ACCESSION: MSBNK-Eawag-EQ367856
RECORD_TITLE: Doxycycline; LC-ESI-QFT; MS2; CE: 90; 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 90 (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: splash10-0006-3890000000-07bb32be2f2e4011348d
PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm)
50.0036 C3N- 1 50.0036 -1.25
51.0239 C4H3- 1 51.024 -1.64
53.0032 C3HO- 1 53.0033 -0.91
55.0189 C3H3O- 1 55.0189 -0.7
57.0345 C3H5O- 1 57.0346 -1.37
59.0138 C2H3O2- 1 59.0139 -0.05
63.024 C5H3- 1 63.024 -0.06
65.0033 C4HO- 1 65.0033 0.33
65.0397 C5H5- 1 65.0397 0.56
65.9985 C3NO- 1 65.9985 -0.26
67.019 C4H3O- 1 67.0189 0.47
68.0142 C3H2NO- 1 68.0142 0.33
68.9982 C3HO2- 1 68.9982 0.39
69.0346 C4H5O- 1 69.0346 0.6
71.0139 C3H3O2- 1 71.0139 1.23
76.0193 C5H2N- 1 76.0193 0.36
78.0349 C5H4N- 1 78.0349 0.22
79.0189 C5H3O- 1 79.0189 -0.74
80.0267 C5H4O- 1 80.0268 -1.29
80.0505 C5H6N- 1 80.0506 -1.28
81.0219 C4H3NO- 1 81.022 -1.26
81.0346 C5H5O- 1 81.0346 0.14
82.0299 C4H4NO- 1 82.0298 0.89
82.0662 C5H8N- 1 82.0662 -0.52
83.0138 C4H3O2- 1 83.0139 -0.64
84.009 C3H2NO2- 1 84.0091 -0.74
85.0295 C4H5O2- 1 85.0295 0.44
86.0248 C3H4NO2- 1 86.0248 0.67
89.0397 C7H5- 1 89.0397 -0.04
90.0348 C6H4N- 1 90.0349 -1.59
91.019 C6H3O- 1 91.0189 0.13
91.0554 C7H7- 1 91.0553 0.4
92.0141 C5H2NO- 1 92.0142 -0.51
93.0345 C6H5O- 1 93.0346 -0.63
94.0298 C5H4NO- 1 94.0298 0.03
95.0138 C5H3O2- 1 95.0139 -0.35
96.0091 C4H2NO2- 1 96.0091 -0.44
96.0455 C5H6NO- 1 96.0455 -0.08
96.9931 C4HO3- 1 96.9931 -0.49
97.0294 C5H5O2- 1 97.0295 -0.96
99.0087 C4H3O3- 1 99.0088 -0.28
100.0767 C5H10NO- 1 100.0768 -0.57
106.0299 C6H4NO- 1 106.0298 1.06
106.0422 C7H6O- 1 106.0424 -1.92
107.0138 C6H3O2- 1 107.0139 -0.96
108.0217 C6H4O2- 1 108.0217 0.02
109.0295 C6H5O2- 1 109.0295 -0.3
110.0249 C5H4NO2- 1 110.0248 1.25
110.0613 C6H8NO- 1 110.0611 1.48
111.0088 C5H3O3- 1 111.0088 0.74
112.0405 C5H6NO2- 1 112.0404 0.43
117.0346 C8H5O- 1 117.0346 0.36
118.0298 C7H4NO- 1 118.0298 -0.74
119.0139 C7H3O2- 1 119.0139 -0.02
119.0502 C8H7O- 1 119.0502 -0.41
120.0091 C6H2NO2- 1 120.0091 0.32
120.0456 C7H6NO- 1 120.0455 1.02
121.0295 C7H5O2- 1 121.0295 0.14
121.0659 C8H9O- 1 121.0659 -0.07
122.0249 C6H4NO2- 1 122.0248 0.8
122.0371 C7H6O2- 1 122.0373 -1.79
123.0088 C6H3O3- 1 123.0088 0.18
123.0328 C6H5NO2- 1 123.0326 2.06
124.0039 C5H2NO3- 1 124.004 -0.78
124.0165 C6H4O3- 1 124.0166 -0.59
124.0403 C6H6NO2- 1 124.0404 -0.5
124.9876 C5HO4- 1 124.988 -3.14
125.0243 C6H5O3- 1 125.0244 -0.62
