ACCESSION: MSBNK-Athens_Univ-AU239606
RECORD_TITLE: Cyproterone; LC-ESI-QTOF; MS2; CE: Ramp 23.1-34.7 eV; R=35000; [M+H]+
DATE: 2019.05.31
AUTHORS: Nikiforos Alygizakis, Katerina Galani, Nikolaos Thomaidis, University of Athens
LICENSE: CC BY
COPYRIGHT: Copyright (C) 2019 Department of Chemistry, University of Athens
COMMENT: CONFIDENCE standard compound
COMMENT: INTERNAL_ID 2396
CH$NAME: Cyproterone
CH$NAME: (1S,2S,3S,5R,11R,12S,15R,16S)-15-acetyl-9-chloro-15-hydroxy-2,16-dimethylpentacyclo[9.7.0.02,8.03,5.012,16]octadeca-7,9-dien-6-one
CH$COMPOUND_CLASS: N/A; Environmental Standard
CH$FORMULA: C22H27ClO3
CH$EXACT_MASS: 374.1648724
CH$SMILES: CC(=O)[C@@]1(O)CC[C@H]2[C@@H]3C=C(Cl)C4=CC(=O)[C@@H]5C[C@@H]5[C@]4(C)[C@H]3CC[C@]12C
CH$IUPAC: InChI=1S/C22H27ClO3/c1-11(24)22(26)7-5-14-12-9-18(23)17-10-19(25)13-8-16(13)21(17,3)15(12)4-6-20(14,22)2/h9-10,12-16,26H,4-8H2,1-3H3/t12-,13+,14-,15-,16-,20-,21-,22-/m0/s1
CH$LINK: CAS
2098-66-0
CH$LINK: CHEBI
50742
CH$LINK: KEGG
D07766
CH$LINK: PUBCHEM
CID:5284537
CH$LINK: INCHIKEY
DUSHUSLJJMDGTE-ZJPMUUANSA-N
CH$LINK: CHEMSPIDER
4447594
CH$LINK: COMPTOX
DTXSID3022873
AC$INSTRUMENT: Bruker maXis Impact
AC$INSTRUMENT_TYPE: LC-ESI-QTOF
AC$MASS_SPECTROMETRY: MS_TYPE MS2
AC$MASS_SPECTROMETRY: ION_MODE POSITIVE
AC$MASS_SPECTROMETRY: IONIZATION ESI
AC$MASS_SPECTROMETRY: FRAGMENTATION_MODE CID
AC$MASS_SPECTROMETRY: COLLISION_ENERGY Ramp 23.1-34.7 eV
AC$MASS_SPECTROMETRY: RESOLUTION 35000
AC$CHROMATOGRAPHY: COLUMN_NAME Acclaim RSLC C18 2.2um, 2.1x100mm, Thermo
AC$CHROMATOGRAPHY: FLOW_GRADIENT 99/1 at 0-1 min, 61/39 at 3 min, 0.1/99.9 at 14-16 min, 99/1 at 16.1-20 min
AC$CHROMATOGRAPHY: FLOW_RATE 200 uL/min at 0-3 min, 400 uL/min at 14 min, 480 uL/min at 16-19 min, 200 uL/min at 19.1-20 min
AC$CHROMATOGRAPHY: RETENTION_TIME 10.101 min
AC$CHROMATOGRAPHY: SOLVENT A 90:10 water:methanol with 0.01% formic acid and 5mM ammonium formate
AC$CHROMATOGRAPHY: SOLVENT B methanol with 0.01% formic acid and 5mM ammonium formate
MS$FOCUSED_ION: BASE_PEAK 375.1723
MS$FOCUSED_ION: PRECURSOR_M/Z 375.1721
MS$FOCUSED_ION: PRECURSOR_TYPE [M+H]+
MS$DATA_PROCESSING: RECALIBRATE identity on assigned fragments and MS1
MS$DATA_PROCESSING: WHOLE RMassBank 2.10.1
PK$SPLASH: splash10-004i-0479000000-5f3349c4734f2a0d52da
PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm)
