ACCESSION: MSBNK-NaToxAq-NA003517
RECORD_TITLE: Protopin; LC-ESI-ITFT; MS2; CE: 100%; 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 100% (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-fb32565d8b0dca89291e
PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm)
65.0386 C5H5+ 1 65.0386 -0.38
77.0385 C6H5+ 1 77.0386 -0.38
79.0542 C6H7+ 1 79.0542 -0.15
81.0696 C6H9+ 1 81.0699 -3.16
89.0385 C7H5+ 1 89.0386 -0.34
91.0542 C7H7+ 1 91.0542 -0.46
93.0699 C7H9+ 1 93.0699 0.5
94.0413 C6H6O+ 1 94.0413 -0.16
102.0463 C8H6+ 1 102.0464 -0.57
103.0542 C8H7+ 1 103.0542 -0.55
105.0334 C7H5O+ 1 105.0335 -0.59
107.0491 C7H7O+ 1 107.0491 -0.57
109.0651 C7H9O+ 1 109.0648 2.54
115.0542 C9H7+ 1 115.0542 -0.49
116.0491 C8H6N+ 1 116.0495 -3.21
117.0334 C8H5O+ 1 117.0335 -0.71
117.0574 C8H7N+ 1 117.0573 0.8
117.0696 C9H9+ 1 117.0699 -2.74
118.065 C8H8N+ 1 118.0651 -0.68
119.0491 C8H7O+ 1 119.0491 -0.23
120.0809 C8H10N+ 1 120.0808 0.62
121.0648 C8H9O+ 1 121.0648 -0.02
130.0651 C9H8N+ 1 130.0651 -0.49
131.0491 C9H7O+ 1 131.0491 0.03
131.0729 C9H9N+ 1 131.073 -0.48
132.0807 C9H10N+ 1 132.0808 -0.59
135.044 C8H7O2+ 1 135.0441 -0.23
136.0518 C8H8O2+ 1 136.0519 -0.45
143.0725 C10H9N+ 1 143.073 -3.46
144.0807 C10H10N+ 1 144.0808 -0.8
146.06 C9H8NO+ 1 146.06 -0.43
147.044 C9H7O2+ 1 147.0441 -0.08
148.0758 C9H10NO+ 1 148.0757 0.49
149.0596 C9H9O2+ 1 149.0597 -0.41
151.0541 C12H7+ 1 151.0542 -0.54
152.0619 C12H8+ 1 152.0621 -0.75
153.0697 C12H9+ 1 153.0699 -1.25
158.06 C10H8NO+ 1 158.06 -0.49
159.044 C10H7O2+ 1 159.0441 -0.17
159.0678 C10H9NO+ 1 159.0679 -0.21
160.0756 C10H10NO+ 1 160.0757 -0.5
161.0598 C10H9O2+ 1 161.0597 0.86
161.0808 C7H13O4+ 1 161.0808 -0.25
163.039 C9H7O3+ 1 163.039 -0.04
164.0621 C13H8+ 1 164.0621 0.53
165.0698 C13H9+ 1 165.0699 -0.59
166.0772 C13H10+ 1 166.0777 -3.07
167.0496 C12H7O+ 1 167.0491 2.84
167.0855 C13H11+ 1 167.0855 -0.41
173.0595 C11H9O2+ 1 173.0597 -1.02
174.0549 C10H8NO2+ 1 174.055 -0.04
175.0387 C10H7O3+ 1 175.039 -1.31
175.0594 C7H11O5+ 1 175.0601 -4.25
175.0623 C10H9NO2+ 1 175.0628 -2.57
176.062 C14H8+ 1 176.0621 -0.51
176.0708 C10H10NO2+ 1 176.0706 1.08
177.0698 C14H9+ 1 177.0699 -0.17
178.0776 C14H10+ 1 178.0777 -0.34
179.0492 C13H7O+ 1 179.0491 0.47
179.0855 C14H11+ 1 179.0855 -0.26
180.0572 C13H8O+ 1 180.057 1.06
181.0647 C13H9O+ 1 181.0648 -0.39
186.0552 C11H8NO2+ 1 186.055 1.06
188.0705 C11H10NO2+ 1 188.0706 -0.58
189.0696 C15H9+ 1 189.0699 -1.66
189.0786 C11H11NO2+ 1 189.0784 0.95
190.087 C11H12NO2+ 1 190.0863 4
191.0854 C15H11+ 1 191.0855 -0.78
192.0567 C14H8O+ 1 192.057 -1.45
193.0648 C14H9O+ 1 193.0648 -0.1
194.0725 C14H10O+ 1 194.0726 -0.5
195.0805 C14H11O+ 1 195.0804 0.2
201.0698 C16H9+ 1 201.0699 -0.42
202.0776 C16H10+ 1 202.0777 -0.28
204.0562 C15H8O+ 1 204.057 -3.61
204.0811 C15H10N+ 1 204.0808 1.52
205.0646 C15H9O+ 1 205.0648 -1
205.0885 C15H11N+ 1 205.0886 -0.36
206.0734 C15H10O+ 1 206.0726 3.96
206.0965 C15H12N+ 1 206.0964 0.23
207.0803 C15H11O+ 1 207.0804 -0.78
209.0595 C14H9O2+ 1 209.0597 -0.97
217.0646 C16H9O+ 1 217.0648 -1.11
218.0733 C16H10O+ 1 218.0726 3.09
218.0968 C16H12N+ 1 218.0964 1.66
