ACCESSION: MSBNK-Eawag-EQ368054
RECORD_TITLE: Chlortetracycline; LC-ESI-QFT; MS2; CE: 60; 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 3680
CH$NAME: Chlortetracycline
CH$NAME: 2-carbamoyl-7-chloro-4-(dimethylazaniumyl)-6,10,11,12a-tetrahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracen-1-olate
CH$COMPOUND_CLASS: N/A; Environmental Standard
CH$FORMULA: C22H23ClN2O8
CH$EXACT_MASS: 478.11429
CH$SMILES: CC1(C2CC3C(C(=O)C(=C(C3(C(=O)C2=C(C4=C(C=CC(=C41)Cl)O)O)O)O)C(=O)N)N(C)C)O
CH$IUPAC: InChI=1S/C22H23ClN2O8/c1-21(32)7-6-8-15(25(2)3)17(28)13(20(24)31)19(30)22(8,33)18(29)11(7)16(27)12-10(26)5-4-9(23)14(12)21/h4-5,7-8,15,26-27,30,32-33H,6H2,1-3H3,(H2,24,31)
CH$LINK: CAS
57-62-5
CH$LINK: PUBCHEM
CID:54677440
CH$LINK: INCHIKEY
DHPRQBPJLMKORJ-UHFFFAOYSA-N
CH$LINK: CHEMSPIDER
10469370
AC$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 60 (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$CHROMATOGRAPHY: RETENTION_TIME 5.4 min
AC$CHROMATOGRAPHY: SOLVENT A water with 0.1% formic acid
AC$CHROMATOGRAPHY: SOLVENT B methanol with 0.1% formic acid
MS$FOCUSED_ION: BASE_PEAK 477.1067
MS$FOCUSED_ION: PRECURSOR_M/Z 477.107
MS$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: splash10-014l-0950000000-5cdd98da2a1032a4efe6
PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm)
57.0346 C3H5O- 1 57.0346 -0.5
59.0138 C2H3O2- 1 59.0139 -0.05
63.0241 C5H3- 1 63.024 0.58
65.0033 C4HO- 1 65.0033 0.33
65.0397 C5H5- 1 65.0397 0.1
65.9985 C3NO- 1 65.9985 -0.11
67.0188 C4H3O- 1 67.0189 -2.66
68.9983 C3HO2- 1 68.9982 0.97
71.0137 C3H3O2- 1 71.0139 -1.87
79.0553 C6H7- 1 79.0553 -0.55
81.0345 C5H5O- 1 81.0346 -0.72
83.0138 C4H3O2- 1 83.0139 -0.4
83.0503 C5H7O- 1 83.0502 0.38
84.009 C3H2NO2- 1 84.0091 -0.74
86.0248 C3H4NO2- 1 86.0248 0.44
87.0087 C3H3O3- 1 87.0088 -0.66
90.0347 C6H4N- 1 90.0349 -2.36
91.019 C6H3O- 1 91.0189 0.24
93.0345 C6H5O- 1 93.0346 -0.63
95.0137 C5H3O2- 1 95.0139 -1.5
95.0503 C6H7O- 1 95.0502 0.12
96.009 C4H2NO2- 1 96.0091 -0.96
96.9931 C4HO3- 1 96.9931 -0.59
97.0294 C5H5O2- 1 97.0295 -0.65
99.0087 C4H3O3- 1 99.0088 -1.09
100.0767 C5H10NO- 1 100.0768 -0.77
102.0561 C4H8NO2- 1 102.0561 0.27
103.0553 C8H7- 1 103.0553 0.06
104.0269 C7H4O- 2 104.0268 1.41
105.0346 C7H5O- 2 105.0346 0.21
107.0139 C6H3O2- 2 107.0139 0.07
107.0502 C7H7O- 2 107.0502 -0.36
108.0216 C6H4O2- 2 108.0217 -0.35
109.0295 C6H5O2- 2 109.0295 -0.39
111.0088 C5H3O3- 2 111.0088 0.2
111.0452 C6H7O2- 2 111.0452 0.06
117.0346 C8H5O- 2 117.0346 0.44
118.0298 C7H4NO- 2 118.0298 -0.32
119.0139 C7H3O2- 2 119.0139 0.31
119.0503 C8H7O- 2 119.0502 0.1
