ACCESSION: MSBNK-Eawag-EQ325002
RECORD_TITLE: Microcystin-RR; LC-ESI-QFT; MS2; CE: 30; 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 30 (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$SPLASH: splash10-00dr-9110000015-bad9a684383a24b24bfb
PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm)
79.0542 C6H7+ 1 79.0542 0.3
84.0445 C4H6NO+ 1 84.0444 0.83
91.0542 C7H7+ 1 91.0542 -0.62
93.0699 C7H9+ 1 93.0699 0.68
102.0548 C4H8NO2+ 1 102.055 -1.22
103.0541 C8H7+ 1 103.0542 -1.13
105.07 C8H9+ 1 105.0699 0.98
107.0856 C8H11+ 1 107.0855 0.87
112.087 C5H10N3+ 1 112.0869 0.86
113.071 C5H9N2O+ 1 113.0709 0.89
114.1027 C5H12N3+ 1 114.1026 1.19
115.0867 C5H11N2O+ 1 115.0866 1.05
117.0699 C9H9+ 1 117.0699 0.37
124.112 C8H14N+ 1 124.1121 -0.85
127.0866 C6H11N2O+ 1 127.0866 0.24
129.1136 C5H13N4+ 1 129.1135 0.6
131.0856 C10H11+ 1 131.0855 0.71
135.0805 C9H11O+ 1 135.0804 0.8
135.1169 C10H15+ 1 135.1168 0.24
138.0549 C7H8NO2+ 1 138.055 -0.18
139.123 C8H15N2+ 1 139.123 0.04
140.0816 C6H10N3O+ 1 140.0818 -1.63
143.0857 C11H11+ 1 143.0855 1.42
155.0816 C7H11N2O2+ 1 155.0815 0.49
156.1244 C6H14N5+ 1 156.1244 0.44
157.1085 C6H13N4O+ 1 157.1084 0.46
158.0925 C6H12N3O2+ 1 158.0924 0.55
163.1118 C11H15O+ 1 163.1117 0.11
167.0814 C8H11N2O2+ 1 167.0815 -0.86
174.1352 C6H16N5O+ 1 174.1349 1.23
175.1189 C6H15N4O2+ 1 175.119 -0.07
183.0878 C7H11N4O2+ 1 183.0877 0.7
186.1241 C8H16N3O2+ 2 186.1237 2.24
195.0763 C9H11N2O3+ 1 195.0764 -0.4
198.1233 C9H16N3O2+ 2 198.1237 -2.14
199.1298 C7H15N6O+ 3 199.1302 -2.14
200.1142 C7H14N5O2+ 1 200.1142 -0.16
209.1323 C16H17+ 4 209.1325 -0.7
211.1192 C9H15N4O2+ 1 211.119 1.13
212.1509 C9H18N5O+ 1 212.1506 1.29
213.0872 C9H13N2O4+ 1 213.087 0.78
213.1348 C9H17N4O2+ 1 213.1346 0.79
217.1341 C13H17N2O+ 1 217.1335 2.53
218.1543 C14H20NO+ 1 218.1539 1.6
223.1197 C10H15N4O2+ 2 223.119 3.35
225.1347 C10H17N4O2+ 1 225.1346 0.61
226.1186 C10H16N3O3+ 1 226.1186 -0.08
226.1591 C16H20N+ 4 226.159 0.42
228.1456 C9H18N5O2+ 1 228.1455 0.26
237.164 C18H21+ 4 237.1638 0.86
238.1189 C11H16N3O3+ 2 238.1186 1.27
239.0667 C10H11N2O5+ 3 239.0662 1.77
240.1459 C10H18N5O2+ 2 240.1455 1.7
241.1298 C10H17N4O3+ 2 241.1295 1.3
243.1447 C10H19N4O3+ 2 243.1452 -1.84
244.1292 C10H18N3O4+ 1 244.1292 -0.13
246.1488 C15H20NO2+ 3 246.1489 -0.22
250.1302 C11H16N5O2+ 2 250.1299 1.23
258.1563 C10H20N5O3+ 2 258.1561 1.06
258.1853 C17H24NO+ 4 258.1852 0.11
265.1589 C19H21O+ 4 265.1587 0.82
268.1411 C11H18N5O3+ 2 268.1404 2.44
269.1121 C10H15N5O4+ 3 269.1119 0.83
269.1247 C11H17N4O4+ 3 269.1244 1
269.1612 C12H21N4O3+ 2 269.1608 1.31
280.214 H28N10O7+ 3 280.2137 1.2
285.167 C11H21N6O3+ 4 285.167 0.16
286.151 C11H20N5O4+ 5 286.151 0.24
292.155 C2H24N6O10+ 5 292.1548 0.51
294.1563 C13H20N5O3+ 2 294.1561 0.83
