ACCESSION: MSBNK-Eawag-EQ325005
RECORD_TITLE: Microcystin-RR; LC-ESI-QFT; MS2; CE: 75; 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 75 (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$SPLASH: splash10-0zfr-3900000000-7a46ae08ed12879d09fb
PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm)
72.0808 C4H10N+ 1 72.0808 0.89
74.0601 C3H8NO+ 1 74.06 0.67
74.0965 C4H12N+ 1 74.0964 1
77.0386 C6H5+ 1 77.0386 0.69
79.0543 C6H7+ 1 79.0542 0.93
80.0495 C5H6N+ 1 80.0495 0.93
81.0336 C5H5O+ 1 81.0335 0.97
81.07 C6H9+ 1 81.0699 1.15
82.0288 C4H4NO+ 1 82.0287 0.61
82.0652 C5H8N+ 1 82.0651 1.27
83.0605 C4H7N2+ 1 83.0604 1.63
84.0445 C4H6NO+ 1 84.0444 1.19
85.0286 C4H5O2+ 1 85.0284 2.05
85.0761 C4H9N2+ 1 85.076 1
86.0601 C4H8NO+ 1 86.06 0.58
86.0715 C3H8N3+ 1 86.0713 2.63
87.0792 C3H9N3+ 1 87.0791 0.82
91.0543 C7H7+ 1 91.0542 0.92
92.0622 C7H8+ 1 92.0621 1.07
93.07 C7H9+ 1 93.0699 1
94.0653 C6H8N+ 1 94.0651 1.43
95.0492 C6H7O+ 1 95.0491 0.83
95.0605 C5H7N2+ 1 95.0604 0.9
96.0445 C5H6NO+ 1 96.0444 0.93
96.0808 C6H10N+ 1 96.0808 0.77
97.0761 C5H9N2+ 1 97.076 1.29
98.0601 C5H8NO+ 1 98.06 0.91
99.019 C3H3N2O2+ 1 99.0189 0.87
99.0918 C5H11N2+ 1 99.0917 1.26
100.0759 C5H10NO+ 1 100.0757 1.99
102.0466 C8H6+ 1 102.0464 1.94
102.0552 C4H8NO2+ 1 102.055 2.79
103.0543 C8H7+ 1 103.0542 1.2
104.0578 C3H8N2O2+ 1 104.058 -2.2
105.0448 C6H5N2+ 1 105.0447 1.1
105.07 C8H9+ 1 105.0699 1.08
106.0527 C6H6N2+ 1 106.0525 1.42
106.0733 C3H10N2O2+ 1 106.0737 -3.29
107.0856 C8H11+ 1 107.0855 1.06
108.0682 C6H8N2+ 1 108.0682 -0.09
108.0808 C7H10N+ 1 108.0808 0.5
109.0649 C7H9O+ 1 109.0648 1.09
109.0761 C6H9N2+ 1 109.076 1.06
110.0238 C5H4NO2+ 1 110.0237 0.96
110.0601 C6H8NO+ 1 110.06 0.18
110.0715 C5H8N3+ 1 110.0713 1.78
110.0966 C7H12N+ 1 110.0964 1.95
111.0553 C5H7N2O+ 1 111.0553 -0.26
111.0918 C6H11N2+ 1 111.0917 1.58
112.0394 C5H6NO2+ 1 112.0393 0.67
112.0871 C5H10N3+ 1 112.0869 1.3
113.0234 C5H5O3+ 1 113.0233 0.88
113.071 C5H9N2O+ 1 113.0709 0.27
114.0551 C5H8NO2+ 1 114.055 1.27
114.1027 C5H12N3+ 1 114.1026 1.02
115.0504 C4H7N2O2+ 1 115.0502 1.44
115.0543 C9H7+ 1 115.0542 0.9
115.0867 C5H11N2O+ 1 115.0866 1.4
116.062 C9H8+ 1 116.0621 -0.79
116.0707 C5H10NO2+ 1 116.0706 1.08
117.07 C9H9+ 1 117.0699 0.8
118.0651 C8H8N+ 1 118.0651 0.04
119.0604 C7H7N2+ 1 119.0604 0.3
119.0856 C9H11+ 1 119.0855 0.36
120.0568 C8H8O+ 1 120.057 -1.14
120.0809 C8H10N+ 1 120.0808 1.28
121.0648 C8H9O+ 1 121.0648 0.24
121.0761 C7H9N2+ 1 121.076 0.62
122.0601 C7H8NO+ 1 122.06 0.9
122.0716 C6H8N3+ 1 122.0713 2.76
122.0965 C8H12N+ 1 122.0964 0.61
123.0554 C6H7N2O+ 1 123.0553 0.49
123.0917 C7H11N2+ 1 123.0917 0.37
124.0395 C6H6NO2+ 1 124.0393 1.82
