MassBank Record: SM874501



 Cyproterone; LC-ESI-QFT; MS2; CE: 35 NCE; R=35000; [M+H]+ 
Mass Spectrum
Chemical Structure


ACCESSION: SM874501
RECORD_TITLE: Cyproterone; LC-ESI-QFT; MS2; CE: 35 NCE; R=35000; [M+H]+
DATE: 2016.12.12
AUTHORS: Krauss M, Schymanski EL, Weidauer C, Schupke H, UFZ and Eawag
LICENSE: CC BY
COPYRIGHT: Copyright (C) 2016 UFZ/Eawag
PUBLICATION: Schymanski, EL et al. Critical Assessment of Small Molecule Identification 2016 - Automated Methods. Submitted.
COMMENT: CONFIDENCE standard compound
COMMENT: INTERNAL_ID 8745

CH$NAME: Cyproterone CH$COMPOUND_CLASS: N/A; Environmental Standard CH$FORMULA: C22H27ClO3 CH$EXACT_MASS: 374.16487 CH$SMILES: CC(=O)C1(O)CCC2C3C=C(Cl)C4=CC(=O)C5CC5C4(C)C3CCC12C CH$IUPAC: InChI=1S/C22H27ClO3/c1-11(24)22(26)7-5-14-12-9-18(23)17-10-19(25)13-8-16(13)21(17,3)15(12)4-6-20(14,22)2/h9-10,12-16,26H,4-8H2,1-3H3 CH$LINK: CAS 2098-66-0 CH$LINK: PUBCHEM CID:3015 CH$LINK: INCHIKEY DUSHUSLJJMDGTE-UHFFFAOYSA-N CH$LINK: CHEMSPIDER 2907
AC$INSTRUMENT: Q Exactive Plus Orbitrap Thermo Scientific AC$INSTRUMENT_TYPE: LC-ESI-QFT AC$MASS_SPECTROMETRY: MS_TYPE MS2 AC$MASS_SPECTROMETRY: IONIZATION ESI AC$MASS_SPECTROMETRY: ION_MODE POSITIVE AC$MASS_SPECTROMETRY: FRAGMENTATION_MODE HCD AC$MASS_SPECTROMETRY: COLLISION_ENERGY 35 (nominal) AC$MASS_SPECTROMETRY: RESOLUTION 35000 AC$CHROMATOGRAPHY: COLUMN_NAME Kinetex C18 EVO 2.6 um, 2.1x50 mm, precolumn 2.1x5 mm, Phenomenex AC$CHROMATOGRAPHY: FLOW_GRADIENT 95/5 at 0 min, 95/5 at 1 min, 0/100 at 13 min, 0/100 at 24 min AC$CHROMATOGRAPHY: FLOW_RATE 300 uL/min AC$CHROMATOGRAPHY: RETENTION_TIME 11.842 min AC$CHROMATOGRAPHY: SOLVENT A water with 0.1% formic acid AC$CHROMATOGRAPHY: SOLVENT B methanol with 0.1% formic acid
MS$FOCUSED_ION: BASE_PEAK 313.2158 MS$FOCUSED_ION: PRECURSOR_M/Z 375.1721 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 2.3.1
PK$SPLASH: splash10-004i-1569000000-a0ff13be629506ff86a3 PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm) 55.0181 C3H3O+ 1 55.0178 4.6 55.0545 C4H7+ 1 55.0542 4.3 59.0493 C3H7O+ 1 59.0491 2.44 61.0285 C2H5O2+ 1 61.0284 1.81 67.0543 C5H7+ 1 67.0542 1.29 69.0335 C4H5O+ 1 69.0335 0.74 69.07 C5H9+ 1 69.0699 1.06 71.0492 C4H7O+ 1 71.0491 0.66 79.0542 C6H7+ 1 79.0542 0.24 81.0699 C6H9+ 1 81.0699 0.28 83.0491 C5H7O+ 1 83.0491 -0.21 85.0648 C5H9O+ 1 85.0648 -0.13 87.044 C4H7O2+ 1 87.0441 -0.11 91.0542 C7H7+ 1 91.0542 -0.67 93.0699 C7H9+ 1 93.0699 -0.28 95.0492 C6H7O+ 1 95.0491 0.36 95.0855 C7H11+ 1 95.0855 -0.05 97.0648 C6H9O+ 1 97.0648 0.18 99.0441 C5H7O2+ 1 99.0441 0.1 99.0804 C6H11O+ 1 99.0804 -0.9 105.0699 C8H9+ 1 105.0699 -0.17 107.0491 C7H7O+ 1 107.0491 -0.15 107.0855 