ACCESSION: MSBNK-Eawag-EQ325004
RECORD_TITLE: Microcystin-RR; 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 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 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$CHROMATOGRAPHY: RETENTION_TIME 9.1 min
AC$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$SPLASH: splash10-0pdr-1900000000-cdf4385b7cfa2554b298
PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm)
72.0808 C4H10N+ 1 72.0808 1.03
74.06 C3H8NO+ 1 74.06 0
77.0385 C6H5+ 1 77.0386 -1.25
79.0543 C6H7+ 1 79.0542 0.93
80.0496 C5H6N+ 1 80.0495 1.05
81.0337 C5H5O+ 1 81.0335 2.58
81.0699 C6H9+ 1 81.0699 0.53
82.0289 C4H4NO+ 1 82.0287 2.07
82.0653 C5H8N+ 1 82.0651 1.64
84.0445 C4H6NO+ 1 84.0444 1.07
85.0285 C4H5O2+ 1 85.0284 0.52
85.0762 C4H9N2+ 1 85.076 1.94
86.0601 C4H8NO+ 1 86.06 1.04
86.0713 C3H8N3+ 1 86.0713 0.89
87.0792 C3H9N3+ 1 87.0791 1.05
88.0758 C4H10NO+ 1 88.0757 0.9
91.0543 C7H7+ 1 91.0542 0.81
93.07 C7H9+ 1 93.0699 0.89
94.0652 C6H8N+ 1 94.0651 1.22
95.0492 C6H7O+ 1 95.0491 0.93
95.0604 C5H7N2+ 1 95.0604 0.69
95.0856 C7H11+ 1 95.0855 0.98
96.0446 C5H6NO+ 1 96.0444 2.18
96.0808 C6H10N+ 1 96.0808 0.15
97.0761 C5H9N2+ 1 97.076 0.67
98.0601 C5H8NO+ 1 98.06 1.12
99.019 C3H3N2O2+ 1 99.0189 1.48
99.0918 C5H11N2+ 1 99.0917 0.76
100.0871 C4H10N3+ 1 100.0869 2.16
101.0709 C4H9N2O+ 1 101.0709 -0.39
102.0465 C8H6+ 1 102.0464 1.06
102.055 C4H8NO2+ 1 102.055 0.54
103.0543 C8H7+ 1 103.0542 1.2
104.0577 C3H8N2O2+ 1 104.058 -3.26
105.0449 C6H5N2+ 1 105.0447 1.77
105.07 C8H9+ 1 105.0699 1.27
106.0653 C7H8N+ 1 106.0651 1.55
106.0733 C3H10N2O2+ 1 106.0737 -3.95
107.0857 C8H11+ 1 107.0855 1.24
108.081 C7H10N+ 1 108.0808 2.26
108.0889 C3H12N2O2+ 1 108.0893 -3.78
109.0649 C7H9O+ 1 109.0648 1.36
109.0761 C6H9N2+ 1 109.076 0.6
110.0602 C6H8NO+ 1 110.06 1.45
110.0966 C7H12N+ 1 110.0964 2.04
111.092 C6H11N2+ 1 111.0917 2.66
112.0394 C5H6NO2+ 1 112.0393 0.49
112.087 C5H10N3+ 1 112.0869 1.04
113.0234 C5H5O3+ 1 113.0233 1.06
113.0711 C5H9N2O+ 1 113.0709 1.07
114.0551 C5H8NO2+ 1 114.055 1.1
114.0664 C4H8N3O+ 1 114.0662 1.68
114.1027 C5H12N3+ 1 114.1026 1.19
115.0543 C9H7+ 1 115.0542 0.81
115.0867 C5H11N2O+ 1 115.0866 1.05
116.0621 C9H8+ 1 116.0621 0.07
116.0707 C5H10NO2+ 1 116.0706 0.82
117.07 C9H9+ 1 117.0699 0.8
119.0603 C7H7N2+ 1 119.0604 -0.71
119.0689 C3H9N3O2+ 1 119.0689 -0.32
119.0856 C9H11+ 1 119.0855 0.7
120.0572 C8H8O+ 1 120.057 1.95
120.0809 C8H10N+ 1 120.0808 1.28
121.0649 C8H9O+ 1 121.0648 1.31
