ACCESSION: MSBNK-Eawag-EQ367809
RECORD_TITLE: Doxycycline; LC-ESI-QFT; MS2; CE: 180; 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 180 (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: splash10-0fri-4900000000-862ed42332f7e53b7e5b
PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm)
50.0151 C4H2+ 1 50.0151 0.57
51.023 C4H3+ 1 51.0229 0.46
52.0308 C4H4+ 1 52.0308 0.93
53.0022 C3HO+ 1 53.0022 0.73
53.0386 C4H5+ 1 53.0386 0.44
53.9975 C2NO+ 1 53.9974 0.55
54.0339 C3H4N+ 1 54.0338 0.45
55.0179 C3H3O+ 1 55.0178 0.16
55.0417 C3H5N+ 1 55.0417 0.35
56.0495 C3H6N+ 1 56.0495 0.44
57.0573 C3H7N+ 1 57.0573 -0.36
58.0651 C3H8N+ 1 58.0651 0.07
61.0072 C5H+ 1 61.0073 -0.76
62.0151 C5H2+ 1 62.0151 -0.02
63.0229 C5H3+ 1 63.0229 -0.1
65.0386 C5H5+ 1 65.0386 0.21
66.01 C4H2O+ 1 66.01 0.06
66.0339 C4H4N+ 1 66.0338 1.43
66.0464 C5H6+ 1 66.0464 -0.18
67.0179 C4H3O+ 1 67.0178 0.88
67.0417 C4H5N+ 1 67.0417 0.14
67.0542 C5H7+ 1 67.0542 0.05
68.0256 C4H4O+ 1 68.0257 -1.27
68.0495 C4H6N+ 1 68.0495 0.51
68.9971 C3HO2+ 1 68.9971 -0.23
70.0651 C4H8N+ 1 70.0651 0.06
72.0444 C3H6NO+ 1 72.0444 0
74.015 C6H2+ 1 74.0151 -0.97
75.0229 C6H3+ 1 75.0229 -0.49
76.0307 C6H4+ 1 76.0308 -0.55
77.0021 C5HO+ 1 77.0022 -1.05
77.0385 C6H5+ 1 77.0386 -0.73
78.0464 C6H6+ 1 78.0464 -0.15
79.0178 C5H3O+ 1 79.0178 -0.39
79.0542 C6H7+ 1 79.0542 -0.46
80.0494 C5H6N+ 1 80.0495 -0.57
81.0335 C5H5O+ 1 81.0335 -0.51
82.0651 C5H8N+ 1 82.0651 -0.19
83.0366 C4H5NO+ 1 83.0366 0.18
84.0444 C4H6NO+ 1 84.0444 0.47
86.015 C7H2+ 1 86.0151 -1.41
87.0229 C7H3+ 1 87.0229 0.15
88.0308 C7H4+ 1 88.0308 0.21
89.0386 C7H5+ 1 89.0386 -0.07
90.0464 C7H6+ 1 90.0464 0.54
91.0542 C7H7+ 1 91.0542 0.26
92.0257 C6H4O+ 1 92.0257 0.69
92.0495 C6H6N+ 1 92.0495 0.16
94.0413 C6H6O+ 1 94.0413 0.36
94.0653 C6H8N+ 1 94.0651 1.64
95.0492 C6H7O+ 1 95.0491 0.2
98.0151 C8H2+ 1 98.0151 -0.32
99.023 C8H3+ 1 99.0229 0.44
101.0386 C8H5+ 1 101.0386 0.23
102.0464 C8H6+ 1 102.0464 0.18
103.0542 C8H7+ 1 103.0542 -0.16
104.0619 C8H8+ 1 104.0621 -1.46
105.0448 C6H5N2+ 1 105.0447 0.34
107.0493 C7H7O+ 1 107.0491 1.76
113.0386 C9H5+ 1 113.0386 -0.15
114.0464 C9H6+ 1 114.0464 -0.01
115.0543 C9H7+ 1 115.0542 0.29
116.062 C9H8+ 1 116.0621 -0.36
117.0702 C9H9+ 1 117.0699 2.85
118.0413 C8H6O+ 1 118.0413 -0.14
119.0492 C8H7O+ 1 119.0491 0.66
125.0386 C10H5+ 1 125.0386 -0.13
126.0464 C10H6+ 1 126.0464 0.3
127.0542 C10H7+ 1 127.0542 0.03
128.0621 C10H8+ 1 128.0621 0.14
129.0447 C8H5N2+ 1 129.0447 0.2
129.0698 C10H9+ 1 129.0699 -0.36
131.0492 C9H7O+ 1 131.0491 0.3
132.057 C9H8O+ 1 132.057 0.41
137.0387 C11H5+ 1 137.0386 0.75
138.0464 C11H6+ 1 138.0464 -0.08
139.0543 C11H7+ 1 139.0542 0.24
140.0621 C11H8+ 1 140.0621 0.49
141.0699 C11H9+ 1 141.0699 -0.19
142.0413 C10H6O+ 1 142.0413 0.1
143.0492 C10H7O+ 1 143.0491 0.27
144.057 C10H8O+ 1 144.057 0.51
145.0648 C10H9O+ 1 145.0648 -0.08
149.0385 C12H5+ 1 149.0386 -0.72
150.0465 C12H6+ 1 150.0464 0.46
151.0543 C12H7+ 1 151.0542 0.49
152.0621 C12H8+ 1 152.0621 0.32
153.0699 C12H9+ 1 153.0699 0.35
155.0493 C11H7O+ 1 155.0491 1.02
155.0604 C10H7N2+ 1 155.0604 0.23
156.0573 C11H8O+ 1 156.057 2.07
157.0649 C11H9O+ 1 157.0648 0.95
161.0599 C10H9O2+ 1 161.0597 1.02
162.0464 C13H6+ 1 162.0464 0.05
163.0542 C13H7+ 1 163.0542 0.14
