ACCESSION: MSBNK-Eawag-EQ367851
RECORD_TITLE: Doxycycline; LC-ESI-QFT; MS2; CE: 15; 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$MASS_SPECTROMETRY: COLLISION_ENERGY 15 (nominal)
AC$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$SPLASH: splash10-0006-0003900000-0a42fbdab90c592b6b37
PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm)
  142.0145 C5H4NO4- 1 142.0146 -0.78
  152.0354 C7H6NO3- 1 152.0353 0.55
  163.0038 C8H3O4- 1 163.0037 1.03
  168.0302 C7H6NO4- 1 168.0302 -0.36
  169.0616 C7H9N2O3- 1 169.0619 -1.34
  173.0607 C11H9O2- 1 173.0608 -0.83
  180.03 C8H6NO4- 1 180.0302 -1.28
  187.0763 C12H11O2- 1 187.0765 -0.55
  196.0251 C8H6NO5- 1 196.0251 -0.13
  197.093 C9H13N2O3- 1 197.0932 -0.64
  207.0774 C10H11N2O3- 1 207.0775 -0.41
  208.0613 C10H10NO4- 1 208.0615 -1.02
  217.0506 C12H9O4- 1 217.0506 -0.33
  225.0881 C10H13N2O4- 1 225.0881 0.13
  229.0502 C13H9O4- 1 229.0506 -1.8
  255.0661 C15H11O4- 1 255.0663 -0.6
  269.0817 C16H13O4- 1 269.0819 -0.75
  273.0768 C15H13O5- 1 273.0768 -0.03
  293.0819 C18H13O4- 1 293.0819 -0.01
  297.0769 C17H13O5- 1 297.0768 0.04
  311.0925 C18H15O5- 1 311.0925 0.14
  323.1399 C19H19N2O3- 1 323.1401 -0.76
  326.1039 C18H16NO5- 1 326.1034 1.51
  336.0883 C19H14NO5- 1 336.0877 1.56
  337.072 C19H13O6- 1 337.0718 0.8
  338.1401 C20H20NO4- 1 338.1398 1
  354.1339 C20H20NO5- 1 354.1347 -2.36
  356.1511 C20H22NO5- 1 356.1503 2.03
  358.1296 C19H20NO6- 1 358.1296 0
  363.1353 C21H19N2O4- 1 363.135 0.71
  364.1191 C21H18NO5- 1 364.119 0.18
  371.1612 C20H23N2O5- 1 371.1612 -0.23
  380.0772 C20H14NO7- 1 380.0776 -0.99
  381.0612 C20H13O8- 1 381.0616 -1
  381.1455 C21H21N2O5- 1 381.1456 -0.33
  382.1295 C21H20NO6- 1 382.1296 -0.34
  399.1562 C21H23N2O6- 1 399.1562 0.02
  400.14 C21H22NO7- 1 400.1402 -0.36
  408.1081 C22H18NO7- 1 408.1089 -1.9
  425.1354 C22H21N2O7- 1 425.1354 -0.06
  426.1195 C22H20NO8- 1 426.1194 0.14
  443.1461 C22H23N2O8- 1 443.146 0.29
  444.1298 C22H22NO9- 2 444.13 -0.46
PK$NUM_PEAK: 43
PK$PEAK: m/z int. rel.int.
  142.0145 56162.2 12
  152.0354 4587.1 1
  163.0038 8614.6 1
  168.0302 36092.5 8
  169.0616 12307.2 2
  173.0607 66146.6 14
  180.03 9634.2 2
  187.0763 23303.8 5
  196.0251 9972.3 2
  197.093 8893.8 2
  207.0774 24112.2 5
  208.0613 7013.8 1
  217.0506 101499.2 22
  225.0881 210462.1 47
  229.0502 4832.5 1
  255.0661 29528.4 6
  269.0817 8705.7 1
  273.0768 202840.4 45
  293.0819 15901.6 3
  297.0769 8712.1 1
  311.0925 7131.2 1
  323.1399 12769.6 2
  326.1039 6004.9 1
  336.0883 7467.3 1
  337.072 23567.7 5
  338.1401 50674.4 11
  354.1339 22072.5 4
  356.1511 21061.8 4
  358.1296 455737.3 103
  363.1353 11330.5 2
  364.1191 84766.2 19
  371.1612 141598.8 32
  380.0772 8105 1
  381.0612 6238.8 1
  381.1455 104610 23
  382.1295 64657.5 14
  399.1562 1447619 327
  400.14 614277.2 139
  408.1081 8249.3 1
  425.1354 60015.7 13
  426.1195 1206098.4 273
  443.1461 4411777 999
  444.1298 169912.8 38
//