ACCESSION: MSBNK-Eawag-EQ367806
RECORD_TITLE: Doxycycline; LC-ESI-QFT; MS2; CE: 90; R=35000; [M+H]+
DATE: 2015.08.25
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$MASS_SPECTROMETRY: ION_MODE POSITIVE
AC$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$CHROMATOGRAPHY: RETENTION_TIME 6.4 min
AC$CHROMATOGRAPHY: SOLVENT A water with 0.1% formic acid
AC$CHROMATOGRAPHY: SOLVENT B methanol with 0.1% formic acid
MS$FOCUSED_ION: BASE_PEAK 445.1595
MS$FOCUSED_ION: PRECURSOR_M/Z 445.1605
MS$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: splash10-00kb-2930000000-584ce7be11c1ed67287a
PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm)
50.0151 C4H2+ 1 50.0151 -0.83
51.0229 C4H3+ 1 51.0229 -0.13
53.0022 C3HO+ 1 53.0022 0.73
53.0386 C4H5+ 1 53.0386 0.25
54.0338 C3H4N+ 1 54.0338 -0.1
55.0178 C3H3O+ 1 55.0178 -0.02
55.0417 C3H5N+ 1 55.0417 0.35
56.0495 C3H6N+ 1 56.0495 -0.1
57.0335 C3H5O+ 1 57.0335 -0.72
57.0573 C3H7N+ 1 57.0573 0.34
58.0651 C3H8N+ 1 58.0651 -0.1
63.0228 C5H3+ 1 63.0229 -1.53
65.0386 C5H5+ 1 65.0386 -0.41
67.0178 C4H3O+ 1 67.0178 -0.76
67.0417 C4H5N+ 1 67.0417 -0.01
67.0542 C5H7+ 1 67.0542 -0.4
68.0495 C4H6N+ 1 68.0495 -0.08
68.9971 C3HO2+ 1 68.9971 -0.52
69.0335 C4H5O+ 1 69.0335 -0.31
70.0651 C4H8N+ 1 70.0651 -0.51
71.0127 C3H3O2+ 1 71.0128 -0.79
71.0365 C3H5NO+ 1 71.0366 -0.35
71.0729 C4H9N+ 1 71.073 -0.15
72.0444 C3H6NO+ 1 72.0444 -0.42
72.0807 C4H10N+ 1 72.0808 -0.63
74.06 C3H8NO+ 1 74.06 -1.08
77.0385 C6H5+ 1 77.0386 -1.38
79.0178 C5H3O+ 1 79.0178 -0.27
79.0542 C6H7+ 1 79.0542 -0.97
80.0494 C5H6N+ 1 80.0495 -0.57
81.0335 C5H5O+ 1 81.0335 -0.26
81.0573 C5H7N+ 1 81.0573 -0.5
82.0651 C5H8N+ 1 82.0651 -0.56
83.0127 C4H3O2+ 1 83.0128 -0.55
83.0365 C4H5NO+ 1 83.0366 -0.54
84.0444 C4H6NO+ 1 84.0444 -0.24
84.0808 C5H10N+ 1 84.0808 -0.07
85.0285 C4H5O2+ 1 85.0284 0.52
86.06 C4H8NO+ 1 86.06 -1.05
89.0385 C7H5+ 1 89.0386 -1.08
91.0542 C7H7+ 1 91.0542 -0.07
92.0496 C6H6N+ 1 92.0495 1.79
93.0336 C6H5O+ 1 93.0335 1.06
93.0573 C6H7N+ 1 93.0573 0.42
93.07 C7H9+ 1 93.0699 0.89
94.0413 C6H6O+ 1 94.0413 0.36
94.0651 C6H8N+ 1 94.0651 -0.49
95.0127 C5H3O2+ 1 95.0128 -0.17
95.0492 C6H7O+ 1 95.0491 0.3
96.0444 C5H6NO+ 1 96.0444 -0.31
96.0808 C6H10N+ 1 96.0808 0.04
97.0284 C5H5O2+ 1 97.0284 -0.27
97.0522 C5H7NO+ 1 97.0522 -0.36
98.06 C5H8NO+ 1 98.06 -0.1
99.0076 C4H3O3+ 1 99.0077 -0.41
100.0756 C5H10NO+ 1 100.0757 -0.5
102.0463 C8H6+ 1 102.0464 -0.8
103.0542 C8H7+ 1 103.0542 -0.45
105.0335 C7H5O+ 1 105.0335 0.46