120.0217 C7H4O2- 2 120.0217 0.18
120.0454 C7H6NO- 2 120.0455 -0.48
121.0297 C7H5O2- 2 121.0295 1.3
121.0658 C8H9O- 2 121.0659 -0.48
122.001 C6H2O3- 2 122.0009 0.64
122.0376 C7H6O2- 2 122.0373 2.15
123.0088 C6H3O3- 2 123.0088 -0.14
123.0451 C7H7O2- 2 123.0452 -0.51
124.004 C5H2NO3- 2 124.004 0.11
124.0166 C6H4O3- 2 124.0166 0.3
124.0767 C7H10NO- 2 124.0768 -0.79
124.9798 C6H2ClO- 1 124.98 -1.25
124.988 C5HO4- 2 124.988 -0.5
125.0242 C6H5O3- 1 125.0244 -1.34
125.072 C6H9N2O- 1 125.072 -0.53
125.9878 C6H3ClO- 1 125.9878 -0.01
126.0196 C5H4NO3- 2 126.0197 -0.53
126.056 C6H8NO2- 2 126.0561 -0.02
126.9956 C6H4ClO- 1 126.9956 -0.13
131.0139 C8H3O2- 2 131.0139 0.59
131.0502 C9H7O- 2 131.0502 -0.29
132.0215 C8H4O2- 2 132.0217 -1.27
133.0295 C8H5O2- 2 133.0295 -0.17
134.0247 C7H4NO2- 2 134.0248 -0.54
134.0373 C8H6O2- 2 134.0373 -0.13
135.0088 C7H3O3- 2 135.0088 0.24
135.0451 C8H7O2- 2 135.0452 -0.1
136.0164 C7H4O3- 1 136.0166 -1.71
136.0403 C7H6NO2- 2 136.0404 -0.68
137.0243 C7H5O3- 2 137.0244 -1
137.0606 C8H9O2- 1 137.0608 -1.77
137.9957 C6H2O4- 2 137.9959 -1.36
138.0321 C7H6O3- 2 138.0322 -1.18
139.0149 C5H3N2O3- 1 139.0149 0.03
139.0401 C7H7O3- 2 139.0401 -0.06
140.0034 C7H5ClO- 1 140.0034 -0.51
141.9827 C6H3ClO2- 1 141.9827 -0.25
142.0147 C5H4NO4- 2 142.0146 0.7
142.9985 C5H3O5- 2 142.9986 -0.47
143.0503 C10H7O- 2 143.0502 0.15
145.0295 C9H5O2- 2 145.0295 0.05
146.0372 C9H6O2- 2 146.0373 -0.67
147.0452 C9H7O2- 2 147.0452 0.52
148.0167 C8H4O3- 2 148.0166 0.46
148.0769 C9H10NO- 2 148.0768 0.62
149.0244 C8H5O3- 2 149.0244 -0.32
149.0608 C9H9O2- 2 149.0608 -0.29
149.996 C7H2O4- 2 149.9959 1.29
150.0194 C7H4NO3- 2 150.0197 -1.51
150.9955 C8H4ClO- 1 150.9956 -0.7
151.0401 C8H7O3- 2 151.0401 -0.05
152.0354 C7H6NO3- 2 152.0353 0.55
152.0715 C8H10NO2- 2 152.0717 -1.33
153.0113 C8H6ClO- 1 153.0113 0.35
153.0176 C5H3N3O3- 1 153.018 -2.81
153.0557 C8H9O3- 2 153.0557 -0.05
154.0385 C6H6N2O3- 1 154.0384 0.84
154.9907 C7H4ClO2- 1 154.9905 0.9
157.0294 C10H5O2- 2 157.0295 -0.72
158.0373 C10H6O2- 2 158.0373 -0.11
159.045 C10H7O2- 2 159.0452 -1.03
160.0166 C9H4O3- 2 160.0166 0.23
161.0244 C9H5O3- 2 161.0244 0.08
162.0197 C8H4NO3- 2 162.0197 0.14
163.0038 C8H3O4- 2 163.0037 0.48
163.0401 C9H7O3- 2 163.0401 -0.11
164.0116 C8H4O4- 2 164.0115 0.44
164.0353 C8H6NO3- 2 164.0353 0.14
164.0715 C9H10NO2- 2 164.0717 -1.29
165.0112 C9H6ClO- 1 165.0113 -0.58
165.043 C8H7NO3- 2 165.0431 -0.86
165.056 C9H9O3- 2 165.0557 1.47
165.067 C8H9N2O2- 1 165.067 0.24
166.0873 C9H12NO2- 2 166.0874 -0.37
166.9905 C8H4ClO2- 1 166.9905 -0.3
167.0223 C7H5NO4- 2 167.0224 -0.88
