ACCESSION: MSBNK-Eawag-EQ325203
RECORD_TITLE: Nodularin; 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 3252
CH$NAME: Nodularin
CH$NAME: (2Z,5R,6S,9S,12S,13S,16R)-9-[3-(diaminomethylideneamino)propyl]-2-ethylidene-12-[(1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dienyl]-1,6,13-trimethyl-3,7,10,14,19-pentaoxo-1,4,8,11,15-pentazacyclononadecane-5,16-dicarboxylic acid
CH$COMPOUND_CLASS: N/A; Environmental Standard
CH$FORMULA: C41H60N8O10
CH$EXACT_MASS: 824.44324
CH$SMILES: NC(=N)NCCC[C@@H]2NC(=O)[C@@H](C)[C@@H](NC(=O)C(=C\C)\N(C)C(=O)CC[C@@H](NC(=O)[C@@H](C)[C@H](/C=C/C(/C)=C/[C@H](C)[C@H](Cc1ccccc1)OC)NC2=O)C(=O)O)C(O)=O
CH$IUPAC: InChI=1S/C41H60N8O10/c1-8-31-38(54)48-34(40(57)58)26(5)36(52)46-29(15-12-20-44-41(42)43)37(53)45-28(25(4)35(51)47-30(39(55)56)18-19-33(50)49(31)6)17-16-23(2)21-24(3)32(59-7)22-27-13-10-9-11-14-27/h8-11,13-14,16-17,21,24-26,28-30,32,34H,12,15,18-20,22H2,1-7H3,(H,45,53)(H,46,52)(H,47,51)(H,48,54)(H,55,56)(H,57,58)(H4,42,43,44)/b17-16+,23-21+,31-8-/t24-,25-,26-,28-,29-,30+,32-,34+/m0/s1
CH$LINK: CAS
118399-22-7
CH$LINK: KEGG
C15713
CH$LINK: PUBCHEM
CID:14217092
CH$LINK: INCHIKEY
IXBQSRWSVIBXNC-HSKGSTCASA-N
CH$LINK: CHEMSPIDER
10471625
CH$LINK: COMPTOX
DTXSID60880022
AC$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$CHROMATOGRAPHY: RETENTION_TIME 9.6 min
AC$CHROMATOGRAPHY: SOLVENT A water with 0.1% formic acid
AC$CHROMATOGRAPHY: SOLVENT B methanol with 0.1% formic acid
MS$FOCUSED_ION: BASE_PEAK 825.4499
MS$FOCUSED_ION: PRECURSOR_M/Z 825.4505
MS$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$SPLASH: splash10-0079-2920000000-f1de77401060fed21da9
PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm)
58.0652 C3H8N+ 1 58.0651 0.94
59.0478 CH5N3+ 1 59.0478 -0.15
60.0557 CH6N3+ 1 60.0556 0.61
65.0386 C5H5+ 1 65.0386 0.05
67.0542 C5H7+ 1 67.0542 -0.4
68.0493 C4H6N+ 1 68.0495 -1.99
69.0335 C4H5O+ 1 69.0335 -0.16
70.0651 C4H8N+ 1 70.0651 -0.37
71.0491 C4H7O+ 1 71.0491 -0.44
72.0807 C4H10N+ 1 72.0808 -1.19
74.0599 C3H8NO+ 1 74.06 -2.03
77.0385 C6H5+ 1 77.0386 -0.99
79.0542 C6H7+ 1 79.0542 -0.34
80.0493 C5H6N+ 1 80.0495 -2.57
81.0697 C6H9+ 1 81.0699 -2.55
82.0651 C5H8N+ 1 82.0651 -0.31
83.049 C5H7O+ 1 83.0491 -1.22
84.0444 C4H6NO+ 1 84.0444 -0.24
85.0284 C4H5O2+ 1 85.0284 -0.54
85.0762 C4H9N2+ 1 85.076 2.18
86.0601 C4H8NO+ 1 86.06 0.58
87.0791 C3H9N3+ 1 87.0791 -0.33
91.0542 C7H7+ 1 91.0542 -0.73
93.0698 C7H9+ 1 93.0699 -0.39
94.0652 C6H8N+ 1 94.0651 0.36
95.0491 C6H7O+ 1 95.0491 -0.33
95.0604 C5H7N2+ 1 95.0604 0.06
95.0855 C7H11+ 1 95.0855 -0.18