105.0447 C6H5N2+ 1 105.0447 -0.23
105.0698 C8H9+ 1 105.0699 -0.44
106.0651 C7H8N+ 1 106.0651 -0.24
107.0127 C6H3O2+ 1 107.0128 -0.24
107.0491 C7H7O+ 1 107.0491 -0.2
108.0442 C6H6NO+ 1 108.0444 -1.48
108.0807 C7H10N+ 1 108.0808 -0.52
109.0284 C6H5O2+ 1 109.0284 -0.24
110.06 C6H8NO+ 1 110.06 -0.82
111.0077 C5H3O3+ 1 111.0077 0.27
111.044 C6H7O2+ 1 111.0441 -0.05
112.0755 C6H10NO+ 1 112.0757 -1.79
114.0464 C9H6+ 1 114.0464 -0.1
115.0542 C9H7+ 1 115.0542 -0.06
116.062 C9H8+ 1 116.0621 -0.01
117.0698 C9H9+ 1 117.0699 -0.4
118.0651 C8H8N+ 1 118.0651 -0.3
119.0128 C7H3O2+ 1 119.0128 0.62
119.049 C8H7O+ 1 119.0491 -0.85
119.0856 C9H11+ 1 119.0855 0.78
121.0284 C7H5O2+ 1 121.0284 -0.38
121.0398 C6H5N2O+ 1 121.0396 1.08
121.0648 C8H9O+ 1 121.0648 -0.26
122.0601 C7H8NO+ 1 122.06 0.57
123.0077 C6H3O3+ 1 123.0077 0.32
123.0439 C7H7O2+ 1 123.0441 -1.1
124.0156 C6H4O3+ 1 124.0155 0.44
124.0394 C6H6NO2+ 1 124.0393 0.44
124.0759 C7H10NO+ 1 124.0757 1.53
125.0233 C6H5O3+ 1 125.0233 -0.4
125.0472 C6H7NO2+ 1 125.0471 0.48
126.0464 C10H6+ 1 126.0464 -0.25
126.0549 C6H8NO2+ 1 126.055 -0.59
127.0542 C10H7+ 1 127.0542 -0.05
128.062 C10H8+ 1 128.0621 -0.25
129.0698 C10H9+ 1 129.0699 -0.44
131.0491 C9H7O+ 1 131.0491 -0.09
131.0855 C10H11+ 1 131.0855 -0.36
132.057 C9H8O+ 1 132.057 0.33
133.0284 C8H5O2+ 1 133.0284 -0.12
133.0646 C9H9O+ 1 133.0648 -1.74
134.06 C8H8NO+ 1 134.06 -0.6
135.0076 C7H3O3+ 1 135.0077 -0.22
135.044 C8H7O2+ 1 135.0441 -0.56
136.0758 C8H10NO+ 1 136.0757 0.95
137.0233 C7H5O3+ 1 137.0233 0.14
138.0551 C7H8NO2+ 1 138.055 1.05
139.0265 C6H5NO3+ 1 139.0264 0.47
139.039 C7H7O3+ 1 139.039 -0.08
139.0542 C11H7+ 1 139.0542 -0.19
140.062 C11H8+ 1 140.0621 -0.23
141.0699 C11H9+ 1 141.0699 -0.12
142.0777 C11H10+ 1 142.0777 -0.36
143.0492 C10H7O+ 1 143.0491 0.34
143.0856 C11H11+ 1 143.0855 0.3
144.057 C10H8O+ 1 144.057 0.1
145.0648 C10H9O+ 1 145.0648 -0.01
147.0074 C8H3O3+ 1 147.0077 -1.91
147.0439 C9H7O2+ 1 147.0441 -1.13
147.0804 C10H11O+ 1 147.0804 -0.35
148.0517 C9H8O2+ 1 148.0519 -1.15
149.0233 C8H5O3+ 1 149.0233 -0.14
149.0599 C9H9O2+ 1 149.0597 1.57
150.055 C8H8NO2+ 1 150.055 0.37
151.0391 C8H7O3+ 1 151.039 0.86
151.054 C12H7+ 1 151.0542 -1.63
152.062 C12H8+ 1 152.0621 -0.01
153.0183 C7H5O4+ 1 153.0182 0.56
153.0699 C12H9+ 1 153.0699 -0.17
154.0494 C7H8NO3+ 1 154.0499 -2.79
154.0777 C12H10+ 1 154.0777 0.25
155.0498 C11H7O+ 1 155.0491 4.57
155.0603 C10H7N2+ 1 155.0604 -0.16
155.0855 C12H11+ 1 155.0855 -0.37
156.057 C11H8O+ 1 156.057 0.28
