ACCESSION: MSBNK-NaToxAq-NA003516
RECORD_TITLE: Protopin; LC-ESI-ITFT; MS2; CE: 95%; R=15000; [M+H]+
DATE: 2020.02.22
AUTHORS: Tobias Schulze, Martin Krauss, Helmholtz Centre for Environmental Research GmbH - UFZ, Leipzig, Germany
LICENSE: CC0
COPYRIGHT: Copyright (C) 2020 by Helmholtz Centre for Environmental Research GmbH - UFZ, Leipzig, Germany
COMMENT: CONFIDENCE Reference Standard (Level 1)
COMMENT: INTERNAL_ID 2281
CH$NAME: Protopin
CH$NAME: Protopine
CH$NAME: 15-methyl-7,9,19,21-tetraoxa-15-azapentacyclo[15.7.0.04,12.06,10.018,22]tetracosa-1(17),4,6(10),11,18(22),23-hexaen-3-one
CH$COMPOUND_CLASS: N/A; Environmental Standard
CH$FORMULA: C20H19NO5
CH$EXACT_MASS: 353.1263
CH$SMILES: CN1CCC2=CC3=C(C=C2C(=O)CC4=C(C1)C5=C(C=C4)OCO5)OCO3
CH$IUPAC: InChI=1S/C20H19NO5/c1-21-5-4-13-7-18-19(25-10-24-18)8-14(13)16(22)6-12-2-3-17-20(15(12)9-21)26-11-23-17/h2-3,7-8H,4-6,9-11H2,1H3
CH$LINK: CAS
130-86-9
CH$LINK: CHEBI
16415
CH$LINK: KEGG
C05189
CH$LINK: PUBCHEM
CID:4970
CH$LINK: INCHIKEY
GPTFURBXHJWNHR-UHFFFAOYSA-N
CH$LINK: CHEMSPIDER
4799
CH$LINK: COMPTOX
DTXSID90156282
AC$INSTRUMENT: LTQ Orbitrap XL Thermo Scientific
AC$INSTRUMENT_TYPE: LC-ESI-ITFT
AC$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 95% (nominal)
AC$MASS_SPECTROMETRY: RESOLUTION 15000
AC$CHROMATOGRAPHY: COLUMN_NAME Kinetex Evo C18 2.6 um 50x2.1 mm, Phenomenex
AC$CHROMATOGRAPHY: FLOW_GRADIENT 95/5 at 0 min, 95/5 at 1 min, 0/100 at 13 min, 0/100 at 24 min, 95/5 at 24.3 min, 95/5/0 at 32 min
AC$CHROMATOGRAPHY: FLOW_RATE 300 uL/min
AC$CHROMATOGRAPHY: RETENTION_TIME 6.681 min
AC$CHROMATOGRAPHY: SOLVENT A water with 0.1% formic acid
AC$CHROMATOGRAPHY: SOLVENT B methanol with 0.1% formic acid
MS$FOCUSED_ION: BASE_PEAK 354.1335
MS$FOCUSED_ION: PRECURSOR_M/Z 354.1336
MS$FOCUSED_ION: PRECURSOR_TYPE [M+H]+
MS$DATA_PROCESSING: RECALIBRATE loess on assigned fragments and MS1
MS$DATA_PROCESSING: REANALYZE Peaks with additional N2/O included
MS$DATA_PROCESSING: WHOLE RMassBank 2.14.1
PK$SPLASH: splash10-000i-0910000000-766cb7c2c199dc4424f2
PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm)
65.0385 C5H5+ 1 65.0386 -1.9
77.0385 C6H5+ 1 77.0386 -0.48
79.0542 C6H7+ 1 79.0542 -0.35
89.0385 C7H5+ 1 89.0386 -0.34
91.0542 C7H7+ 1 91.0542 -0.37
93.0697 C7H9+ 1 93.0699 -1.72
94.0415 C6H6O+ 1 94.0413 1.79
95.049 C6H7O+ 1 95.0491 -1.2
103.0542 C8H7+ 1 103.0542 -0.25
105.0334 C7H5O+ 1 105.0335 -0.88
107.0491 C7H7O+ 1 107.0491 -0.28
115.0541 C9H7+ 1 115.0542 -1.08
116.0495 C8H6N+ 1 116.0495 -0.05
117.0334 C8H5O+ 1 117.0335 -0.71
117.0572 C8H7N+ 1 117.0573 -0.63
117.0699 C9H9+ 1 117.0699 0.19
118.0651 C8H8N+ 1 118.0651 -0.42
119.0491 C8H7O+ 1 119.0491 -0.17
120.0806 C8H10N+ 1 120.0808 -1.67
121.0647 C8H9O+ 1 121.0648 -0.96
130.0651 C9H8N+ 1 130.0651 -0.37
131.0491 C9H7O+ 1 131.0491 -0.55
131.0729 C9H9N+ 1 131.073 -0.36
132.0565 C9H8O+ 1 132.057 -3.67
132.0807 C9H10N+ 1 132.0808 -0.59
135.044 C8H7O2+ 1 135.0441 -0.12
136.0519 C8H8O2+ 1 136.0519 0.44
143.0493 C10H7O+ 1 143.0491 1.38