168.0669 C5H13ClN2O2- 2 168.0671 -1.33
169.0062 C8H6ClO2- 1 169.0062 0.23
170.0374 C11H6O2- 2 170.0373 0.19
170.9855 C7H4ClO3- 1 170.9854 0.09
171.0452 C11H7O2- 2 171.0452 0.1
172.0164 C10H4O3- 2 172.0166 -1.35
172.0528 C11H8O2- 2 172.053 -1.33
173.0244 C10H5O3- 2 173.0244 -0.04
174.0322 C10H6O3- 2 174.0322 -0.36
175.0038 C9H3O4- 2 175.0037 0.79
175.0326 C11H8Cl- 2 175.032 3.53
175.04 C10H7O3- 2 175.0401 -0.67
177.0112 C10H6ClO- 1 177.0113 -0.26
177.0308 C8H5N2O3- 1 177.0306 1.32
178.9905 C9H4ClO2- 1 178.9905 -0.12
179.9983 C9H5ClO2- 1 179.9984 -0.31
180.0301 C8H6NO4- 2 180.0302 -0.73
181.0062 C9H6ClO2- 1 181.0062 0.38
181.0142 C8H5O5- 2 181.0142 -0.26
181.0503 C9H9O4- 2 181.0506 -1.95
182.0142 C9H7ClO2- 1 182.014 1.23
182.0369 C12H6O2- 2 182.0373 -2.13
183.0453 C12H7O2- 2 183.0452 0.97
185.0607 C12H9O2- 2 185.0608 -0.72
186.0325 C11H6O3- 2 186.0322 1.17
187.04 C11H7O3- 2 187.0401 -0.63
188.048 C11H8O3- 2 188.0479 0.73
189.0193 C10H5O4- 2 189.0193 -0.01
189.0556 C11H9O3- 2 189.0557 -0.73
190.0272 C10H6O4- 2 190.0272 0.17
191.0267 C11H8ClO- 1 191.0269 -1.18
191.0351 C10H7O4- 2 191.035 0.83
191.9983 C10H5ClO2- 1 191.9984 -0.24
192.1026 C11H14NO2- 2 192.103 -1.99
193.0062 C10H6ClO2- 1 193.0062 0.15
193.0505 C10H9O4- 2 193.0506 -0.63
193.0657 C14H9O- 2 193.0659 -0.77
194.0139 C10H7ClO2- 1 194.014 -0.54
194.9854 C9H4ClO3- 1 194.9854 -0.28
195.9932 C9H5ClO3- 1 195.9933 -0.61
196.0532 C13H8O2- 2 196.053 0.98
197.001 C9H6ClO3- 1 197.0011 -0.48
197.0608 C13H9O2- 2 197.0608 -0.12
198.0325 C12H6O3- 2 198.0322 1.2
199.0395 C12H7O3- 1 199.0401 -2.8
199.0764 C13H11O2- 2 199.0765 -0.17
201.0197 C8H8ClNO3- 2 201.0198 -0.39
203.027 C12H8ClO- 1 203.0269 0.51
205.0064 C11H6ClO2- 1 205.0062 1.02
206.0139 C11H7ClO2- 1 206.014 -0.42
207.0217 C11H8ClO2- 1 207.0218 -0.44
207.9932 C10H5ClO3- 1 207.9933 -0.34
208.0526 C14H8O2- 2 208.053 -1.67
209.0609 C14H9O2- 2 209.0608 0.27
209.0932 C10H13N2O3- 1 209.0932 0.12
211.04 C13H7O3- 2 211.0401 -0.42
211.0766 C14H11O2- 2 211.0765 0.89
212.048 C13H8O3- 2 212.0479 0.55
213.0557 C13H9O3- 2 213.0557 -0.18
214.0269 C12H6O4- 2 214.0272 -1.39
215.026 C13H8ClO- 2 215.0269 -4.35
215.0356 C9H10ClNO3- 2 215.0355 0.56
217.0059 C12H6ClO2- 1 217.0062 -1.11
217.0424 C13H10ClO- 1 217.0426 -0.72
219.0218 C12H8ClO2- 1 219.0218 0.04
220.0296 C12H9ClO2- 1 220.0297 -0.44
221.001 C11H6ClO3- 1 221.0011 -0.25
221.0375 C12H10ClO2- 1 221.0375 0.22
221.0608 C15H9O2- 2 221.0608 0.03
222.0086 C11H7ClO3- 1 222.0089 -1.58
222.0322 C14H6O3- 2 222.0322 -0.06
223.0168 C11H8ClO3- 1 223.0167 0.33
223.0406 C11H10ClNO2- 2 223.0406 0.38