96.0445 C5H6NO+ 1 96.0444 0.73
96.0808 C6H10N+ 1 96.0808 0.15
97.076 C5H9N2+ 1 97.076 0.26
98.0601 C5H8NO+ 1 98.06 0.1
100.0756 C5H10NO+ 1 100.0757 -0.8
100.0871 C4H10N3+ 1 100.0869 1.76
102.0549 C4H8NO2+ 1 102.055 -0.73
103.0542 C8H7+ 1 103.0542 0.03
105.0699 C8H9+ 1 105.0699 0.13
107.0855 C8H11+ 1 107.0855 0.03
108.0806 C7H10N+ 1 108.0808 -1.81
109.0649 C7H9O+ 1 109.0648 1
109.0763 C6H9N2+ 1 109.076 2.71
110.0599 C6H8NO+ 1 110.06 -1.27
110.0964 C7H12N+ 1 110.0964 -0.69
112.0869 C5H10N3+ 1 112.0869 -0.12
113.0232 C5H5O3+ 1 113.0233 -0.8
113.0709 C5H9N2O+ 1 113.0709 0.09
114.0549 C5H8NO2+ 1 114.055 -0.48
114.1026 C5H12N3+ 1 114.1026 -0.03
115.0542 C9H7+ 1 115.0542 -0.06
115.0866 C5H11N2O+ 1 115.0866 0.01
116.0705 C5H10NO2+ 1 116.0706 -0.47
117.0699 C9H9+ 1 117.0699 -0.14
119.0855 C9H11+ 1 119.0855 0.03
120.0569 C8H8O+ 1 120.057 -0.64
120.0808 C8H10N+ 1 120.0808 -0.13
121.0647 C8H9O+ 1 121.0648 -0.59
121.101 C9H13+ 1 121.1012 -1.13
122.0964 C8H12N+ 1 122.0964 -0.46
124.0757 C7H10NO+ 1 124.0757 0.32
124.0871 C6H10N3+ 1 124.0869 1.1
124.112 C8H14N+ 1 124.1121 -0.69
125.0709 C6H9N2O+ 1 125.0709 -0.15
126.055 C6H8NO2+ 1 126.055 0.28
126.0661 C5H8N3O+ 1 126.0662 -0.94
126.0913 C7H12NO+ 1 126.0913 -0.32
127.0865 C6H11N2O+ 1 127.0866 -0.78
127.0978 C5H11N4+ 1 127.0978 -0.02
127.123 C7H15N2+ 1 127.123 -0.2
128.0818 C5H10N3O+ 1 128.0818 -0.46
129.0698 C10H9+ 1 129.0699 -0.28
129.1134 C5H13N4+ 1 129.1135 -0.41
130.0499 C5H8NO3+ 1 130.0499 0.46
130.0975 C5H12N3O+ 1 130.0975 0.4
131.0856 C10H11+ 1 131.0855 0.63
132.0808 C9H10N+ 1 132.0808 0.56
132.1132 C5H14N3O+ 1 132.1131 0.24
133.0646 C9H9O+ 1 133.0648 -1.21
133.1012 C10H13+ 1 133.1012 -0.13
135.0804 C9H11O+ 1 135.0804 -0.23
135.1167 C10H15+ 1 135.1168 -0.94
136.0756 C8H10NO+ 1 136.0757 -0.59
136.0836 C4H12N2O3+ 1 136.0842 -4.58
137.1074 C8H13N2+ 1 137.1073 0.26
138.0661 C6H8N3O+ 1 138.0662 -0.64
138.0912 C8H12NO+ 1 138.0913 -1.31
139.0976 C6H11N4+ 1 139.0978 -1.46
139.1229 C8H15N2+ 1 139.123 -0.75
140.0703 C7H10NO2+ 1 140.0706 -1.82
140.0817 C6H10N3O+ 1 140.0818 -1.2
141.0656 C6H9N2O2+ 1 141.0659 -1.52
142.0861 C7H12NO2+ 1 142.0863 -1.09
142.0976 C6H12N3O+ 1 142.0975 1.14
143.0857 C11H11+ 1 143.0855 1.21
145.1012 C11H13+ 1 145.1012 0.3
146.0965 C10H12N+ 1 146.0964 0.3
146.1087 C11H14+ 1 146.109 -1.86
147.0807 C10H11O+ 1 147.0804 1.96
147.0917 C9H11N2+ 1 147.0917 -0.03
147.1166 C11H15+ 1 147.1168 -1.81
150.0913 C9H12NO+ 1 150.0913 -0.07
150.1024 C8H12N3+ 1 150.1026 -1.49
151.0864 C8H11N2O+ 1 151.0866 -1.25
152.0706 C8H10NO2+ 1 152.0706 -0.03