125.0719 C6H9N2O- 1 125.072 -1.17
126.0196 C5H4NO3- 1 126.0197 -0.29
126.056 C6H8NO2- 1 126.0561 -0.33
129.071 C10H9- 1 129.071 -0.11
130.0424 C9H6O- 1 130.0424 -0.1
131.05 C9H7O- 1 131.0502 -1.51
133.0165 C7H3NO2- 1 133.0169 -3.21
133.0292 C8H5O2- 1 133.0295 -2.35
133.0661 C9H9O- 1 133.0659 1.81
134.0248 C7H4NO2- 1 134.0248 0.28
135.0088 C7H3O3- 1 135.0088 0.24
135.045 C8H7O2- 1 135.0452 -1.28
136.0405 C7H6NO2- 1 136.0404 0.79
137.0243 C7H5O3- 1 137.0244 -0.49
138.0196 C6H4NO3- 1 138.0197 -0.63
139.0149 C5H3N2O3- 1 139.0149 0.03
141.0712 C11H9- 1 141.071 1.67
142.9986 C5H3O5- 1 142.9986 0.02
143.0502 C10H7O- 1 143.0502 -0.62
144.058 C10H8O- 1 144.0581 -0.44
145.0294 C9H5O2- 1 145.0295 -0.37
145.0658 C10H9O- 1 145.0659 -0.61
146.0247 C8H4NO2- 1 146.0248 -0.42
146.0375 C9H6O2- 1 146.0373 0.84
147.0202 C7H3N2O2- 1 147.02 1.22
147.0327 C8H5NO2- 1 147.0326 0.77
147.0455 C9H7O2- 1 147.0452 2.5
148.0042 C7H2NO3- 1 148.004 1.17
148.0404 C8H6NO2- 1 148.0404 0.32
149.0118 C7H3NO3- 1 149.0118 -0.21
149.0356 C7H5N2O2- 1 149.0357 -0.54
150.0196 C7H4NO3- 1 150.0197 -0.18
151.0039 C7H3O4- 1 151.0037 1.44
151.0278 C7H5NO3- 1 151.0275 1.98
152.0118 C7H4O4- 1 152.0115 1.86
152.0352 C7H6NO3- 1 152.0353 -0.7
155.0504 C11H7O- 1 155.0502 0.72
156.058 C11H8O- 1 156.0581 -0.73
157.0659 C11H9O- 1 157.0659 -0.18
158.0373 C10H6O2- 1 158.0373 0.01
159.0452 C10H7O2- 1 159.0452 0.04
159.0815 C11H11O- 1 159.0815 -0.18
161.0243 C9H5O3- 1 161.0244 -0.85
161.0608 C10H9O2- 1 161.0608 0.04
162.0197 C8H4NO3- 1 162.0197 -0.04
163.004 C8H3O4- 1 163.0037 1.89
163.015 C7H3N2O3- 1 163.0149 0.46
163.0276 C8H5NO3- 1 163.0275 0.54
164.0356 C8H6NO3- 1 164.0353 1.97
167.0503 C12H7O- 1 167.0502 0.43
168.0577 C12H8O- 1 168.0581 -2.4
169.03 C11H5O2- 1 169.0295 3.24
169.066 C12H9O- 1 169.0659 0.84
170.0375 C11H6O2- 1 170.0373 0.78
171.0452 C11H7O2- 1 171.0452 0.1
171.0816 C12H11O- 1 171.0815 0.36
172.053 C11H8O2- 1 172.053 -0.16
173.0607 C11H9O2- 1 173.0608 -0.36
174.0323 C10H6O3- 1 174.0322 0.5
175.0765 C11H11O2- 1 175.0765 0.5
177.0305 C8H5N2O3- 1 177.0306 -0.65
178.0145 C8H4NO4- 1 178.0146 -0.4
180.058 C13H8O- 1 180.0581 -0.19
181.0661 C13H9O- 1 181.0659 1.22
182.0375 C12H6O2- 1 182.0373 0.73
183.0451 C12H7O2- 1 183.0452 -0.18
183.0817 C13H11O- 1 183.0815 0.99
184.0534 C12H8O2- 1 184.053 2.35
185.0608 C12H9O2- 1 185.0608 -0.12
186.0321 C11H6O3- 1 186.0322 -0.71
186.0686 C12H10O2- 1 186.0686 0.12
187.0401 C11H7O3- 1 187.0401 -0.09
188.047 C11H8O3- 1 188.0479 -4.64
