ACCESSION: MSBNK-Eawag-EQ361055
RECORD_TITLE: Oxytetracycline; 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 3610
CH$NAME: Oxytetracycline
CH$NAME: (4S,4aR,5S,5aR,6S,12aS)-4-(Dimethylamino)-3,5,6,10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-2-tetracenecarboxamide
CH$NAME: 2-carbamoyl-4-(dimethylazaniumyl)-5,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracen-1-olate
CH$COMPOUND_CLASS: N/A; Environmental Standard
CH$FORMULA: C22H24N2O9
CH$EXACT_MASS: 460.14818
CH$SMILES: CC1(C2C(C3C(C(=O)C(=C(C3(C(=O)C2=C(C4=C1C=CC=C4O)O)O)O)C(=O)N)N(C)C)O)O
CH$IUPAC: InChI=1S/C22H24N2O9/c1-21(32)7-5-4-6-8(25)9(7)15(26)10-12(21)17(28)13-14(24(2)3)16(27)11(20(23)31)19(30)22(13,33)18(10)29/h4-6,12-14,17,25-26,28,30,32-33H,1-3H3,(H2,23,31)
CH$LINK: CAS
79-57-2
CH$LINK: PUBCHEM
CID:54686003
CH$LINK: INCHIKEY
OWFJMIVZYSDULZ-UHFFFAOYSA-N
CH$LINK: CHEMSPIDER
10482174
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 4.3 min
AC$CHROMATOGRAPHY: SOLVENT A water with 0.1% formic acid
AC$CHROMATOGRAPHY: SOLVENT B methanol with 0.1% formic acid
MS$FOCUSED_ION: BASE_PEAK 459.1405
MS$FOCUSED_ION: PRECURSOR_M/Z 459.1409
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$SPLASH: splash10-0fe0-2940000000-4b5e52328498b1485857
PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm)
50.0035 C3N- 1 50.0036 -1.65
51.0239 C4H3- 1 51.024 -2.03
55.0189 C3H3O- 1 55.0189 -0.7
57.0345 C3H5O- 1 57.0346 -1.02
58.0298 C2H4NO- 1 58.0298 -0.47
59.0138 C2H3O2- 1 59.0139 -0.22
63.024 C5H3- 1 63.024 -0.06
65.0033 C4HO- 1 65.0033 0.33
65.0397 C5H5- 1 65.0397 0.25
65.9985 C3NO- 1 65.9985 -0.11
67.019 C4H3O- 1 67.0189 0.32
68.0143 C3H2NO- 1 68.0142 1.07
68.9982 C3HO2- 1 68.9982 0.39
69.0346 C4H5O- 1 69.0346 0.17
71.014 C3H3O2- 1 71.0139 1.79
72.9932 C2HO3- 1 72.9931 0.86
73.0296 C3H5O2- 1 73.0295 1.74
75.024 C6H3- 1 75.024 -0.45
78.035 C5H4N- 1 78.0349 0.48
79.0189 C5H3O- 1 79.0189 -0.74
80.0268 C5H4O- 1 80.0268 0.58
81.0346 C5H5O- 1 81.0346 0.02
83.0139 C4H3O2- 1 83.0139 0.21
84.009 C3H2NO2- 1 84.0091 -0.74
85.0295 C4H5O2- 1 85.0295 0.08
87.0087 C3H3O3- 1 87.0088 -0.55
89.0397 C7H5- 1 89.0397 0.63
90.0349 C6H4N- 1 90.0349 -0.25
91.0189 C6H3O- 1 91.0189 -0.53
91.0553 C7H7- 1 91.0553 0.07
92.0268 C6H4O- 1 92.0268 0.29
93.0345 C6H5O- 1 93.0346 -0.63
95.0138 C5H3O2- 1 95.0139 -0.14
96.0091 C4H2NO2- 1 96.0091 0.29
96.0455 C5H6NO- 1 96.0455 0.55
96.9931 C4HO3- 1 96.9931 -0.59
97.0294 C5H5O2- 1 97.0295 -0.75
98.0247 C4H4NO2- 1 98.0248 -0.94
99.0087 C4H3O3- 1 99.0088 -0.28
99.0451 C5H7O2- 1 99.0452 -0.94