157.0648 C11H9O+ 1 157.0648 0.25
157.1013 C12H13+ 1 157.1012 0.78
158.0727 C11H10O+ 1 158.0726 0.78
159.0439 C10H7O2+ 1 159.0441 -0.98
159.0805 C11H11O+ 1 159.0804 0.12
160.0519 C10H8O2+ 1 160.0519 -0.19
161.0233 C9H5O3+ 1 161.0233 -0.06
161.0598 C10H9O2+ 1 161.0597 0.65
162.0552 C9H8NO2+ 1 162.055 1.64
163.039 C9H7O3+ 1 163.039 0.36
163.0541 C13H7+ 1 163.0542 -0.53
164.062 C13H8+ 1 164.0621 -0.13
165.0183 C8H5O4+ 1 165.0182 0.33
165.0699 C13H9+ 1 165.0699 0.2
166.0498 C8H8NO3+ 1 166.0499 -0.42
166.0777 C13H10+ 1 166.0777 0.05
167.0855 C13H11+ 1 167.0855 -0.16
168.057 C12H8O+ 1 168.057 0.02
169.0649 C12H9O+ 1 169.0648 0.88
169.0757 C11H9N2+ 1 169.076 -2.04
170.0726 C12H10O+ 1 170.0726 -0.27
171.0439 C11H7O2+ 1 171.0441 -0.97
171.0804 C12H11O+ 1 171.0804 -0.13
172.0518 C11H8O2+ 1 172.0519 -0.41
173.0234 C10H5O3+ 1 173.0233 0.63
173.0597 C11H9O2+ 1 173.0597 0.08
174.0676 C11H10O2+ 1 174.0675 0.11
175.0755 C11H11O2+ 1 175.0754 0.94
176.0621 C14H8+ 1 176.0621 0.05
177.0699 C14H9+ 1 177.0699 0.08
178.0777 C14H10+ 1 178.0777 -0.23
179.0602 C12H7N2+ 1 179.0604 -0.92
179.0855 C14H11+ 1 179.0855 -0.43
180.057 C13H8O+ 1 180.057 0.13
181.0648 C13H9O+ 1 181.0648 -0.06
182.0726 C13H10O+ 1 182.0726 -0.03
183.0554 C11H7N2O+ 1 183.0553 0.39
183.0804 C13H11O+ 1 183.0804 -0.01
184.0518 C12H8O2+ 1 184.0519 -0.33
185.0596 C12H9O2+ 1 185.0597 -0.46
185.071 C11H9N2O+ 1 185.0709 0.11
185.0961 C13H13O+ 1 185.0961 0.05
186.0311 C11H6O3+ 1 186.0311 -0.14
186.0676 C12H10O2+ 1 186.0675 0.16
187.0391 C11H7O3+ 1 187.039 0.69
187.0754 C12H11O2+ 1 187.0754 0.02
188.0625 C15H8+ 1 188.0621 2.28
189.0698 C15H9+ 1 189.0699 -0.46
190.0776 C15H10+ 1 190.0777 -0.32
191.0339 C10H7O4+ 1 191.0339 0.23
191.0854 C15H11+ 1 191.0855 -0.77
192.057 C14H8O+ 1 192.057 0.02
193.0649 C14H9O+ 1 193.0648 0.51
193.0759 C13H9N2+ 1 193.076 -0.85
194.0727 C14H10O+ 1 194.0726 0.33
195.0805 C14H11O+ 1 195.0804 0.04
196.0519 C13H8O2+ 1 196.0519 -0.06
197.0598 C13H9O2+ 1 197.0597 0.22
197.0959 C14H13O+ 1 197.0961 -0.77
198.0675 C13H10O2+ 1 198.0675 0
199.0388 C12H7O3+ 1 199.039 -0.76
199.0752 C13H11O2+ 1 199.0754 -0.88
200.0468 C12H8O3+ 1 200.0468 0.17
200.0618 C16H8+ 1 200.0621 -1.41
201.0546 C12H9O3+ 1 201.0546 -0.1
202.0775 C16H10+ 1 202.0777 -1.05
203.0706 C12H11O3+ 1 203.0703 1.52
203.0855 C16H11+ 1 203.0855 -0.38
204.0571 C15H8O+ 1 204.057 0.41
205.0496 C11H9O4+ 1 205.0495 0.46
205.0649 C15H9O+ 1 205.0648 0.53
206.0728 C15H10O+ 1 206.0726 0.65
207.0441 C14H7O2+ 1 207.0441 0.41