55.0534 C4H7+ 1 55.0542 -14.77
59.0489 C3H7O+ 1 59.0491 -4.83
61.0279 C2H5O2+ 1 61.0284 -7.54
67.0534 C5H7+ 1 67.0542 -12.87
69.032 C4H5O+ 1 69.0335 -21.98
69.0697 C5H9+ 1 69.0699 -2.37
71.0482 C4H7O+ 1 71.0491 -12.99
79.0541 C6H7+ 1 79.0542 -1.81
81.07 C6H9+ 1 81.0699 1.28
83.0487 C5H7O+ 1 83.0491 -5.91
85.0646 C5H9O+ 1 85.0648 -1.96
87.0436 C4H7O2+ 1 87.0441 -5.29
91.0546 C7H7+ 1 91.0542 4.04
93.0699 C7H9+ 2 93.0699 -0.18
95.0494 C6H7O+ 1 95.0491 3.02
95.0855 C7H11+ 2 95.0855 -0.59
97.0639 C6H9O+ 2 97.0648 -8.73
105.07 C8H9+ 2 105.0699 1.49
107.0501 C7H7O+ 1 107.0491 8.9
107.0859 C8H11+ 2 107.0855 3.47
109.0649 C7H9O+ 2 109.0648 1.36
109.1024 C8H13+ 1 109.1012 11.29
111.0809 C7H11O+ 2 111.0804 4.42
117.0687 C3H14ClO2+ 2 117.0677 8.98
119.0849 C9H11+ 2 119.0855 -5.37
121.0638 C8H9O+ 2 121.0648 -8.11
121.0996 C3H18ClO2+ 2 121.099 5.17
123.0793 C2H16ClO3+ 2 123.0782 8.89
129.0685 C4H14ClO2+ 2 129.0677 6.54
131.0841 C4H16ClO2+ 2 131.0833 5.9
133.0629 C3H14ClO3+ 2 133.0626 2.13
133.1 C10H13+ 2 133.1012 -8.62
134.1041 C9[13]CH13+ 1 134.1051 -6.94
135.0795 C9H11O+ 2 135.0804 -7.13
135.1162 C10H15+ 2 135.1168 -4.61
137.0947 C3H18ClO3+ 2 137.0939 6.19
141.0685 C5H14ClO2+ 2 141.0677 5.43
142.0768 C11H10+ 2 142.0777 -6.2
143.0846 C11H11+ 2 143.0855 -6.34
144.0881 C5H17ClO2+ 1 144.0912 -21.27
145.0634 C4H14ClO3+ 2 145.0626 5.31
145.0998 C11H13+ 2 145.1012 -9.76
146.1032 C10[13]CH13+ 1 146.1051 -13.16
147.0791 C4H16ClO3+ 2 147.0782 5.6
147.1154 C11H15+ 2 147.1168 -9.6
148.1187 C10[13]CH15+ 1 148.1207 -13.64
149.095 C10H13O+ 2 149.0961 -7.12
151.1098 C4H20ClO3+ 2 151.1095 1.94
155.0841 C6H16ClO2+ 2 155.0833 4.7
156.0916 C6H17ClO2+ 2 156.0912 2.61
157.0633 C5H14ClO3+ 2 157.0626 4.62
157.1 C6H18ClO2+ 2 157.099 6.54
159.0793 C5H16ClO3+ 2 159.0782 6.78
159.1157 C12H15+ 2 159.1168 -6.94
160.12 C11[13]CH15+ 1 160.1207 -4.83
161.0949 C5H18ClO3+ 2 161.0939 6.39
163.1103 C5H20ClO3+ 2 163.1095 4.42
165.0454 C10H10Cl+ 1 165.0466 -6.75
167.0851 C13H11+ 2 167.0855 -2.8
169.0403 C9H10ClO+ 1 169.0415 -7.02
169.1 C7H18ClO2+ 2 169.099 5.95
171.0792 C6H16ClO3+ 2 171.0782 5.42
171.1156 C7H20ClO2+ 2 171.1146 5.35
173.0933 C6H18ClO3+ 2 173.0939 -3.68
173.1302 C7H22ClO2+ 2 173.1303 -0.5
175.1106 C12H15O+ 2 175.1117 -6.51
176.1141 C11[13]CH15O+ 1 176.1156 -8.67
