ACCESSION: MSBNK-Eawag-EQ367858
RECORD_TITLE: Doxycycline; LC-ESI-QFT; MS2; CE: 150; 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 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$CHROMATOGRAPHY: RETENTION_TIME 6.3 min
AC$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: splash10-014i-8920000000-f3249d1185e212d78155
PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm)
50.0036 C3N- 1 50.0036 -1.05
51.024 C4H3- 1 51.024 -0.86
53.0032 C3HO- 1 53.0033 -1.29
55.0189 C3H3O- 1 55.0189 -0.51
63.024 C5H3- 1 63.024 0.26
64.0192 C4H2N- 1 64.0193 -0.51
65.0033 C4HO- 1 65.0033 0.18
65.0397 C5H5- 1 65.0397 -0.21
65.9986 C3NO- 1 65.9985 0.35
67.019 C4H3O- 1 67.0189 0.62
68.0142 C3H2NO- 1 68.0142 0.63
68.9982 C3HO2- 1 68.9982 0.54
76.0195 C5H2N- 1 76.0193 2.33
79.019 C5H3O- 1 79.0189 0.65
81.022 C4H3NO- 1 81.022 -0.52
84.0091 C3H2NO2- 1 84.0091 -0.5
89.0397 C7H5- 1 89.0397 -0.04
90.0349 C6H4N- 1 90.0349 -0.7
91.019 C6H3O- 1 91.0189 0.9
91.0554 C7H7- 1 91.0553 0.4
93.0345 C6H5O- 1 93.0346 -0.84
95.0138 C5H3O2- 1 95.0139 -0.14
96.0091 C4H2NO2- 1 96.0091 -0.12
101.0394 C8H5- 1 101.0397 -2.61
102.0473 C8H6- 1 102.0475 -2.14
108.0217 C6H4O2- 1 108.0217 -0.07
109.0295 C6H5O2- 1 109.0295 0.34
113.0397 C9H5- 1 113.0397 0.5
115.0555 C9H7- 1 115.0553 1.79
117.0345 C8H5O- 1 117.0346 -0.41
119.0503 C8H7O- 1 119.0502 0.43
120.0091 C6H2NO2- 1 120.0091 -0.35
121.0294 C7H5O2- 1 121.0295 -0.77
123.0087 C6H3O3- 1 123.0088 -0.55
130.0424 C9H6O- 1 130.0424 0.13
131.0503 C9H7O- 1 131.0502 0.24
137.0396 C11H5- 1 137.0397 -0.32
138.0477 C11H6- 1 138.0475 1.24
139.0554 C11H7- 1 139.0553 0.62
141.0345 C10H5O- 1 141.0346 -0.41
143.0503 C10H7O- 1 143.0502 0.22
144.0588 C10H8O- 1 144.0581 4.84
145.0295 C9H5O2- 1 145.0295 -0.3
145.0656 C10H9O- 1 145.0659 -2.2
147.0199 C7H3N2O2- 1 147.02 -0.35
147.0453 C9H7O2- 1 147.0452 1.07
148.004 C7H2NO3- 1 148.004 -0.04
154.0424 C11H6O- 1 154.0424 -0.15
155.0505 C11H7O- 1 155.0502 1.49
157.066 C11H9O- 1 157.0659 0.58
158.0373 C10H6O2- 1 158.0373 -0.49
159.0452 C10H7O2- 1 159.0452 0.3
161.0249 C9H5O3- 1 161.0244 2.93
165.0344 C12H5O- 1 165.0346 -0.9
167.0503 C12H7O- 1 167.0502 0.31
169.0294 C11H5O2- 1 169.0295 -0.55
169.0657 C12H9O- 1 169.0659 -0.88
171.0452 C11H7O2- 1 171.0452 0.27
173.0607 C11H9O2- 1 173.0608 -0.83
180.0581 C13H8O- 1 180.0581 0.2
181.0655 C13H9O- 1 181.0659 -2.15
182.0372 C12H6O2- 1 182.0373 -0.54
183.0451 C12H7O2- 1 183.0452 -0.18
187.0397 C11H7O3- 1 187.0401 -1.91
191.0503 C14H7O- 1 191.0502 0.22
193.0294 C13H5O2- 1 193.0295 -0.48
195.0451 C13H7O2- 1 195.0452 -0.53
196.0531 C13H8O2- 1 196.053 0.88
197.0607 C13H9O2- 1 197.0608 -0.32
204.058 C15H8O- 1 204.0581 -0.51
207.0451 C14H7O2- 1 207.0452 -0.21
208.0527 C14H8O2- 1 208.053 -1.29
209.0609 C14H9O2- 1 209.0608 0.61
210.0322 C13H6O3- 1 210.0322 -0.11
211.0402 C13H7O3- 1 211.0401 0.39
220.0533 C15H8O2- 1 220.053 1.28
224.048 C14H8O3- 1 224.0479 0.61
225.0559 C14H9O3- 1 225.0557 0.81
239.034 C14H7O4- 1 239.035 -4.15
PK$NUM_PEAK: 79
PK$PEAK: m/z int. rel.int.
50.0036 15817.1 118
51.024 2051.2 15
53.0032 6308.2 47
55.0189 4003.3 29
63.024 10482.3 78
64.0192 5154.3 38
65.0033 27006.3 201
65.0397 7793.2 58
65.9986 133609.2 999
67.019 7812 58
68.0142 6895.8 51
68.9982 48040 359
76.0195 1068.1 7
79.019 4536.4 33
81.022 1080.8 8
84.0091 4277.9 31
89.0397 9008.2 67
90.0349 1672.4 12
91.019 1993.6 14
91.0554 5590.6 41
93.0345 7354.7 54
95.0138 25599 191
96.0091 10866.1 81
101.0394 1337.9 10
102.0473 814.5 6
108.0217 4298.1 32
109.0295 4005.3 29
113.0397 1777.9 13
115.0555 4315.2 32
117.0345 13781.8 103
119.0503 8459.4 63
120.0091 6011.1 44
121.0294 1154.5 8
123.0087 5912.8 44
130.0424 21976.9 164
131.0503 3883.5 29
137.0396 12313.7 92
138.0477 3618.4 27
139.0554 6550.2 48
141.0345 6109.7 45
143.0503 20640.1 154
144.0588 1017 7
145.0295 1155.4 8
145.0656 1278.6 9
147.0199 855.4 6
147.0453 3925.8 29
148.004 2037.4 15
154.0424 18700.7 139
155.0505 12759.6 95
157.066 1122.3 8
158.0373 14955.5 111
159.0452 12639.5 94
161.0249 1575.2 11
165.0344 16037.2 119
167.0503 20091.8 150
169.0294 926.4 6
169.0657 3699.5 27
171.0452 6029.9 45
173.0607 1306.5 9
180.0581 3269.7 24
181.0655 1623.3 12
182.0372 31301.2 234
183.0451 56041.3 419
187.0397 3618.3 27
191.0503 1351 10
193.0294 1238.7 9
195.0451 5159.2 38
196.0531 4372 32
197.0607 1561.4 11
204.058 1513.6 11
207.0451 1150.1 8
208.0527 1544.6 11
209.0609 2157.6 16
210.0322 5935.3 44
211.0402 84667.9 633
220.0533 1108.3 8
224.048 1169.8 8
225.0559 871.8 6
239.034 1865.5 13
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