ACCESSION: MSBNK-Eawag-EQ367808
RECORD_TITLE: Doxycycline; LC-ESI-QFT; MS2; CE: 150; 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 150 (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: splash10-014r-2900000000-713ff54567cd65afe965
PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm)
50.0151 C4H2+ 1 50.0151 0.17
51.0229 C4H3+ 1 51.0229 -0.13
52.0307 C4H4+ 1 52.0308 -0.22
53.0022 C3HO+ 1 53.0022 0.55
53.0386 C4H5+ 1 53.0386 0.44
53.9974 C2NO+ 1 53.9974 -0.56
54.0338 C3H4N+ 1 54.0338 0.08
55.0179 C3H3O+ 1 55.0178 0.16
55.0417 C3H5N+ 1 55.0417 0.17
56.0495 C3H6N+ 1 56.0495 -0.28
57.0334 C3H5O+ 1 57.0335 -1.6
57.0573 C3H7N+ 1 57.0573 0.16
58.0651 C3H8N+ 1 58.0651 0.07
61.0072 C5H+ 1 61.0073 -0.6
62.015 C5H2+ 1 62.0151 -1.31
63.0229 C5H3+ 1 63.0229 -0.26
65.0386 C5H5+ 1 65.0386 0.05
66.01 C4H2O+ 1 66.01 -0.7
66.0463 C5H6+ 1 66.0464 -1.08
67.0178 C4H3O+ 1 67.0178 -0.32
67.0416 C4H5N+ 1 67.0417 -0.31
67.0542 C5H7+ 1 67.0542 -0.84
68.0255 C4H4O+ 1 68.0257 -1.71
68.0494 C4H6N+ 1 68.0495 -0.52
68.9971 C3HO2+ 1 68.9971 -0.37
69.0334 C4H5O+ 1 69.0335 -1.03
70.0651 C4H8N+ 1 70.0651 -0.37
71.0127 C3H3O2+ 1 71.0128 -1.07
71.0731 C4H9N+ 1 71.073 2.24
72.0444 C3H6NO+ 1 72.0444 0
72.0808 C4H10N+ 1 72.0808 0.2
74.0149 C6H2+ 1 74.0151 -2.45
74.0599 C3H8NO+ 1 74.06 -1.76
75.0229 C6H3+ 1 75.0229 -1.02
76.0307 C6H4+ 1 76.0308 -0.41
77.0021 C5HO+ 1 77.0022 -1.05
77.0385 C6H5+ 1 77.0386 -1.12
78.0464 C6H6+ 1 78.0464 -0.28
79.0177 C5H3O+ 1 79.0178 -1.28
79.0542 C6H7+ 1 79.0542 -0.21
80.0494 C5H6N+ 1 80.0495 -0.94
81.0335 C5H5O+ 1 81.0335 -0.01
81.0573 C5H7N+ 1 81.0573 -0.25
82.0651 C5H8N+ 1 82.0651 0.17
83.0126 C4H3O2+ 1 83.0128 -1.64
83.0365 C4H5NO+ 1 83.0366 -0.3
84.0807 C5H10N+ 1 84.0808 -1.26
86.0148 C7H2+ 1 86.0151 -3.04
87.0229 C7H3+ 1 87.0229 -0.19
88.0308 C7H4+ 1 88.0308 0.66
89.0386 C7H5+ 1 89.0386 -0.3
90.0464 C7H6+ 1 90.0464 -0.02
91.0542 C7H7+ 1 91.0542 0.26
92.0495 C6H6N+ 1 92.0495 0.37
93.0573 C6H7N+ 1 93.0573 -0.33
94.0413 C6H6O+ 1 94.0413 -0.49
94.0653 C6H8N+ 1 94.0651 1.32
95.0491 C6H7O+ 1 95.0491 0.09
96.0443 C5H6NO+ 1 96.0444 -0.52
98.0151 C8H2+ 1 98.0151 -0.02
98.0601 C5H8NO+ 1 98.06 0.1
99.0228 C8H3+ 1 99.0229 -0.97
101.0385 C8H5+ 1 101.0386 -0.76
102.0464 C8H6+ 1 102.0464 0.18
103.0542 C8H7+ 1 103.0542 0.03
104.062 C8H8+ 1 104.0621 -0.11
105.0334 C7H5O+ 1 105.0335 -0.58
105.0447 C6H5N2+ 1 105.0447 0.24
107.0129 C6H3O2+ 1 107.0128 1.25
107.0491 C7H7O+ 1 107.0491 -0.11
113.0386 C9H5+ 1 113.0386 0.03
114.0464 C9H6+ 1 114.0464 0.42
115.0542 C9H7+ 1 115.0542 0.2
116.062 C9H8+ 1 116.0621 -0.27
117.0699 C9H9+ 1 117.0699 -0.14