100.0768 C5H10NO- 1 100.0768 -0.18
103.0554 C8H7- 1 103.0553 0.45
105.0345 C7H5O- 1 105.0346 -1.03
106.0299 C6H4NO- 1 106.0298 0.4
107.0138 C6H3O2- 1 107.0139 -0.68
107.0503 C7H7O- 1 107.0502 1.04
107.0615 C6H7N2- 1 107.0615 0.08
108.0217 C6H4O2- 1 108.0217 -0.07
109.0295 C6H5O2- 1 109.0295 -0.3
110.0249 C5H4NO2- 1 110.0248 1.62
111.0088 C5H3O3- 1 111.0088 0.02
115.055 C9H7- 1 115.0553 -2.55
117.0346 C8H5O- 1 117.0346 0.36
118.03 C7H4NO- 1 118.0298 1.21
119.0139 C7H3O2- 1 119.0139 0.31
119.0502 C8H7O- 1 119.0502 -0.66
120.0091 C6H2NO2- 1 120.0091 -0.02
121.0295 C7H5O2- 1 121.0295 0.31
121.0534 C7H7NO- 1 121.0533 0.56
122.025 C6H4NO2- 1 122.0248 1.7
122.0374 C7H6O2- 1 122.0373 0.26
122.0611 C7H8NO- 1 122.0611 -0.22
123.0088 C6H3O3- 1 123.0088 0.26
123.0327 C6H5NO2- 1 123.0326 1
124.0165 C6H4O3- 1 124.0166 -0.5
124.0404 C6H6NO2- 1 124.0404 -0.02
124.9878 C5HO4- 1 124.988 -1.46
125.0243 C6H5O3- 1 125.0244 -0.54
125.072 C6H9N2O- 1 125.072 0.03
126.0195 C5H4NO3- 1 126.0197 -1.16
126.0561 C6H8NO2- 1 126.0561 0.06
129.0348 C9H5O- 1 129.0346 1.49
129.0711 C10H9- 1 129.071 0.67
130.0422 C9H6O- 1 130.0424 -1.79
131.0135 C8H3O2- 1 131.0139 -2.46
131.0502 C9H7O- 1 131.0502 -0.22
132.0218 C8H4O2- 1 132.0217 0.62
133.017 C7H3NO2- 1 133.0169 0.7
133.0293 C8H5O2- 1 133.0295 -1.68
133.0661 C9H9O- 1 133.0659 1.29
134.0248 C7H4NO2- 1 134.0248 0.06
134.0373 C8H6O2- 1 134.0373 -0.43
135.0088 C7H3O3- 1 135.0088 0.46
135.0452 C8H7O2- 1 135.0452 0.27
136.0164 C7H4O3- 1 136.0166 -1.49
136.0402 C7H6NO2- 1 136.0404 -1.12
136.0762 C8H10NO- 1 136.0768 -4.17
136.9881 C6HO4- 1 136.988 0.86
137.0244 C7H5O3- 1 137.0244 -0.13
137.0483 C7H7NO2- 1 137.0482 0.61
138.0196 C6H4NO3- 1 138.0197 -0.41
138.0323 C7H6O3- 1 138.0322 0.27
138.0561 C7H8NO2- 1 138.0561 0.2
139.0149 C5H3N2O3- 1 139.0149 -0.11
140.0718 C7H10NO2- 1 140.0717 0.48
141.0193 C6H5O4- 1 141.0193 -0.44
142.0144 C5H4NO4- 1 142.0146 -1.14
142.9986 C5H3O5- 1 142.9986 0.23
143.0502 C10H7O- 1 143.0502 -0.41
144.058 C10H8O- 1 144.0581 -0.23
145.0294 C9H5O2- 1 145.0295 -0.5
145.0658 C10H9O- 1 145.0659 -0.82
146.0247 C8H4NO2- 1 146.0248 -0.08
146.037 C9H6O2- 1 146.0373 -2.52
147.02 C7H3N2O2- 1 147.02 0.27
147.0327 C8H5NO2- 1 147.0326 1.11
147.0452 C9H7O2- 1 147.0452 0.52
148.004 C7H2NO3- 1 148.004 -0.45
148.0168 C8H4O3- 1 148.0166 1.06
148.0403 C8H6NO2- 1 148.0404 -0.82
149.0118 C7H3NO3- 1 149.0118 -0.41
149.0243 C8H5O3- 1 149.0244 -0.45
149.0353 C7H5N2O2- 1 149.0357 -2.42
149.0481 C8H7NO2- 1 149.0482 -0.58
149.996 C7H2O4- 1 149.9959 0.75
150.0196 C7H4NO3- 1 150.0197 -0.38
