ACCESSION: MSBNK-Eawag-EQ325204
RECORD_TITLE: Nodularin; LC-ESI-QFT; MS2; CE: 60; 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 60 (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$SPLASH: splash10-0kmr-4900000000-fd0515ed1a847892d922
PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm)
58.0652 C3H8N+ 1 58.0651 1.28
59.0478 CH5N3+ 1 59.0478 0.87
60.0557 CH6N3+ 1 60.0556 0.77
65.0386 C5H5+ 1 65.0386 -0.1
67.0542 C5H7+ 1 67.0542 0.35
68.0495 C4H6N+ 1 68.0495 0.06
69.0335 C4H5O+ 1 69.0335 0.27
69.0699 C5H9+ 1 69.0699 -0.39
70.0651 C4H8N+ 1 70.0651 -0.37
71.0492 C4H7O+ 1 71.0491 0.55
72.0807 C4H10N+ 1 72.0808 -0.63
73.0634 C2H7N3+ 1 73.0634 -0.8
74.0237 C2H4NO2+ 1 74.0237 0.34
74.0602 C3H8NO+ 1 74.06 2.7
77.0385 C6H5+ 1 77.0386 -0.86
79.0542 C6H7+ 1 79.0542 -0.08
80.0495 C5H6N+ 1 80.0495 -0.07
81.0335 C5H5O+ 1 81.0335 0.48
81.0699 C6H9+ 1 81.0699 0.66
82.0288 C4H4NO+ 1 82.0287 0.12
82.0652 C5H8N+ 1 82.0651 0.66
83.0491 C5H7O+ 1 83.0491 -0.02
84.0444 C4H6NO+ 1 84.0444 -0.12
85.0284 C4H5O2+ 1 85.0284 0.4
85.076 C4H9N2+ 1 85.076 -0.17
86.0599 C4H8NO+ 1 86.06 -1.75
87.0792 C3H9N3+ 1 87.0791 0.93
89.0384 C7H5+ 1 89.0386 -2.43
91.0542 C7H7+ 1 91.0542 -0.18
92.062 C7H8+ 1 92.0621 -0.56
93.0699 C7H9+ 1 93.0699 -0.18
94.0651 C6H8N+ 1 94.0651 -0.38
95.0491 C6H7O+ 1 95.0491 -0.22
95.0603 C5H7N2+ 1 95.0604 -0.26
95.0855 C7H11+ 1 95.0855 0.14
96.0444 C5H6NO+ 1 96.0444 0.41
96.0681 C5H8N2+ 1 96.0682 -1.14
96.0807 C6H10N+ 1 96.0808 -0.48
97.076 C5H9N2+ 1 97.076 0.26
98.0601 C5H8NO+ 1 98.06 0.2
99.0189 C3H3N2O2+ 1 99.0189 -0.04
100.0756 C5H10NO+ 1 100.0757 -0.4
102.0465 C8H6+ 1 102.0464 1.06
102.055 C4H8NO2+ 1 102.055 0.64
103.0542 C8H7+ 1 103.0542 0.23
104.0577 C3H8N2O2+ 1 104.058 -2.78
105.0699 C8H9+ 1 105.0699 0.13
106.0651 C7H8N+ 1 106.0651 -0.05
107.0855 C8H11+ 1 107.0855 -0.06
108.0808 C7H10N+ 1 108.0808 -0.05
109.0648 C7H9O+ 1 109.0648 -0.2
109.076 C6H9N2+ 1 109.076 -0.59
110.0237 C5H4NO2+ 1 110.0237 0.14
110.0714 C5H8N3+ 1 110.0713 0.88
110.0963 C7H12N+ 1 110.0964 -0.87
112.0869 C5H10N3+ 1 112.0869 -0.03
113.0234 C5H5O3+ 1 113.0233 0.35
113.0709 C5H9N2O+ 1 113.0709 0.01
114.0547 C5H8NO2+ 1 114.055 -2.32
114.1026 C5H12N3+ 1 114.1026 0.4
115.0542 C9H7+ 1 115.0542 0.12
115.0866 C5H11N2O+ 1 115.0866 0.18
116.062 C9H8+ 1 116.0621 -0.1