118.0412 C8H6O+ 1 118.0413 -1.15
119.0492 C8H7O+ 1 119.0491 0.66
121.0285 C7H5O2+ 1 121.0284 1.19
125.0386 C10H5+ 1 125.0386 0.11
126.0464 C10H6+ 1 126.0464 0.3
127.0542 C10H7+ 1 127.0542 0.03
128.062 C10H8+ 1 128.0621 -0.01
129.0447 C8H5N2+ 1 129.0447 0.2
129.0699 C10H9+ 1 129.0699 0.03
130.0411 C9H6O+ 1 130.0413 -1.36
131.0492 C9H7O+ 1 131.0491 0.37
132.057 C9H8O+ 1 132.057 0.1
134.06 C8H8NO+ 1 134.06 0.07
137.0386 C11H5+ 1 137.0386 0.32
138.0464 C11H6+ 1 138.0464 -0.08
139.0542 C11H7+ 1 139.0542 0.17
140.0621 C11H8+ 1 140.0621 0.06
141.0699 C11H9+ 1 141.0699 0.02
142.0411 C10H6O+ 1 142.0413 -1.31
142.0778 C11H10+ 1 142.0777 0.34
143.0492 C10H7O+ 1 143.0491 0.13
144.057 C10H8O+ 1 144.057 0.16
145.0648 C10H9O+ 1 145.0648 0.2
149.0384 C12H5+ 1 149.0386 -1.25
150.0465 C12H6+ 1 150.0464 0.46
151.0542 C12H7+ 1 151.0542 0.15
152.0621 C12H8+ 1 152.0621 0.19
153.0699 C12H9+ 1 153.0699 0.02
154.0778 C12H10+ 1 154.0777 0.57
155.0604 C10H7N2+ 1 155.0604 -0.03
156.0571 C11H8O+ 1 156.057 0.6
157.0648 C11H9O+ 1 157.0648 0.06
160.052 C10H8O2+ 1 160.0519 0.43
162.0466 C13H6+ 1 162.0464 1.1
163.0542 C13H7+ 1 163.0542 0.02
164.062 C13H8+ 1 164.0621 -0.19
165.07 C13H9+ 1 165.0699 0.5
166.0777 C13H10+ 1 166.0777 0.23
167.0491 C12H7O+ 1 167.0491 -0.25
168.057 C12H8O+ 1 168.057 0.26
169.0648 C12H9O+ 1 169.0648 0.11
173.0599 C11H9O2+ 1 173.0597 1.41
174.0465 C14H6+ 1 174.0464 0.51
175.0539 C14H7+ 1 175.0542 -1.69
176.0621 C14H8+ 1 176.0621 0.33
177.0699 C14H9+ 1 177.0699 0.02
178.0777 C14H10+ 1 178.0777 0.21
179.049 C13H7O+ 1 179.0491 -0.73
179.0604 C12H7N2+ 1 179.0604 0.25
180.0569 C13H8O+ 1 180.057 -0.42
181.0648 C13H9O+ 1 181.0648 -0.06
182.0727 C13H10O+ 1 182.0726 0.46
184.0519 C12H8O2+ 1 184.0519 -0.11
185.0596 C12H9O2+ 1 185.0597 -0.41
187.0542 C15H7+ 1 187.0542 0.12
188.0618 C15H8+ 1 188.0621 -1.13
189.0699 C15H9+ 1 189.0699 -0.14
190.0651 C14H8N+ 1 190.0651 -0.4
190.0779 C15H10+ 1 190.0777 1.25
191.0726 C14H9N+ 1 191.073 -2.1
191.0854 C15H11+ 1 191.0855 -0.61
192.057 C14H8O+ 1 192.057 -0.08
193.0648 C14H9O+ 1 193.0648 -0.11
194.0364 C13H6O2+ 1 194.0362 0.67
194.0726 C14H10O+ 1 194.0726 -0.29
195.044 C13H7O2+ 1 195.0441 -0.24
195.0801 C14H11O+ 1 195.0804 -1.85
196.0519 C13H8O2+ 1 196.0519 -0.11
197.0598 C13H9O2+ 1 197.0597 0.27
200.0622 C16H8+ 1 200.0621 0.74
201.0698 C16H9+ 1 201.0699 -0.23
202.0781 C16H10+ 1 202.0777 1.77
203.0602 C14H7N2+ 1 203.0604 -1.06
205.065 C15H9O+ 1 205.0648 1.21
208.0512 C14H8O2+ 1 208.0519 -3.32
218.0722 C16H10O+ 1 218.0726 -1.96
220.0514 C15H8O2+ 1 220.0519 -2.19
221.0595 C15H9O2+ 1 221.0597 -1.11
PK$NUM_PEAK: 153
PK$PEAK: m/z int. rel.int.