121.0761 C7H9N2+ 1 121.076 0.29
121.1013 C9H13+ 1 121.1012 0.93
122.0601 C7H8NO+ 1 122.06 0.73
122.0714 C6H8N3+ 1 122.0713 0.87
122.0965 C8H12N+ 1 122.0964 0.53
123.0554 C6H7N2O+ 1 123.0553 1.06
123.0918 C7H11N2+ 1 123.0917 0.85
124.0759 C7H10NO+ 1 124.0757 1.69
124.0872 C6H10N3+ 1 124.0869 1.98
124.1122 C8H14N+ 1 124.1121 1.08
125.0711 C6H9N2O+ 1 125.0709 0.96
125.1073 C7H13N2+ 1 125.1073 -0.2
126.0553 C6H8NO2+ 1 126.055 3.05
126.0663 C5H8N3O+ 1 126.0662 1.04
127.0867 C6H11N2O+ 1 127.0866 0.95
128.0342 C5H6NO3+ 1 128.0342 -0.23
128.0622 C10H8+ 1 128.0621 1.16
128.0707 C6H10NO2+ 1 128.0706 0.66
128.0899 CH12N4O3+ 1 128.0904 -3.99
129.0702 C10H9+ 1 129.0699 2.5
130.0501 C5H8NO3+ 1 130.0499 1.62
130.0651 C9H8N+ 1 130.0651 0.11
130.0781 C10H10+ 1 130.0777 2.75
130.0976 C5H12N3O+ 1 130.0975 0.47
131.0857 C10H11+ 1 131.0855 1.09
132.0807 C9H10N+ 1 132.0808 -0.27
133.1013 C10H13+ 1 133.1012 1.15
135.0805 C9H11O+ 1 135.0804 0.66
135.1169 C10H15+ 1 135.1168 0.47
136.0757 C8H10NO+ 1 136.0757 0.44
136.0839 C4H12N2O3+ 1 136.0842 -2.89
137.071 C7H9N2O+ 1 137.0709 0.15
137.1074 C8H13N2+ 1 137.1073 0.4
138.055 C7H8NO2+ 1 138.055 0.69
138.0662 C6H8N3O+ 1 138.0662 0.45
138.0914 C8H12NO+ 1 138.0913 0.07
138.1029 C7H12N3+ 1 138.1026 2.58
139.0867 C7H11N2O+ 1 139.0866 0.94
139.0979 C6H11N4+ 1 139.0978 0.77
139.1228 C8H15N2+ 1 139.123 -1.26
140.0707 C7H10NO2+ 1 140.0706 0.75
140.0818 C6H10N3O+ 1 140.0818 -0.2
141.0658 C6H9N2O2+ 1 141.0659 -0.31
141.1023 C7H13N2O+ 1 141.1022 0.15
143.0859 C11H11+ 1 143.0855 2.61
144.0811 C10H10N+ 1 144.0808 2.18
145.1015 C11H13+ 1 145.1012 2.23
146.0967 C10H12N+ 1 146.0964 2.01
147.0805 C10H11O+ 1 147.0804 0.4
149.0711 C8H9N2O+ 1 149.0709 1.35
150.1029 C8H12N3+ 1 150.1026 2.04
151.0868 C8H11N2O+ 1 151.0866 1.39
152.071 C8H10NO2+ 1 152.0706 2.33
152.0821 C7H10N3O+ 1 152.0818 1.59
152.1185 C8H14N3+ 1 152.1182 2.08
153.1025 C8H13N2O+ 1 153.1022 1.83
155.0815 C7H11N2O2+ 1 155.0815 -0.28
155.1182 C8H15N2O+ 1 155.1179 1.94
156.1247 C6H14N5+ 1 156.1244 1.91
157.1085 C6H13N4O+ 1 157.1084 0.53
158.0924 C6H12N3O2+ 1 158.0924 -0.02
159.1168 C12H15+ 1 159.1168 -0.23
161.0962 C11H13O+ 1 161.0961 0.67
162.1029 C9H12N3+ 1 162.1026 2.07
163.0868 C9H11N2O+ 1 163.0866 1.6
163.1118 C11H15O+ 1 163.1117 0.36
164.0709 C9H10NO2+ 1 164.0706 1.55
164.0819 C8H10N3O+ 1 164.0818 0.56
164.1184 C9H14N3+ 1 164.1182 0.83
165.1022 C9H13N2O+ 1 165.1022 -0.24
166.086 C9H12NO2+ 1 166.0863 -1.29
