ACCESSION: MSBNK-Eawag-EQ325006
RECORD_TITLE: Microcystin-RR; LC-ESI-QFT; MS2; CE: 90; 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 90 (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$SPLASH: splash10-0udi-6900000000-4ba182a55859b53adcf4
PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm)
72.0808 C4H10N+ 1 72.0808 1.03
74.0601 C3H8NO+ 1 74.06 0.67
77.0386 C6H5+ 1 77.0386 0.56
79.0543 C6H7+ 1 79.0542 1.31
80.0496 C5H6N+ 1 80.0495 1.3
81.0336 C5H5O+ 1 81.0335 1.22
81.0699 C6H9+ 1 81.0699 0.29
82.0289 C4H4NO+ 1 82.0287 1.34
82.0653 C5H8N+ 1 82.0651 1.51
83.0604 C4H7N2+ 1 83.0604 0.79
84.0445 C4H6NO+ 1 84.0444 1.07
85.0285 C4H5O2+ 1 85.0284 0.99
85.0761 C4H9N2+ 1 85.076 1.24
86.0602 C4H8NO+ 1 86.06 1.39
86.0715 C3H8N3+ 1 86.0713 2.86
91.0543 C7H7+ 1 91.0542 0.81
92.0621 C7H8+ 1 92.0621 0.52
93.07 C7H9+ 1 93.0699 0.79
94.0652 C6H8N+ 1 94.0651 0.9
95.0492 C6H7O+ 1 95.0491 0.93
95.0604 C5H7N2+ 1 95.0604 0.69
96.0446 C5H6NO+ 1 96.0444 1.66
96.0808 C6H10N+ 1 96.0808 0.67
97.0761 C5H9N2+ 1 97.076 1.19
98.0601 C5H8NO+ 1 98.06 0.91
99.0191 C3H3N2O2+ 1 99.0189 1.78
99.0918 C5H11N2+ 1 99.0917 1.16
100.0757 C5H10NO+ 1 100.0757 0.4
102.0465 C8H6+ 1 102.0464 1.36
102.0552 C4H8NO2+ 1 102.055 2.6
103.0543 C8H7+ 1 103.0542 1.2
104.0576 C3H8N2O2+ 1 104.058 -3.64
105.0448 C6H5N2+ 1 105.0447 0.91
105.07 C8H9+ 1 105.0699 1.17
106.0524 C6H6N2+ 1 106.0525 -0.94
106.0652 C7H8N+ 1 106.0651 0.23
107.0856 C8H11+ 1 107.0855 0.96
108.0446 C6H6NO+ 1 108.0444 1.48
108.0683 C6H8N2+ 1 108.0682 0.65
108.0809 C7H10N+ 1 108.0808 0.78
109.065 C7H9O+ 1 109.0648 1.64
109.0763 C6H9N2+ 1 109.076 2.43
110.0238 C5H4NO2+ 1 110.0237 1.5
110.0601 C6H8NO+ 1 110.06 0.63
110.0714 C5H8N3+ 1 110.0713 1.06
110.0966 C7H12N+ 1 110.0964 1.4
111.0553 C5H7N2O+ 1 111.0553 0.19
111.0919 C6H11N2+ 1 111.0917 2.12
112.0395 C5H6NO2+ 1 112.0393 1.3
112.087 C5H10N3+ 1 112.0869 0.95
113.0235 C5H5O3+ 1 113.0233 1.94
113.071 C5H9N2O+ 1 113.0709 0.98
114.0551 C5H8NO2+ 1 114.055 1.54
114.1027 C5H12N3+ 1 114.1026 0.76
115.0543 C9H7+ 1 115.0542 0.64
115.0867 C5H11N2O+ 1 115.0866 1.22
116.0622 C9H8+ 1 116.0621 1.36
116.0709 C5H10NO2+ 1 116.0706 2.2
117.07 C9H9+ 1 117.0699 0.8
118.0653 C8H8N+ 1 118.0651 1.39
119.0494 C8H7O+ 1 119.0491 2.09
119.0605 C7H7N2+ 1 119.0604 1.22
119.0856 C9H11+ 1 119.0855 0.87
120.057 C8H8O+ 1 120.057 -0.05
120.0808 C8H10N+ 1 120.0808 0.45
121.0761 C7H9N2+ 1 121.076 0.62
122.0602 C7H8NO+ 1 122.06 1.14
122.0965 C8H12N+ 1 122.0964 0.85
123.0556 C6H7N2O+ 1 123.0553 2.53
123.0918 C7H11N2+ 1 123.0917 1.18
124.0759 C7H10NO+ 1 124.0757 2.01
124.0871 C6H10N3+ 1 124.0869 1.42
125.071 C6H9N2O+ 1 125.0709 0.57
127.0867 C6H11N2O+ 1 127.0866 0.79
128.0623 C10H8+ 1 128.0621 1.94
129.0699 C10H9+ 1 129.0699 0.34
130.0503 C5H8NO3+ 1 130.0499 2.93
130.0654 C9H8N+ 1 130.0651 2.26
130.0976 C5H12N3O+ 1 130.0975 0.86
131.0858 C10H11+ 1 131.0855 2.16