50.0151 229761.9 50
51.0229 185072 40
52.0307 7574.1 1
53.0022 146567.5 32
53.0386 405564.8 89
53.9974 7025.8 1
54.0338 100989.9 22
55.0179 386578.1 84
55.0417 183789.9 40
56.0495 121511.8 26
57.0334 5993.5 1
57.0573 13946.8 3
58.0651 592849.8 130
61.0072 10830.5 2
62.015 65039.8 14
63.0229 356867.6 78
65.0386 662788.1 145
66.01 6460.9 1
66.0463 14092.8 3
67.0178 65172.7 14
67.0416 70038.8 15
67.0542 25601.6 5
68.0255 20704.7 4
68.0494 107334.3 23
68.9971 577569.5 126
69.0334 29273.7 6
70.0651 143888.7 31
71.0127 8777.3 1
71.0731 6645 1
72.0444 46189.7 10
72.0808 9989.5 2
74.0149 45525.5 10
74.0599 8832.1 1
75.0229 235037.1 51
76.0307 75781.8 16
77.0021 34142.2 7
77.0385 365862.6 80
78.0464 207513.1 45
79.0177 88879.4 19
79.0542 100065.9 21
80.0494 64238.9 14
81.0335 101257 22
81.0573 23862.2 5
82.0651 64521.6 14
83.0126 10283.3 2
83.0365 74494.6 16
84.0807 10216.7 2
86.0148 8012.2 1
87.0229 45743.4 10
88.0308 46060.1 10
89.0386 514978 113
90.0464 81411.4 17
91.0542 1404626.2 308
92.0495 9339.4 2
93.0573 10851.7 2
94.0413 13579.4 2
94.0653 41598.4 9
95.0491 902390.1 198
96.0443 10335.8 2
98.0151 13166.2 2
98.0601 75641 16
99.0228 31556.2 6
101.0385 68622.2 15
102.0464 522887.3 114
103.0542 434318.3 95
104.062 27758.8 6
105.0334 51396.3 11
105.0447 705928.4 155
107.0129 10350.3 2
107.0491 83829.8 18
113.0386 199990.1 43
114.0464 156061.3 34
115.0542 4286261 942
116.062 338487.8 74
117.0699 102977.7 22
118.0412 55985.7 12
119.0492 76459.9 16
121.0285 6760.6 1
125.0386 70313.9 15
126.0464 764101.9 167
127.0542 879963.4 193
128.062 1849034 406
129.0447 213823.8 47
129.0699 126536.8 27
130.0411 10174.3 2
131.0492 353466.5 77
132.057 155416.7 34
134.06 7220 1
137.0386 25462 5
138.0464 57196 12
139.0542 4543955 999
140.0621 635402.5 139
141.0699 557225.6 122
142.0411 31785.4 6
142.0778 11006 2
143.0492 23963.9 5
144.057 211426.7 46
145.0648 345769.5 76
149.0384 27100.4 5
150.0465 506379.6 111
151.0542 243480.2 53
152.0621 2953802.2 649
153.0699 438938.4 96
154.0778 23396.5 5
155.0604 800808.2 176
156.0571 29214.4 6
157.0648 58556.7 12
160.052 37833.8 8
162.0466 25394.8 5
163.0542 1038472.9 228
164.062 461140.1 101
165.07 2033209.8 447
166.0777 45921 10
167.0491 39626.3 8
168.057 810136 178
169.0648 950092.8 208
173.0599 23301.4 5
174.0465 62940.9 13
175.0539 14126.8 3
176.0621 816473.3 179
177.0699 155392.1 34
178.0777 241624.6 53
179.049 39727.1 8
179.0604 317991.2 69
180.0569 27144.9 5
181.0648 263113 57
182.0727 7071.7 1
184.0519 12785.1 2
185.0596 13386.1 2
187.0542 151616.2 33
188.0618 48543.2 10
189.0699 444014.4 97
190.0651 10593.7 2
190.0779 9843.6 2
191.0726 9466.1 2
191.0854 9254.9 2
192.057 59397.4 13
193.0648 64766.5 14
194.0364 6785.1 1
194.0726 24765.2 5
195.044 8336.9 1
195.0801 7651.4 1
196.0519 113214.3 24
197.0598 96234.8 21
200.0622 76278.7 16
201.0698 9265.4 2
202.0781 43549.9 9
203.0602 18921.3 4
205.065 83083 18
208.0512 7198.9 1
218.0722 10972.7 2
220.0514 6022.6 1
221.0595 11832.7 2
//