116.0706 C5H10NO2+ 1 116.0706 0.3
117.0699 C9H9+ 1 117.0699 -0.23
118.0653 C8H8N+ 1 118.0651 1.05
119.0604 C7H7N2+ 1 119.0604 0.04
119.0855 C9H11+ 1 119.0855 0.11
120.057 C8H8O+ 1 120.057 0.03
120.0808 C8H10N+ 1 120.0808 0.45
120.0934 C9H12+ 1 120.0934 -0.02
121.0648 C8H9O+ 1 121.0648 0.32
121.1012 C9H13+ 1 121.1012 0.19
122.0601 C7H8NO+ 1 122.06 0.73
122.0965 C8H12N+ 1 122.0964 1.02
123.0553 C6H7N2O+ 1 123.0553 -0.08
123.0802 C8H11O+ 1 123.0804 -1.72
123.0917 C7H11N2+ 1 123.0917 -0.04
124.0392 C6H6NO2+ 1 124.0393 -1.01
124.0757 C7H10NO+ 1 124.0757 -0.08
124.112 C8H14N+ 1 124.1121 -0.21
125.0709 C6H9N2O+ 1 125.0709 -0.23
126.055 C6H8NO2+ 1 126.055 0.12
126.0662 C5H8N3O+ 1 126.0662 -0.15
126.0914 C7H12NO+ 1 126.0913 0.39
127.0866 C6H11N2O+ 1 127.0866 0.08
127.1232 C7H15N2+ 1 127.123 1.69
128.0343 C5H6NO3+ 1 128.0342 0.47
128.062 C10H8+ 1 128.0621 -0.09
129.0698 C10H9+ 1 129.0699 -0.9
130.0499 C5H8NO3+ 1 130.0499 0.46
130.0652 C9H8N+ 1 130.0651 0.88
130.0778 C10H10+ 1 130.0777 0.68
130.0975 C5H12N3O+ 1 130.0975 0.32
131.0855 C10H11+ 1 131.0855 -0.28
132.0807 C9H10N+ 1 132.0808 -0.88
133.0647 C9H9O+ 1 133.0648 -0.61
133.1011 C10H13+ 1 133.1012 -0.28
135.0804 C9H11O+ 1 135.0804 -0.31
135.0912 C8H11N2+ 1 135.0917 -3.44
135.1167 C10H15+ 1 135.1168 -0.72
136.0756 C8H10NO+ 1 136.0757 -0.74
136.0995 C8H12N2+ 1 136.0995 -0.29
137.0711 C7H9N2O+ 1 137.0709 0.81
137.1074 C8H13N2+ 1 137.1073 0.69
138.0661 C6H8N3O+ 1 138.0662 -0.35
138.0913 C8H12NO+ 1 138.0913 -0.65
139.0978 C6H11N4+ 1 139.0978 -0.38
139.1228 C8H15N2+ 1 139.123 -0.97
140.0703 C7H10NO2+ 1 140.0706 -2.18
140.0817 C6H10N3O+ 1 140.0818 -0.99
141.0657 C6H9N2O2+ 1 141.0659 -0.95
142.0863 C7H12NO2+ 1 142.0863 0.6
142.0976 C6H12N3O+ 1 142.0975 1
143.0855 C11H11+ 1 143.0855 0.02
145.1014 C11H13+ 1 145.1012 1.4
146.0965 C10H12N+ 1 146.0964 0.64
146.1091 C11H14+ 1 146.109 0.6
147.0807 C10H11O+ 1 147.0804 1.49
147.0921 C9H11N2+ 1 147.0917 2.96
147.1172 C11H15+ 1 147.1168 2.2
148.112 C10H14N+ 1 148.1121 -0.58
150.0918 C9H12NO+ 1 150.0913 2.8
150.1027 C8H12N3+ 1 150.1026 0.97
151.0867 C8H11N2O+ 1 151.0866 0.47
152.0706 C8H10NO2+ 1 152.0706 -0.16
152.1182 C8H14N3+ 1 152.1182 -0.16
153.0658 C7H9N2O2+ 1 153.0659 -0.29
153.1021 C8H13N2O+ 1 153.1022 -0.58
154.0862 C8H12NO2+ 1 154.0863 -0.16
