ACCESSION: MSBNK-Eawag-EQ325003
RECORD_TITLE: Microcystin-RR; LC-ESI-QFT; MS2; CE: 45; R=35000; [M+H]+
DATE: 2015.08.25
AUTHORS: Beck B, Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag
LICENSE: CC BY
COPYRIGHT: Copyright (C) 2015 Eawag, Duebendorf, Switzerland
COMMENT: CONFIDENCE standard compound
COMMENT: EAWAG_UCHEM_ID 3250
CH$NAME: Microcystin-RR
CH$NAME: (5R,8R,11R,12S,15S,18S,19S,22R)-8,15-bis[3-(diaminomethylideneamino)propyl]-18-[(1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dienyl]-1,5,12,19-tetramethyl-2-methylidene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptazacyclopentacosane-11,22-dicarboxylic acid
CH$COMPOUND_CLASS: N/A; Environmental Standard
CH$FORMULA: C49H75N13O12
CH$EXACT_MASS: 1037.56581
CH$SMILES: O=C2N[C@@H](\C=C\C(=C\[C@H](C)[C@@H](OC)Cc1ccccc1)C)[C@@H](C(=O)N[C@@H](C(=O)O)CCC(=O)N(/C(=C)C(=O)N[C@@H](C(=O)N[C@@H](C(=O)N[C@@H](C(=O)O)[C@@H](C(=O)N[C@H]2CCC/N=C(\N)N)C)CCC/N=C(\N)N)C)C)C
CH$IUPAC: InChI=1S/C49H75N13O12/c1-26(24-27(2)37(74-8)25-32-14-10-9-11-15-32)18-19-33-28(3)40(64)60-36(46(70)71)20-21-38(63)62(7)31(6)43(67)56-30(5)42(66)59-35(17-13-23-55-49(52)53)45(69)61-39(47(72)73)29(4)41(65)58-34(44(68)57-33)16-12-22-54-48(50)51/h9-11,14-15,18-19,24,27-30,33-37,39H,6,12-13,16-17,20-23,25H2,1-5,7-8H3,(H,56,67)(H,57,68)(H,58,65)(H,59,66)(H,60,64)(H,61,69)(H,70,71)(H,72,73)(H4,50,51,54)(H4,52,53,55)/b19-18+,26-24+/t27-,28-,29-,30+,33-,34-,35+,36+,37-,39+/m0/s1
CH$LINK: CAS
111755-37-4
CH$LINK: PUBCHEM
CID:23305170
CH$LINK: INCHIKEY
JIGDOBKZMULDHS-CJYJKAEFSA-N
CH$LINK: CHEMSPIDER
4942840
AC$INSTRUMENT: Q Exactive 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 45 (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$CHROMATOGRAPHY: RETENTION_TIME 9.1 min
AC$CHROMATOGRAPHY: SOLVENT A water with 0.1% formic acid
AC$CHROMATOGRAPHY: SOLVENT B methanol with 0.1% formic acid
MS$FOCUSED_ION: BASE_PEAK 519.7909
MS$FOCUSED_ION: PRECURSOR_M/Z 1038.5731
MS$FOCUSED_ION: PRECURSOR_TYPE [M+H]+
MS$DATA_PROCESSING: DEPROFILE Spline
MS$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$SPLASH: splash10-0550-0920000000-823d2e1b2009397584a2
PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm)
72.0808 C4H10N+ 1 72.0808 0.75
77.0386 C6H5+ 1 77.0386 -0.09
79.0543 C6H7+ 1 79.0542 1.56
82.0288 C4H4NO+ 1 82.0287 0.49
82.0652 C5H8N+ 1 82.0651 0.91
83.0605 C4H7N2+ 1 83.0604 1.39