C8H11+ 1 107.0855 0.13 109.0648 C7H9O+ 1 109.0648 -0.35 109.1012 C8H13+ 1 109.1012 -0.07 111.0805 C7H11O+ 1 111.0804 0.5 113.0597 C6H9O2+ 1 113.0597 0.17 115.0544 C9H7+ 1 115.0542 1.66 117.0699 C9H9+ 1 117.0699 0.21 119.0855 C9H11+ 1 119.0855 -0.16 121.0648 C8H9O+ 1 121.0648 0.11 121.1012 C9H13+ 1 121.1012 0.23 123.0805 C8H11O+ 1 123.0804 0.31 127.031 C7H8Cl+ 1 127.0309 0.82 129.0699 C10H9+ 1 129.0699 0.16 130.0776 C10H10+ 1 130.0777 -0.91 131.0855 C10H11+ 1 131.0855 -0.21 133.0649 C9H9O+ 1 133.0648 0.51 133.1011 C10H13+ 1 133.1012 -0.24 135.0805 C9H11O+ 1 135.0804 0.14 135.1167 C10H15+ 1 135.1168 -1.05 137.0961 C9H13O+ 1 137.0961 -0.03 139.0308 C8H8Cl+ 1 139.0309 -0.67 141.0465 C8H10Cl+ 1 141.0466 -0.33 141.0699 C11H9+ 1 141.0699 0.38 142.0775 C11H10+ 1 142.0777 -1.17 143.0855 C11H11+ 1 143.0855 -0.26 144.0568 C10H8O+ 1 144.057 -1 144.0932 C11H12+ 1 144.0934 -1.27 145.0648 C10H9O+ 1 145.0648 0.01 145.1011 C11H13+ 1 145.1012 -0.47 146.0724 C10H10O+ 1 146.0726 -1.19 147.0803 C10H11O+ 1 147.0804 -0.94 147.1168 C11H15+ 1 147.1168 -0.48 149.0963 C10H13O+ 1 149.0961 1.2 151.1118 C10H15O+ 1 151.1117 0.45 154.0777 C12H10+ 1 154.0777 0.05 155.0261 C8H8ClO+ 1 155.0258 1.56 155.0854 C12H11+ 1 155.0855 -0.81 156.0934 C12H12+ 1 156.0934 0.1 157.0413 C8H10ClO+ 1 157.0415 -0.85 157.0647 C11H9O+ 1 157.0648 -0.5 157.1012 C12H13+ 1 157.1012 -0.07 158.0725 C11H10O+ 1 158.0726 -0.86 159.0805 C11H11O+ 1 159.0804 0.22 159.1169 C12H15+ 1 159.1168 0.36 161.0961 C11H13O+ 1 161.0961 0.36 161.1323 C12H17+ 1 161.1325 -1.02 163.0308 C10H8Cl+ 1 163.0309 -0.66 163.1117 C11H15O+ 1 163.1117 -0.26 165.0466 C10H10Cl+ 1 165.0466 0.23 165.0701 C13H9+ 1 165.0699 1.57 166.0778 C13H10+ 1 166.0777 0.48 167.0258 C9H8ClO+ 1 167.0258 -0.32 167.0855 C13H11+ 1 167.0855 0.05 168.0934 C13H12+ 1 168.0934 0.25 169.0413 C9H10ClO+ 1 169.0415 -0.72 169.0648 C12H9O+ 1 169.0648 -0.13 169.1011 C13H13+ 1 169.1012 -0.27 171.0804 C12H11O+ 1 171.0804 -0.08 171.117 C13H15+ 1 171.1168 0.94 172.088 C12H12O+ 1 172.0883 -1.3 173.0962 C12H13O+ 1 173.0961 0.49 175.1118 C12H15O+ 1 175.1117 0.35 177.0465 C11H10Cl+ 1 177.0466 -0.07 177.1274 C12H17O+ 1 177.1274 -0.13 178.0776 C14H10+ 1 178.0777 -0.34 179.0256 C10H8ClO+ 1 179.0258 -1.09 179.0622 C11H12Cl+ 1 179.0622 -0.2 179.0853 C14H11+ 1 179.0855 -1.17 180.0933 C14H12+ 1 180.0934 -0.55 181.0414 C10H10ClO+ 1 181.0415 -0.61 181.0778 C11H14Cl+ 1 181.0779 -0.24 181.1012 C14H13+ 1 181.1012 -0.11 182.1091 C14H14+ 1 182.109 0.42 183.0572 C10H12ClO+ 1 183.0571 0.6 183.0804 C13H11O+ 1 183.0804 -0.44 183.1168 C14H15+ 1 183.1168 0.1 184.0884 C13H12O+ 1 184.0883 0.75 184.125 C14H16+ 1 184.1247 1.78 185.0962 C13H13O+ 1 185.0961 