207.0804 C15H11O+ 1 207.0804 -0.01
208.0519 C14H8O2+ 1 208.0519 -0.1
208.0883 C15H12O+ 1 208.0883 0.4
209.0597 C14H9O2+ 1 209.0597 0.12
209.0961 C15H13O+ 1 209.0961 -0.1
210.0675 C14H10O2+ 1 210.0675 -0.1
211.039 C13H7O3+ 1 211.039 0.19
211.0754 C14H11O2+ 1 211.0754 0.07
212.0468 C13H8O3+ 1 212.0468 0.02
212.0831 C14H12O2+ 1 212.0832 -0.24
213.0546 C13H9O3+ 1 213.0546 -0.05
213.091 C14H13O2+ 1 213.091 -0.08
214.0621 C13H10O3+ 1 214.0624 -1.66
217.0647 C16H9O+ 1 217.0648 -0.28
218.0727 C16H10O+ 1 218.0726 0.43
219.0804 C16H11O+ 1 219.0804 -0.01
220.0519 C15H8O2+ 1 220.0519 0.18
221.0598 C15H9O2+ 1 221.0597 0.29
222.0676 C15H10O2+ 1 222.0675 0.09
223.0389 C14H7O3+ 1 223.039 -0.32
223.0754 C15H11O2+ 1 223.0754 0.2
224.0468 C14H8O3+ 1 224.0468 0.2
225.0548 C14H9O3+ 1 225.0546 0.71
225.0908 C15H13O2+ 1 225.091 -0.74
226.0625 C14H10O3+ 1 226.0624 0.06
227.0703 C14H11O3+ 1 227.0703 0.09
229.0648 C17H9O+ 1 229.0648 0.17
229.0759 C16H9N2+ 1 229.076 -0.76
231.0808 C17H11O+ 1 231.0804 1.55
232.0519 C16H8O2+ 1 232.0519 -0.05
233.0596 C16H9O2+ 1 233.0597 -0.67
234.0676 C16H10O2+ 1 234.0675 0.29
234.0912 C16H12NO+ 1 234.0913 -0.51
235.0753 C16H11O2+ 1 235.0754 -0.2
236.0465 C15H8O3+ 1 236.0468 -1.04
236.0831 C16H12O2+ 1 236.0832 -0.43
237.0545 C15H9O3+ 1 237.0546 -0.55
237.0908 C16H13O2+ 1 237.091 -0.91
238.0624 C15H10O3+ 1 238.0624 -0.36
239.0703 C15H11O3+ 1 239.0703 0.21
240.0417 C14H8O4+ 1 240.0417 -0.21
240.0782 C15H12O3+ 1 240.0781 0.6
241.0502 C14H9O4+ 1 241.0495 2.92
241.0859 C15H13O3+ 1 241.0859 -0.09
242.0573 C14H10O4+ 1 242.0574 -0.33
245.0598 C17H9O2+ 1 245.0597 0.18
246.0681 C17H10O2+ 1 246.0675 2.31
247.0755 C17H11O2+ 1 247.0754 0.54
248.0464 C16H8O3+ 1 248.0468 -1.68
248.0829 C17H12O2+ 1 248.0832 -1.09
249.0548 C16H9O3+ 1 249.0546 0.84
250.0625 C16H10O3+ 1 250.0624 0.18
251.0699 C16H11O3+ 1 251.0703 -1.56
252.0417 C15H8O4+ 1 252.0417 0.04
253.0499 C15H9O4+ 1 253.0495 1.4
253.0856 C16H13O3+ 1 253.0859 -1.11
254.0572 C15H10O4+ 1 254.0574 -0.75
255.0641 C15H11O4+ 1 255.0652 -4.14
260.0472 C17H8O3+ 1 260.0468 1.63
261.0545 C17H9O3+ 1 261.0546 -0.62
262.0626 C17H10O3+ 1 262.0624 0.51
262.0864 C17H12NO2+ 1 262.0863 0.48
263.0706 C17H11O3+ 1 263.0703 1.29
263.0939 C17H13NO2+ 1 263.0941 -0.61
264.0408 C16H8O4+ 1 264.0417 -3.6
264.079 C17H12O3+ 1 264.0781 3.31
265.0496 C16H9O4+ 1 265.0495 0.17
265.0855 C17H13O3+ 1 265.0859 -1.7
266.0569 C16H10O4+ 1 266.0574 -1.69
267.0652 C16H11O4+ 1 267.0652 -0.13
270.0521 C15H10O5+ 1 270.0523 -0.76