84.0445 C4H6NO+ 1 84.0444 1.07
85.0761 C4H9N2+ 1 85.076 0.77
86.0602 C4H8NO+ 1 86.06 2.44
87.0792 C3H9N3+ 1 87.0791 0.7
91.0542 C7H7+ 1 91.0542 0.15
93.07 C7H9+ 1 93.0699 0.89
94.0653 C6H8N+ 1 94.0651 1.53
95.0492 C6H7O+ 1 95.0491 0.62
95.0605 C5H7N2+ 1 95.0604 0.79
95.0857 C7H11+ 1 95.0855 1.3
96.0443 C5H6NO+ 1 96.0444 -0.84
96.081 C6H10N+ 1 96.0808 2.13
97.0761 C5H9N2+ 1 97.076 1.29
98.0601 C5H8NO+ 1 98.06 0.91
99.0917 C5H11N2+ 1 99.0917 0.36
100.0757 C5H10NO+ 1 100.0757 0.1
100.087 C4H10N3+ 1 100.0869 0.86
101.0712 C4H9N2O+ 1 101.0709 2.18
102.0467 C8H6+ 1 102.0464 3.22
102.055 C4H8NO2+ 1 102.055 0.64
103.0543 C8H7+ 1 103.0542 1.1
104.0577 C3H8N2O2+ 1 104.058 -3.06
105.07 C8H9+ 1 105.0699 1.17
107.0856 C8H11+ 1 107.0855 1.06
108.0889 C3H12N2O2+ 1 108.0893 -3.69
109.0649 C7H9O+ 1 109.0648 1.36
109.0762 C6H9N2+ 1 109.076 1.33
110.0601 C6H8NO+ 1 110.06 0.91
110.0716 C5H8N3+ 1 110.0713 3.33
112.087 C5H10N3+ 1 112.0869 1.04
113.071 C5H9N2O+ 1 113.0709 0.89
114.0551 C5H8NO2+ 1 114.055 1.18
114.0663 C4H8N3O+ 1 114.0662 0.72
114.1027 C5H12N3+ 1 114.1026 1.02
115.0544 C9H7+ 1 115.0542 1.68
115.0867 C5H11N2O+ 1 115.0866 1.13
116.0707 C5H10NO2+ 1 116.0706 1.08
117.07 C9H9+ 1 117.0699 0.97
119.0691 C3H9N3O2+ 1 119.0689 1.53
119.0857 C9H11+ 1 119.0855 1.29
120.057 C8H8O+ 1 120.057 -0.14
120.0808 C8H10N+ 1 120.0808 0.54
121.0647 C8H9O+ 1 121.0648 -0.75
121.1012 C9H13+ 1 121.1012 0.03
123.0916 C7H11N2+ 1 123.0917 -0.36
124.076 C7H10NO+ 1 124.0757 2.33
124.0872 C6H10N3+ 1 124.0869 1.98
124.1123 C8H14N+ 1 124.1121 1.64
125.0711 C6H9N2O+ 1 125.0709 0.96
126.0662 C5H8N3O+ 1 126.0662 -0.15
127.0867 C6H11N2O+ 1 127.0866 1.03
128.0707 C6H10NO2+ 1 128.0706 1.05
128.0899 CH12N4O3+ 1 128.0904 -3.53
129.0702 C10H9+ 1 129.0699 2.89
129.1135 C5H13N4+ 1 129.1135 0.21
130.05 C5H8NO3+ 1 130.0499 0.85
130.0976 C5H12N3O+ 1 130.0975 1.17
131.0857 C10H11+ 1 131.0855 1.32
132.081 C9H10N+ 1 132.0808 1.85
133.1014 C10H13+ 1 133.1012 1.75
135.0805 C9H11O+ 1 135.0804 0.58
135.1169 C10H15+ 1 135.1168 0.39
136.0838 C4H12N2O3+ 1 136.0842 -3.63
136.1119 C9H14N+ 1 136.1121 -1
137.0709 C7H9N2O+ 1 137.0709 -0.21
137.1077 C8H13N2+ 1 137.1073 2.37
138.055 C7H8NO2+ 1 138.055 0.18
138.0664 C6H8N3O+ 1 138.0662 1.46
138.0914 C8H12NO+ 1 138.0913 0.21
139.0866 C7H11N2O+ 1 139.0866 -0.14
139.0977 C6H11N4+ 1 139.0978 -0.52
139.1231 C8H15N2+ 1 139.123 0.68