155.0855 C12H11+ 1 155.0855 -0.24
155.118 C8H15N2O+ 1 155.1179 0.52
156.1244 C6H14N5+ 1 156.1244 0.5
157.1083 C6H13N4O+ 1 157.1084 -0.68
158.0925 C6H12N3O2+ 1 158.0924 0.49
159.1169 C12H15+ 1 159.1168 0.59
161.0959 C11H13O+ 1 161.0961 -0.88
162.0921 C10H12NO+ 1 162.0913 4.93
162.1027 C9H12N3+ 1 162.1026 0.47
163.0865 C9H11N2O+ 1 163.0866 -0.55
163.1117 C11H15O+ 1 163.1117 -0.44
164.0703 C9H10NO2+ 1 164.0706 -1.62
164.1184 C9H14N3+ 1 164.1182 0.83
165.1021 C9H13N2O+ 1 165.1022 -0.91
166.0864 C9H12NO2+ 1 166.0863 0.57
167.0858 C13H11+ 1 167.0855 1.46
170.0811 C8H12NO3+ 1 170.0812 -0.59
170.0969 C12H12N+ 1 170.0964 2.67
171.0763 C7H11N2O3+ 1 171.0764 -0.87
171.1125 C8H15N2O2+ 1 171.1128 -1.84
172.1121 C12H14N+ 1 172.1121 0.08
173.0961 C12H13O+ 1 173.0961 0.34
174.1353 C6H16N5O+ 1 174.1349 1.8
176.1068 C11H14NO+ 1 176.107 -1.02
176.1428 C12H18N+ 1 176.1434 -3.21
178.0973 C9H12N3O+ 1 178.0975 -0.89
180.0933 C14H12+ 2 180.0934 -0.57
180.1131 C9H14N3O+ 1 180.1131 -0.05
181.097 C9H13N2O2+ 1 181.0972 -1.07
182.0812 C9H12NO3+ 1 182.0812 0.28
182.1036 C7H12N5O+ 1 182.1036 -0.15
182.1288 C9H16N3O+ 1 182.1288 -0.05
183.0876 C7H11N4O2+ 1 183.0877 -0.12
183.1123 C9H15N2O2+ 2 183.1128 -2.64
186.0916 C12H12NO+ 1 186.0913 1.18
188.1066 C12H14NO+ 2 188.107 -2.24
192.1133 C10H14N3O+ 1 192.1131 0.68
195.1241 C9H15N4O+ 1 195.124 0.58
197.1074 C13H13N2+ 1 197.1073 0.38
198.1237 C9H16N3O2+ 1 198.1237 -0.02
199.1073 C9H15N2O3+ 2 199.1077 -2.3
200.1141 C7H14N5O2+ 1 200.1142 -0.46
201.0979 C7H13N4O3+ 1 201.0982 -1.62
204.1383 C13H18NO+ 1 204.1383 0.14
206.0925 C10H12N3O2+ 1 206.0924 0.57
207.0769 C10H11N2O3+ 1 207.0764 2.08
208.1081 C10H14N3O2+ 1 208.1081 0.37
209.092 C10H13N2O3+ 1 209.0921 -0.47
210.0762 C10H12NO4+ 1 210.0761 0.65
210.1243 C10H16N3O2+ 2 210.1237 2.98
213.1355 C9H17N4O2+ 2 213.1346 4.35
218.1545 C14H20NO+ 1 218.1539 2.43
223.1193 C10H15N4O2+ 2 223.119 1.47
224.1027 C10H14N3O3+ 2 224.103 -1.06
225.0872 C10H13N2O4+ 2 225.087 1.05
225.135 C10H17N4O2+ 2 225.1346 1.68
226.1183 C10H16N3O3+ 2 226.1186 -1.27
227.1025 C10H15N2O4+ 1 227.1026 -0.72
228.0868 C10H14NO5+ 2 228.0866 0.66
249.1231 C13H17N2O3+ 2 249.1234 -0.92
253.0819 C11H13N2O5+ 1 253.0819 -0.07
267.1344 C13H19N2O4+ 2 267.1339 1.71
PK$NUM_PEAK: 192
PK$PEAK: m/z int. rel.int.