303.1775 C11H23N6O4+ 5 303.1775 0.07
311.1831 C13H23N6O3+ 3 311.1826 1.59
312.1661 C13H22N5O4+ 3 312.1666 -1.73
328.2098 C13H26N7O3+ 3 328.2092 2
329.1934 C13H25N6O4+ 6 329.1932 0.73
357.1874 C13H19N13+ 5 357.1881 -1.93
368.241 C2H32N12O9+ 5 368.241 0.1
383.2045 C2H29N11O11+ 6 383.2043 0.59
389.2053 C3H27N13O9+ 7 389.2049 0.95
397.2602 C9H35N9O8+ 8 397.2603 -0.33
407.2159 C3H29N13O10+ 8 407.2155 1.02
408.1995 C3H28N12O11+ 8 408.1995 -0.13
440.226 C4H32N12O12+ 10 440.2257 0.55
469.3293 C12H43N11O8+ 7 469.3291 0.47
484.2147 C33H28N2O2+ 9 484.2145 0.35
523.2647 C38H35O2+ 10 523.2632 2.97
554.3047 C24H46N2O12+ 12 554.3045 0.3
571.316 C19H43N10O10+ 11 571.3158 0.33
571.3607 C16H49N11O11+ 11 571.3608 -0.13
595.343 C40H43N4O+ 12 595.3431 -0.15
599.3555 C17H49N11O12+ 11 599.3557 -0.23
620.3443 C33H50NO10+ 12 620.3429 2.27
664.3511 C44H46N3O3+ 13 664.3534 -3.35
700.4037 C36H50N11O4+ 12 700.4042 -0.64
728.3983 C36H54N7O9+ 12 728.3978 0.77
753.4301 C39H53N12O4+ 10 753.4307 -0.78
754.4121 C36H54N10O8+ 11 754.4121 -0.01
865.4461 C43H61N8O11+ 7 865.4454 0.75
866.469 C38H64N11O12+ 7 866.473 -4.71
869.464 C42H63N9O11+ 6 869.4642 -0.19
876.5087 C44H66N11O8+ 8 876.509 -0.4
882.4709 C41H62N12O10+ 5 882.4706 0.34
887.4745 C42H65N9O12+ 5 887.4747 -0.27
890.5358 C44H68N13O7+ 7 890.5359 -0.17
899.5044 C49H63N12O5+ 3 899.5039 0.61
909.5309 C44H69N12O9+ 6 909.5305 0.45
910.5188 C49H68N9O8+ 6 910.5185 0.26
924.5718 C49H72N12O6+ 3 924.5692 2.81
926.558 C46H74N10O10+ 5 926.5584 -0.42
929.4893 C49H67N7O11+ 3 929.4893 -0.01
933.5658 C44H75N11O11+ 3 933.5642 1.71
947.5025 C49H69N7O12+ 2 947.4999 2.73
949.5641 C49H75N9O10+ 2 949.5631 1.02
950.5381 C49H68N13O7+ 3 950.5359 2.34
952.5671 C49H76N8O11+ 2 952.5628 4.54
959.547 C48H71N12O9+ 2 959.5461 0.86
960.53 C48H70N11O10+ 2 960.5302 -0.21
961.5176 C48H69N10O11+ 2 961.5142 3.51
966.5909 C47H76N13O9+ 1 966.5883 2.62
968.5531 C47H74N11O11+ 2 968.5564 -3.36
971.5118 C48H67N12O10+ 1 971.5098 2.08
974.5588 C48H72N13O9+ 2 974.557 1.79
975.5412 C48H71N12O10+ 1 975.5411 0.13
977.5596 C48H73N12O10+ 1 977.5567 2.95
978.5415 C48H72N11O11+ 1 978.5407 0.78
985.5238 C49H69N12O10+ 1 985.5254 -1.68
986.5138 C49H68N11O11+ 1 986.5094 4.39
989.5219 C48H69N12O11+ 1 989.5203 1.62
992.5694 C48H74N13O10+ 1 992.5676 1.78
993.5527 C48H73N12O11+ 1 993.5516 1.09
996.552 C48H74N11O12+ 1 996.5513 0.66
997.5571 C48H75N11O12+ 1 997.5591 -1.97
1002.5522 C49H72N13O10+ 1 1002.552 0.28
1003.5366 C49H71N12O11+ 1 1003.536 0.6
1004.5323 C48H70N13O11+ 1 1004.5312 1.07
1010.5809 C48H76N13O11+ 1 1010.5782 2.69
1020.5628 C49H74N13O11+ 1 1020.5625 0.25
1021.5496 C49H73N12O12+ 1 1021.5465 2.96
1038.5737 C49H76N13O12+ 1 1038.5731 0.61
1040.5753 C48H76N14O12+ 1 1040.5762 -0.83
PK$NUM_PEAK: 141
PK$PEAK: m/z int. rel.int.
