H4NO- 1 82.0298 0.64
83.0139 C4H3O2- 1 83.0139 -0.04
84.009 C3H2NO2- 1 84.0091 -0.86
85.0295 C4H5O2- 1 85.0295 -0.39
86.0247 C3H4NO2- 1 86.0248 -0.95
90.0349 C6H4N- 1 90.0349 -0.59
91.0189 C6H3O- 1 91.0189 -0.09
93.0345 C6H5O- 1 93.0346 -0.52
94.0296 C5H4NO- 1 94.0298 -2.1
95.0138 C5H3O2- 1 95.0139 -0.35
96.0091 C4H2NO2- 1 96.0091 -0.02
96.0454 C5H6NO- 1 96.0455 -0.6
96.9931 C4HO3- 1 96.9931 -0.59
97.0294 C5H5O2- 1 97.0295 -0.65
99.0089 C4H3O3- 1 99.0088 1.14
100.0768 C5H10NO- 1 100.0768 -0.27
106.0298 C6H4NO- 1 106.0298 0.12
107.0138 C6H3O2- 1 107.0139 -0.77
108.0217 C6H4O2- 1 108.0217 0.3
109.0295 C6H5O2- 1 109.0295 -0.39
110.0248 C5H4NO2- 1 110.0248 0.07
110.061 C6H8NO- 1 110.0611 -1.61
111.0088 C5H3O3- 1 111.0088 0.29
117.0346 C8H5O- 1 117.0346 0.36
118.0298 C7H4NO- 1 118.0298 0.02
119.0139 C7H3O2- 1 119.0139 0.06
119.0502 C8H7O- 1 119.0502 -0.15
120.0091 C6H2NO2- 1 120.0091 0.07
120.0455 C7H6NO- 1 120.0455 0.44
121.0295 C7H5O2- 1 121.0295 -0.11
121.0535 C7H7NO- 1 121.0533 1.63
121.0658 C8H9O- 1 121.0659 -0.4
122.0248 C6H4NO2- 1 122.0248 0.72
122.0611 C7H8NO- 1 122.0611 0.1
123.0088 C6H3O3- 1 123.0088 0.18
123.0324 C6H5NO2- 1 123.0326 -1.36
124.0165 C6H4O3- 1 124.0166 -0.42
124.0404 C6H6NO2- 1 124.0404 -0.26
124.9879 C5HO4- 1 124.988 -0.9
125.0242 C6H5O3- 1 125.0244 -1.34
125.072 C6H9N2O- 1 125.072 -0.29
126.0196 C5H4NO3- 1 126.0197 -0.45
126.056 C6H8NO2- 1 126.0561 -0.33
129.0712 C10H9- 1 129.071 1.44
130.0424 C9H6O- 1 130.0424 0.13
133.0168 C7H3NO2- 1 133.0169 -1.03
133.0658 C9H9O- 1 133.0659 -0.89
134.0247 C7H4NO2- 1 134.0248 -0.09
135.0088 C7H3O3- 1 135.0088 0.02
135.0452 C8H7O2- 1 135.0452 0.2
136.0167 C7H4O3- 1 136.0166 0.64
136.0403 C7H6NO2- 1 136.0404 -0.53
136.0767 C8H10NO- 1 136.0768 -0.94
137.0244 C7H5O3- 1 137.0244 -0.35
137.0482 C7H7NO2- 1 137.0482 -0.2
138.0196 C6H4NO3- 1 138.0197 -0.26
138.0562 C7H8NO2- 1 138.0561 0.78
139.0149 C5H3N2O3- 1 139.0149 0.03
141.0195 C6H5O4- 1 141.0193 0.91
142.9986 C5H3O5- 1 142.9986 -0.05
143.0502 C10H7O- 1 143.0502 -0.13
144.0581 C10H8O- 1 144.0581 0.39
145.0295 C9H5O2- 1 145.0295 -0.02
145.0659 C10H9O- 1 145.0659 0.08
146.0246 C8H4NO2- 1 146.0248 -1.11
146.0377 C9H6O2- 1 146.0373 2.2
147.0452 C9H7O2- 1 147.0452 0.05
148.0039 C7H2NO3- 1 148.004 -0.58
