ACCESSION: MSBNK-Eawag-EQ368052
RECORD_TITLE: Chlortetracycline; LC-ESI-QFT; MS2; CE: 30; 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 30 (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: splash10-0006-0119100000-f81cbed646ea3c626cd4
PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm)
67.0068 ClH4N2- 1 67.0068 -0.59
84.0091 C3H2NO2- 1 84.0091 -0.26
99.0087 C4H3O3- 1 99.0088 -0.58
100.0767 C5H10NO- 1 100.0768 -1.27
109.0294 C6H5O2- 1 109.0295 -0.85
124.004 C5H2NO3- 2 124.004 -0.13
125.072 C6H9N2O- 1 125.072 -0.53
126.0197 C5H4NO3- 2 126.0197 0.58
126.0559 C6H8NO2- 2 126.0561 -1.13
126.9952 C6H4ClO- 1 126.9956 -3.2
135.0087 C7H3O3- 2 135.0088 -0.2
136.0405 C7H6NO2- 2 136.0404 0.57
142.0145 C5H4NO4- 2 142.0146 -0.64
142.9984 C5H3O5- 2 142.9986 -1.03
152.0354 C7H6NO3- 2 152.0353 0.55
154.0384 C6H6N2O3- 1 154.0384 -0.2
161.0245 C9H5O3- 2 161.0244 0.39
162.0196 C8H4NO3- 2 162.0197 -0.41
163.0037 C8H3O4- 2 163.0037 0.05
166.0873 C9H12NO2- 2 166.0874 -0.31
169.006 C8H6ClO2- 1 169.0062 -1.25
169.0618 C7H9N2O3- 1 169.0619 -0.45
170.9854 C7H4ClO3- 1 170.9854 -0.56
175.0401 C10H7O3- 2 175.0401 0.36
180.0302 C8H6NO4- 2 180.0302 -0.01
181.0383 C8H7NO4- 2 181.0381 1.13
191.0351 C10H7O4- 2 191.035 0.35
192.0667 C10H10NO3- 2 192.0666 0.64
193.0061 C10H6ClO2- 1 193.0062 -0.63
193.0506 C10H9O4- 2 193.0506 -0.06
194.9853 C9H4ClO3- 1 194.9854 -0.54
195.0217 C10H8ClO2- 1 195.0218 -0.67
197.001 C9H6ClO3- 1 197.0011 -0.28
206.013 C11H7ClO2- 2 206.014 -4.64
207.0218 C11H8ClO2- 1 207.0218 -0.25
207.993 C10H5ClO3- 1 207.9933 -1.16
209.0932 C10H13N2O3- 1 209.0932 -0.03
221.0375 C12H10ClO2- 1 221.0375 0.09
223.0167 C11H8ClO3- 1 223.0167 -0.16
235.0167 C12H8ClO3- 1 235.0167 -0.19
235.0531 C13H12ClO2- 1 235.0531 0.04
236.0929 C12H14NO4- 2 236.0928 0.21
245.0372 C14H10ClO2- 1 245.0375 -1.06
247.0168 C13H8ClO3- 1 247.0167 0.06
248.0245 C13H9ClO3- 1 248.0246 -0.24
251.0119 C12H8ClO4- 1 251.0117 0.88
253.0506 C15H9O4- 2 253.0506 -0.17
257.0372 C15H10ClO2- 1 257.0375 -1.21
259.0155 C14H8ClO3- 2 259.0167 -4.69
259.0534 C15H12ClO2- 1 259.0531 0.92
261.0325 C14H10ClO3- 1 261.0324 0.29
263.048 C14H12ClO3- 1 263.048 -0.29
265.0271 C13H10ClO4- 1 265.0273 -0.79
271.0169 C15H8ClO3- 1 271.0167 0.5
271.0532 C16H12ClO2- 1 271.0531 0.11
273.0324 C15H10ClO3- 1 273.0324 -0.17
275.0486 C15H12ClO3- 1 275.048 2.16
279.0065 C13H8ClO5- 1 279.0066 -0.37
279.0988 C13H15N2O5- 1 279.0986 0.7
285.0319 C16H10ClO3- 2 285.0324 -1.77