140.0708 C7H10NO2+ 1 140.0706 1.11
140.0818 C6H10N3O+ 1 140.0818 -0.35
141.0658 C6H9N2O2+ 1 141.0659 -0.45
141.1021 C7H13N2O+ 1 141.1022 -0.63
142.0976 C6H12N3O+ 1 142.0975 0.5
143.0859 C11H11+ 1 143.0855 2.33
145.1014 C11H13+ 1 145.1012 1.26
146.1093 C11H14+ 1 146.109 1.97
147.0808 C10H11O+ 1 147.0804 2.71
149.0712 C8H9N2O+ 1 149.0709 1.75
150.1029 C8H12N3+ 1 150.1026 2.11
150.1279 C10H16N+ 1 150.1277 1.36
151.0867 C8H11N2O+ 1 151.0866 0.67
152.0707 C8H10NO2+ 1 152.0706 0.3
152.0812 C7H10N3O+ 2 152.0818 -4.33
152.1182 C8H14N3+ 1 152.1182 -0.35
153.1023 C8H13N2O+ 1 153.1022 0.2
154.0976 C7H12N3O+ 1 154.0975 0.98
155.0816 C7H11N2O2+ 1 155.0815 0.49
156.1246 C6H14N5+ 1 156.1244 1.21
157.1085 C6H13N4O+ 1 157.1084 0.91
158.0924 C6H12N3O2+ 1 158.0924 0.17
159.1169 C12H15+ 1 159.1168 0.4
160.1121 C11H14N+ 1 160.1121 -0.1
161.0963 C11H13O+ 1 161.0961 1.17
162.1032 C9H12N3+ 2 162.1026 3.62
162.1277 C11H16N+ 1 162.1277 -0.34
163.0867 C9H11N2O+ 1 163.0866 0.86
163.1118 C11H15O+ 1 163.1117 0.6
164.0708 C9H10NO2+ 1 164.0706 1.07
164.1187 C9H14N3+ 1 164.1182 2.9
165.1024 C9H13N2O+ 1 165.1022 0.85
166.0864 C9H12NO2+ 1 166.0863 0.63
166.0976 C8H12N3O+ 1 166.0975 0.67
167.0816 C8H11N2O2+ 1 167.0815 0.34
168.0652 C8H10NO3+ 1 168.0655 -1.9
169.0966 C8H13N2O2+ 2 169.0972 -3.51
171.1124 C8H15N2O2+ 1 171.1128 -2.3
173.0967 C12H13O+ 1 173.0961 3.34
174.1351 C6H16N5O+ 1 174.1349 0.65
175.119 C6H15N4O2+ 1 175.119 0.39
178.0974 C9H12N3O+ 1 178.0975 -0.33
179.0811 C9H11N2O2+ 1 179.0815 -2.42
180.1132 C9H14N3O+ 1 180.1131 0.4
181.0972 C9H13N2O2+ 1 181.0972 0.47
181.1446 C9H17N4+ 1 181.1448 -0.73
182.0818 C9H12NO3+ 1 182.0812 3.57
182.1039 C7H12N5O+ 1 182.1036 1.34
182.1295 C9H16N3O+ 2 182.1288 3.85
183.0878 C7H11N4O2+ 1 183.0877 0.81
185.1398 C8H17N4O+ 1 185.1397 0.39
186.1242 C8H16N3O2+ 2 186.1237 2.51
188.1071 C12H14NO+ 1 188.107 0.48
190.0977 C10H12N3O+ 1 190.0975 0.9
191.0816 C10H11N2O2+ 1 191.0815 0.29
192.1135 C10H14N3O+ 1 192.1131 1.62
193.0972 C10H13N2O2+ 1 193.0972 0.39
194.0925 C9H12N3O2+ 1 194.0924 0.5
194.1287 C10H16N3O+ 1 194.1288 -0.61
195.0765 C9H11N2O3+ 1 195.0764 0.31
195.1169 C15H15+ 3 195.1168 0.22
195.1244 C9H15N4O+ 2 195.124 2.01
196.0599 C9H10NO4+ 2 196.0604 -2.83
196.1082 C9H14N3O2+ 1 196.1081 0.9
197.1398 C9H17N4O+ 1 197.1397 0.42
198.1237 C9H16N3O2+ 1 198.1237 -0.12
199.1075 C9H15N2O3+ 1 199.1077 -1.25