177.0441 C11H10Cl+ 1 177.0466 -13.7
177.1264 C12H17O+ 2 177.1274 -5.45
179.0842 C8H16ClO2+ 2 179.0833 4.72
181.0396 C10H10ClO+ 1 181.0415 -10.29
181.076 C11H14Cl+ 1 181.0779 -10.07
181.1001 C14H13+ 2 181.1012 -6.02
182.1057 C8H19ClO2+ 2 182.1068 -6.28
183.0358 C10H10[37]ClO+ 1 183.0391 -17.59
183.0562 C10H12ClO+ 1 183.0571 -5.07
183.0794 C13H11O+ 2 183.0804 -5.55
183.1157 C14H15+ 2 183.1168 -6.01
184.0866 C7H17ClO3+ 2 184.0861 3.06
184.1207 C13[13]CH15+ 1 184.1207 -0.27
185.0951 C13H13O+ 2 185.0961 -5.58
185.1311 C8H22ClO2+ 2 185.1303 4.61
186.0981 C12[13]CH13O+ 1 186.1 -10.16
187.0762 C12H11O2+ 1 187.0754 4.4
187.1094 C7H20ClO3+ 2 187.1095 -1
189.0457 C12H10Cl+ 1 189.0466 -4.34
189.1265 C13H17O+ 2 189.1274 -4.88
191.0235 C11H8ClO+ 1 191.0258 -12.04
191.0612 C12H12Cl+ 1 191.0622 -5.06
192.0915 C9H17ClO2+ 2 192.0912 1.78
193.0407 C11H10ClO+ 1 193.0415 -4.2
193.0998 C9H18ClO2+ 2 193.099 4.2
193.1216 C12H17O2+ 1 193.1223 -3.49
194.1062 C9H19ClO2+ 2 194.1068 -3.05
195.0549 C11H12ClO+ 1 195.0571 -11.62
195.1153 C9H20ClO2+ 2 195.1146 3.41
196.1214 C9H21ClO2+ 2 196.1225 -5.58
197.0953 C14H13O+ 2 197.0961 -3.89
197.1304 C9H22ClO2+ 2 197.1303 0.42
199.1105 C8H20ClO3+ 2 199.1095 4.79
199.1447 C9H24ClO2+ 2 199.1459 -6.39
201.1269 C14H17O+ 2 201.1274 -2.3
203.0607 C13H12Cl+ 1 203.0622 -7.34
205.0395 C12H10ClO+ 1 205.0415 -9.58
205.0772 C13H14Cl+ 1 205.0779 -3.15
205.101 C16H13+ 2 205.1012 -1.03
206.1066 C10H19ClO2+ 2 206.1068 -1.05
207.0373 C12H10[37]ClO+ 1 207.0391 -8.46
207.0563 C12H12ClO+ 1 207.0571 -4.15
207.1153 C16H15+ 2 207.1168 -7.41
208.1207 C15[13]CH15+ 1 208.1207 0.06
209.0951 C15H13O+ 2 209.0961 -4.86
209.1318 C16H17+ 2 209.1325 -3.31
210.1015 C9H19ClO3+ 2 210.1017 -0.96
210.1372 C10H23ClO2+ 2 210.1381 -4.28
211.1104 C9H20ClO3+ 2 211.1095 4.24
211.1469 C10H24ClO2+ 2 211.1459 4.55
213.1263 C9H22ClO3+ 2 213.1252 5.06
215.0612 C14H12Cl+ 1 215.0622 -4.82
217.0766 C14H14Cl+ 1 217.0779 -5.89
217.1002 C17H13+ 2 217.1012 -4.51
218.1084 C17H14+ 2 218.109 -2.94
219.056 C13H12ClO+ 1 219.0571 -5.22
219.1154 C11H20ClO2+ 2 219.1146 3.63
220.0587 C12[13]CH12ClO+ 1 220.061 -10.63
220.1231 C11H21ClO2+ 2 220.1225 3.13
221.0525 C13H12[37]ClO+ 1 221.0547 -9.85
221.0686 C13H14ClO+ 1 221.0728 -18.94
221.0939 C10H18ClO3+ 2 221.0939 -0.03
221.131 C17H17+ 2 221.1325 -6.51