149.0118 C7H3NO3- 1 149.0118 -0.55
149.0243 C8H5O3- 1 149.0244 -0.72
149.048 C8H7NO2- 1 149.0482 -1.19
149.0607 C9H9O2- 1 149.0608 -0.49
149.9959 C7H2O4- 1 149.9959 0.15
150.0196 C7H4NO3- 1 150.0197 -0.18
151.0037 C7H3O4- 1 151.0037 -0.08
151.0274 C7H5NO3- 1 151.0275 -0.34
152.0115 C7H4O4- 1 152.0115 0.15
152.0354 C7H6NO3- 1 152.0353 0.35
152.0716 C8H10NO2- 1 152.0717 -0.93
153.0194 C7H5O4- 1 153.0193 0.38
154.0382 C6H6N2O3- 1 154.0384 -1.56
155.0501 C11H7O- 1 155.0502 -0.76
156.058 C11H8O- 1 156.0581 -0.73
157.0658 C11H9O- 1 157.0659 -0.31
158.0373 C10H6O2- 1 158.0373 -0.3
159.0451 C10H7O2- 1 159.0452 -0.14
159.0816 C11H11O- 1 159.0815 0.2
161.0245 C9H5O3- 1 161.0244 0.45
161.0607 C10H9O2- 1 161.0608 -0.83
162.0197 C8H4NO3- 1 162.0197 0.02
163.0037 C8H3O4- 1 163.0037 0.05
163.0274 C8H5NO3- 1 163.0275 -0.75
164.0117 C8H4O4- 1 164.0115 1.3
164.0355 C8H6NO3- 1 164.0353 1.06
166.0511 C8H8NO3- 1 166.051 0.86
167.0223 C7H5NO4- 1 167.0224 -0.82
167.051 C12H7O- 1 167.0502 4.62
168.0666 C8H10NO3- 1 168.0666 -0.04
169.0256 C6H5N2O4- 1 169.0255 0.89
169.0658 C12H9O- 1 169.0659 -0.41
171.0451 C11H7O2- 1 171.0452 -0.37
171.0816 C12H11O- 1 171.0815 0.53
172.0531 C11H8O2- 1 172.053 0.48
173.0607 C11H9O2- 1 173.0608 -0.54
174.0323 C10H6O3- 1 174.0322 0.21
175.0764 C11H11O2- 1 175.0765 -0.53
177.0307 C8H5N2O3- 1 177.0306 0.48
178.0145 C8H4NO4- 1 178.0146 -0.4
180.0581 C13H8O- 1 180.0581 0.37
181.0661 C13H9O- 1 181.0659 1.06
182.0373 C12H6O2- 1 182.0373 -0.21
183.0451 C12H7O2- 1 183.0452 -0.45
183.0815 C13H11O- 1 183.0815 0.01
184.0532 C12H8O2- 1 184.053 1.15
185.0608 C12H9O2- 1 185.0608 -0.12
186.0318 C11H6O3- 1 186.0322 -2.22
186.0686 C12H10O2- 1 186.0686 -0.04
187.04 C11H7O3- 1 187.0401 -0.2
187.0764 C12H11O2- 1 187.0765 -0.34
188.0479 C11H8O3- 1 188.0479 0.25
193.0661 C14H9O- 1 193.0659 1.25
194.0736 C14H10O- 1 194.0737 -0.43
195.0454 C13H7O2- 1 195.0452 1.11
195.0818 C14H11O- 1 195.0815 1.14
196.0529 C13H8O2- 1 196.053 -0.5
197.0608 C13H9O2- 1 197.0608 -0.12
198.0321 C12H6O3- 1 198.0322 -0.67
198.0685 C13H10O2- 1 198.0686 -0.5
199.04 C12H7O3- 1 199.0401 -0.19
199.0765 C13H11O2- 1 199.0765 0.29
201.0192 C11H5O4- 1 201.0193 -0.56
201.0557 C12H9O3- 1 201.0557 -0.09
203.0352 C11H7O4- 1 203.035 1.12