151.0037 C7H3O4- 1 151.0037 0.18
151.0275 C7H5NO3- 1 151.0275 -0.21
152.0118 C7H4O4- 1 152.0115 2.06
152.0356 C7H6NO3- 1 152.0353 1.6
152.0714 C8H10NO2- 1 152.0717 -1.86
153.0195 C7H5O4- 1 153.0193 1.29
155.0501 C11H7O- 1 155.0502 -0.89
156.058 C11H8O- 1 156.0581 -0.34
157.0658 C11H9O- 1 157.0659 -0.37
158.0373 C10H6O2- 1 158.0373 0.01
159.0452 C10H7O2- 1 159.0452 0.04
160.0163 C9H4O3- 1 160.0166 -1.7
160.0401 C9H6NO2- 1 160.0404 -1.7
161.0245 C9H5O3- 1 161.0244 0.2
162.0197 C8H4NO3- 1 162.0197 0.02
162.0323 C9H6O3- 1 162.0322 0.11
163.004 C8H3O4- 1 163.0037 1.7
163.0152 C7H3N2O3- 1 163.0149 1.81
163.0276 C8H5NO3- 1 163.0275 0.66
163.0401 C9H7O3- 1 163.0401 -0.11
164.0115 C8H4O4- 1 164.0115 -0.04
164.0353 C8H6NO3- 1 164.0353 -0.16
165.0193 C8H5O4- 1 165.0193 -0.44
165.0712 C13H9- 1 165.071 1.67
167.0221 C7H5NO4- 1 167.0224 -2.07
167.0501 C12H7O- 1 167.0502 -0.89
168.0664 C8H10NO3- 1 168.0666 -1.05
169.025 C6H5N2O4- 1 169.0255 -3.02
169.066 C12H9O- 1 169.0659 0.54
170.0372 C11H6O2- 1 170.0373 -0.93
171.0452 C11H7O2- 1 171.0452 0.27
172.053 C11H8O2- 1 172.053 0.3
173.0244 C10H5O3- 1 173.0244 -0.33
173.0607 C11H9O2- 1 173.0608 -0.65
174.0322 C10H6O3- 1 174.0322 -0.36
175.04 C10H7O3- 1 175.0401 -0.62
176.035 C9H6NO3- 1 176.0353 -1.91
177.0306 C8H5N2O3- 1 177.0306 0.02
178.0146 C8H4NO4- 1 178.0146 0.27
180.0583 C13H8O- 1 180.0581 1.09
181.066 C13H9O- 1 181.0659 0.56
182.0368 C12H6O2- 1 182.0373 -2.9
183.0449 C12H7O2- 1 183.0452 -1.16
183.0815 C13H11O- 1 183.0815 -0.16
184.0528 C12H8O2- 1 184.053 -0.8
185.0244 C11H5O3- 1 185.0244 -0.31
185.0608 C12H9O2- 1 185.0608 -0.12
186.0323 C11H6O3- 1 186.0322 0.09
186.0686 C12H10O2- 1 186.0686 -0.1
187.0401 C11H7O3- 1 187.0401 -0.04
188.0479 C11H8O3- 1 188.0479 -0.17
189.0193 C10H5O4- 1 189.0193 -0.33
189.0557 C11H9O3- 1 189.0557 -0.31
190.051 C10H8NO3- 1 190.051 0.23
191.0348 C10H7O4- 1 191.035 -1.01
191.0507 C14H7O- 1 191.0502 2.42
191.0714 C11H11O3- 1 191.0714 0.12
192.0305 C9H6NO4- 1 192.0302 1.19
193.0659 C14H9O- 1 193.0659 0.01
195.0459 C13H7O2- 1 195.0452 3.62
195.0814 C14H11O- 1 195.0815 -0.45
196.053 C13H8O2- 1 196.053 -0.04
197.0608 C13H9O2- 1 197.0608 -0.27
198.0319 C12H6O3- 1 198.0322 -1.68
198.069 C13H10O2- 1 198.0686 1.62
199.0397 C12H7O3- 1 199.0401 -1.7
199.0764 C13H11O2- 1 199.0765 -0.37
200.048 C12H8O3- 1 200.0479 0.59
201.0557 C12H9O3- 1 201.0557 -0.14
202.0271 C11H6O4- 1 202.0272 -0.18
203.0349 C11H7O4- 1 203.035 -0.26
203.0713 C12H11O3- 1 203.0714 -0.14
204.0424 C11H8O4- 1 204.0428 -2.09
204.0584 C15H8O- 1 204.0581 1.6
205.0656 C15H9O- 1 205.0659 -1.41