143.0727 C10H9N+ 1 143.073 -1.65
144.0807 C10H10N+ 1 144.0808 -0.59
146.06 C9H8NO+ 1 146.06 -0.01
147.044 C9H7O2+ 1 147.0441 -0.08
148.0756 C9H10NO+ 1 148.0757 -0.75
149.0596 C9H9O2+ 1 149.0597 -0.51
151.0541 C12H7+ 1 151.0542 -1.05
152.062 C12H8+ 1 152.0621 -0.05
153.0696 C12H9+ 1 153.0699 -1.85
158.0602 C10H8NO+ 1 158.06 1.15
159.0441 C10H7O2+ 1 159.0441 0.11
159.0678 C10H9NO+ 1 159.0679 -0.11
160.0756 C10H10NO+ 1 160.0757 -0.69
161.0598 C10H9O2+ 1 161.0597 0.58
161.0801 C7H13O4+ 1 161.0808 -4.61
163.0389 C9H7O3+ 1 163.039 -0.32
164.0621 C13H8+ 1 164.0621 0.53
165.0546 C9H9O3+ 1 165.0546 -0.24
165.0698 C13H9+ 1 165.0699 -0.41
166.0773 C13H10+ 1 166.0777 -2.34
167.0855 C13H11+ 1 167.0855 -0.23
172.0514 C11H8O2+ 1 172.0519 -2.62
172.076 C11H10NO+ 1 172.0757 1.96
173.0596 C11H9O2+ 1 173.0597 -0.58
174.0549 C10H8NO2+ 1 174.055 -0.04
175.039 C10H7O3+ 1 175.039 0.25
176.062 C14H8+ 1 176.0621 -0.34
177.0698 C14H9+ 1 177.0699 -0.34
177.0785 C10H11NO2+ 1 177.0784 0.21
178.0777 C14H10+ 1 178.0777 -0.26
179.0855 C14H11+ 1 179.0855 -0.26
180.057 C13H8O+ 1 180.057 0.46
181.0647 C13H9O+ 1 181.0648 -0.3
186.0551 C11H8NO2+ 1 186.055 0.57
188.0705 C11H10NO2+ 1 188.0706 -0.58
189.0696 C15H9+ 1 189.0699 -1.66
189.0786 C11H11NO2+ 1 189.0784 0.71
190.0869 C11H12NO2+ 1 190.0863 3.35
191.0854 C15H11+ 1 191.0855 -0.86
192.0567 C14H8O+ 1 192.057 -1.29
193.0653 C14H9O+ 1 193.0648 2.74
194.0724 C14H10O+ 1 194.0726 -1.29
195.0803 C14H11O+ 1 195.0804 -0.5
201.0696 C16H9+ 1 201.0699 -1.49
202.0772 C16H10+ 1 202.0777 -2.39
204.0809 C15H10N+ 1 204.0808 0.47
205.0646 C15H9O+ 1 205.0648 -1.07
205.0887 C15H11N+ 1 205.0886 0.69
206.0805 C11H12NO3+ 1 206.0812 -3.04
207.0803 C15H11O+ 1 207.0804 -0.86
208.052 C14H8O2+ 1 208.0519 0.58
209.0595 C14H9O2+ 1 209.0597 -1.04
217.0646 C16H9O+ 1 217.0648 -0.83
218.0959 C16H12N+ 1 218.0964 -2.53
219.0805 C16H11O+ 1 219.0804 0.36
220.0518 C15H8O2+ 1 220.0519 -0.17
220.1117 C16H14N+ 1 220.1121 -1.9
221.0594 C15H9O2+ 1 221.0597 -1.41
222.0672 C15H10O2+ 1 222.0675 -1.28
223.0759 C15H11O2+ 1 223.0754 2.56
232.0764 C16H10NO+ 1 232.0757 3.24
233.06 C16H9O2+ 1 233.0597 1.42
233.0844 C16H11NO+ 1 233.0835 3.69
234.0674 C16H10O2+ 1 234.0675 -0.48
234.0921 C16H12NO+ 1 234.0913 3.41
235.0752 C16H11O2+ 1 235.0754 -0.74
237.0549 C15H9O3+ 1 237.0546 0.98
237.0905 C16H13O2+ 1 237.091 -2.09
245.0593 C17H9O2+ 1 245.0597 -1.84
246.0677 C17H10O2+ 1 246.0675 0.59
247.0752 C17H11O2+ 1 247.0754 -0.65
248.1068 C17H14NO+ 1 248.107 -0.67
249.054 C16H9O3+ 1 249.0546 -2.38
250.0636 C16H10O3+ 1 250.0624 4.65
262.0862 C17H12NO2+ 1 262.0863 -0.27
263.0692 C17H11O3+ 1 263.0703 -3.9
263.0948 C17H13NO2+ 1 263.0941 2.58
265.0862 C17H13O3+ 1 265.0859 1.21
266.0571 C16H10O4+ 1 266.0574 -1.11
275.0692 C18H11O3+ 1 275.0703 -4
276.1017 C18H14NO2+ 1 276.1019 -0.73
290.0816 C18H12NO3+ 1 290.0812 1.44
292.0957 C18H14NO3+ 1 292.0968 -3.77
304.0976 C19H14NO3+ 1 304.0968 2.4
320.0912 C19H14NO4+ 1 320.0917 -1.72
PK$NUM_PEAK: 113
PK$PEAK: m/z int. rel.int.