287.0122 C15H8ClO4- 1 287.0117 1.88
287.0486 C16H12ClO3- 1 287.048 1.86
288.0797 C16H15ClNO2- 2 288.0797 -0.1
289.0272 C15H10ClO4- 1 289.0273 -0.31
290.0355 C15H11ClO4- 1 290.0351 1.09
291.0433 C15H12ClO4- 1 291.043 1.06
299.0482 C17H12ClO3- 1 299.048 0.65
301.0278 C16H10ClO4- 1 301.0273 1.49
303.043 C16H12ClO4- 1 303.043 0.2
305.0224 C15H10ClO5- 1 305.0222 0.54
306.09 C16H17ClNO3- 2 306.0902 -0.77
307.0379 C15H12ClO5- 1 307.0379 -0.05
309.0329 C18H10ClO3- 1 309.0324 1.76
312.02 C17H9ClO4- 1 312.0195 1.75
315.0437 C17H12ClO4- 1 315.043 2.29
319.0382 C16H12ClO5- 1 319.0379 1.08
325.0276 C18H10ClO4- 1 325.0273 0.8
327.0074 C17H8ClO5- 1 327.0066 2.43
327.0432 C18H12ClO4- 1 327.043 0.61
329.0222 C17H10ClO5- 1 329.0222 -0.08
331.0373 C17H12ClO5- 2 331.0379 -1.65
332.0695 C17H15ClNO4- 2 332.0695 -0.03
342.0544 C18H13ClNO4- 2 342.0539 1.55
343.038 C18H12ClO5- 1 343.0379 0.39
345.0182 C17H10ClO6- 2 345.0171 3.07
345.0537 C18H14ClO5- 1 345.0535 0.65
347.0325 C17H12ClO6- 2 347.0328 -0.81
348.1009 C18H19ClNO4- 2 348.1008 0.17
353.0221 C19H10ClO5- 2 353.0222 -0.35
354.0892 C20H17ClNO3- 2 354.0902 -2.84
356.0088 C18H9ClO6- 2 356.0093 -1.44
356.0694 C19H15ClNO4- 2 356.0695 -0.39
356.1137 C19H18NO6- 2 356.114 -0.68
359.0336 C18H12ClO6- 1 359.0328 2.37
360.0649 C18H15ClNO5- 2 360.0644 1.38
369.0171 C19H10ClO6- 2 369.0171 -0.21
370.0328 C15H13ClNO8- 1 370.0335 -1.83
370.0855 C20H17ClNO4- 1 370.0852 1.03
371.0327 C19H12ClO6- 2 371.0328 -0.29
372.1012 C20H19ClNO4- 1 372.1008 1.13
373.0122 C18H10ClO7- 1 373.0121 0.42
374.0796 C22H14O6- 2 374.0796 0.09
387.0276 C19H12ClO7- 2 387.0277 -0.17
388.0959 C20H19ClNO5- 1 388.0957 0.56
389.0434 C19H14ClO7- 2 389.0434 0.09
390.1108 C20H21ClNO5- 1 390.1114 -1.39
392.0908 C19H19ClNO6- 2 392.0906 0.28
397.012 C20H10ClO7- 2 397.0121 -0.11
398.0807 C21H17ClNO5- 1 398.0801 1.57
399.9992 C19H9ClO8- 2 399.9991 0.19
404.0538 C22H12O8- 2 404.0538 0.18
405.1212 C20H22ClN2O5- 1 405.1223 -2.6
414.0378 C20H13ClNO7- 1 414.0386 -2.06
415.0226 C20H12ClO8- 2 415.0226 -0.17
415.107 C21H20ClN2O5- 1 415.1066 0.81
416.0906 C21H19ClNO6- 1 416.0906 -0.07
432.0512 C20H15ClNO8- 1 432.0492 4.75
434.1011 C21H21ClNO7- 1 434.1012 -0.26
442.0699 C22H17ClNO7- 1 442.0699 0.04
459.0965 C22H20ClN2O7- 1 459.0965 0.15
460.0804 C22H19ClNO8- 1 460.0805 -0.15
477.1072 C22H22ClN2O8- 1 477.107 0.4
478.0914 C22H21ClNO9- 2 478.091 0.83
PK$NUM_PEAK: 123
PK$PEAK: m/z int. rel.int.