206.0211 C10H6O5- 1 206.0221 -4.77
207.0451 C14H7O2- 1 207.0452 -0.06
207.0815 C15H11O- 1 207.0815 0.06
208.0532 C14H8O2- 1 208.053 1.07
209.0608 C14H9O2- 1 209.0608 -0.11
210.0322 C13H6O3- 1 210.0322 -0.39
210.0684 C14H10O2- 1 210.0686 -0.9
211.04 C13H7O3- 1 211.0401 -0.18
211.0764 C14H11O2- 1 211.0765 -0.16
212.048 C13H8O3- 1 212.0479 0.41
213.0556 C13H9O3- 1 213.0557 -0.36
214.0269 C12H6O4- 1 214.0272 -0.97
214.0636 C13H10O3- 1 214.0635 0.22
215.0351 C12H7O4- 1 215.035 0.64
215.0716 C13H11O3- 1 215.0714 0.99
216.0427 C12H8O4- 1 216.0428 -0.73
217.0507 C12H9O4- 1 217.0506 0.36
217.0661 C16H9O- 1 217.0659 0.93
218.0223 C11H6O5- 1 218.0221 1.05
218.059 C12H10O4- 1 218.0585 2.49
219.0449 C15H7O2- 1 219.0452 -0.97
220.0531 C15H8O2- 1 220.053 0.33
221.0607 C15H9O2- 1 221.0608 -0.42
222.0683 C15H10O2- 1 222.0686 -1.48
223.0401 C14H7O3- 1 223.0401 0.32
223.0763 C15H11O2- 1 223.0765 -0.55
224.0479 C14H8O3- 1 224.0479 0.12
224.0714 C14H10NO2- 1 224.0717 -1.48
225.0557 C14H9O3- 1 225.0557 -0.12
225.0924 C15H13O2- 1 225.0921 1.19
226.027 C13H6O4- 1 226.0272 -0.7
226.0635 C14H10O3- 1 226.0635 -0.32
227.035 C13H7O4- 1 227.035 -0.05
227.0713 C14H11O3- 1 227.0714 -0.12
228.043 C13H8O4- 1 228.0428 1.06
229.0511 C13H9O4- 1 229.0506 1.82
230.0218 C12H6O5- 1 230.0221 -1.05
230.0581 C13H10O4- 1 230.0585 -1.42
231.03 C12H7O5- 1 231.0299 0.36
232.0531 C16H8O2- 1 232.053 0.44
233.0608 C16H9O2- 1 233.0608 -0.14
234.0686 C16H10O2- 1 234.0686 0.01
235.0401 C15H7O3- 1 235.0401 -0.08
235.0762 C16H11O2- 1 235.0765 -0.91
236.0482 C15H8O3- 1 236.0479 1.34
236.0716 C15H10NO2- 1 236.0717 -0.39
237.0557 C15H9O3- 1 237.0557 0.01
237.0921 C16H13O2- 1 237.0921 -0.22
238.0272 C14H6O4- 1 238.0272 0.14
238.0637 C15H10O3- 1 238.0635 0.66
238.0877 C15H12NO2- 1 238.0874 1.63
239.035 C14H7O4- 1 239.035 -0.09
239.0713 C15H11O3- 1 239.0714 -0.07
240.0426 C14H8O4- 1 240.0428 -0.78
241.051 C14H9O4- 1 241.0506 1.48
241.0874 C15H13O3- 1 241.087 1.42
243.0664 C14H11O4- 1 243.0663 0.32
245.0602 C17H9O2- 1 245.0608 -2.3
246.0684 C17H10O2- 1 246.0686 -0.76
247.0402 C16H7O3- 1 247.0401 0.5
247.0764 C17H11O2- 1 247.0765 -0.26
248.0476 C16H8O3- 1 248.0479 -1.02
249.0557 C16H9O3- 1 249.0557 -0.27
250.0277 C15H6O4- 1 250.0272 2.37
250.0637 C16H10O3- 1 250.0635 0.75
250.0875 C16H12NO2- 1 250.0874 0.51
251.0347 C15H7O4- 1 251.035 -1.12
251.0712 C16H11O3- 1 251.0714 -0.47
252.0428 C15H8O4- 1 252.0428 -0.19
252.1027 C16H14NO2- 1 252.103 -1.32
253.0506 C15H9O4- 1 253.0506 -0.05
254.0586 C15H10O4- 1 254.0585 0.68
255.03 C14H7O5- 1 255.0299 0.21