193.0656 C14H9O- 1 193.0659 -1.29
194.0738 C14H10O- 1 194.0737 0.5
195.0451 C13H7O2- 1 195.0452 -0.22
195.0816 C14H11O- 1 195.0815 0.11
196.0529 C13H8O2- 1 196.053 -0.3
197.0608 C13H9O2- 1 197.0608 -0.27
198.0324 C12H6O3- 1 198.0322 0.64
198.0683 C13H10O2- 1 198.0686 -1.56
199.0395 C12H7O3- 1 199.0401 -2.85
199.0764 C13H11O2- 1 199.0765 -0.02
201.056 C12H9O3- 1 201.0557 1.35
203.0349 C11H7O4- 1 203.035 -0.26
203.0716 C12H11O3- 1 203.0714 1.09
204.0428 C11H8O4- 1 204.0428 -0.13
204.058 C15H8O- 1 204.0581 -0.41
205.0657 C15H9O- 1 205.0659 -1.16
206.074 C15H10O- 1 206.0737 1.29
207.0452 C14H7O2- 1 207.0452 0.03
207.0819 C15H11O- 1 207.0815 1.89
208.0531 C14H8O2- 1 208.053 0.39
209.0608 C14H9O2- 1 209.0608 0.13
210.0326 C13H6O3- 1 210.0322 1.89
210.056 C13H8NO2- 1 210.0561 -0.34
210.0682 C14H10O2- 1 210.0686 -2.04
211.0401 C13H7O3- 1 211.0401 0.11
211.076 C14H11O2- 1 211.0765 -2.24
212.048 C13H8O3- 1 212.0479 0.41
213.0559 C13H9O3- 1 213.0557 0.86
213.092 C14H13O2- 1 213.0921 -0.48
214.0271 C12H6O4- 1 214.0272 -0.45
219.0452 C15H7O2- 1 219.0452 0.03
220.0529 C15H8O2- 1 220.053 -0.17
221.0607 C15H9O2- 1 221.0608 -0.42
222.0324 C14H6O3- 1 222.0322 0.57
222.0687 C15H10O2- 1 222.0686 0.41
223.0402 C14H7O3- 1 223.0401 0.46
223.065 C14H9NO2- 1 223.0639 4.81
223.0762 C15H11O2- 1 223.0765 -0.91
224.0479 C14H8O3- 1 224.0479 0.26
225.0557 C14H9O3- 1 225.0557 -0.12
225.0922 C15H13O2- 1 225.0921 0.56
226.0872 C14H12NO2- 1 226.0874 -0.85
227.035 C13H7O4- 1 227.035 0.08
227.0709 C14H11O3- 1 227.0714 -1.93
232.053 C16H8O2- 1 232.053 -0.08
233.0609 C16H9O2- 1 233.0608 0.33
234.0677 C16H10O2- 1 234.0686 -4.05
235.0403 C15H7O3- 1 235.0401 0.9
235.0766 C16H11O2- 1 235.0765 0.45
236.0484 C15H8O3- 1 236.0479 2.19
236.0718 C15H10NO2- 1 236.0717 0.5
237.0558 C15H9O3- 1 237.0557 0.22
237.0793 C15H11NO2- 1 237.0795 -1.08
238.0635 C15H10O3- 1 238.0635 -0.22
238.0876 C15H12NO2- 1 238.0874 0.91
239.035 C14H7O4- 1 239.035 0.16
240.0429 C14H8O4- 1 240.0428 0.34
241.0499 C14H9O4- 1 241.0506 -3.2
246.0683 C17H10O2- 1 246.0686 -1.37
247.0639 C16H9NO2- 1 247.0639 0.13
247.0756 C17H11O2- 1 247.0765 -3.29
248.0477 C16H8O3- 1 248.0479 -0.7
248.0715 C16H10NO2- 1 248.0717 -0.73
249.0557 C16H9O3- 1 249.0557 -0.19
250.0509 C15H8NO3- 1 250.051 -0.19
250.0635 C16H10O3- 1 250.0635 -0.25
250.0874 C16H12NO2- 1 250.0874 0.35
251.0349 C15H7O4- 1 251.035 -0.45
251.071 C16H11O3- 1 251.0714 -1.58
252.0669 C15H10NO3- 1 252.0666 1.08
253.0505 C15H9O4- 1 253.0506 -0.52