58.0652 30302.9 1
59.0478 23907.1 1
60.0557 537865.4 23
65.0386 294430.1 12
67.0542 162125.1 7
68.0495 444074.6 19
69.0335 574467.9 24
69.0699 164462.7 7
70.0651 23021199.6 999
71.0492 246075.3 10
72.0807 498646.9 21
73.0634 26662.3 1
74.0237 41891.3 1
74.0602 32059.8 1
77.0385 433225.3 18
79.0542 1797567.9 78
80.0495 104412.2 4
81.0335 56973.5 2
81.0699 165249.6 7
82.0288 193336.3 8
82.0652 128299.4 5
83.0491 381384.4 16
84.0444 3123567.7 135
85.0284 204160.5 8
85.076 157102.4 6
86.0599 203454.9 8
87.0792 244306.5 10
89.0384 28624 1
91.0542 4652352.1 201
92.062 23223.9 1
93.0699 3360018.1 145
94.0651 355325.4 15
95.0491 2480278.8 107
95.0603 583190 25
95.0855 253067.4 10
96.0444 307143.4 13
96.0681 30917.4 1
96.0807 244954.7 10
97.076 1238157 53
98.0601 1340974.9 58
99.0189 288625.4 12
100.0756 175919.5 7
102.0465 221030.4 9
102.055 114293.1 4
103.0542 16588454.1 719
104.0577 32174.1 1
105.0699 10347564.9 449
106.0651 25137.9 1
107.0855 9997218.4 433
108.0808 259443.9 11
109.0648 653144.4 28
109.076 49880.3 2
110.0237 30179.5 1
110.0714 27199.4 1
110.0963 160418.2 6
112.0869 2686568.5 116
113.0234 396080.7 17
113.0709 587566.3 25
114.0547 197136.2 8
114.1026 627030.2 27
115.0542 2102056.8 91
115.0866 1773489.9 76
116.062 134303.1 5
116.0706 369334.7 16
117.0699 3932060.3 170
118.0653 49956.3 2
119.0604 169675.3 7
119.0855 526734.9 22
120.057 375958.4 16
120.0808 584476.3 25
120.0934 42047.1 1
121.0648 51864.3 2
121.1012 171719.6 7
122.0601 53027.7 2
122.0965 137625.9 5
123.0553 116418.7 5
123.0802 33246.5 1
123.0917 28594.6 1
124.0392 103627.4 4
124.0757 688212.3 29
124.112 132431.9 5
125.0709 792984.7 34
126.055 247259.9 10
126.0662 30753.8 1
126.0914 331760.2 14
127.0866 602783.1 26
127.1232 45276.7 1
128.0343 52900.6 2
128.062 127410.5 5
129.0698 216853.7 9
130.0499 725462.7 31
130.0652 38880.4 1
130.0778 54734.1 2
130.0975 379516.7 16
131.0855 343160.4 14
132.0807 48701.8 2
133.0647 33467.2 1
133.1011 298985.4 12
135.0804 10729022.7 465
135.0912 750924.1 32
135.1167 3262555.5 141
136.0756 443890.2 19
136.0995 114472.1 4
137.0711 28739.2 1
137.1074 264796.5 11
138.0661 123855.2 5
138.0913 232368 10
139.0978 240783.6 10
139.1228 57456.1 2
140.0703 100540.3 4
140.0817 672343.7 29
141.0657 1399747.2 60
142.0863 29101.6 1
142.0976 32399 1
143.0855 245586.2 10
145.1014 358740.3 15
146.0965 36969 1
146.1091 48026.1 2
147.0807 49163.8 2
147.0921 43317.8 1
147.1172 48949.1 2
148.112 28886.1 1
150.0918 42977.4 1
150.1027 30339 1
151.0867 137516.6 5
152.0706 647390.5 28
152.1182 111954.6 4
153.0658 114363.8 4
153.1021 1140694.2 49
154.0862 179412.8 7
155.0855 53560 2
155.118 110762 4
156.1244 37504.4 1
157.1083 480563.4 20
158.0925 150502 6
159.1169 46312.3 2
161.0959 41026.3 1
162.0921 32892.4 1
162.1027 122999.7 5
163.0865 1001116 43
163.1117 801705.5 34
164.0703 244261.6 10
164.1184 139021.5 6
165.1021 537407.4 23
166.0864 147723.9 6
167.0858 42297.3 1
170.0811 121024.8 5
170.0969 37235.1 1
171.0763 209833.6 9
171.1125 35969.5 1
172.1121 178619 7
173.0961 63313.3 2
174.1353 187301.8 8
176.1068 43098.5 1
176.1428 30608 1
178.0973 207334.1 8
180.0933 42777 1
180.1131 238194.3 10
181.097 3531369.2 153
182.0812 659897.5 28
182.1036 434848.9 18
182.1288 102185.3 4
183.0876 288140.5 12
183.1123 270901.6 11
186.0916 36475.5 1
188.1066 47852.8 2
192.1133 141698.2 6
195.1241 36219.7 1
197.1074 34832.2 1
198.1237 111593.3 4
199.1073 291387.5 12
200.1141 402491.6 17
201.0979 360609.5 15
204.1383 53276.7 2
206.0925 135217.2 5
207.0769 46651.7 2
208.1081 146237.2 6
209.092 1815784.5 78
210.0762 211100.1 9
210.1243 25454.1 1
213.1355 27153.4 1
218.1545 30716.5 1
223.1193 110194.8 4
224.1027 100895 4
225.0872 118018 5
225.135 43172.3 1
226.1183 271187.4 11
227.1025 1369296.7 59
228.0868 63547.4 2
249.1231 49625.2 2
253.0819 180698.2 7
267.1344 100056 4
//