132.0808 C9H10N+ 1 132.0808 -0.12
133.1015 C10H13+ 1 133.1012 2.13
135.0806 C9H11O+ 1 135.0804 1.17
135.1171 C10H15+ 1 135.1168 1.73
137.1071 C8H13N2+ 1 137.1073 -1.79
138.0549 C7H8NO2+ 1 138.055 -0.4
138.0662 C6H8N3O+ 1 138.0662 0.45
138.0914 C8H12NO+ 1 138.0913 0.72
139.0867 C7H11N2O+ 1 139.0866 1.08
141.0657 C6H9N2O2+ 1 141.0659 -1.02
146.0966 C10H12N+ 1 146.0964 1.33
149.0712 C8H9N2O+ 1 149.0709 1.75
149.1078 C9H13N2+ 1 149.1073 3.39
151.0868 C8H11N2O+ 1 151.0866 1.2
152.0711 C8H10NO2+ 1 152.0706 3.32
162.1025 C9H12N3+ 1 162.1026 -0.7
163.0867 C9H11N2O+ 1 163.0866 0.74
164.0822 C8H10N3O+ 1 164.0818 2.26
165.0703 C13H9+ 1 165.0699 2.56
165.1025 C9H13N2O+ 1 165.1022 1.7
166.0974 C8H12N3O+ 1 166.0975 -0.59
167.0813 C8H11N2O2+ 1 167.0815 -1.34
170.0966 C12H12N+ 1 170.0964 0.79
178.0978 C9H12N3O+ 1 178.0975 1.81
195.0766 C9H11N2O3+ 1 195.0764 0.98
PK$NUM_PEAK: 105
PK$PEAK: m/z int. rel.int.
72.0808 7692 11
74.0601 1417.4 2
77.0386 43469 65
79.0543 83407.3 124
80.0496 33536 50
81.0336 7029.3 10
81.0699 6119 9
82.0289 19518.8 29
82.0653 36563.4 54
83.0604 2091.2 3
84.0445 72036.2 107
85.0285 15640.8 23
85.0761 11969.4 17
86.0602 9804.6 14
86.0715 2109.9 3
91.0543 284207.2 425
92.0621 5895.4 8
93.07 44508.7 66
94.0652 17829.8 26
95.0492 289652.4 433
95.0604 39481.7 59
96.0446 18434.5 27
96.0808 9538.9 14
97.0761 39060 58
98.0601 41941.5 62
99.0191 9994.1 14
99.0918 29949 44
100.0757 5597 8
102.0465 23356.8 34
102.0552 2641.8 3
103.0543 667406.6 999
104.0576 10037.4 15
105.0448 44284.9 66
105.07 180198.9 269
106.0524 2344 3
106.0652 1911.4 2
107.0856 83096.2 124
108.0446 1748.1 2
108.0683 2375.9 3
108.0809 10413.3 15
109.065 19828.6 29
109.0763 3203.3 4
110.0238 2070.1 3
110.0601 9850.3 14
110.0714 2295.3 3
110.0966 5360.8 8
111.0553 1755.7 2
111.0919 1863.6 2
112.0395 3032.1 4
112.087 47653.2 71
113.0235 18108.7 27
113.071 6680.6 9
114.0551 3343.4 5
114.1027 5590.1 8
115.0543 98220.8 147
115.0867 14764.2 22
116.0622 9047.9 13
116.0709 5640.5 8
117.07 44263.2 66
118.0653 3415.1 5
119.0494 1383.6 2
119.0605 6721.6 10
119.0856 9302.1 13
120.057 9709 14
120.0808 10006.3 14
121.0761 25793.8 38
122.0602 6500.7 9
122.0965 2323 3
123.0556 1380.7 2
123.0918 9548.4 14
124.0759 2679.3 4
124.0871 2527.6 3
125.071 10206 15
127.0867 114802.1 171
128.0623 11352.8 16
129.0699 9645.5 14
130.0503 2533.6 3
130.0654 2033.5 3
130.0976 6434.9 9
131.0858 5570 8
132.0808 2995.4 4
133.1015 1517.4 2
135.0806 23125.6 34
135.1171 1927.7 2
137.1071 1382.1 2
138.0549 1630 2
138.0662 1961.1 2
138.0914 1667.2 2
139.0867 3976.6 5
141.0657 10237.4 15
146.0966 2098.5 3
149.0712 15602.3 23
149.1078 1965 2
151.0868 5905.6 8
152.0711 2189.8 3
162.1025 1595.3 2
163.0867 6256.8 9
164.0822 1371.1 2
165.0703 6544.8 9
165.1025 6115.4 9
166.0974 1625.6 2
167.0813 16122.2 24
170.0966 5862.2 8
178.0978 2546.6 3
195.0766 2964.7 4
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