203.0715 C12H11O3- 1 203.0714 0.7
204.0426 C11H8O4- 1 204.0428 -1.07
204.058 C15H8O- 1 204.0581 -0.51
206.0741 C15H10O- 1 206.0737 1.68
207.045 C14H7O2- 1 207.0452 -0.93
207.0819 C15H11O- 1 207.0815 1.84
208.0528 C14H8O2- 1 208.053 -0.76
209.0608 C14H9O2- 1 209.0608 0.18
210.0685 C14H10O2- 1 210.0686 -0.51
211.04 C13H7O3- 1 211.0401 -0.18
211.0764 C14H11O2- 1 211.0765 -0.35
212.0481 C13H8O3- 1 212.0479 0.79
213.0556 C13H9O3- 1 213.0557 -0.65
213.092 C14H13O2- 1 213.0921 -0.39
214.0272 C12H6O4- 1 214.0272 0.2
217.0504 C12H9O4- 1 217.0506 -0.89
220.0528 C15H8O2- 1 220.053 -0.72
221.0611 C15H9O2- 1 221.0608 1.3
222.0323 C14H6O3- 1 222.0322 0.35
222.0687 C15H10O2- 1 222.0686 0.46
223.0397 C14H7O3- 1 223.0401 -1.83
223.065 C14H9NO2- 1 223.0639 4.94
223.0764 C15H11O2- 1 223.0765 -0.19
224.0479 C14H8O3- 1 224.0479 0.26
225.0557 C14H9O3- 1 225.0557 -0.08
225.0921 C15H13O2- 1 225.0921 0.16
226.064 C14H10O3- 1 226.0635 1.89
226.0871 C14H12NO2- 1 226.0874 -1.12
227.0713 C14H11O3- 1 227.0714 -0.12
229.0506 C13H9O4- 1 229.0506 0.08
229.0872 C14H13O3- 1 229.087 0.66
232.0529 C16H8O2- 1 232.053 -0.55
233.0608 C16H9O2- 1 233.0608 -0.06
234.0683 C16H10O2- 1 234.0686 -1.57
235.0399 C15H7O3- 1 235.0401 -0.59
235.0764 C16H11O2- 1 235.0765 -0.18
236.0483 C15H8O3- 1 236.0479 1.89
236.0727 C15H10NO2- 1 236.0717 4.06
236.0846 C16H12O2- 1 236.0843 1.45
237.0558 C15H9O3- 1 237.0557 0.52
237.0926 C16H13O2- 1 237.0921 1.97
238.0635 C15H10O3- 1 238.0635 -0.35
238.0873 C15H12NO2- 1 238.0874 -0.43
239.0351 C14H7O4- 1 239.035 0.28
239.0713 C15H11O3- 1 239.0714 -0.28
240.0429 C14H8O4- 1 240.0428 0.59
241.0507 C14H9O4- 1 241.0506 0.28
241.0869 C15H13O3- 1 241.087 -0.57
246.0684 C17H10O2- 1 246.0686 -0.76
247.0637 C16H9NO2- 1 247.0639 -0.55
247.0766 C17H11O2- 1 247.0765 0.55
248.048 C16H8O3- 1 248.0479 0.59
248.071 C16H10NO2- 1 248.0717 -2.95
249.0556 C16H9O3- 1 249.0557 -0.63
250.0514 C15H8NO3- 1 250.051 1.85
250.0631 C16H10O3- 1 250.0635 -1.97
250.087 C16H12NO2- 1 250.0874 -1.41
251.0345 C15H7O4- 1 251.035 -2.08
251.0712 C16H11O3- 1 251.0714 -0.71
252.0432 C15H8O4- 1 252.0428 1.56
252.0668 C15H10NO3- 1 252.0666 0.77
252.1031 C16H14NO2- 1 252.103 0.31
253.0508 C15H9O4- 1 253.0506 0.74
253.087 C16H13O3- 1 253.087 -0.15