0.51 185.1323 C14H17+ 1 185.1325 -1.1 187.1119 C13H15O+ 1 187.1117 0.79 189.0466 C12H10Cl+ 1 189.0466 0.4 189.1271 C13H17O+ 1 189.1274 -1.6 191.0257 C11H8ClO+ 1 191.0258 -0.64 191.0621 C12H12Cl+ 1 191.0622 -0.68 191.0854 C15H11+ 1 191.0855 -0.56 192.0934 C15H12+ 1 192.0934 0.02 193.0414 C11H10ClO+ 1 193.0415 -0.2 193.078 C12H14Cl+ 1 193.0779 0.95 193.1012 C15H13+ 1 193.1012 0.04 194.1088 C15H14+ 1 194.109 -0.8 195.0572 C11H12ClO+ 1 195.0571 0.55 195.0804 C14H11O+ 1 195.0804 -0.42 195.1169 C15H15+ 1 195.1168 0.16 196.1246 C15H16+ 1 196.1247 -0.29 197.0963 C14H13O+ 1 197.0961 1.17 197.1326 C15H17+ 1 197.1325 0.59 199.1121 C14H15O+ 1 199.1117 1.89 201.0464 C13H10Cl+ 1 201.0466 -0.68 201.127 C14H17O+ 1 201.1274 -2.18 203.0621 C13H12Cl+ 1 203.0622 -0.33 203.0855 C16H11+ 1 203.0855 -0.14 204.0932 C16H12+ 1 204.0934 -0.56 205.0414 C12H10ClO+ 1 205.0415 -0.46 205.0778 C13H14Cl+ 1 205.0779 -0.28 205.1011 C16H13+ 1 205.1012 -0.16 206.109 C16H14+ 1 206.109 0.08 207.0571 C12H12ClO+ 1 207.0571 -0.19 207.1168 C16H15+ 1 207.1168 -0.34 208.0883 C15H12O+ 1 208.0883 -0.05 208.1245 C16H16+ 1 208.1247 -0.61 209.0963 C15H13O+ 1 209.0961 0.99 209.1323 C16H17+ 1 209.1325 -0.87 210.104 C15H14O+ 1 210.1039 0.5 210.1398 C16H18+ 1 210.1403 -2.3 211.1116 C15H15O+ 1 211.1117 -0.63 211.148 C16H19+ 1 211.1481 -0.53 213.1275 C15H17O+ 1 213.1274 0.28 215.0625 C14H12Cl+ 1 215.0622 1.52 217.0781 C14H14Cl+ 1 217.0779 1.06 217.1011 C17H13+ 1 217.1012 -0.24 218.109 C17H14+ 1 218.109 -0.21 219.0572 C13H12ClO+ 1 219.0571 0.16 219.1168 C17H15+ 1 219.1168 -0.32 220.1246 C17H16+ 1 220.1247 -0.44 221.0728 C13H14ClO+ 1 221.0728 0 221.0961 C16H13O+ 1 221.0961 -0.17 221.1326 C17H17+ 1 221.1325 0.76 222.1038 C16H14O+ 1 222.1039 -0.41 222.1406 C17H18+ 1 222.1403 1.26 223.1117 C16H15O+ 1 223.1117 -0.32 223.1483 C17H19+ 1 223.1481 0.6 224.1197 C16H16O+ 1 224.1196 0.59 225.1275 C16H17O+ 1 225.1274 0.27 226.1354 C16H18O+ 1 226.1352 0.77 227.1427 C16H19O+ 1 227.143 -1.7 229.0778 C15H14Cl+ 1 229.0779 -0.32 229.1011 C18H13+ 1 229.1012 -0.42 230.1092 C18H14+ 1 230.109 0.8 231.0575 C14H12ClO+ 1 231.0571 1.82 231.0934 C15H16Cl+ 1 231.0935 -0.66 231.1169 C18H15+ 1 231.1168 0.43 232.1246 C18H16+ 1 232.1247 -0.4 233.0727 C14H14ClO+ 1 233.0728 -0.51 233.1326 C18H17+ 1 233.1325 0.74 234.104 C17H14O+ 1 234.1039 0.47 234.1403 C18H18+ 1 234.1403 -0.09 235.0884 C14H16ClO+ 1 235.0884 0.07 235.1118 C17H15O+ 1 235.1117 0.43 235.1481 C18H19+ 1 235.1481 -0.13 236.1194 C17H16O+ 1 236.1196 -0.91 236.1559 C18H20+ 1 236.156 -0.3 237.1276 C17H17O+ 1 237.1274 0.86 237.1635 C18H21+ 1 237.1638 -1.11 238.1351 C17H18O+ 1 238.1352 -0.47 239.143 C17H19O+ 1 239.143 -0.12 241.0778 