ACCESSION: MSBNK-Eawag-EQ367857
RECORD_TITLE: Doxycycline; LC-ESI-QFT; MS2; CE: 120; 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 120 (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: splash10-03xr-5960000000-615a60dad7e8412f2e60
PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm)
50.0036 C3N- 1 50.0036 -0.85
51.0239 C4H3- 1 51.024 -2.03
53.0032 C3HO- 1 53.0033 -1.29
55.0189 C3H3O- 1 55.0189 -1.24
59.0138 C2H3O2- 1 59.0139 -0.73
63.024 C5H3- 1 63.024 0.1
64.0192 C4H2N- 1 64.0193 -0.67
65.0033 C4HO- 1 65.0033 0.33
65.0397 C5H5- 1 65.0397 0.4
65.9986 C3NO- 1 65.9985 0.35
67.019 C4H3O- 1 67.0189 0.47
68.0143 C3H2NO- 1 68.0142 1.07
68.9982 C3HO2- 1 68.9982 0.54
69.0346 C4H5O- 1 69.0346 0.31
71.0138 C3H3O2- 1 71.0139 -0.6
76.0192 C5H2N- 1 76.0193 -0.3
78.0349 C5H4N- 1 78.0349 -0.93
79.019 C5H3O- 1 79.0189 0.27
81.0345 C5H5O- 1 81.0346 -1.46
83.0138 C4H3O2- 1 83.0139 -0.52
84.009 C3H2NO2- 1 84.0091 -0.86
85.0295 C4H5O2- 1 85.0295 0.08
89.0396 C7H5- 1 89.0397 -0.6
90.0349 C6H4N- 1 90.0349 -0.25
91.0189 C6H3O- 1 91.0189 -0.42
91.0553 C7H7- 1 91.0553 -0.59
92.014 C5H2NO- 1 92.0142 -1.93
93.0346 C6H5O- 1 93.0346 0.13
94.0298 C5H4NO- 1 94.0298 -0.4
95.0139 C5H3O2- 1 95.0139 -0.03
96.0091 C4H2NO2- 1 96.0091 -0.23
96.993 C4HO3- 1 96.9931 -1
97.0295 C5H5O2- 1 97.0295 -0.34
106.0424 C7H6O- 1 106.0424 0.25
107.014 C6H3O2- 1 107.0139 1.75
108.0217 C6H4O2- 1 108.0217 0.11
109.0294 C6H5O2- 1 109.0295 -0.94
115.0553 C9H7- 1 115.0553 -0.47
117.0347 C8H5O- 1 117.0346 0.95
118.0299 C7H4NO- 1 118.0298 0.62
119.0502 C8H7O- 1 119.0502 -0.24
120.0092 C6H2NO2- 1 120.0091 0.9
120.0455 C7H6NO- 1 120.0455 0.44
121.0295 C7H5O2- 1 121.0295 0.31
121.066 C8H9O- 1 121.0659 0.59
122.0247 C6H4NO2- 1 122.0248 -0.43
123.0088 C6H3O3- 1 123.0088 0.67
124.0166 C6H4O3- 1 124.0166 -0.02
124.0402 C6H6NO2- 1 124.0404 -1.55
126.056 C6H8NO2- 1 126.0561 -0.49
130.0424 C9H6O- 1 130.0424 -0.33
131.05 C9H7O- 1 131.0502 -2.05
133.0294 C8H5O2- 1 133.0295 -0.4
133.0665 C9H9O- 1 133.0659 4.22
134.0246 C7H4NO2- 1 134.0248 -1.36
135.0091 C7H3O3- 1 135.0088 2.39
137.0246 C7H5O3- 1 137.0244 1.33
137.0397 C11H5- 1 137.0397 0.56
138.0196 C6H4NO3- 1 138.0197 -0.26
138.0474 C11H6- 1 138.0475 -0.93
139.0149 C5H3N2O3- 1 139.0149 -0.18
139.0553 C11H7- 1 139.0553 0.12
141.0346 C10H5O- 1 141.0346 0.22
141.0712 C11H9- 1 141.071 1.67
143.0502 C10H7O- 1 143.0502 0.01
144.058 C10H8O- 1 144.0581 -0.44