255.0665 C15H11O4- 1 255.0663 1.01
256.0377 C14H8O5- 1 256.0377 -0.05
261.0553 C17H9O3- 1 261.0557 -1.75
262.064 C17H10O3- 1 262.0635 1.59
263.0351 C16H7O4- 1 263.035 0.64
263.0586 C16H9NO3- 1 263.0588 -0.88
263.0713 C17H11O3- 1 263.0714 -0.07
264.0427 C16H8O4- 1 264.0428 -0.33
264.0667 C16H10NO3- 1 264.0666 0.24
265.0503 C16H9O4- 1 265.0506 -1.18
265.087 C17H13O3- 1 265.087 -0.07
266.0584 C16H10O4- 1 266.0585 -0.18
267.066 C16H11O4- 1 267.0663 -0.91
268.0613 C15H10NO4- 1 268.0615 -0.83
269.0459 C15H9O5- 1 269.0455 1.42
271.0616 C15H11O5- 1 271.0612 1.3
273.056 C18H9O3- 1 273.0557 1.03
274.0639 C18H10O3- 1 274.0635 1.3
275.0716 C18H11O3- 1 275.0714 0.92
276.0428 C17H8O4- 1 276.0428 -0.1
277.0504 C17H9O4- 1 277.0506 -0.8
278.0579 C17H10O4- 1 278.0585 -2.04
278.0824 C17H12NO3- 1 278.0823 0.59
279.0293 C16H7O5- 1 279.0299 -2.28
279.0666 C17H11O4- 1 279.0663 0.99
280.0382 C16H8O5- 1 280.0377 1.85
282.0539 C16H10O5- 1 282.0534 1.73
289.0507 C18H9O4- 1 289.0506 0.16
291.066 C18H11O4- 1 291.0663 -0.97
292.0374 C17H8O5- 1 292.0377 -1.07
293.0456 C17H9O5- 1 293.0455 0.11
303.0299 C18H7O5- 1 303.0299 -0.02
304.0618 C18H10NO4- 1 304.0615 1.05
305.0452 C18H9O5- 1 305.0455 -1.1
316.0629 C19H10NO4- 2 316.0615 4.36
PK$NUM_PEAK: 299
PK$PEAK: m/z int. rel.int.
50.0035 1838.4 2
51.0239 2031.4 3
55.0189 31414.3 48
57.0345 7882.2 12
58.0298 2461.6 3
59.0138 8775.9 13
63.024 27271.7 42
65.0033 22429.1 34
65.0397 26781.4 41
65.9985 50594.7 78
67.019 14604.1 22
68.0143 3740.9 5
68.9982 112250.4 173
69.0346 40439.5 62
71.014 18728.7 28
72.9932 6401.9 9
73.0296 2547.2 3
75.024 2047.1 3
78.035 2793.8 4
79.0189 29614.4 45
80.0268 10909.8 16
81.0346 22342.6 34
83.0139 80375.7 123
84.009 93594.6 144
85.0295 8855.3 13
87.0087 50520.9 77
89.0397 8302.5 12
90.0349 7323 11
91.0189 64416.8 99
91.0553 7782.5 12
92.0268 9890.3 15
93.0345 84340.9 130
95.0138 86274.1 133
96.0091 26102.8 40
96.0455 2091.9 3
96.9931 110074.5 169
97.0294 48789 75
98.0247 2211.1 3
99.0087 19447 29
99.0451 2509.9 3
100.0768 9607.8 14
103.0554 1764.8 2
105.0345 11469.2 17
106.0299 2807 4
107.0138 22902.5 35
107.0503 8634.1 13
107.0615 2047 3
108.0217 81493.4 125
109.0295 87081.4 134
110.0249 2832.3 4
111.0088 68746.9 106
115.055 1962.8 3
117.0346 48969.4 75
118.03 2054.9 3
119.0139 9653.2 14
119.0502 23297 35
120.0091 8126.5 12
121.0295 45180 69
121.0534 2395.1 3
122.025 12686.6 19
122.0374 7455.8 11
122.0611 2077.2 3
123.0088 79115.1 122
123.0327 8365.7 12
124.0165 55165.3 85
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//