223.0764 C15H11O2- 2 223.0765 -0.28
224.0478 C14H8O3- 2 224.0479 -0.24
225.0556 C14H9O3- 2 225.0557 -0.75
226.0275 C10H9ClNO3- 2 226.0276 -0.77
227.0714 C14H11O3- 2 227.0714 0.14
229.0056 C13H6ClO2- 1 229.0062 -2.58
229.0419 C14H10ClO- 1 229.0426 -2.95
230.0134 C13H7ClO2- 1 230.014 -2.55
231.0216 C13H8ClO2- 1 231.0218 -1.13
231.993 C12H5ClO3- 1 231.9933 -1.12
233.0015 C12H6ClO3- 1 233.0011 1.57
233.0376 C13H10ClO2- 1 233.0375 0.68
233.0602 C16H9O2- 2 233.0608 -2.5
235.0169 C12H8ClO3- 1 235.0167 0.74
235.0401 C15H7O3- 2 235.0401 0.18
235.0528 C13H12ClO2- 1 235.0531 -1.24
235.988 C11H5ClO4- 1 235.9882 -0.66
236.0479 C15H8O3- 2 236.0479 0.12
237.0323 C12H10ClO3- 1 237.0324 -0.49
237.0557 C15H9O3- 2 237.0557 0.01
238.0038 C11H7ClO4- 1 238.0038 -0.1
238.0271 C14H6O4- 2 238.0272 -0.32
239.0716 C15H11O3- 2 239.0714 0.93
240.0429 C14H8O4- 2 240.0428 0.34
243.0215 C14H8ClO2- 1 243.0218 -1.16
244.0294 C14H9ClO2- 1 244.0297 -1.09
245.0012 C13H6ClO3- 1 245.0011 0.63
245.0374 C14H10ClO2- 1 245.0375 -0.33
246.0084 C13H7ClO3- 1 246.0089 -2.32
247.0167 C13H8ClO3- 1 247.0167 -0.31
247.0395 C16H7O3- 2 247.0401 -2.1
247.0531 C14H12ClO2- 1 247.0531 -0.29
248.0245 C13H9ClO3- 1 248.0246 -0.24
248.0478 C16H8O3- 2 248.0479 -0.21
248.9967 C12H6ClO4- 1 248.996 2.69
249.0323 C13H10ClO3- 1 249.0324 -0.54
249.0559 C16H9O3- 2 249.0557 0.65
250.0041 C12H7ClO4- 1 250.0038 0.98
250.0271 C15H6O4- 2 250.0272 -0.39
251.0116 C12H8ClO4- 1 251.0117 -0.4
251.0348 C15H7O4- 2 251.035 -0.57
252.0426 C15H8O4- 2 252.0428 -0.66
253.0049 C16HN2O2- 1 253.0044 2.21
253.016 C17H3NO2- 2 253.0169 -3.78
254.0221 C14H6O5- 2 254.0221 0.19
255.0206 C16H3N2O2- 2 255.02 2.19
257.0374 C15H10ClO2- 1 257.0375 -0.16
258.0183 C10H9ClNO5- 1 258.0175 3.13
259.0168 C14H8ClO3- 1 259.0167 0.02
259.0527 C15H12ClO2- 1 259.0531 -1.78
259.9884 C13H5ClO4- 1 259.9882 0.94
260.0246 C14H9ClO3- 1 260.0246 0.19
260.9957 C13H6ClO4- 1 260.996 -1.11
261.0322 C14H10ClO3- 1 261.0324 -0.79
263.0479 C14H12ClO3- 1 263.048 -0.4
263.983 C12H5ClO5- 1 263.9831 -0.38
264.0199 C13H9ClO4- 1 264.0195 1.42
264.0425 C16H8O4- 2 264.0428 -1.13
265.0273 C13H10ClO4- 1 265.0273 0.11
265.0507 C16H9O4- 2 265.0506 0.1
266.0219 C15H6O5- 2 266.0221 -0.72
267.0218 C16H8ClO2- 1 267.0218 -0.04
267.0659 C16H11O4- 2 267.0663 -1.47
268.0376 C15H8O5- 2 268.0377 -0.34
270.009 C15H7ClO3- 1 270.0089 0.3
271.0167 C15H8ClO3- 1 271.0167 -0.2
273.0323 C15H10ClO3- 1 273.0324 -0.39
273.0559 C18H9O3- 2 273.0557 0.48
274.0035 C14H7ClO4- 1 274.0038 -1.3
275.0115 C14H8ClO4- 1 275.0117 -0.69
275.0351 C17H7O4- 2 275.035 0.39