65.0385 2852.6 7
77.0385 17986.4 49
79.0542 24901.7 68
89.0385 6479.5 17
91.0542 84378 231
93.0697 4048.7 11
94.0415 1326.1 3
95.049 2532.7 6
103.0542 23200.3 63
105.0334 7201.8 19
107.0491 36818.2 101
115.0541 7629.8 20
116.0495 1862.8 5
117.0334 4691.5 12
117.0572 2925.9 8
117.0699 3913.3 10
118.0651 11084.2 30
119.0491 42749.4 117
120.0806 3780.9 10
121.0647 3251.2 8
130.0651 41929.7 115
131.0491 16107.7 44
131.0729 73930.3 203
132.0565 1395.6 3
132.0807 15739.7 43
135.044 49983.2 137
136.0519 1606 4
143.0493 2249.3 6
143.0727 2846.1 7
144.0807 14006.3 38
146.06 8864.2 24
147.044 60974.4 167
148.0756 3990.8 10
149.0596 88992 244
151.0541 5549.1 15
152.062 17716.7 48
153.0696 8268.2 22
158.0602 6251 17
159.0441 13149.7 36
159.0678 62001.1 170
160.0756 53356.5 146
161.0598 5949.6 16
161.0801 3621.1 9
163.0389 24125.2 66
164.0621 3226.6 8
165.0546 2365.8 6
165.0698 21984.4 60
166.0773 8958 24
167.0855 37850.4 104
172.0514 2251.8 6
172.076 1497.4 4
173.0596 2501.9 6
174.0549 35049.2 96
175.039 5543.3 15
176.062 8797.8 24
177.0698 38736.7 106
177.0785 2342.9 6
178.0777 50512.6 138
179.0855 76265.4 209
180.057 1330.5 3
181.0647 5257.1 14
186.0551 1693.6 4
188.0705 363458.9 999
189.0696 173579.4 477
189.0786 67355.5 185
190.0869 3777.2 10
191.0854 17538.4 48
192.0567 4652.7 12
193.0653 2536.7 6
194.0724 3440.7 9
195.0803 15801.5 43
201.0696 2764 7
202.0772 1574.3 4
204.0809 2505.2 6
205.0646 29143.5 80
205.0887 2094.2 5
206.0805 5610.4 15
207.0803 40548.2 111
208.052 2619.6 7
209.0595 61067 167
217.0646 43879.1 120
218.0959 1575.4 4
219.0805 10720.8 29
220.0518 1874.6 5
220.1117 1642.8 4
221.0594 2518 6
222.0672 14204.5 39
223.0759 3246.1 8
232.0764 1413.5 3
233.06 2988.6 8
233.0844 2607.3 7
234.0674 2877.3 7
234.0921 1975.3 5
235.0752 18905.3 51
237.0549 4663.4 12
237.0905 7813.3 21
245.0593 2448.1 6
246.0677 5867.2 16
247.0752 26342 72
248.1068 1335.8 3
249.054 1626.9 4
250.0636 1816.2 4
262.0862 8067.1 22
263.0692 2176.9 5
263.0948 3034.3 8
265.0862 2125.8 5
266.0571 2360.8 6
275.0692 4371.5 12
276.1017 3313.6 9
290.0816 3350.2 9
292.0957 3374 9
304.0976 1684.1 4
320.0912 8456.8 23
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