200.1141 C7H14N5O2+ 1 200.1142 -0.36
201.0982 C7H13N4O3+ 1 201.0982 0.12
205.0975 C11H13N2O2+ 1 205.0972 1.64
206.0927 C10H12N3O2+ 1 206.0924 1.44
208.1081 C10H14N3O2+ 1 208.1081 0.18
209.0922 C10H13N2O3+ 1 209.0921 0.53
209.1324 C16H17+ 4 209.1325 -0.18
210.124 C10H16N3O2+ 1 210.1237 1.32
211.0715 C9H11N2O4+ 1 211.0713 0.84
211.1191 C9H15N4O2+ 1 211.119 0.89
212.1035 C9H14N3O3+ 2 212.103 2.37
212.1513 C9H18N5O+ 2 212.1506 3.22
213.0871 C9H13N2O4+ 1 213.087 0.36
213.1346 C9H17N4O2+ 1 213.1346 0.13
214.1342 C13H16N3+ 2 214.1339 1.48
214.1667 C9H20N5O+ 2 214.1662 1.93
217.1336 C13H17N2O+ 1 217.1335 0.46
218.1539 C14H20NO+ 1 218.1539 -0.32
219.1239 C11H15N4O+ 1 219.124 -0.49
220.1085 C11H14N3O2+ 2 220.1081 1.94
221.0923 C11H13N2O3+ 1 221.0921 0.96
222.1241 C11H16N3O2+ 2 222.1237 1.56
223.1083 C11H15N2O3+ 1 223.1077 2.47
223.1193 C10H15N4O2+ 2 223.119 1.78
224.103 C10H14N3O3+ 1 224.103 0.28
225.1347 C10H17N4O2+ 1 225.1346 0.43
226.1187 C10H16N3O3+ 1 226.1186 0.45
226.1589 C16H20N+ 4 226.159 -0.65
227.1028 C10H15N2O4+ 1 227.1026 0.65
228.146 C9H18N5O2+ 2 228.1455 2.27
229.1305 C9H17N4O3+ 2 229.1295 4.33
234.1242 C12H16N3O2+ 2 234.1237 2.29
237.1637 C18H21+ 4 237.1638 -0.49
238.1187 C11H16N3O3+ 1 238.1186 0.51
239.0664 C10H11N2O5+ 2 239.0662 0.51
240.1453 C10H18N5O2+ 3 240.1455 -0.71
241.1293 C10H17N4O3+ 3 241.1295 -0.86
243.1452 C10H19N4O3+ 1 243.1452 0.3
244.1293 C10H18N3O4+ 3 244.1292 0.69
244.1409 C9H18N5O3+ 2 244.1404 2.11
246.1488 C15H20NO2+ 3 246.1489 -0.06
248.1033 C12H14N3O3+ 2 248.103 1.42
250.1302 C11H16N5O2+ 2 250.1299 1.59
251.1143 C11H15N4O3+ 2 251.1139 1.88
251.1504 C12H19N4O2+ 2 251.1503 0.63
252.0976 C11H14N3O4+ 2 252.0979 -1.2
252.1341 C12H18N3O3+ 2 252.1343 -0.82
258.1564 C10H20N5O3+ 2 258.1561 1.29
258.1858 C3H26N6O7+ 4 258.1857 0.35
263.1141 C12H15N4O3+ 2 263.1139 0.7
263.1867 C14H23N4O+ 3 263.1866 0.39
265.1587 C19H21O+ 4 265.1587 0.03
267.1568 C11H19N6O2+ 2 267.1564 1.46
268.1406 C11H18N5O3+ 2 268.1404 0.61
269.1248 C11H17N4O4+ 3 269.1244 1.52
269.1612 C12H21N4O3+ 2 269.1608 1.31
272.1354 C10H18N5O4+ 3 272.1353 0.37
277.1302 C13H17N4O3+ 4 277.1295 2.61
278.1501 C14H20N3O3+ 3 278.1499 0.55
280.1408 C12H18N5O3+ 2 280.1404 1.19
280.2131 C14H26N5O+ 4 280.2132 -0.31
282.1855 C19H24NO+ 4 282.1852 0.88
283.1879 C12H23N6O2+ 2 283.1877 0.63
285.1673 C11H21N6O3+ 2 285.167 1.07