124.0756 C7H10NO+ 1 124.0757 -0.49
124.0869 C6H10N3+ 1 124.0869 -0.11
124.1124 C8H14N+ 1 124.1121 2.21
125.0713 C6H9N2O+ 1 125.0709 3.04
125.1075 C7H13N2+ 1 125.1073 1.08
126.0663 C5H8N3O+ 1 126.0662 0.89
127.0867 C6H11N2O+ 1 127.0866 0.95
128.0344 C5H6NO3+ 1 128.0342 1.25
128.062 C10H8+ 1 128.0621 -0.25
128.0708 C6H10NO2+ 1 128.0706 1.84
128.0901 CH12N4O3+ 1 128.0904 -2.04
129.0699 C10H9+ 1 129.0699 0.26
130.0501 C5H8NO3+ 1 130.0499 1.62
130.0652 C9H8N+ 1 130.0651 0.88
130.0779 C10H10+ 1 130.0777 1.29
130.0977 C5H12N3O+ 1 130.0975 1.32
131.0855 C10H11+ 1 131.0855 0.1
132.0808 C9H10N+ 1 132.0808 0.41
133.1016 C10H13+ 1 133.1012 2.8
135.0805 C9H11O+ 1 135.0804 0.58
135.1169 C10H15+ 1 135.1168 0.62
136.0758 C8H10NO+ 1 136.0757 0.95
136.1123 C9H14N+ 1 136.1121 1.35
137.0714 C7H9N2O+ 1 137.0709 3.36
137.1078 C8H13N2+ 1 137.1073 3.39
138.0552 C7H8NO2+ 1 138.055 1.63
138.0662 C6H8N3O+ 1 138.0662 0.37
138.0915 C8H12NO+ 1 138.0913 1.08
138.1028 C7H12N3+ 1 138.1026 2
139.0867 C7H11N2O+ 1 139.0866 0.87
140.0708 C7H10NO2+ 1 140.0706 1.11
140.0819 C6H10N3O+ 1 140.0818 0.65
141.0658 C6H9N2O2+ 1 141.0659 -0.24
141.1025 C7H13N2O+ 1 141.1022 1.85
143.0859 C11H11+ 1 143.0855 2.47
144.0809 C10H10N+ 1 144.0808 1.07
145.1013 C11H13+ 1 145.1012 0.99
146.0962 C10H12N+ 1 146.0964 -1.82
147.0807 C10H11O+ 1 147.0804 1.62
149.0712 C8H9N2O+ 1 149.0709 1.75
150.103 C8H12N3+ 1 150.1026 3.17
151.0866 C8H11N2O+ 1 151.0866 0.4
152.0709 C8H10NO2+ 1 152.0706 1.87
152.082 C7H10N3O+ 1 152.0818 0.93
153.1024 C8H13N2O+ 1 153.1022 0.98
155.0816 C7H11N2O2+ 1 155.0815 0.94
157.1085 C6H13N4O+ 1 157.1084 0.72
158.0919 C6H12N3O2+ 1 158.0924 -2.87
160.1119 C11H14N+ 1 160.1121 -1.41
162.1029 C9H12N3+ 1 162.1026 1.89
163.0865 C9H11N2O+ 1 163.0866 -0.67
163.1117 C11H15O+ 1 163.1117 -0.32
164.0707 C9H10NO2+ 1 164.0706 0.52
164.0822 C8H10N3O+ 1 164.0818 1.96
165.0703 C13H9+ 1 165.0699 2.69
165.1026 C9H13N2O+ 1 165.1022 1.88
166.0976 C8H12N3O+ 1 166.0975 0.79
167.0814 C8H11N2O2+ 1 167.0815 -0.5
168.0656 C8H10NO3+ 1 168.0655 0.18
169.0973 C8H13N2O2+ 1 169.0972 0.74
170.0966 C12H12N+ 1 170.0964 0.79
172.1123 C12H14N+ 1 172.1121 1.48
177.1026 C10H13N2O+ 1 177.1022 2.09
178.0979 C9H12N3O+ 1 178.0975 2.14
180.1132 C9H14N3O+ 1 180.1131 0.17
181.0975 C9H13N2O2+ 1 181.0972 2.13
182.1038 C7H12N5O+ 1 182.1036 1.01
182.1287 C9H16N3O+ 1 182.1288 -0.43
194.0921 C9H12N3O2+ 1 194.0924 -1.41
195.0765 C9H11N2O3+ 1 195.0764 0.31
196.0603 C9H10NO4+ 1 196.0604 -0.53
199.1084 C9H15N2O3+ 1 199.1077 3.57
201.098 C7H13N4O3+ 1 201.0982 -1.08
209.0925 C10H13N2O3+ 1 209.0921 1.82
213.087 C9H13N2O4+ 1 213.087 0.27
239.0666 C10H11N2O5+ 3 239.0662 1.43
PK$NUM_PEAK: 150
PK$PEAK: m/z int. rel.int.