153.0656 C7H9N2O2+ 1 153.0659 -1.79
153.1022 C8H13N2O+ 1 153.1022 -0.39
154.0863 C8H12NO2+ 1 154.0863 0.1
155.0925 C6H11N4O+ 1 155.0927 -1.6
155.1177 C8H15N2O+ 1 155.1179 -1.22
156.1245 C6H14N5+ 1 156.1244 0.88
157.1083 C6H13N4O+ 1 157.1084 -0.43
158.0922 C6H12N3O2+ 1 158.0924 -1.35
159.1167 C12H15+ 1 159.1168 -0.61
161.0962 C11H13O+ 1 161.0961 0.43
162.1027 C9H12N3+ 1 162.1026 0.66
163.0865 C9H11N2O+ 1 163.0866 -0.67
163.1116 C11H15O+ 1 163.1117 -0.68
164.0705 C9H10NO2+ 1 164.0706 -0.52
164.118 C9H14N3+ 1 164.1182 -1.12
165.1022 C9H13N2O+ 1 165.1022 -0.36
166.0861 C9H12NO2+ 1 166.0863 -0.93
167.086 C13H11+ 1 167.0855 2.71
169.1011 C13H13+ 1 169.1012 -0.63
170.081 C8H12NO3+ 1 170.0812 -1.23
170.1287 C8H16N3O+ 1 170.1288 -0.34
171.0759 C7H11N2O3+ 2 171.0764 -3.27
171.113 C8H15N2O2+ 1 171.1128 1.26
172.0713 C6H10N3O3+ 1 172.0717 -1.85
172.1119 C12H14N+ 1 172.1121 -1.08
173.0961 C12H13O+ 1 173.0961 -0.18
174.1349 C6H16N5O+ 1 174.1349 -0.32
175.1188 C6H15N4O2+ 1 175.119 -0.87
176.1069 C11H14NO+ 1 176.107 -0.8
176.1431 C12H18N+ 1 176.1434 -1.57
178.0972 C9H12N3O+ 1 178.0975 -1.62
178.1224 C11H16NO+ 1 178.1226 -1.07
179.0813 C9H11N2O2+ 1 179.0815 -1.2
180.1131 C9H14N3O+ 1 180.1131 -0.21
181.097 C9H13N2O2+ 1 181.0972 -0.96
182.0811 C9H12NO3+ 1 182.0812 -0.33
182.1036 C7H12N5O+ 1 182.1036 0.07
182.1285 C9H16N3O+ 1 182.1288 -1.47
183.0875 C7H11N4O2+ 1 183.0877 -0.67
183.1126 C9H15N2O2+ 1 183.1128 -1.06
184.0967 C9H14NO3+ 1 184.0968 -0.54
186.0912 C12H12NO+ 1 186.0913 -0.81
188.107 C12H14NO+ 1 188.107 -0.16
190.0976 C10H12N3O+ 1 190.0975 0.43
190.1225 C12H16NO+ 1 190.1226 -0.58
191.0814 C10H11N2O2+ 1 191.0815 -0.65
192.1131 C10H14N3O+ 1 192.1131 -0.04
195.1165 C15H15+ 2 195.1168 -1.83
195.1243 C9H15N4O+ 1 195.124 1.4
196.1077 C9H14N3O2+ 1 196.1081 -1.7
197.0921 C9H13N2O3+ 1 197.0921 0.11
197.107 C13H13N2+ 1 197.1073 -1.5
198.1232 C9H16N3O2+ 2 198.1237 -2.39
199.1075 C9H15N2O3+ 1 199.1077 -1.3
200.1139 C7H14N5O2+ 1 200.1142 -1.3
201.098 C7H13N4O3+ 1 201.0982 -1.03
201.1268 C14H17O+ 2 201.1274 -2.69
204.1382 C13H18NO+ 1 204.1383 -0.2
205.1088 C12H15NO2+ 2 205.1097 -4.29
205.1338 C12H17N2O+ 1 205.1335 1.32
206.0925 C10H12N3O2+ 1 206.0924 0.52
207.0761 C10H11N2O3+ 2 207.0764 -1.54
207.1241 C10H15N4O+ 1 207.124 0.3
208.1081 C10H14N3O2+ 1 208.1081 0.37
209.092 C10H13N2O3+ 1 209.0921 -0.28
209.1321 C16H17+ 3 209.1325 -1.71
210.076 C10H12NO4+ 1 210.0761 -0.45
210.1242 C10H16N3O2+ 2 210.1237 2.27
211.1071 C10H15N2O3+ 2 211.1077 -2.93
212.1506 C9H18N5O+ 1 212.1506 -0.13
213.1344 C9H17N4O2+ 1 213.1346 -0.85