C16H14Cl+ 1 241.0779 -0.03 243.0937 C16H16Cl+ 1 243.0935 0.71 243.1164 C19H15+ 1 243.1168 -1.64 244.1247 C19H16+ 1 244.1247 0.21 245.0731 C15H14ClO+ 1 245.0728 1.22 245.1093 C16H18Cl+ 1 245.1092 0.57 245.1324 C19H17+ 1 245.1325 -0.27 246.14 C19H18+ 1 246.1403 -1.3 247.0889 C15H16ClO+ 1 247.0884 1.94 247.1117 C18H15O+ 1 247.1117 0 247.148 C19H19+ 1 247.1481 -0.65 248.1198 C18H16O+ 1 248.1196 1.01 248.1557 C19H20+ 1 248.156 -0.99 249.1272 C18H17O+ 1 249.1274 -0.69 249.1637 C19H21+ 1 249.1638 -0.42 250.1353 C18H18O+ 1 250.1352 0.37 250.1713 C19H22+ 1 250.1716 -1.18 251.1432 C18H19O+ 1 251.143 0.52 251.1792 C19H23+ 1 251.1794 -0.85 252.1507 C18H20O+ 1 252.1509 -0.61 253.1586 C18H21O+ 1 253.1587 -0.47 255.0938 C17H16Cl+ 1 255.0935 1.12 257.1092 C17H18Cl+ 1 257.1092 0.2 259.0882 C16H16ClO+ 1 259.0884 -0.78 259.1118 C19H15O+ 1 259.1117 0.13 259.1482 C20H19+ 1 259.1481 0.22 260.1557 C20H20+ 1 260.156 -1.11 261.1043 C16H18ClO+ 1 261.1041 1.02 261.1272 C19H17O+ 1 261.1274 -0.88 261.1638 C20H21+ 1 261.1638 -0.09 262.1354 C19H18O+ 1 262.1352 0.6 262.1722 C20H22+ 1 262.1716 2.2 263.143 C19H19O+ 1 263.143 -0.13 264.1513 C19H20O+ 1 264.1509 1.68 265.1228 C18H17O2+ 1 265.1223 1.78 265.1586 C19H21O+ 1 265.1587 -0.43 269.1099 C18H18Cl+ 1 269.1092 2.7 270.1397 C21H18+ 1 270.1403 -2.11 271.0886 C17H16ClO+ 1 271.0884 0.73 271.1248 C18H20Cl+ 1 271.1248 0.02 273.1038 C17H18ClO+ 1 273.1041 -1.02 273.1271 C20H17O+ 1 273.1274 -0.94 273.1632 C21H21+ 1 273.1638 -1.97 274.1121 C17H19ClO+ 1 274.1119 0.61 275.1196 C17H20ClO+ 1 275.1197 -0.31 275.1427 C20H19O+ 1 275.143 -1.33 275.1794 C21H23+ 1 275.1794 -0.14 277.1587 C20H21O+ 1 277.1587 0.04 278.1665 C20H22O+ 1 278.1665 0 279.1744 C20H23O+ 1 279.1743 0.19 281.1087 C19H18Cl+ 1 281.1092 -1.53 283.0887 C18H16ClO+ 1 283.0884 0.92 285.1038 C18H18ClO+ 1 285.1041 -0.87 285.1636 C22H21+ 1 285.1638 -0.49 287.1193 C18H20ClO+ 1 287.1197 -1.36 288.1509 C21H20O+ 1 288.1509 0.28 289.1348 C18H22ClO+ 1 289.1354 -2.05 291.1738 C21H23O+ 1 291.1743 -1.71 293.1536 C20H21O2+ 1 293.1536 0.14 293.1895 C21H25O+ 1 293.19 -1.56 295.1697 C20H23O2+ 1 295.1693 1.41 296.133 C20H21Cl+ 1 296.1326 1.33 297.1402 C20H22Cl+ 1 297.1405 -0.87 297.1853 C20H25O2+ 1 297.1849 1.43 299.1198 C19H20ClO+ 1 299.1197 0.22 301.1346 C19H22ClO+ 1 301.1354 -2.59 303.1745 C22H23O+ 1 303.1743 0.56 306.1612 C21H22O2+ 1 306.1614 -0.72 313.1353 C20H22ClO+ 1 313.1354 -0.08 314.143 C20H23ClO+ 1 314.1432 -0.5 315.151 C20H24ClO+ 1 315.151 -0.05 321.185 C22H25O2+ 1 321.1849 0.23 322.1929 C22H26O2+ 1 322.1927 0.48 329.1668 C21H26ClO+ 1 329.1667 0.33 331.1469 C20H24ClO2+ 1 331.1459 3.05 333.161 C20H26ClO2+ 1 333.1616 -1.89 339.1512 C22H24ClO+ 