285.2035 C12H25N6O2+ 2 285.2034 0.52
286.1511 C11H20N5O4+ 3 286.151 0.42
294.1563 C13H20N5O3+ 2 294.1561 0.73
303.1774 C11H23N6O4+ 5 303.1775 -0.3
311.1829 C13H23N6O3+ 3 311.1826 0.98
312.1671 C13H22N5O4+ 4 312.1666 1.66
328.2098 C13H26N7O3+ 3 328.2092 1.88
329.1935 C13H25N6O4+ 4 329.1932 0.97
345.1921 C18H25N4O3+ 6 345.1921 0.04
347.1976 C20H23N6+ 5 347.1979 -0.72
357.1889 H27N11O11+ 6 357.1886 0.75
365.1936 C2H27N11O10+ 7 365.1937 -0.16
368.2409 C2H32N12O9+ 7 368.241 -0.11
383.2035 C15H21N13+ 7 383.2037 -0.7
389.2065 C3H27N13O9+ 6 389.2049 3.98
408.2003 C3H28N12O11+ 9 408.1995 2.01
469.3293 C12H43N11O8+ 7 469.3291 0.47
488.3234 C26H42N5O4+ 8 488.3231 0.47
523.2641 C38H35O2+ 10 523.2632 1.9
571.3606 C16H49N11O11+ 10 571.3608 -0.32
659.3913 C36H55N2O9+ 13 659.3902 1.69
PK$NUM_PEAK: 230
PK$PEAK: m/z int. rel.int.
72.0808 1351.8 1
77.0386 3165.3 4
79.0543 17552.2 25
82.0288 3715 5
82.0652 8547.8 12
83.0605 1588 2
84.0445 69770.6 102
85.0761 6271.8 9
86.0602 3671.9 5
87.0792 7821.8 11
91.0542 67744.8 99
93.07 52597.2 77
94.0653 2499.1 3
95.0492 25313.9 37
95.0605 9922.5 14
95.0857 10133.7 14
96.0443 2225.5 3
96.081 5989.4 8
97.0761 23241.5 34
98.0601 21252.2 31
99.0917 12719.6 18
100.0757 2120 3
100.087 3419.7 5
101.0712 2062.3 3
102.0467 1649.3 2
102.055 9228 13
103.0543 142790 209
104.0577 1407.2 2
105.07 136096 199
107.0856 255230.4 374
108.0889 3321.8 4
109.0649 7062.7 10
109.0762 1852.7 2
110.0601 3776.5 5
110.0716 1488.9 2
112.087 209526.9 307
113.071 51929.2 76
114.0551 2492.4 3
114.0663 3208.6 4
114.1027 32749.4 48
115.0544 23399.1 34
115.0867 159257.6 233
116.0707 11673.2 17
117.07 65156.8 95
119.0691 2380.5 3
119.0857 14544.8 21
120.057 2397.1 3
120.0808 19976.7 29
121.0647 2140.1 3
121.1012 3318.1 4
123.0916 6437.7 9
124.076 9411.1 13
124.0872 2558.4 3
124.1123 18520.1 27
125.0711 11650.9 17
126.0662 2383.5 3
127.0867 451678.3 663
128.0707 2631.2 3
128.0899 2773.8 4
129.0702 2795 4
129.1135 5664.7 8
130.05 17086.3 25
130.0976 12466.6 18
131.0857 24744.9 36
132.081 1880.1 2
133.1014 11976.7 17
135.0805 680238.2 999
135.1169 204586 300
136.0838 3784.8 5
136.1119 1706.8 2
137.0709 2512.7 3
137.1077 2361.3 3
138.055 31722.7 46
138.0664 6518 9
138.0914 2345.2 3
139.0866 11117.5 16
139.0977 15102 22
139.1231 6932.5 10
140.0708 4420.8 6
140.0818 47176.2 69
141.0658 22608.7 33
141.1021 3635.9 5
142.0976 1697.2 2