214.1339 C13H16N3+ 1 214.1339 0.12
217.1336 C13H17N2O+ 1 217.1335 0.32
218.1536 C14H20NO+ 2 218.1539 -1.33
220.1441 C12H18N3O+ 2 220.1444 -1.67
223.1184 C10H15N4O2+ 3 223.119 -2.25
224.1028 C10H14N3O3+ 1 224.103 -0.53
224.1505 C10H18N5O+ 1 224.1506 -0.61
225.0871 C10H13N2O4+ 1 225.087 0.34
225.1344 C10H17N4O2+ 1 225.1346 -0.81
226.1184 C10H16N3O3+ 1 226.1186 -0.87
226.1586 C16H20N+ 2 226.159 -1.93
227.1024 C10H15N2O4+ 2 227.1026 -0.94
228.138 C15H18NO+ 3 228.1383 -1.23
232.1698 C15H22NO+ 1 232.1696 0.77
237.1238 C12H17N2O3+ 1 237.1234 1.82
237.1635 C18H21+ 3 237.1638 -1.38
240.1451 C10H18N5O2+ 3 240.1455 -1.5
241.1294 C10H17N4O3+ 1 241.1295 -0.36
242.1609 C10H20N5O2+ 3 242.1612 -0.87
245.1131 C10H17N2O5+ 2 245.1132 -0.56
246.1236 C13H16N3O2+ 1 246.1237 -0.22
246.1488 C15H20NO2+ 2 246.1489 -0.43
248.139 C13H18N3O2+ 2 248.1394 -1.58
249.1231 C13H17N2O3+ 2 249.1234 -1.12
250.1298 C11H16N5O2+ 1 250.1299 -0.24
250.1555 C13H20N3O2+ 2 250.155 1.83
251.1141 C11H15N4O3+ 2 251.1139 0.93
252.0976 C11H14N3O4+ 2 252.0979 -1.2
253.0816 C11H13N2O5+ 2 253.0819 -1.02
255.1452 C11H19N4O3+ 1 255.1452 -0.03
257.1727 C12H23N3O3+ 2 257.1734 -2.54
258.1565 C10H20N5O3+ 2 258.1561 1.8
263.1865 C14H23N4O+ 3 263.1866 -0.64
267.1345 C13H19N2O4+ 2 267.1339 2.16
268.14 C11H18N5O3+ 3 268.1404 -1.48
269.1242 C11H17N4O4+ 3 269.1244 -0.97
280.213 C14H26N5O+ 3 280.2132 -0.74
282.1849 C19H24NO+ 3 282.1852 -1.07
283.1289 C13H19N2O5+ 3 283.1288 0.04
285.1672 C11H21N6O3+ 2 285.167 0.93
286.1506 C11H20N5O4+ 3 286.151 -1.19
291.1453 C14H19N4O3+ 4 291.1452 0.35
292.1286 C14H18N3O4+ 3 292.1292 -1.86
293.1132 C14H17N2O5+ 3 293.1132 -0.1
293.1608 C14H21N4O3+ 4 293.1608 -0.06
295.1287 C14H19N2O5+ 2 295.1288 -0.64
295.1762 C14H23N4O3+ 3 295.1765 -0.87
303.1776 C11H23N6O4+ 3 303.1775 0.33
310.1386 C14H20N3O5+ 3 310.1397 -3.86
319.2133 C17H27N4O2+ 3 319.2129 1.28
320.1716 C15H22N5O3+ 4 320.1717 -0.36
322.1874 C15H24N5O3+ 4 322.1874 0.2
323.1715 C15H23N4O4+ 5 323.1714 0.49
338.1351 C15H20N3O6+ 3 338.1347 1.18
338.1828 C15H24N5O4+ 2 338.1823 1.62
339.1185 C15H19N2O7+ 4 339.1187 -0.46
341.1813 C15H25N4O5+ 3 341.1819 -1.98
348.167 C18H24N2O5+ 4 348.168 -2.8
356.2409 C15H30N7O3+ 3 356.2405 1.22
365.1954 C18H27N3O5+ 4 365.1945 2.54
366.1771 C16H24N5O5+ 4 366.1772 -0.15
389.2066 C21H29N2O5+ 3 389.2071 -1.18
406.2086 C19H28N5O5+ 4 406.2085 0.18
409.257 C21H35N3O5+ 4 409.2571 -0.4
449.216 C22H31N3O7+ 5 449.2157 0.71
467.2299 C25H31N4O5+ 4 467.2289 2.19
488.3229 C26H42N5O4+ 5 488.3231 -0.58
PK$NUM_PEAK: 243
PK$PEAK: m/z int. rel.int.