222.102 C10H19ClO3+ 2 222.1017 1.12
222.1361 C16[13]CH17+ 1 222.1364 -1.15
223.0678 C13H14[37]ClO+ 1 223.0704 -11.62
223.1106 C10H20ClO3+ 2 223.1095 4.77
223.1468 C11H24ClO2+ 2 223.1459 3.95
224.1171 C10H21ClO3+ 2 224.1174 -1.08
225.1267 C16H17O+ 2 225.1274 -3.28
225.1627 C11H26ClO2+ 2 225.1616 4.79
226.1332 C10H23ClO3+ 2 226.133 0.6
227.1054 C15H15O2+ 1 227.1067 -5.35
227.1413 C10H24ClO3+ 2 227.1408 2.02
227.1794 C17H23+ 2 227.1794 -0.23
231.0922 C15H16Cl+ 1 231.0935 -5.73
231.1158 C18H15+ 2 231.1168 -4.35
232.1229 C12H21ClO2+ 2 232.1225 1.78
233.0719 C14H14ClO+ 1 233.0728 -3.84
233.1313 C12H22ClO2+ 2 233.1303 4.42
234.1382 C12H23ClO2+ 2 234.1381 0.6
235.1102 C11H20ClO3+ 2 235.1095 2.92
235.1474 C18H19+ 2 235.1481 -2.96
236.1174 C11H21ClO3+ 2 236.1174 -0.09
236.1524 C17[13]CH19+ 1 236.152 1.55
237.1263 C17H17O+ 2 237.1274 -4.57
237.1631 C18H21+ 2 237.1638 -3.04
238.1325 C16[13]CH17O+ 1 238.1313 4.92
238.167 C17[13]CH21+ 1 238.1677 -2.74
239.1414 C11H24ClO3+ 2 239.1408 2.18
241.1575 C11H26ClO3+ 2 241.1565 4.33
243.0927 C16H16Cl+ 1 243.0935 -3.15
245.0717 C15H14ClO+ 1 245.0728 -4.43
245.1092 C16H18Cl+ 1 245.1092 0.21
245.1323 C19H17+ 2 245.1325 -0.55
245.1883 C17H25O+ 1 245.19 -7.06
246.0763 C14[13]CH14ClO+ 1 246.0767 -1.45
246.1388 C13H23ClO2+ 2 246.1381 3
246.1919 C16[13]CH25O+ 1 246.1939 -8.16
247.0691 C15H14[37]ClO+ 1 247.0704 -5.2
247.1099 C12H20ClO3+ 2 247.1095 1.56
247.1471 C19H19+ 2 247.1481 -4.27
248.1155 C12H21ClO3+ 2 248.1174 -7.7
248.1533 C18[13]CH19+ 1 248.152 5.04
249.1261 C12H22ClO3+ 2 249.1252 3.67
249.1623 C13H26ClO2+ 2 249.1616 2.9
250.1337 C12H23ClO3+ 2 250.133 2.61
250.1677 C13H27ClO2+ 2 250.1694 -6.82
251.1426 C18H19O+ 2 251.143 -1.94
251.1786 C19H23+ 2 251.1794 -3.47
252.1486 C17[13]CH19O+ 1 252.1469 6.57
252.1828 C18[13]CH23+ 1 252.1833 -2.04
253.1567 C12H26ClO3+ 2 253.1565 0.76
255.0917 C17H16Cl+ 1 255.0935 -6.95
257.1099 C17H18Cl+ 1 257.1092 2.79
259.0868 C16H16ClO+ 1 259.0884 -6.16
259.1477 C20H19+ 2 259.1481 -1.83
260.1541 C14H25ClO2+ 2 260.1538 1.44
261.1049 C16H18ClO+ 1 261.1041 3.31
261.1258 C13H22ClO3+ 2 261.1252 2.19
261.1629 C20H21+ 2 261.1638 -3.24
262.1335 C13H23ClO3+ 2 262.133 1.69
262.1665 C19[13]CH21+ 1 262.1677 -4.53
263.1421 C19H19O+ 2 263.143 -3.57
264.1476 C18[13]CH19O+ 1 264.1469 2.51