166.0976 C8H12N3O+ 1 166.0975 0.49
167.0815 C8H11N2O2+ 1 167.0815 -0.26
168.0656 C8H10NO3+ 1 168.0655 0.18
169.0973 C8H13N2O2+ 1 169.0972 0.57
170.0967 C12H12N+ 1 170.0964 1.85
171.1125 C8H15N2O2+ 1 171.1128 -1.72
172.1125 C12H14N+ 1 172.1121 2.35
173.0964 C12H13O+ 1 173.0961 1.61
174.1352 C6H16N5O+ 1 174.1349 1.4
175.1193 C6H15N4O2+ 1 175.119 1.82
177.1023 C10H13N2O+ 1 177.1022 0.17
178.0975 C9H12N3O+ 1 178.0975 0.23
179.0814 C9H11N2O2+ 1 179.0815 -0.8
180.1132 C9H14N3O+ 1 180.1131 0.17
181.0977 C9H13N2O2+ 1 181.0972 2.85
182.1038 C7H12N5O+ 1 182.1036 1.17
182.1289 C9H16N3O+ 1 182.1288 0.72
183.088 C7H11N4O2+ 1 183.0877 1.68
190.0982 C10H12N3O+ 2 190.0975 3.59
191.082 C10H11N2O2+ 1 191.0815 2.6
192.1131 C10H14N3O+ 1 192.1131 0.01
193.0973 C10H13N2O2+ 1 193.0972 0.76
194.0926 C9H12N3O2+ 1 194.0924 1.07
194.129 C10H16N3O+ 1 194.1288 0.99
195.0764 C9H11N2O3+ 1 195.0764 0.11
195.1165 C15H15+ 3 195.1168 -1.47
196.0605 C9H10NO4+ 1 196.0604 0.54
196.1082 C9H14N3O2+ 1 196.1081 0.75
197.1395 C9H17N4O+ 1 197.1397 -0.9
199.1071 C9H15N2O3+ 2 199.1077 -3.16
200.1141 C7H14N5O2+ 1 200.1142 -0.41
201.0983 C7H13N4O3+ 1 201.0982 0.27
205.0974 C11H13N2O2+ 1 205.0972 0.96
205.1082 C10H13N4O+ 1 205.1084 -0.96
206.0926 C10H12N3O2+ 1 206.0924 0.81
207.1245 C10H15N4O+ 2 207.124 2.33
208.1082 C10H14N3O2+ 1 208.1081 0.8
209.0923 C10H13N2O3+ 1 209.0921 0.87
210.1241 C10H16N3O2+ 2 210.1237 2.03
211.0713 C9H11N2O4+ 1 211.0713 0.03
211.1189 C9H15N4O2+ 1 211.119 -0.48
212.1033 C9H14N3O3+ 2 212.103 1.47
213.0871 C9H13N2O4+ 1 213.087 0.36
214.167 C9H20N5O+ 2 214.1662 3.38
217.1339 C13H17N2O+ 1 217.1335 1.75
218.1544 C14H20NO+ 1 218.1539 2.11
220.108 C11H14N3O2+ 1 220.1081 -0.01
221.0921 C11H13N2O3+ 1 221.0921 0.28
222.1239 C11H16N3O2+ 1 222.1237 0.89
223.1186 C10H15N4O2+ 3 223.119 -1.58
224.1031 C10H14N3O3+ 1 224.103 0.59
225.1345 C10H17N4O2+ 1 225.1346 -0.28
226.1188 C10H16N3O3+ 2 226.1186 0.98
226.1589 C16H20N+ 4 226.159 -0.78
227.1029 C10H15N2O4+ 2 227.1026 1.39
234.1242 C12H16N3O2+ 2 234.1237 1.95
235.1194 C11H15N4O2+ 2 235.119 2.03
239.0665 C10H11N2O5+ 3 239.0662 1.22
241.1296 C10H17N4O3+ 1 241.1295 0.43
251.1503 C12H19N4O2+ 1 251.1503 0.07
252.0975 C11H14N3O4+ 2 252.0979 -1.68
252.1345 C12H18N3O3+ 2 252.1343 1.08
263.1869 C14H23N4O+ 3 263.1866 0.92
269.1246 C11H17N4O4+ 3 269.1244 0.59
272.1358 C10H18N5O4+ 3 272.1353 1.69
278.15 C14H20N3O3+ 3 278.1499 0.4
280.2135 H28N10O7+ 3 280.2137 -0.52
PK$NUM_PEAK: 202
PK$PEAK: m/z int. rel.int.