1 339.151 0.44 339.1955 C22H27O3+ 1 339.1955 0.12 357.1616 C22H26ClO2+ 1 357.1616 0.15 375.1722 C22H28ClO3+ 1 375.1721 0.11 PK$NUM_PEAK: 258 PK$PEAK: m/z int. rel.int. 55.0181 192647.1 2 55.0545 190021.8 2 59.0493 542676.2 8 61.0285 411086.2 6 67.0543 518599.9 8 69.0335 249738.3 3 69.07 256281.4 3 71.0492 258783 4 79.0542 494690.1 7 81.0699 730966.4 11 83.0491 628078.8 9 85.0648 535478.1 8 87.044 1029085.4 16 91.0542 735393.2 11 93.0699 994426.6 15 95.0492 632071.4 9 95.0855 617716.2 9 97.0648 521552.8 8 99.0441 79454.9 1 99.0804 172932 2 105.0699 1612391.1 25 107.0491 301218 4 107.0855 888890.4 13 109.0648 904125.3 14 109.1012 397672.1 6 111.0805 972079.2 15 113.0597 138187.7 2 115.0544 77125.6 1 117.0699 575223.2 8 119.0855 1424519.1 22 121.0648 871066.9 13 121.1012 684927.9 10 123.0805 423348 6 127.031 148091.8 2 129.0699 589816.7 9 130.0776 74261.5 1 131.0855 885858.5 13 133.0649 155676.8 2 133.1011 2356329.5 36 135.0805 350592.8 5 135.1167 299902.4 4 137.0961 233039.2 3 139.0308 154663.2 2 141.0465 85496.7 1 141.0699 355453.7 5 142.0775 445145.3 6 143.0855 772761.6 12 144.0568 88401 1 144.0932 86451.7 1 145.0648 720872 11 145.1011 1332579 20 146.0724 157254.5 2 147.0803 718373.6 11 147.1168 2182265.5 33 149.0963 273409.9 4 151.1118 267338.4 4 154.0777 74214.5 1 155.0261 173554 2 155.0854 984383.3 15 156.0934 229136.5 3 157.0413 78692.5 1 157.0647 245636 3 157.1012 1069628.4 16 158.0725 191556.8 2 159.0805 690789.8 10 159.1169 631413.1 9 161.0961 377316.7 5 161.1323 68010.8 1 163.0308 80529.1 1 163.1117 431921.2 6 165.0466 240133.6 3 165.0701 291826.7 4 166.0778 72069.3 1 167.0258 187263.7 2 167.0855 313367.9 4 168.0934 313040.1 4 169.0413 229001.4 3 169.0648 68032.1 1 169.1011 753806.9 11 171.0804 586837.8 9 171.117 480517 7 172.088 74481.7 1 173.0962 351927.2 5 175.1118 1086644.9 16 177.0465 730370.2 11 177.1274 170225.2 2 178.0776 79773.6 1 179.0256 175446 2 179.0622 202520.1 3 179.0853 327149.6 5 180.0933 234946.5 3 181.0414 777492.4 12 181.0778 239158.4 3 181.1012 841926.9 13 182.1091 238756.4 3 183.0572 288734 4 183.0804 351384.3 5 183.1168 1007493.4 15 184.0884 386790.8 6 184.125 81686.7 1 185.0962 1144822.5 17 185.1323 245785.8 3 187.1119 315384.3 4 189.0466 386512.8 6 189.1271 262585.2 4 191.0257 457736.8 7 191.0621 392843.8 6 191.0854 164863.5 2 192.0934 227398.9 3 193.0414 270079 4 193.078 149164.7 2 193.1012 865996.1 13 194.1088 202837.7 3 195.0572 276302.4 4 195.0804 162753.6 2 195.1169 1392105.4 21 196.1246 365542.5 5 197.0963 322863.9 5 197.1326 386304.6 6 199.1121 277796.3 4 201.0464 196073.4 3 201.127 323294.2 5 203.0621 347663.6 5 203.0855 175848.5 2 204.0932 80018.4 1 