265.1565 C13H26ClO3+ 2 265.1565 0.1
269.109 C18H18Cl+ 1 269.1092 -0.67
271.087 C17H16ClO+ 1 271.0884 -5.07
271.1241 C18H20Cl+ 1 271.1248 -2.55
272.0907 C17H17ClO+ 1 272.0962 -20.47
273.1034 C17H18ClO+ 1 273.1041 -2.3
273.1256 C14H22ClO3+ 2 273.1252 1.31
275.1053 C17H18[37]ClO+ 1 275.1017 13.21
275.1178 C17H20ClO+ 1 275.1197 -6.96
275.1393 C14H24ClO3+ 2 275.1408 -5.66
275.1793 C21H23+ 2 275.1794 -0.39
277.1585 C20H21O+ 2 277.1587 -0.52
277.1935 C21H25+ 1 277.1951 -5.67
278.1653 C14H27ClO3+ 2 278.1643 3.62
279.1736 C20H23O+ 2 279.1743 -2.58
280.1773 C19[13]CH23O+ 1 280.1782 -3.51
285.1029 C18H18ClO+ 1 285.1041 -4.24
285.1618 C16H26ClO2+ 2 285.1616 0.85
287.1184 C18H20ClO+ 1 287.1197 -4.66
288.15 C21H20O+ 2 288.1509 -3.01
289.1176 C18H20[37]ClO+ 1 289.1173 0.95
289.1349 C18H22ClO+ 1 289.1354 -1.57
293.1537 C20H21O2+ 1 293.1536 0.29
293.1895 C21H25O+ 1 293.19 -1.53
294.1571 C19[13]CH21O2+ 1 294.1575 -1.49
294.1911 C20[13]CH25O+ 1 294.1939 -9.65
295.1664 C20H23O2+ 1 295.1693 -9.69
295.2042 C21H27O+ 1 295.2056 -4.91
297.1408 C20H22Cl+ 1 297.1405 1.15
297.1844 C20H25O2+ 1 297.1849 -1.56
299.1189 C19H20ClO+ 1 299.1197 -2.79
301.1186 C19H20[37]ClO+ 1 301.1173 4.37
301.1343 C19H22ClO+ 1 301.1354 -3.44
303.1318 C21H19O2+ 1 303.138 -20.36
303.173 C22H23O+ 2 303.1743 -4.54
304.1783 C21[13]CH23O+ 1 304.1782 0.27
306.1606 C21H22O2+ 1 306.1614 -2.87
307.1658 C20[13]CH22O2+ 1 307.1653 1.42
311.1585 C21H24Cl+ 2 311.1561 7.76
313.1345 C20H22ClO+ 1 313.1354 -2.82
314.1409 C20H23ClO+ 1 314.1432 -7.19
315.1487 C20H24ClO+ 1 315.151 -7.32
316.1482 C19[13]CH24ClO+ 1 316.1549 -21.33
317.1469 C20H24[37]ClO+ 1 317.1486 -5.34
321.1848 C22H25O2+ 1 321.1849 -0.39
322.188 C21[13]CH25O2+ 1 322.1888 -2.56
323.1939 C20[13]C2H25O2+ 1 323.1922 5.47
329.1655 C21H26ClO+ 1 329.1667 -3.45
332.1522 C20H25ClO2+ 1 332.1538 -4.8
333.1625 C20H26ClO2+ 1 333.1616 2.72
339.1492 C22H24ClO+ 1 339.151 -5.43
339.1955 C22H27O3+ 1 339.1955 -0.03
340.1992 C21[13]CH27O3+ 1 340.1994 -0.59
341.1491 C22H24[37]ClO+ 1 341.1486 1.5
357.1609 C22H26ClO2+ 1 357.1616 -1.96
358.1648 C21[13]CH26ClO2+ 1 358.1655 -2.01
359.1598 C22H26[37]ClO2+ 1 359.1592 1.59
375.1723 C22H28ClO3+ 1 375.1721 0.53
376.1753 C21[13]CH28ClO3+ 1 376.1761 -2.05
377.1699 C22H28[37]ClO3+ 1 377.1697 0.31
PK$NUM_PEAK: 252
PK$PEAK: m/z int. rel.int.