145.0294 C9H5O2- 1 145.0295 -0.37
145.0659 C10H9O- 1 145.0659 0.42
147.02 C7H3N2O2- 1 147.02 0.27
147.0453 C9H7O2- 1 147.0452 0.86
148.0041 C7H2NO3- 1 148.004 0.43
149.0118 C7H3NO3- 1 149.0118 -0.55
149.0359 C7H5N2O2- 1 149.0357 1.67
150.0197 C7H4NO3- 1 150.0197 0.56
154.0426 C11H6O- 1 154.0424 1.34
155.0504 C11H7O- 1 155.0502 0.78
156.058 C11H8O- 1 156.0581 -0.15
157.0656 C11H9O- 1 157.0659 -1.58
158.0373 C10H6O2- 1 158.0373 0.01
159.0452 C10H7O2- 1 159.0452 0.23
161.0243 C9H5O3- 1 161.0244 -0.98
163.0151 C7H3N2O3- 1 163.0149 1.13
165.0344 C12H5O- 1 165.0346 -1.08
167.0503 C12H7O- 1 167.0502 0.43
169.0296 C11H5O2- 1 169.0295 0.63
169.0657 C12H9O- 1 169.0659 -0.94
170.0373 C11H6O2- 1 170.0373 -0.22
171.0452 C11H7O2- 1 171.0452 0.16
172.053 C11H8O2- 1 172.053 0.01
173.0607 C11H9O2- 1 173.0608 -0.54
180.0581 C13H8O- 1 180.0581 0.37
181.0655 C13H9O- 1 181.0659 -1.98
182.0373 C12H6O2- 1 182.0373 0.01
183.045 C12H7O2- 1 183.0452 -0.62
184.0529 C12H8O2- 1 184.053 -0.64
185.0608 C12H9O2- 1 185.0608 -0.29
186.0324 C11H6O3- 1 186.0322 1.06
187.0401 C11H7O3- 1 187.0401 0.12
191.05 C14H7O- 1 191.0502 -1.14
193.0295 C13H5O2- 1 193.0295 0.19
193.0658 C14H9O- 1 193.0659 -0.61
194.0735 C14H10O- 1 194.0737 -1.31
195.0452 C13H7O2- 1 195.0452 0.29
196.0529 C13H8O2- 1 196.053 -0.45
197.0607 C13H9O2- 1 197.0608 -0.52
199.0763 C13H11O2- 1 199.0765 -0.52
204.058 C15H8O- 1 204.0581 -0.26
205.0658 C15H9O- 1 205.0659 -0.29
207.0448 C14H7O2- 1 207.0452 -1.61
208.0527 C14H8O2- 1 208.053 -1.19
209.0608 C14H9O2- 1 209.0608 0.18
210.0319 C13H6O3- 1 210.0322 -1.77
210.0561 C13H8NO2- 1 210.0561 0.09
210.0687 C14H10O2- 1 210.0686 0.48
211.0402 C13H7O3- 1 211.0401 0.39
213.0556 C13H9O3- 1 213.0557 -0.51
219.0451 C15H7O2- 1 219.0452 -0.06
220.0531 C15H8O2- 1 220.053 0.46
221.0499 C2H11N3O9- 1 221.0501 -0.98
221.0607 C15H9O2- 1 221.0608 -0.65
222.0684 C15H10O2- 1 222.0686 -0.98
223.0402 C14H7O3- 1 223.0401 0.64
224.0481 C14H8O3- 1 224.0479 0.79
225.0559 C14H9O3- 1 225.0557 0.94
232.0529 C16H8O2- 1 232.053 -0.16
233.0607 C16H9O2- 1 233.0608 -0.27
235.0408 C15H7O3- 1 235.0401 3.03
237.056 C15H9O3- 1 237.0557 1.32
239.0351 C14H7O4- 1 239.035 0.28
240.043 C14H8O4- 1 240.0428 0.68
248.0479 C16H8O3- 1 248.0479 -0.01
249.0559 C16H9O3- 1 249.0557 0.85
250.0512 C15H8NO3- 1 250.051 1.09
253.0509 C15H9O4- 1 253.0506 1.18
261.0557 C17H9O3- 1 261.0557 0.01
PK$NUM_PEAK: 135
PK$PEAK: m/z int. rel.int.