254.0585 C15H10O4- 1 254.0585 0.29
254.083 C15H12NO3- 1 254.0823 2.96
255.0663 C15H11O4- 1 255.0663 -0.09
261.0556 C17H9O3- 1 261.0557 -0.45
262.0644 C17H10O3- 1 262.0635 3.12
262.087 C17H12NO2- 1 262.0874 -1.46
263.0713 C17H11O3- 1 263.0714 -0.18
264.0427 C16H8O4- 1 264.0428 -0.56
264.0665 C16H10NO3- 1 264.0666 -0.56
265.0505 C16H9O4- 1 265.0506 -0.5
265.0742 C16H11NO3- 1 265.0744 -0.95
265.0874 C17H13O3- 1 265.087 1.44
266.0583 C16H10O4- 1 266.0585 -0.52
266.0821 C16H12NO3- 1 266.0823 -0.55
267.0659 C16H11O4- 1 267.0663 -1.24
269.0819 C16H13O4- 1 269.0819 0.03
275.0583 C17H9NO3- 1 275.0588 -1.93
275.0717 C18H11O3- 1 275.0714 1.28
276.0425 C17H8O4- 1 276.0428 -0.97
276.0664 C17H10NO3- 1 276.0666 -0.75
277.0505 C17H9O4- 1 277.0506 -0.44
278.058 C17H10O4- 1 278.0585 -1.61
279.0667 C17H11O4- 1 279.0663 1.42
280.0382 C16H8O5- 1 280.0377 1.74
280.0983 C17H14NO3- 1 280.0979 1.37
281.0822 C17H13O4- 1 281.0819 0.77
290.0221 C17H6O5- 1 290.0221 0.06
290.0821 C18H12NO3- 1 290.0823 -0.51
291.0527 C17H9NO4- 1 291.0537 -3.35
291.0669 C18H11O4- 1 291.0663 2.19
293.046 C17H9O5- 1 293.0455 1.48
293.1057 C18H15NO3- 1 293.1057 -0.14
PK$NUM_PEAK: 247
PK$PEAK: m/z int. rel.int.
55.0189 4720.5 2
57.0345 2682.6 1
59.0138 2285.4 1
63.024 61446 31
65.0033 21553.1 11
65.0396 12680.9 6
65.9985 59529.6 30
67.019 14533 7
68.0142 4498.6 2
68.9982 71479.8 37
69.0346 28350.4 14
71.0139 12840.4 6
72.9933 2342 1
78.0349 5286.7 2
79.0189 20106.2 10
80.0268 12403.3 6
81.022 5449.3 2
81.0346 16231.9 8
82.0299 2309.3 1
83.0139 16282.7 8
84.009 86944.9 45
85.0295 5347.8 2
86.0247 2222 1
90.0349 2151.4 1
91.0189 23442.5 12
93.0345 25631.8 13
94.0296 2137.5 1
95.0138 116377.3 60
96.0091 31408.6 16
96.0454 5196.8 2
96.9931 64243.5 33
97.0294 22981.6 11
99.0089 9699.8 5
100.0768 2831.5 1
106.0298 5081.2 2
107.0138 20977.3 10
108.0217 54353.6 28
109.0295 69050.8 35
110.0248 2356.4 1
110.061 4760.6 2
111.0088 11598.2 6
117.0346 23834.9 12
118.0298 2847.7 1
119.0139 30133.4 15
119.0502 90299.5 46
120.0091 4223.3 2
120.0455 2646.7 1
121.0295 15271.3 7
121.0535 2658.1 1
121.0658 39488.2 20
122.0248 13773.6 7
122.0611 1977.7 1
123.0088 66153.5 34
123.0324 8978.9 4
124.0165 33533.9 17
124.0404 7056 3
124.9879 7625.6 3