271.0596 C15H11O5+ 1 271.0601 -2.03
275.0702 C18H11O3+ 1 275.0703 -0.22
276.0416 C17H8O4+ 1 276.0417 -0.44
277.0497 C17H9O4+ 1 277.0495 0.74
278.0575 C17H10O4+ 1 278.0574 0.47
279.0644 C17H11O4+ 1 279.0652 -2.85
280.096 C17H14NO3+ 1 280.0968 -3
285.0765 C16H13O5+ 1 285.0757 2.81
288.0656 C18H10NO3+ 1 288.0655 0.38
291.0653 C18H11O4+ 1 291.0652 0.39
292.0978 C18H14NO3+ 1 292.0968 3.18
306.0518 C18H10O5+ 1 306.0523 -1.49
334.0468 C19H10O6+ 1 334.0472 -1.23
PK$NUM_PEAK: 291
PK$PEAK: m/z int. rel.int.
50.0151 10705.7 4
51.0229 30142.5 13
53.0022 57190.9 25
53.0386 114536.3 51
54.0338 24414.2 10
55.0178 488917.4 219
55.0417 49275.2 22
56.0495 225818.6 101
57.0335 13538.2 6
57.0573 30485.7 13
58.0651 1478945 663
63.0228 21363.9 9
65.0386 159816.2 71
67.0178 92191.1 41
67.0417 25068.9 11
67.0542 24267.6 10
68.0495 170092.2 76
68.9971 461693.5 207
69.0335 87915.5 39
70.0651 831041.2 372
71.0127 14699.9 6
71.0365 46499.9 20
71.0729 13480.6 6
72.0444 230545.1 103
72.0807 77869.3 34
74.06 14230.4 6
77.0385 47595.8 21
79.0178 142217 63
79.0542 55057.7 24
80.0494 85915 38
81.0335 188806.5 84
81.0573 36818.3 16
82.0651 172415.9 77
83.0127 271925 121
83.0365 53103.7 23
84.0444 152321.1 68
84.0808 117697.8 52
85.0285 13289.4 5
86.06 58668 26
89.0385 34454.6 15
91.0542 565827.9 253
92.0496 5945 2
93.0336 39259 17
93.0573 9993.2 4
93.07 34446.2 15
94.0413 8640 3
94.0651 93224.4 41
95.0127 202217 90
95.0492 110728 49
96.0444 35969.4 16
96.0808 25410.4 11
97.0284 61696 27
97.0522 11282.7 5
98.06 2139517 959
99.0076 12708.9 5
100.0756 52206.3 23
102.0463 13787.4 6
103.0542 261912.6 117
105.0335 63438.1 28
105.0447 65265.1 29
105.0698 75534 33
106.0651 34525.4 15
107.0127 102472 45
107.0491 144198.4 64
108.0442 48830.4 21
108.0807 28835.4 12
109.0284 130931.9 58
110.06 33474.5 15
111.0077 106301.2 47
111.044 24008.6 10
112.0755 11698.8 5
114.0464 10939.4 4
115.0542 1021262 457
116.062 108018.3 48
117.0698 664471.8 297
118.0651 26918 12
119.0128 55000.6 24
119.049 108519.4 48
119.0856 85073.7 38
121.0284 179364.9 80
121.0398 26206.2 11
121.0648 74851.6 33
122.0601 33526.6 15
123.0077 57302.3 25
123.0439 25891.9 11
124.0156 13968 6
124.0394 74784.6 33
124.0759 14652.2 6
125.0233 44186.4 19
125.0472 7781.4 3
126.0464 29034.8 13
126.0549 46198.3 20
127.0542 882519.9 395
128.062 510894.5 229
129.0698 495784.6 222
131.0491 264270.5 118
131.0855 137040.5 61
132.057 80909.5 36
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//