50.0036 11406.7 34
51.0239 5714.4 17
53.0032 6900.1 20
55.0189 5765.4 17
59.0138 4408.2 13
63.024 36121.4 108
64.0192 4035.3 12
65.0033 29999.1 89
65.0397 10712.5 32
65.9986 112945.6 337
67.019 12456.6 37
68.0143 9310.3 27
68.9982 84769.1 253
69.0346 10574.6 31
71.0138 1826.4 5
76.0192 1598.9 4
78.0349 1903.1 5
79.019 17640.2 52
81.0345 3587.8 10
83.0138 1806.9 5
84.009 19994.4 59
85.0295 1202.2 3
89.0396 7928.1 23
90.0349 4440.9 13
91.0189 8867.5 26
91.0553 5915.7 17
92.014 1662.1 4
93.0346 14346.9 42
94.0298 1113 3
95.0139 55204.8 165
96.0091 41759.8 124
96.993 5627.6 16
97.0295 9598 28
106.0424 1505.6 4
107.014 1387.6 4
108.0217 12115 36
109.0294 16466 49
115.0553 5161.7 15
117.0347 15745.8 47
118.0299 1175.7 3
119.0502 36580.3 109
120.0092 7093.9 21
120.0455 1834.1 5
121.0295 17455.8 52
121.066 4324.6 12
122.0247 5234.8 15
123.0088 21248 63
124.0166 5471.6 16
124.0402 1452.3 4
126.056 1402.9 4
130.0424 51647.1 154
131.05 6896.5 20
133.0294 892.7 2
133.0665 1021.6 3
134.0246 8655.6 25
135.0091 1381 4
137.0246 3466.5 10
137.0397 1621.2 4
138.0196 2353.6 7
138.0474 1471.2 4
139.0149 13606.6 40
139.0553 4315.3 12
141.0346 7931.1 23
141.0712 1270.4 3
143.0502 37877.7 113
144.058 2272.4 6
145.0294 5057.9 15
145.0659 5617.2 16
147.02 1789.2 5
147.0453 1088.2 3
148.0041 9850 29
149.0118 3673.2 10
149.0359 1092.2 3
150.0197 3616.2 10
154.0426 6404.7 19
155.0504 11582.3 34
156.058 7765.9 23
157.0656 8842.4 26
158.0373 43763.9 130
159.0452 58844.3 176
161.0243 5837.8 17
163.0151 1639.8 4
165.0344 5214.6 15
167.0503 33795.9 101
169.0296 3927.9 11
169.0657 9842.3 29
170.0373 4258.9 12
171.0452 27221.2 81
172.053 17397.2 52
173.0607 30501.7 91
180.0581 13531.2 40
181.0655 9200.5 27
182.0373 15128.3 45
183.045 79023.9 236
184.0529 2442 7
185.0608 14222.7 42
186.0324 1417.4 4
187.0401 29907.5 89
191.05 5665.8 16
193.0295 1999.4 5
193.0658 5845.9 17
194.0735 1402.4 4
195.0452 18564.7 55
196.0529 19382.3 57
197.0607 20155.5 60
199.0763 3726.9 11
204.058 5722.8 17
205.0658 1129.8 3
207.0448 6143.1 18
208.0527 9237.3 27
209.0608 27395.4 81
210.0319 8409.7 25
210.0561 5957.7 17
210.0687 1340.6 4
211.0402 333849.1 999
213.0556 1655.9 4
219.0451 2129.1 6
220.0531 4527.4 13
221.0499 1010.9 3
221.0607 4420.3 13
222.0684 1319.7 3
223.0402 4261.2 12
224.0481 13184.5 39
225.0559 12472.5 37
232.0529 2240.6 6
233.0607 5175.9 15
235.0408 4567.3 13
237.056 13357.3 39
239.0351 84923.7 254
240.043 26800 80
248.0479 5472.9 16
249.0559 2082.4 6
250.0512 1088.4 3
253.0509 2331.2 6
261.0557 1977.4 5
//