219.0805 C16H11O+ 1 219.0804 0.08
220.0512 C15H8O2+ 1 220.0519 -3.15
220.1112 C16H14N+ 1 220.1121 -3.84
221.0602 C15H9O2+ 1 221.0597 2.45
222.0673 C15H10O2+ 1 222.0675 -0.86
223.0759 C15H11O2+ 1 223.0754 2.49
233.0595 C16H9O2+ 1 233.0597 -0.67
233.083 C16H11NO+ 1 233.0835 -2.34
234.0677 C16H10O2+ 1 234.0675 0.89
234.0913 C16H12NO+ 1 234.0913 -0.31
235.0751 C16H11O2+ 1 235.0754 -0.93
237.0538 C15H9O3+ 1 237.0546 -3.4
237.0915 C16H13O2+ 1 237.091 2.16
246.0676 C17H10O2+ 1 246.0675 0.28
247.0756 C17H11O2+ 1 247.0754 0.96
250.0635 C16H10O3+ 1 250.0624 4.16
262.0862 C17H12NO2+ 1 262.0863 -0.04
263.0698 C17H11O3+ 1 263.0703 -1.69
263.095 C17H13NO2+ 1 263.0941 3.62
275.0692 C18H11O3+ 1 275.0703 -4
276.103 C18H14NO2+ 1 276.1019 3.8
290.0814 C18H12NO3+ 1 290.0812 0.71
292.0971 C18H14NO3+ 1 292.0968 1.03
304.0979 C19H14NO3+ 1 304.0968 3.71
318.0751 C19H12NO4+ 1 318.0761 -3.19
320.0916 C19H14NO4+ 1 320.0917 -0.57
PK$NUM_PEAK: 111
PK$PEAK: m/z int. rel.int.
65.0386 4918.5 17
77.0385 19734.4 69
79.0542 29653.1 103
81.0696 1336.9 4
89.0385 9888.2 34
91.0542 88800.8 310
93.0699 4653.9 16
94.0413 1397.7 4
102.0463 4171 14
103.0542 26709.9 93
105.0334 7674.8 26
107.0491 27135.5 95
109.0651 1388.2 4
115.0542 8148.6 28
116.0491 2269.4 7
117.0334 6405.6 22
117.0574 3998.9 14
117.0696 4849.8 16
118.065 10425 36
119.0491 37985.3 133
120.0809 4133.5 14
121.0648 3172.7 11
130.0651 48552.6 170
131.0491 15337.7 53
131.0729 73843.1 258
132.0807 16814.4 58
135.044 43445.5 152
136.0518 1253.7 4
143.0725 2946.8 10
144.0807 14755.4 51
146.06 7893.4 27
147.044 55193.9 193
148.0758 4759.2 16
149.0596 58904.2 206
151.0541 8634.4 30
152.0619 21563.4 75
153.0697 10016.3 35
158.06 6773.7 23
159.044 10622.3 37
159.0678 46509.7 162
160.0756 49600.9 173
161.0598 3862.6 13
161.0808 3136.4 10
163.039 17785.4 62
164.0621 3446.2 12
165.0698 30346.8 106
166.0772 8181 28
167.0496 2270.8 7
167.0855 30809.7 107
173.0595 1842.9 6
174.0549 25645.9 89
175.0387 3290 11
175.0594 1295.8 4
175.0623 1282.2 4
176.062 11522 40
176.0708 3138.4 10
177.0698 39260.1 137
178.0776 63269.9 221
179.0492 4356.7 15
179.0855 65065.4 227
180.0572 2266.9 7
181.0647 4284 15
186.0552 1697.4 5
188.0705 285266.2 999
189.0696 171068 599
189.0786 39520.1 138
190.087 2221.7 7
191.0854 14312.9 50
192.0567 4484.6 15
193.0648 3299.6 11
194.0725 3337.1 11
195.0805 8980.2 31
201.0698 2585.3 9
202.0776 2265.6 7
204.0562 1403.5 4
204.0811 3196.9 11
205.0646 21690.9 75
205.0885 2925.3 10
206.0734 5201 18
206.0965 1454.2 5
207.0803 27854.4 97
209.0595 49051.3 171
217.0646 26648.5 93
218.0733 5358 18
218.0968 1468.5 5
219.0805 6363 22
220.0512 2184.1 7
220.1112 1591.7 5
221.0602 2678.5 9
222.0673 10918.8 38
223.0759 1926.5 6
233.0595 1342 4
233.083 1967 6
234.0677 2674.8 9
234.0913 1650.1 5
235.0751 13160.4 46
237.0538 2070.7 7
237.0915 2819.1 9
246.0676 6506.3 22
247.0756 12951 45
250.0635 1946.4 6
262.0862 6239.9 21
263.0698 2132.9 7
263.095 1433.4 5
275.0692 2051.1 7
276.103 1718.2 6
290.0814 3362.2 11
292.0971 2017.1 7
304.0979 1247.3 4
318.0751 1704.8 5
320.0916 4368.1 15
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