58.0652 40153.8 1
59.0478 48433.5 2
60.0557 578308.8 24
65.0386 44901.3 1
67.0542 31587.2 1
68.0493 193753.4 8
69.0335 459453.4 19
70.0651 19598861.6 815
71.0491 127633.7 5
72.0807 258029.5 10
74.0599 25353.2 1
77.0385 127398.4 5
79.0542 732529.4 30
80.0493 25168.4 1
81.0697 75588.7 3
82.0651 66712.7 2
83.049 146237.8 6
84.0444 1913673 79
85.0284 43551.9 1
85.0762 49343 2
86.0601 142742.4 5
87.0791 296429.9 12
91.0542 2167477 90
93.0698 2294172.3 95
94.0652 102097.1 4
95.0491 556856.8 23
95.0604 339853.3 14
95.0855 298452 12
96.0445 129562.7 5
96.0808 161833 6
97.076 739168.8 30
98.0601 718188.7 29
100.0756 106100 4
100.0871 39597.8 1
102.0549 40309.4 1
103.0542 6256507.5 260
105.0699 5999135 249
107.0855 9760159.8 405
108.0806 59520.9 2
109.0649 233390.9 9
109.0763 29637.7 1
110.0599 48370.5 2
110.0964 51228.6 2
112.0869 4522736.4 188
113.0232 108500.7 4
113.0709 1424242.9 59
114.0549 58689.7 2
114.1026 894683.3 37
115.0542 720561.7 29
115.0866 3292695.8 136
116.0705 1024695.8 42
117.0699 2891693 120
119.0855 382951.7 15
120.0569 185644 7
120.0808 693460.7 28
121.0647 56926.9 2
121.101 232401.3 9
122.0964 44721.6 1
124.0757 680301.3 28
124.0871 37070.3 1
124.112 296725.2 12
125.0709 930601.6 38
126.055 284518.8 11
126.0661 120551.1 5
126.0913 352378.8 14
127.0865 339166.3 14
127.0978 36874.7 1
127.123 61510.4 2
128.0818 36248.5 1
129.0698 145780.9 6
129.1134 30312.1 1
130.0499 840753.7 34
130.0975 484738.5 20
131.0856 547080.7 22
132.0808 56998.6 2
132.1132 41236.2 1
133.0646 50126.9 2
133.1012 332641.5 13
135.0804 24020505.3 999
135.1167 8073786.8 335
136.0756 404320.4 16
136.0836 45857.9 1
137.1074 196693.3 8
138.0661 43209.6 1
138.0912 203106.7 8
139.0976 487969.8 20
139.1229 66766.8 2
140.0703 156985.6 6
140.0817 1197235.9 49
141.0656 922189.9 38
142.0861 60862.9 2
142.0976 28068.2 1
143.0857 317981.8 13
145.1012 587355.9 24
146.0965 104402.4 4
146.1087 102583 4
147.0807 48703.5 2
147.0917 32451.2 1
147.1166 40501 1
150.0913 102787.5 4
150.1024 33365.1 1
151.0864 132924.4 5
152.0706 1706338.5 70
153.0656 92487.7 3
153.1022 707696.9 29
154.0863 262662.7 10
155.0925 65842.1 2
155.1177 282008.7 11
156.1245 305094.7 12
157.1083 2406398.7 100
158.0922 469879 19
159.1167 155772.3 6
161.0962 247355.1 10
162.1027 139849.2 5
163.0865 1023252.7 42
163.1116 4065174.7 169
164.0705 225972.6 9
164.118 150716.6 6
165.1022 455240.8 18
166.0861 301051 12
167.086 45692.6 1
169.1011 45626.4 1
170.081 333835.5 13
170.1287 38153.3 1
171.0759 104406.6 4
171.113 231962 9
172.0713 30613.1 1
172.1119 249132.9 10
173.0961 114003.7 4
174.1349 2030600.4 84
175.1188 494300.1 20
176.1069 29820 1
176.1431 41676.9 1
178.0972 169035.2 7
178.1224 50330.3 2
179.0813 49819.1 2
180.1131 511935.1 21
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//