164.062 C13H8+ 1 164.0621 -0.01
165.07 C13H9+ 1 165.0699 0.5
167.0491 C12H7O+ 1 167.0491 -0.25
168.057 C12H8O+ 1 168.057 0.44
169.0648 C12H9O+ 1 169.0648 0.05
174.0464 C14H6+ 1 174.0464 -0.12
175.0544 C14H7+ 1 175.0542 1.16
176.0621 C14H8+ 1 176.0621 0.33
177.0696 C14H9+ 1 177.0699 -1.28
178.0779 C14H10+ 1 178.0777 1.34
179.0604 C12H7N2+ 1 179.0604 0.2
181.0645 C13H9O+ 1 181.0648 -1.33
183.0809 C13H11O+ 1 183.0804 2.67
185.0597 C12H9O2+ 1 185.0597 -0.09
187.0543 C15H7+ 1 187.0542 0.23
188.0619 C15H8+ 1 188.0621 -0.97
189.07 C15H9+ 1 189.0699 0.44
192.0569 C14H8O+ 1 192.057 -0.45
193.0648 C14H9O+ 1 193.0648 -0.01
194.0365 C13H6O2+ 1 194.0362 1.13
196.0519 C13H8O2+ 1 196.0519 0.05
200.062 C16H8+ 1 200.0621 -0.36
203.0601 C14H7N2+ 1 203.0604 -1.35
203.0725 C15H9N+ 1 203.073 -2.27
220.0519 C15H8O2+ 1 220.0519 0
PK$NUM_PEAK: 120
PK$PEAK: m/z int. rel.int.
50.0151 466775.4 120
51.023 356071 91
52.0308 8174.1 2
53.0022 215263.2 55
53.0386 354567.6 91
53.9975 11722.1 3
54.0339 120094.8 30
55.0179 218907.1 56
55.0417 137586.2 35
56.0495 82779.9 21
57.0573 10743.5 2
58.0651 209314.3 53
61.0072 38694.3 9
62.0151 204368.7 52
63.0229 778672.7 200
65.0386 1111137.2 285
66.01 13062.6 3
66.0339 7079 1
66.0464 39171.9 10
67.0179 27121.8 6
67.0417 49693.6 12
67.0542 23573.8 6
68.0256 12006.6 3
68.0495 58823.2 15
68.9971 450709.7 115
70.0651 32182.9 8
72.0444 20112.8 5
74.015 203529 52
75.0229 628555 161
76.0307 237181.7 61
77.0021 52897.9 13
77.0385 459420.9 118
78.0464 363178.6 93
79.0178 37617.3 9
79.0542 41580.1 10
80.0494 38467.6 9
81.0335 68351 17
82.0651 26697.4 6
83.0366 40440.1 10
84.0444 10019.6 2
86.015 68566.6 17
87.0229 230706.1 59
88.0308 164561.6 42
89.0386 1229805.4 316
90.0464 72698.7 18
91.0542 907687.4 233
92.0257 7238.4 1
92.0495 9380.3 2
94.0413 24247.3 6
94.0653 9491.8 2
95.0492 973781.5 250
98.0151 77907.6 20
99.023 78966.8 20
101.0386 96242.4 24
102.0464 794600.5 204
103.0542 320484.8 82
104.0619 7633.9 1
105.0448 717826.9 184
107.0493 26135.9 6
113.0386 526012.2 135
114.0464 162447 41
115.0543 3725813.5 958
116.062 89816.5 23
117.0702 5832.2 1
118.0413 74350.7 19
119.0492 60801.3 15
125.0386 94351.1 24
126.0464 929152.5 238
127.0542 392648.2 100
128.0621 1040333.4 267
129.0447 177446.4 45
129.0698 28178.4 7
131.0492 153643.4 39
132.057 83390 21
137.0387 108791.5 27
138.0464 96292.2 24
139.0543 3884082 999
140.0621 130416.2 33
141.0699 190175.3 48
142.0413 8578.8 2
143.0492 10953.9 2
144.057 29418.3 7
145.0648 149763.3 38
149.0385 40016.1 10
150.0465 982308.6 252
151.0543 204732.4 52
152.0621 1671023.6 429
153.0699 106292 27
155.0493 38534.2 9
155.0604 365509.7 94
156.0573 12634.5 3
157.0649 8090 2
161.0599 5045.7 1
162.0464 78762.9 20
163.0542 1161592 298
164.062 262360.9 67
165.07 783835.3 201
167.0491 25761.1 6
168.057 200395.9 51
169.0648 747609.2 192
174.0464 96584.3 24
175.0544 21310.9 5
176.0621 422097.2 108
177.0696 45729.6 11
178.0779 46936.8 12
179.0604 287672.5 73
181.0645 44240.9 11
183.0809 8018 2
185.0597 26392.4 6
187.0543 183011.3 47
188.0619 45595.2 11
189.07 138957.6 35
192.0569 24651.7 6
193.0648 56830.5 14
194.0365 28149.7 7
196.0519 61011.9 15
200.062 50162.8 12
203.0601 19780.6 5
203.0725 5975.7 1
220.0519 9332.3 2
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