67.0068 4667.4 1
84.0091 6676.3 1
99.0087 7663.9 1
100.0767 5953.3 1
109.0294 7942.8 2
124.004 7076.2 1
125.072 26492.6 6
126.0197 7503 1
126.0559 10775.6 2
126.9952 8076.4 2
135.0087 8826.6 2
136.0405 17200.4 4
142.0145 68419.1 17
142.9984 11436.4 2
152.0354 11857.6 3
154.0384 5739.6 1
161.0245 6599 1
162.0196 7094 1
163.0037 15965.4 4
166.0873 4378.7 1
169.006 52213.8 13
169.0618 63294.6 16
170.9854 7572.9 1
175.0401 22097.4 5
180.0302 203044 52
181.0383 5298.3 1
191.0351 6327.8 1
192.0667 6660.8 1
193.0061 5280.5 1
193.0506 6316.8 1
194.9853 111742.7 28
195.0217 20664.6 5
197.001 255931.9 66
206.013 8812.4 2
207.0218 24875.6 6
207.993 4997.4 1
209.0932 105146.7 27
221.0375 250134.6 64
223.0167 47026.2 12
235.0167 14345.2 3
235.0531 50774.1 13
236.0929 44860.3 11
245.0372 29538.2 7
247.0168 6729.3 1
248.0245 25187.6 6
251.0119 6088.2 1
253.0506 5469.8 1
257.0372 8595.4 2
259.0155 7926 2
259.0534 5320.5 1
261.0325 4533.4 1
263.048 145460 37
265.0271 4909.8 1
271.0169 7696.9 1
271.0532 7701.4 1
273.0324 5005.4 1
275.0486 9850.2 2
279.0065 19053 4
279.0988 7349.9 1
285.0319 22598 5
287.0122 6573.2 1
287.0486 4965.5 1
288.0797 5009.2 1
289.0272 68156 17
290.0355 5609.6 1
291.0433 7432.6 1
299.0482 19220.2 4
301.0278 7983.5 2
303.043 32999 8
305.0224 48885.9 12
306.09 5000.6 1
307.0379 329673.2 85
309.0329 5152 1
312.02 7204.5 1
315.0437 6801.2 1
319.0382 37892.7 9
325.0276 18730.2 4
327.0074 10268.4 2
327.0432 48860.5 12
329.0222 39178.6 10
331.0373 8067.9 2
332.0695 4928.8 1
342.0544 23255 6
343.038 38852.4 10
345.0182 11032.1 2
345.0537 26424.7 6
347.0325 87005 22
348.1009 23809.8 6
353.0221 23124.3 5
354.0892 12864.6 3
356.0088 14873.4 3
356.0694 4484.5 1
356.1137 6447 1
359.0336 8089.1 2
360.0649 24815.7 6
369.0171 18954.3 4
370.0328 5237.3 1
370.0855 21629.7 5
371.0327 126329 32
372.1012 41052.9 10
373.0122 10631.3 2
374.0796 30706.9 7
387.0276 73675.4 19
388.0959 79115.5 20
389.0434 148758 38
390.1108 27826.6 7
392.0908 3871747.2 999
397.012 17300.5 4
398.0807 16910.8 4
399.9992 23708.1 6
404.0538 5547 1
405.1212 5919.3 1
414.0378 11227.3 2
415.0226 164583.9 42
415.107 10392.8 2
416.0906 80559.4 20
432.0512 11124.9 2
434.1011 163658.5 42
442.0699 12540.8 3
459.0965 20372 5
460.0804 220617.1 56
477.1072 18307 4
478.0914 17686.3 4
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