254.0583 C15H10O4- 1 254.0585 -0.46
255.0662 C15H11O4- 1 255.0663 -0.21
260.0717 C17H10NO2- 1 260.0717 0.15
261.0559 C17H9O3- 1 261.0557 0.85
262.0633 C17H10O3- 1 262.0635 -0.96
263.0348 C16H7O4- 1 263.035 -0.62
263.0713 C17H11O3- 1 263.0714 -0.3
264.0426 C16H8O4- 1 264.0428 -0.9
264.0668 C16H10NO3- 1 264.0666 0.58
265.0507 C16H9O4- 1 265.0506 0.22
265.0743 C16H11NO3- 1 265.0744 -0.72
265.0879 C17H13O3- 1 265.087 3.4
275.0589 C17H9NO3- 1 275.0588 0.5
276.0433 C17H8O4- 1 276.0428 1.78
277.0499 C17H9O4- 1 277.0506 -2.64
279.0312 C16H7O5- 2 279.0299 4.85
280.0374 C16H8O5- 1 280.0377 -1.01
290.0216 C17H6O5- 1 290.0221 -1.52
291.053 C17H9NO4- 1 291.0537 -2.43
PK$NUM_PEAK: 231
PK$PEAK: m/z int. rel.int.
50.0036 2681.8 3
51.0239 2502.9 3
53.0032 2254.9 2
55.0189 6422.9 7
57.0345 2120.9 2
59.0138 5895.4 7
63.024 74966.4 91
65.0033 29308.7 35
65.0397 16393.3 20
65.9985 71386.8 87
67.019 20726.8 25
68.0142 2644 3
68.9982 86779.1 106
69.0346 25322.5 31
71.0139 10374.1 12
76.0193 1077.5 1
78.0349 4715 5
79.0189 29889.3 36
80.0267 4953.9 6
80.0505 1191.8 1
81.0219 2662.2 3
81.0346 8181.4 10
82.0299 1461.9 1
82.0662 1758.9 2
83.0138 12199.1 14
84.009 72682.9 88
85.0295 2019 2
86.0248 1563.2 1
89.0397 1936.6 2
90.0348 1956.1 2
91.019 18294.9 22
91.0554 2642.6 3
92.0141 1293.1 1
93.0345 23708.1 29
94.0298 4799.8 5
95.0138 103811.4 127
96.0091 41821.2 51
96.0455 2138 2
96.9931 32030.5 39
97.0294 19733.7 24
99.0087 1664.7 2
100.0767 1372.4 1
106.0299 1528.8 1
106.0422 1390.6 1
107.0138 13796.6 16
108.0217 35132.7 43
109.0295 48157.7 58
110.0249 2192.4 2
110.0613 4467.2 5
111.0088 4663.6 5
112.0405 2055.4 2
117.0346 26382.3 32
118.0298 1516.3 1
119.0139 11609.5 14
119.0502 82240.7 100
120.0091 5273.5 6
120.0456 5443.1 6
121.0295 18756 22
121.0659 29263.5 35
122.0249 14532 17
122.0371 1265 1
123.0088 48251.3 59
123.0328 3945.4 4
124.0039 2232.1 2
124.0165 21109.6 25
124.0403 2243.4 2
124.9876 1141.6 1
125.0243 6308.3 7
125.0719 1127.7 1
126.0196 1554 1
126.056 21831 26
129.071 2675.3 3
130.0424 33997 41
131.05 1332.4 1
133.0165 1237.9 1
133.0292 2069.8 2
133.0661 4650.1 5
134.0248 25275.4 30
135.0088 27684.5 33
135.045 1484.4 1
136.0405 2696 3
137.0243 9431.8 11
138.0196 11624.6 14
139.0149 64706.4 79
141.0712 1430.7 1
142.9986 4718.8 5
143.0502 35476.8 43
144.058 12262.2 15
145.0294 5748.6 7
145.0658 9194.5 11
146.0247 4428.9 5
146.0375 9296.2 11
147.0202 1517.9 1
147.0327 1209 1
147.0455 2054.5 2
148.0042 9040.5 11
148.0404 5171.4 6
149.0118 9849.1 12