143.0859 7899 11
145.1014 15990.5 23
146.1093 1996.2 2
147.0808 2282.3 3
149.0712 9258.7 13
150.1029 9553.4 14
150.1279 2137.4 3
151.0867 11676.7 17
152.0707 14733.8 21
152.0812 1738.2 2
152.1182 3589.1 5
153.1023 18837.2 27
154.0976 2954.2 4
155.0816 164154.3 241
156.1246 21651.1 31
157.1085 111783 164
158.0924 46354.1 68
159.1169 2051.8 3
160.1121 2349.6 3
161.0963 9733.1 14
162.1032 2132.9 3
162.1277 9527.1 13
163.0867 7280.5 10
163.1118 102899.4 151
164.0708 2188.6 3
164.1187 3396.3 4
165.1024 10314.1 15
166.0864 3225.5 4
166.0976 2886.4 4
167.0816 77760.2 114
168.0652 12116.4 17
169.0966 10770.2 15
171.1124 14932.1 21
173.0967 2753.6 4
174.1351 71803.7 105
175.119 56650.5 83
178.0974 11640 17
179.0811 2130.8 3
180.1132 9479.1 13
181.0972 5891.4 8
181.1446 1713.1 2
182.0818 1480.4 2
182.1039 12156.6 17
182.1295 2441 3
183.0878 32717.5 48
185.1398 2952.1 4
186.1242 2649.3 3
188.1071 1846.8 2
190.0977 6793.8 9
191.0816 10616.5 15
192.1135 1907.6 2
193.0972 12366.1 18
194.0925 2882.4 4
194.1287 2377.9 3
195.0765 57745.6 84
195.1169 5232.5 7
195.1244 4900.2 7
196.0599 12515.8 18
196.1082 15528 22
197.1398 21962.6 32
198.1237 14383.5 21
199.1075 2965.2 4
200.1141 82863.4 121
201.0982 24416.2 35
205.0975 1495 2
206.0927 8670.5 12
208.1081 18456.1 27
209.0922 23760 34
209.1324 16601.5 24
210.124 12986.6 19
211.0715 14550.1 21
211.1191 48186.3 70
212.1035 2433.7 3
212.1513 3046.2 4
213.0871 221313.7 325
213.1346 43303.7 63
214.1342 2273 3
214.1667 5757.8 8
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222.1241 15562.3 22
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224.103 15866.7 23
225.1347 26633.9 39
226.1187 49335 72
226.1589 19256.7 28
227.1028 12807.9 18
228.146 3774 5
229.1305 2730.3 4
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244.1409 2325.1 3
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280.1408 2667.4 3
280.2131 20188.1 29
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286.1511 23347 34
294.1563 48436.1 71
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328.2098 7244.2 10
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357.1889 6411.9 9
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383.2035 2454.5 3
389.2065 1688.3 2
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488.3234 7187.8 10
523.2641 6628.3 9
571.3606 9888.6 14
659.3913 2632.5 3
//