205.0414 715097.5 11 205.0778 214679.6 3 205.1011 888888.2 13 206.109 236803.7 3 207.0571 361559.1 5 207.1168 1231500.9 19 208.0883 86803.8 1 208.1245 211587.9 3 209.0963 473381.6 7 209.1323 815210.9 12 210.104 75689.2 1 210.1398 207892.2 3 211.1116 481208.3 7 211.148 158825.2 2 213.1275 220110.1 3 215.0625 278373.1 4 217.0781 274455.5 4 217.1011 382234.4 5 218.109 280256.8 4 219.0572 3506608 54 219.1168 919658.7 14 220.1246 272300.2 4 221.0728 405873.7 6 221.0961 308928.3 4 221.1326 932637.1 14 222.1038 205557.4 3 222.1406 136205.6 2 223.1117 635280.4 9 223.1483 394035.2 6 224.1197 185082.9 2 225.1275 369882.8 5 226.1354 75728.6 1 227.1427 79387.8 1 229.0778 210082.2 3 229.1011 85046.6 1 230.1092 174775 2 231.0575 140847.8 2 231.0934 226848.7 3 231.1169 395033.1 6 232.1246 326519.2 5 233.0727 206907.8 3 233.1326 936646.2 14 234.104 84522.8 1 234.1403 175690.9 2 235.0884 161223.4 2 235.1118 627631.5 9 235.1481 1245929 19 236.1194 346672.3 5 236.1559 142030.3 2 237.1276 848038.9 13 237.1635 459262.8 7 238.1351 201071.9 3 239.143 616999.4 9 241.0778 228826.3 3 243.0937 194176 3 243.1164 168557.6 2 244.1247 209549 3 245.0731 694306.6 10 245.1093 242449 3 245.1324 472762.9 7 246.14 430161.8 6 247.0889 87456 1 247.1117 329312.6 5 247.148 841346.5 13 248.1198 205586.6 3 248.1557 184461.5 2 249.1272 671142 10 249.1637 853259 13 250.1353 371636.4 5 250.1713 248224.5 3 251.1432 1041635.5 16 251.1792 526692.8 8 252.1507 75271.6 1 253.1586 350119.5 5 255.0938 311206.9 4 257.1092 216924.1 3 259.0882 362161.1 5 259.1118 70328.4 1 259.1482 392788.9 6 260.1557 505097.7 7 261.1043 142903.7 2 261.1272 373535 5 261.1638 1145031.5 17 262.1354 314642.4 4 262.1722 64333.4 1 263.143 2509484 39 264.1513 283160.8 4 265.1228 133294.6 2 265.1586 508567.7 7 269.1099 189883.9 2 270.1397 171733.8 2 271.0886 159077.5 2 271.1248 140513.7 2 273.1038 621713.1 9 273.1271 77086.9 1 273.1632 84670.2 1 274.1121 64425.8 1 275.1196 241102.2 3 275.1427 160069.6 2 275.1794 658349.5 10 277.1587 1994559.2 31 278.1665 1500193.2 23 279.1744 3972948.8 61 281.1087 78211.3 1 283.0887 71976.1 1 285.1038 199202.5 3 285.1636 228820.5 3 287.1193 355099.2 5 288.1509 199872.3 3 289.1348 170238.6 2 291.1738 66186.6 1 293.1536 2232677.5 34 293.1895 823003.7 12 295.1697 75997 1 296.133 71451.8 1 297.1402 238641 3 297.1853 277503.6 4 299.1198 560230.6 8 301.1346 192642.6 2 303.1745 1323281.2 20 306.1612 525230.9 8 313.1353 1685755.1 26 314.143 1304698 20 315.151 1250162.6 19 321.185 7460905.5 116 322.1929 226258.1 3 329.1668 406632.7 6 331.1469 64472 1 333.161 143621.8 2 339.1512 448769.7 6 339.1955 420008.5 6 357.1616 2844915.2 44 375.1722 64210540 999 //