55.0534 796 5
59.0489 1208 8
61.0279 908 6
67.0534 1416 9
69.032 968 6
69.0697 744 5
71.0482 1392 9
79.0541 864 6
81.07 1292 9
83.0487 1844 13
85.0646 1436 10
87.0436 2480 17
91.0546 1116 7
93.0699 1712 12
95.0494 1400 9
95.0855 1112 7
97.0639 720 5
105.07 1364 9
107.0501 908 6
107.0859 1232 8
109.0649 1432 10
109.1024 1132 7
111.0809 1404 9
117.0687 1220 8
119.0849 2988 21
121.0638 2360 16
121.0996 1664 11
123.0793 2136 15
129.0685 1764 12
131.0841 3004 21
133.0629 936 6
133.1 9728 68
134.1041 924 6
135.0795 1940 13
135.1162 1116 7
137.0947 1156 8
141.0685 1116 7
142.0768 1036 7
143.0846 3284 23
144.0881 792 5
145.0634 2764 19
145.0998 6436 45
146.1032 984 6
147.0791 2672 18
147.1154 11272 79
148.1187 1432 10
149.095 1968 13
151.1098 1772 12
155.0841 2796 19
156.0916 760 5
157.0633 832 5
157.1 4648 32
159.0793 2384 16
159.1157 3532 24
160.12 728 5
161.0949 2072 14
163.1103 2700 19
165.0454 928 6
167.0851 1024 7
169.0403 1344 9
169.1 2576 18
171.0792 2008 14
171.1156 3600 25
173.0933 1420 10
173.1302 760 5
175.1106 7248 51
176.1141 856 6
177.0441 2460 17
177.1264 1448 10
179.0842 1248 8
181.0396 4012 28
181.076 1048 7
181.1001 2796 19
182.1057 856 6
183.0358 1104 7
183.0562 1140 8
183.0794 1384 9
183.1157 4440 31
184.0866 1184 8
184.1207 1000 7
185.0951 6852 48
185.1311 1860 13
186.0981 1020 7
187.0762 768 5
187.1094 2280 16
189.0457 2056 14
189.1265 2844 20
191.0235 876 6
191.0612 2392 16
192.0915 948 6
193.0407 1836 12
193.0998 2504 17
193.1216 964 6
194.1062 1288 9
195.0549 1344 9
195.1153 5800 40
196.1214 2132 15
197.0953 2356 16
197.1304 2464 17
199.1105 2380 16
199.1447 860 6
201.1269 2984 21
203.0607 2036 14
205.0395 2764 19
205.0772 1052 7
205.101 2028 14
206.1066 1300 9
207.0373 1164 8
207.0563 2016 14
207.1153 3456 24
208.1207 1000 7
209.0951 1392 9
209.1318 3100 21
210.1015 932 6
210.1372 1208 8
211.1104 2368 16
211.1469 852 6
213.1263 2140 15
215.0612 1032 7
217.0766 1108 7
217.1002 856 6
218.1084 1148 8
219.056 17824 125
219.1154 2784 19
220.0587 2156 15
220.1231 1256 8
221.0525 4276 30
221.0686 2116 14
221.0939 1016 7
221.131 3660 25
222.102 1164 8
222.1361 1104 7
223.0678 780 5
223.1106 2756 19
223.1468 2400 16
224.1171 988 6
225.1267 2124 14
225.1627 932 6
226.1332 992 6
227.1054 888 6
227.1413 1028 7
227.1794 1016 7
231.0922 1476 10
231.1158 1028 7
232.1229 1460 10
233.0719 768 5
233.1313 3392 23
234.1382 1288 9
235.1102 2852 20
235.1474 5756 40
236.1174 1404 9
236.1524 1332 9
237.1263 5512 38
237.1631 4068 28
238.1325 1624 11
238.167 904 6
239.1414 3060 21
241.1575 860 6
243.0927 1108 7
245.0717 3844 27
245.1092 1380 9
245.1323 1312 9
245.1883 5148 36
246.0763 928 6
246.1388 2044 14
246.1919 1160 8
247.0691 1152 8
247.1099 984 6
247.1471 3772 26
248.1155 808 5
248.1533 1344 9
249.1261 2812 19
249.1623 5080 35
250.1337 1404 9
250.1677 2024 14
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251.1786 3400 23
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255.0917 824 5
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261.1049 776 5
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263.1421 12564 88
264.1476 3796 26
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269.109 940 6
271.087 1000 7
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272.0907 720 5
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273.1256 844 5
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275.1793 2908 20
277.1585 11832 83
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278.1653 12268 86
279.1736 28552 201
280.1773 5344 37
285.1029 884 6
285.1618 1024 7
287.1184 1780 12
288.15 1068 7
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289.1349 1072 7
293.1537 9076 63
293.1895 3728 26
294.1571 2320 16
294.1911 1080 7
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297.1408 1904 13
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299.1189 2728 19
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303.173 8556 60
304.1783 2448 17
306.1606 4540 32
307.1658 1200 8
311.1585 728 5
313.1345 9632 67
314.1409 9120 64
315.1487 9208 64
316.1482 2652 18
317.1469 2604 18
321.1848 60316 425
322.188 15248 107
323.1939 1848 13
329.1655 2544 17
332.1522 788 5
333.1625 1424 10
339.1492 2528 17
339.1955 3524 24
340.1992 1004 7
341.1491 764 5
357.1609 19168 135
358.1648 4844 34
359.1598 6716 47
375.1723 141692 999
376.1753 36012 253
377.1699 54148 381
//