79.0542 1790.9 2
84.0445 2683.5 3
91.0542 3618.7 4
93.0699 1826 2
102.0548 1518.5 1
103.0541 2254.2 2
105.07 3704.8 4
107.0856 24806.5 31
112.087 26798.2 34
113.071 3794.1 4
114.1027 2361.8 3
115.0867 22186.6 28
117.0699 1997.3 2
124.112 1919.2 2
127.0866 28797 36
129.1136 2196 2
131.0856 2128.2 2
135.0805 92283.3 117
135.1169 24889 31
138.0549 2233.9 2
139.123 6005.7 7
140.0816 2259.5 2
143.0857 2695.9 3
155.0816 24555.6 31
156.1244 20563.3 26
157.1085 35231.6 44
158.0925 3502.5 4
163.1118 39233.4 50
167.0814 3349.6 4
174.1352 42370.9 54
175.1189 10069.4 12
183.0878 3227.6 4
186.1241 5937.9 7
195.0763 11346.6 14
198.1233 1808.4 2
199.1298 3440.3 4
200.1142 14161.6 18
209.1323 3060.1 3
211.1192 3797.1 4
212.1509 2324.1 2
213.0872 49048.2 62
213.1348 20596.3 26
217.1341 1968.4 2
218.1543 2875.7 3
223.1197 2397.1 3
225.1347 8461.4 10
226.1186 4425.6 5
226.1591 3426.3 4
228.1456 2263.2 2
237.164 13445.3 17
238.1189 10568.7 13
239.0667 6955.4 8
240.1459 3543.3 4
241.1298 3346.2 4
243.1447 6994.5 8
244.1292 11278.5 14
246.1488 9080.2 11
250.1302 2020.1 2
258.1563 6286.9 8
258.1853 21994.6 28
265.1589 11878 15
268.1411 11130.3 14
269.1121 3173.6 4
269.1247 11493.1 14
269.1612 14538.5 18
280.214 2701.6 3
285.167 48165.7 61
286.151 49915.8 63
292.155 6399.8 8
294.1563 19338.2 24
303.1775 74024.4 94
311.1831 25549.4 32
312.1661 5781.8 7
328.2098 11042.3 14
329.1934 36034.8 45
357.1874 6484.3 8
368.241 9407.6 12
383.2045 3060.5 3
389.2053 1933.1 2
397.2602 1913.2 2
407.2159 7531.5 9
408.1995 3631.7 4
440.226 65793.8 83
469.3293 10070.2 12
484.2147 12882.3 16
523.2647 10966.9 13
554.3047 17674.6 22
571.316 5032.6 6
571.3607 22569.4 28
595.343 15700.2 20
599.3555 100063.1 127
620.3443 17967.8 22
664.3511 16262.4 20
700.4037 18553.4 23
728.3983 106533.1 135
753.4301 19555.3 24
754.4121 32385.3 41
865.4461 32968 42
866.469 5872.7 7
867.5098 162274.9393 207
869.464 13463.3 17
876.5087 6747.9 8
882.4709 22332.3 28
887.4745 10371.9 13
890.5358 7765.9 9
899.5044 13509.1 17
909.5309 70399.4 89
910.5188 14412.3 18
924.5718 3073.6 3
926.558 50450.8 64
929.4893 7279.9 9
933.5658 2799.9 3
947.5025 1865.7 2
949.5641 21804.4 27
950.5381 15249.1 19
952.5671 11136.1 14
959.547 23895.9 30
960.53 39300.8 50
961.5176 28254.5 36
966.5909 16559.4 21
968.5531 6998.3 8
971.5118 6188.4 7
974.5588 2412 3
975.5412 35120.1 44
977.5596 12921.5 16
978.5415 231145.2 295
985.5238 8913.8 11
986.5138 2804.8 3
989.5219 12519.2 15
992.5694 21601.9 27
993.5527 51471.3 65
996.552 473694.4 604
997.5571 32563.7 41
1002.5522 52110.5 66
1003.5366 276892.7 353
1004.5323 44042.3 56
1010.5809 9926.5 12
1020.5628 782678.3 999
1021.5496 412296.3 526
1038.5737 540775.1 690
1040.5753 3067.8 3
//