125.0242 14969.8 7
125.072 10222.1 5
126.0196 7512 3
126.056 44069.9 22
129.0712 4121.3 2
130.0424 15643.7 8
133.0168 2201.3 1
133.0658 2273.7 1
134.0247 34729 17
135.0088 67156.6 34
135.0452 5915.4 3
136.0167 2666.1 1
136.0403 2700.8 1
136.0767 4408.3 2
137.0244 17994.7 9
137.0482 7882.3 4
138.0196 21201.3 10
138.0562 4997.6 2
139.0149 77513.8 40
141.0195 7672.9 3
142.9986 26260.2 13
143.0502 19982.4 10
144.0581 12815.2 6
145.0295 5333.4 2
145.0659 5463.6 2
146.0246 2583 1
146.0377 11178.5 5
147.0452 6645.6 3
148.0039 5764.8 2
149.0118 11586.9 6
149.0243 4266.5 2
149.048 2597.8 1
149.0607 6555.4 3
149.9959 10315.9 5
150.0196 56398 29
151.0037 12977.6 6
151.0274 4649.8 2
152.0115 5089.5 2
152.0354 11727.9 6
152.0716 2745.1 1
153.0194 4864 2
154.0382 2268.1 1
155.0501 2723.1 1
156.058 5099.7 2
157.0658 41404 21
158.0373 73847.7 38
159.0451 51835.9 26
159.0816 18905.7 9
161.0245 8977.7 4
161.0607 2790.2 1
162.0197 16649.6 8
163.0037 10649.4 5
163.0274 5554.3 2
164.0117 5953.4 3
164.0355 5643.1 2
166.0511 2034.5 1
167.0223 2162.7 1
167.051 2061.2 1
168.0666 5991.3 3
169.0256 2809 1
169.0658 16744.3 8
171.0451 17585.8 9
171.0816 9112.1 4
172.0531 71262.5 36
173.0607 453496.1 235
174.0323 5858.2 3
175.0764 7399.1 3
177.0307 12659.1 6
178.0145 15848.8 8
180.0581 10590.1 5
181.0661 19738.9 10
182.0373 2460.4 1
183.0451 20725.7 10
183.0815 11778.5 6
184.0532 9503.8 4
185.0608 73054.7 37
186.0318 13578.1 7
186.0686 18021.2 9
187.04 98132.4 50
187.0764 18766.3 9
188.0479 5545.4 2
193.0661 8892.6 4
194.0736 7879.3 4
195.0454 13286.7 6
195.0818 15185.7 7
196.0529 91888.1 47
197.0608 54759.7 28
198.0321 7228.7 3
198.0685 5570.6 2
199.04 4606.5 2
199.0765 30068.3 15
201.0192 9116.6 4
201.0557 22103.1 11
203.0352 2292.2 1
203.0715 30014.7 15
204.0426 9132.2 4
204.058 5543.6 2
206.0741 2257 1
207.045 2323.2 1
207.0819 14014.9 7
208.0528 14019.9 7
209.0608 66078.1 34
210.0685 22573.4 11
211.04 73360.8 38
211.0764 34168.2 17
212.0481 33186.9 17
213.0556 17416.6 9
213.092 18102.7 9
214.0272 28405.6 14
217.0504 7304.7 3
220.0528 11568.6 5
221.0611 19576.2 10
222.0323 1960.2 1
222.0687 26017.3 13
223.0397 8145.3 4
223.065 2069.3 1
223.0764 35804.5 18
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//