72.0808 6982.3 13
74.06 2897.3 5
77.0385 15043.5 28
79.0543 49688.5 94
80.0496 9501.6 18
81.0337 2107.1 3
81.0699 1950 3
82.0289 13288.5 25
82.0653 34677.9 65
84.0445 100738.8 191
85.0285 6085.6 11
85.0762 13483.7 25
86.0601 10046.2 19
86.0713 2430.1 4
87.0792 6792.4 12
88.0758 6501.6 12
91.0543 155074.7 294
93.07 65438.9 124
94.0652 10004.5 18
95.0492 98029.3 186
95.0604 34501.9 65
95.0856 6598.9 12
96.0446 10689.3 20
96.0808 7402 14
97.0761 57506 109
98.0601 49027.2 93
99.019 10230.9 19
99.0918 53551 101
100.0871 1939.2 3
101.0709 2372.1 4
102.0465 7696.1 14
102.055 10929.4 20
103.0543 402415.3 763
104.0577 3384.4 6
105.0449 15723.7 29
105.07 273517.9 519
106.0653 1681.6 3
106.0733 1511.5 2
107.0857 280584.9 532
108.081 6995.8 13
108.0889 2169.6 4
109.0649 18322.6 34
109.0761 2085.8 3
110.0602 16200 30
110.0966 6248.9 11
111.092 7255.9 13
112.0394 16964.1 32
112.087 193890.6 367
113.0234 3510 6
113.0711 31157.7 59
114.0551 7729.2 14
114.0664 1803.4 3
114.1027 31040.3 58
115.0543 66071.2 125
115.0867 108043.5 205
116.0621 6473.7 12
116.0707 19545.4 37
117.07 106321.2 201
119.0603 2149.1 4
119.0689 1796.7 3
119.0856 14271.4 27
120.0572 15058.1 28
120.0809 28116.4 53
121.0649 2037.7 3
121.0761 13276.1 25
121.1013 3037.8 5
122.0601 6351.3 12
122.0714 2669.1 5
122.0965 7316.2 13
123.0554 2873.8 5
123.0918 17337.4 32
124.0759 7907.1 15
124.0872 6137.4 11
124.1122 8544.5 16
125.0711 19401.9 36
125.1073 3395.6 6
126.0553 1623.8 3
126.0663 2260.2 4
127.0867 526430.9 999
128.0342 2425.6 4
128.0622 3620.1 6
128.0707 8275.2 15
128.0899 2226.6 4
129.0702 6435.9 12
130.0501 18906.7 35
130.0651 5333.2 10
130.0781 1565.3 2
130.0976 18212.4 34
131.0857 17833.6 33
132.0807 2307.2 4
133.1013 8434.5 16
135.0805 355400.2 674
135.1169 103475.2 196
136.0757 8312.5 15
136.0839 2912.1 5
137.071 2272.2 4
137.1074 6197.9 11
138.055 28172.9 53
138.0662 8516.1 16
138.0914 2296.1 4
138.1029 1531.7 2
139.0867 26808.6 50
139.0979 8548.7 16
139.1228 3519.3 6
140.0707 6958.6 13
140.0818 40563.3 76
141.0658 58359.1 110
141.1023 3042.9 5
143.0859 5562.3 10
144.0811 1823.9 3
145.1015 13010.2 24
146.0967 1987.7 3
147.0805 2830.9 5
149.0711 29679.6 56
150.1029 11073.1 21
151.0868 12865.5 24
152.071 10765.2 20
152.0821 2932.1 5
152.1185 2469.6 4
153.1025 16632.8 31
155.0815 57806.2 109
155.1182 7086.6 13
156.1247 2031.1 3
157.1085 34639.7 65
158.0924 24962.1 47
159.1168 3514.7 6
161.0962 3528.2 6
162.1029 10876.4 20
163.0868 10817.7 20
163.1118 31487.2 59
164.0709 12005.8 22
164.0819 7999 15
164.1184 2231.3 4
165.1022 13330.7 25
166.086 1711.5 3
166.0976 6712.5 12
167.0815 93154.1 176
168.0656 16690 31
169.0973 9866.1 18
170.0967 2786.5 5
171.1125 2800.5 5
172.1125 17468.2 33
173.0964 2119 4
174.1352 8097.5 15
175.1193 21877 41
177.1023 5879.2 11
178.0975 11773.3 22
179.0814 2206.5 4
180.1132 9039.2 17
181.0977 8900.6 16
182.1038 11396.8 21
182.1289 2958.8 5
183.088 21739.8 41
190.0982 3822.3 7
191.082 6892.1 13
192.1131 2142.2 4
193.0973 9797 18
194.0926 2224.2 4
194.129 1977 3
195.0764 46340.4 87
195.1165 2639.2 5
196.0605 11984.6 22
196.1082 8038.7 15
197.1395 22618.2 42
199.1071 2245.3 4
200.1141 22308.4 42
201.0983 16981.2 32
205.0974 1613.1 3
205.1082 1819.4 3
206.0926 3597.1 6
207.1245 2275.2 4
208.1082 12779.5 24
209.0923 14282.3 27
210.1241 2574.3 4
211.0713 11584.3 21
211.1189 17998.6 34
212.1033 4206.7 7
213.0871 75987.5 144
214.167 2335.1 4
217.1339 1881.4 3
218.1544 2485.9 4
220.108 1654.7 3
221.0921 5555.6 10
222.1239 2915.1 5
223.1186 10473.6 19
224.1031 5754.6 10
225.1345 6181 11
226.1188 19492.2 36
226.1589 5891.8 11
227.1029 5836.1 11
234.1242 3541.7 6
235.1194 2275.1 4
239.0665 21527.7 40
241.1296 2822.9 5
251.1503 2474.3 4
252.0975 2084 3
252.1345 2773.9 5
263.1869 2356.8 4
269.1246 7640.7 14
272.1358 2669.1 5
278.15 1802.3 3
280.2135 1694.1 3
//