149.0356 2661.1 3
150.0196 28127.7 34
151.0039 4482.5 5
151.0278 1716.2 2
152.0118 1488.1 1
152.0352 7598.3 9
155.0504 5845.9 7
156.058 12043.7 14
157.0659 38561.1 47
158.0373 97392 119
159.0452 70631.3 86
159.0815 5123.2 6
161.0243 9684 11
161.0608 4175.3 5
162.0197 8671.3 10
163.004 2416.1 2
163.015 2116.8 2
163.0276 1497.4 1
164.0356 1507.3 1
167.0503 15162.1 18
168.0577 1124.3 1
169.03 1132.5 1
169.066 13386.1 16
170.0375 7781.3 9
171.0452 28890.5 35
171.0816 5215.6 6
172.053 69038.2 84
173.0607 257330.6 315
174.0323 4274.4 5
175.0765 2741.2 3
177.0305 4685.1 5
178.0145 6018.5 7
180.058 16440.1 20
181.0661 21529.2 26
182.0375 9133.4 11
183.0451 37486 45
183.0817 7398.7 9
184.0534 8254.7 10
185.0608 54427.7 66
186.0321 17042.6 20
186.0686 2657.7 3
187.0401 79923.3 97
188.047 1544 1
193.0656 10525.6 12
194.0738 5979.2 7
195.0451 22504.4 27
195.0816 7222.7 8
196.0529 57865.5 70
197.0608 57861.1 70
198.0324 5230.7 6
198.0683 1475.3 1
199.0395 1577.9 1
199.0764 22163.4 27
201.056 10437.7 12
203.0349 1075.6 1
203.0716 6512 7
204.0428 9962.8 12
204.058 7644.6 9
205.0657 4089.3 5
206.074 2046.1 2
207.0452 6891.2 8
207.0819 4457.6 5
208.0531 16927.3 20
209.0608 71057.1 86
210.0326 1635.6 2
210.056 4728 5
210.0682 7820.8 9
211.0401 161977.2 198
211.076 10689.2 13
212.048 11887 14
213.0559 13554.7 16
213.092 4626.3 5
214.0271 10965.9 13
219.0452 2397 2
220.0529 12097.7 14
221.0607 23895.5 29
222.0324 6552.7 8
222.0687 11500.1 14
223.0402 8956 10
223.065 2017.1 2
223.0762 20705.5 25
224.0479 50320.2 61
225.0557 42023.8 51
225.0922 6052.1 7
226.0872 5700.8 6
227.035 1790.5 2
227.0709 8595.7 10
232.053 10081 12
233.0609 23100.9 28
234.0677 1369.9 1
235.0403 15672.4 19
235.0766 7461.2 9
236.0484 4148.6 5
236.0718 2021.4 2
237.0558 34420.5 42
237.0793 1895 2
238.0635 10038.7 12
238.0876 1299.8 1
239.035 258596.9 316
240.0429 816001.3 999
241.0499 6513.5 7
246.0683 2168.5 2
247.0639 6481.7 7
247.0756 1623.6 1
248.0477 18999.3 23
248.0715 4831.1 5
249.0557 21502 26
250.0509 6630 8
250.0635 2193.1 2
250.0874 2112.2 2
251.0349 1672.7 2
251.071 8482.6 10
252.0669 1563.5 1
253.0505 16823.7 20
254.0583 7155.9 8
255.0662 1958.3 2
260.0717 1631.5 1
261.0559 10558.3 12
262.0633 4096.2 5
263.0348 1803.5 2
263.0713 4304.5 5
264.0426 5246.7 6
264.0668 1784.7 2
265.0507 2387.6 2
265.0743 1576.1 1
265.0879 1212.3 1
275.0589 1166.6 1
276.0433 4183.3 5
277.0499 7801.7 9
279.0312 1333.9 1
280.0374 2411.4 2
290.0216 5856.3 7
291.053 1389.6 1
//