275.0483 C15H12ClO3- 1 275.048 1.07
276.043 C14H11ClNO3- 2 276.0433 -0.96
276.9909 C13H6ClO5- 1 276.9909 -0.09
277.0506 C17H9O4- 2 277.0506 -0.23
277.9982 C13H7ClO5- 2 277.9987 -2.08
278.022 C16H6O5- 2 278.0221 -0.37
279.0433 C14H12ClO4- 1 279.043 1.22
281.0371 C17H10ClO2- 1 281.0375 -1.21
283.0166 C16H8ClO3- 1 283.0167 -0.62
284.033 C12H11ClNO5- 2 284.0331 -0.47
284.9964 C15H6ClO4- 1 284.996 1.33
285.0324 C16H10ClO3- 1 285.0324 0.16
286.0038 C15H7ClO4- 1 286.0038 0.02
286.0411 C16H11ClO3- 2 286.0402 2.97
287.0113 C15H8ClO4- 2 287.0117 -1.39
288.0192 C15H9ClO4- 1 288.0195 -0.82
289.0273 C15H10ClO4- 1 289.0273 0.1
291.0426 C15H12ClO4- 1 291.043 -1.24
292.0142 C14H9ClO5- 1 292.0144 -0.65
292.0381 C14H11ClNO4- 2 292.0382 -0.24
292.1114 C16H19ClNO2- 2 292.111 1.47
293.046 C14H12ClNO4- 2 293.046 -0.18
296.0329 C13H11ClNO5- 2 296.0331 -0.79
297.0321 C17H10ClO3- 1 297.0324 -1.13
299.0117 C16H8ClO4- 1 299.0117 0.27
299.0478 C17H12ClO3- 1 299.048 -0.79
300.027 C15H8O7- 2 300.0276 -1.74
300.0436 C16H11ClNO3- 2 300.0433 1.02
301.0271 C16H10ClO4- 1 301.0273 -0.63
301.9984 C15H7ClO5- 2 301.9987 -1.16
302.0355 C16H11ClO4- 1 302.0351 1.04
307.0378 C15H12ClO5- 1 307.0379 -0.24
308.9951 C17H6ClO4- 2 308.996 -2.85
309.032 C18H10ClO3- 2 309.0324 -1.18
310.0035 C17H7ClO4- 2 310.0038 -1.11
311.011 C17H8ClO4- 2 311.0117 -2.22
312.0202 C17H9ClO4- 1 312.0195 2.16
313.0269 C17H10ClO4- 2 313.0273 -1.21
313.9987 C16H7ClO5- 1 313.9987 -0.25
319.0383 C16H12ClO5- 1 319.0379 1.18
320.0319 C18H8O6- 3 320.0326 -2.4
322.0113 C17H6O7- 2 322.0119 -1.87
324.0271 C17H8O7- 2 324.0276 -1.27
325.0274 C18H10ClO4- 1 325.0273 0.43
327.0064 C17H8ClO5- 1 327.0066 -0.38
327.0426 C18H12ClO4- 2 327.043 -1.25
328.023 C13H11ClNO7- 2 328.023 0.2
328.0746 C18H15ClNO3- 2 328.0746 0.11
329.0218 C17H10ClO5- 2 329.0222 -1.29
329.993 C16H7ClO6- 2 329.9937 -2.13
330.0909 C18H17ClNO3- 2 330.0902 1.86
331.0363 C17H12ClO5- 2 331.0379 -4.67
338.001 C21H5ClNO2- 1 338.0014 -1.21
338.0432 C18H10O7- 2 338.0432 0.06
341.9929 C17H7ClO6- 2 341.9937 -2.32
347.0327 C17H12ClO6- 2 347.0328 -0.29
351.0062 C19H8ClO5- 2 351.0066 -1.15
352.0213 C18H8O8- 2 352.0225 -3.2
354.0538 C19H13ClNO4- 2 354.0539 -0.14
356.0697 C19H15ClNO4- 2 356.0695 0.4
357.989 C17H7ClO7- 1 357.9886 1.06
368.0167 C15H11ClNO8- 1 368.0179 -3.28
370.0335 C15H13ClNO8- 1 370.0335 -0.18
PK$NUM_PEAK: 323
PK$PEAK: m/z int. rel.int.
57.0346 1711.5 2
59.0138 26418.6 35
63.0241 13501.1 18
65.0033 4678.1 6
65.0397 11493.4 15
65.9985 16517.9 22
67.0188 1266.9 1
68.9983 16840.6 22
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//