72.0808 11469.5 19
74.0601 2570.6 4
74.0965 2156.6 3
77.0386 24815.7 42
79.0543 77985.6 133
80.0495 18351.6 31
81.0336 7148.2 12
81.07 3280.7 5
82.0288 20866.6 35
82.0652 44281.7 75
83.0605 2057.3 3
84.0445 82159.3 140
85.0286 10819.5 18
85.0761 13159.4 22
86.0601 17551.5 30
86.0715 1921.7 3
87.0792 2861.3 4
91.0543 216233.5 370
92.0622 1947.8 3
93.07 63310.6 108
94.0653 20354.9 34
95.0492 181887.5 311
95.0605 40464.5 69
96.0445 16134.1 27
96.0808 9893.5 16
97.0761 53868.6 92
98.0601 49198.2 84
99.019 13513.2 23
99.0918 53465.9 91
100.0759 5661 9
102.0466 13707.3 23
102.0552 5687 9
103.0543 582825.4 999
104.0578 6411 10
105.0448 32342.2 55
105.07 252985.6 433
106.0527 2217 3
106.0733 1702.2 2
107.0856 159635.3 273
108.0682 2626.5 4
108.0808 8753.9 15
109.0649 24609.7 42
109.0761 2910.2 4
110.0238 1507.4 2
110.0601 15980.3 27
110.0715 2379.5 4
110.0966 6196 10
111.0553 1743.9 2
111.0918 6838.1 11
112.0394 7463.4 12
112.0871 99284.9 170
113.0234 17412.7 29
113.071 21913.2 37
114.0551 7938 13
114.1027 9557.5 16
115.0504 4745.6 8
115.0543 78359.5 134
115.0867 41383.4 70
116.062 2720.1 4
116.0707 10220.2 17
117.07 74002.4 126
118.0651 2807.5 4
119.0604 7501.3 12
119.0856 19233 32
120.0568 10804.4 18
120.0809 15447.1 26
121.0648 2293.2 3
121.0761 21581.1 36
122.0601 8259.5 14
122.0716 3484.8 5
122.0965 7542.7 12
123.0554 6240.5 10
123.0917 15040.7 25
124.0395 1694.3 2
124.0756 2944.5 5
124.0869 3512.3 6
124.1124 1977.1 3
125.0713 11900 20
125.1075 1778.4 3
126.0663 1586.6 2
127.0867 271879.1 466
128.0344 6231.5 10
128.062 10286.4 17
128.0708 1821.1 3
128.0901 1522.8 2
129.0699 6703 11
130.0501 9880.3 16
130.0652 2196.9 3
130.0779 1685.5 2
130.0977 8570.3 14
131.0855 13524.8 23
132.0808 2621.8 4
133.1016 2824.9 4
135.0805 96700.9 165
135.1169 19714 33
136.0758 7932.9 13
136.1123 1687.5 2
137.0714 2059.2 3
137.1078 2428.9 4
138.0552 7334.1 12
138.0662 6392.3 10
138.0915 3522.4 6
138.1028 3166 5
139.0867 13829 23
140.0708 2670.7 4
140.0819 10873.7 18
141.0658 31828.6 54
141.1025 1697.9 2
143.0859 2905.1 4
144.0809 2116.4 3
145.1013 5596.9 9
146.0962 1946.9 3
147.0807 1719.7 2
149.0712 18378 31
150.103 7430.4 12
151.0866 12393.7 21
152.0709 7024.8 12
152.082 2511.5 4
153.1024 6132.5 10
155.0816 6886.9 11
157.1085 7980.7 13
158.0919 2826 4
160.1119 1507.7 2
162.1029 2500.1 4
163.0865 10479 17
163.1117 3159.2 5
164.0707 9524.6 16
164.0822 1835.5 3
165.0703 2321.3 3
165.1026 6015.1 10
166.0976 3074.7 5
167.0814 47294.8 81
168.0656 8202.5 14
169.0973 1518.9 2
170.0966 7749.3 13
172.1123 9373 16
177.1026 1504.8 2
178.0979 6278.1 10
180.1132 4201.9 7
181.0975 2299 3
182.1038 3375.9 5
182.1287 2356.4 4
194.0921 2255.5 3
195.0765 14644.8 25
196.0603 2749.3 4
199.1084 1594.7 2
201.098 3505.5 6
209.0925 2664.6 4
213.087 7131.5 12
239.0666 1869.1 3
//
