ACCESSION: MSBNK-NaToxAq-NA003518
RECORD_TITLE: Protopin; LC-ESI-ITFT; MS2; CE: 105%; 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 105% (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-1910000000-5d044675abcefe883e57
PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm)
65.0385 C5H5+ 1 65.0386 -1.2
77.0386 C6H5+ 1 77.0386 0.02
79.0542 C6H7+ 1 79.0542 -0.25
89.0385 C7H5+ 1 89.0386 -0.51
91.0542 C7H7+ 1 91.0542 -0.29
93.0698 C7H9+ 1 93.0699 -0.9
94.0412 C6H6O+ 1 94.0413 -1.29
95.049 C6H7O+ 1 95.0491 -1.36
102.0463 C8H6+ 1 102.0464 -0.79
103.0542 C8H7+ 1 103.0542 -0.48
105.0335 C7H5O+ 1 105.0335 -0.3
105.0699 C8H9+ 1 105.0699 -0.09
107.0491 C7H7O+ 1 107.0491 -0.64
115.0542 C9H7+ 1 115.0542 -0.09
116.0494 C8H6N+ 1 116.0495 -0.71
117.0336 C8H5O+ 1 117.0335 0.79
117.0573 C8H7N+ 1 117.0573 -0.24
117.0699 C9H9+ 1 117.0699 -0.13
118.0651 C8H8N+ 1 118.0651 -0.03
119.0491 C8H7O+ 1 119.0491 -0.1
120.0809 C8H10N+ 1 120.0808 0.88
121.065 C8H9O+ 1 121.0648 1.74
130.0651 C9H8N+ 1 130.0651 -0.25
131.049 C9H7O+ 1 131.0491 -0.79
131.0729 C9H9N+ 1 131.073 -0.25
132.0807 C9H10N+ 1 132.0808 -0.59
135.044 C8H7O2+ 1 135.0441 -0.23
143.0731 C10H9N+ 1 143.073 0.91
144.0806 C10H10N+ 1 144.0808 -0.9
146.0601 C9H8NO+ 1 146.06 0.2
147.044 C9H7O2+ 1 147.0441 -0.19
148.0758 C9H10NO+ 1 148.0757 0.49
149.0596 C9H9O2+ 1 149.0597 -0.51
151.0542 C12H7+ 1 151.0542 -0.34
152.062 C12H8+ 1 152.0621 -0.45
153.0697 C12H9+ 1 153.0699 -1.45
158.06 C10H8NO+ 1 158.06 -0.2
159.0441 C10H7O2+ 1 159.0441 0.5
159.0678 C10H9NO+ 1 159.0679 -0.31
160.0757 C10H10NO+ 1 160.0757 -0.21
161.0599 C10H9O2+ 1 161.0597 1.05
161.0802 C7H13O4+ 1 161.0808 -4.23
163.039 C9H7O3+ 1 163.039 -0.04
164.0619 C13H8+ 1 164.0621 -0.68
165.0698 C13H9+ 1 165.0699 -0.31
166.0775 C13H10+ 1 166.0777 -1.42
167.0494 C12H7O+ 1 167.0491 1.47
167.0854 C13H11+ 1 167.0855 -0.69
173.0599 C11H9O2+ 1 173.0597 1.09
174.0549 C10H8NO2+ 1 174.055 -0.04
175.0393 C10H7O3+ 1 175.039 1.91
175.0625 C10H9NO2+ 1 175.0628 -1.78
176.062 C14H8+ 1 176.0621 -0.25
177.0699 C14H9+ 1 177.0699 0.09
178.0776 C14H10+ 1 178.0777 -0.34
179.0488 C13H7O+ 1 179.0491 -2.17
179.0855 C14H11+ 1 179.0855 -0.35
180.0565 C13H8O+ 1 180.057 -2.67
181.0648 C13H9O+ 1 181.0648 0.12
186.0553 C11H8NO2+ 1 186.055 1.72
187.0637 C11H9NO2+ 1 187.0628 4.73
188.0705 C11H10NO2+ 1 188.0706 -0.5
189.0697 C15H9+ 1 189.0699 -1.02
189.0786 C11H11NO2+ 1 189.0784 0.79
190.0862 C11H12NO2+ 1 190.0863 -0.26
191.0853 C15H11+ 1 191.0855 -1.18
192.0567 C14H8O+ 1 192.057 -1.61
193.0647 C14H9O+ 1 193.0648 -0.66
194.0727 C14H10O+ 1 194.0726 0.68
195.0806 C14H11O+ 1 195.0804 0.83
202.0775 C16H10+ 1 202.0777 -0.96
204.0578 C15H8O+ 1 204.057 3.87
204.0808 C15H10N+ 1 204.0808 -0.13
205.0645 C15H9O+ 1 205.0648 -1.29
205.0883 C15H11N+ 1 205.0886 -1.32
206.0732 C15H10O+ 1 206.0726 2.92
206.0969 C15H12N+ 1 206.0964 2.38
207.0803 C15H11O+ 1 207.0804 -0.63
208.052 C14H8O2+ 1 208.0519 0.36
209.0595 C14H9O2+ 1 209.0597 -0.97
217.0646 C16H9O+ 1 217.0648 -0.76
218.0728 C16H10O+ 1 218.0726 0.99
218.0961 C16H12N+ 1 218.0964 -1.55
219.0802 C16H11O+ 1 219.0804 -1.04
220.0508 C15H8O2+ 1 220.0519 -4.95
221.0595 C15H9O2+ 1 221.0597 -0.72
222.0672 C15H10O2+ 1 222.0675 -1.62
232.0746 C16H10NO+ 1 232.0757 -4.58
233.0837 C16H11NO+ 1 233.0835 0.94
234.0678 C16H10O2+ 1 234.0675 1.28
234.0907 C16H12NO+ 1 234.0913 -2.52
235.0751 C16H11O2+ 1 235.0754 -1
237.0545 C15H9O3+ 1 237.0546 -0.51
237.0914 C16H13O2+ 1 237.091 1.45
246.0675 C17H10O2+ 1 246.0675 -0.16
247.0752 C17H11O2+ 1 247.0754 -0.71
250.0614 C16H10O3+ 1 250.0624 -4.32
262.0861 C17H12NO2+ 1 262.0863 -0.74
290.0805 C18H12NO3+ 1 290.0812 -2.45
292.0966 C18H14NO3+ 1 292.0968 -0.85
320.0919 C19H14NO4+ 1 320.0917 0.48
PK$NUM_PEAK: 101
PK$PEAK: m/z int. rel.int.
65.0385 4287.3 17
77.0386 21974 88
79.0542 28957.4 117
89.0385 14654.3 59
91.0542 89680 362
93.0698 4742.1 19
94.0412 2180.7 8
95.049 2102.5 8
102.0463 4485.7 18
103.0542 28965.6 117
105.0335 8050 32
105.0699 1288.7 5
107.0491 26048.7 105
115.0542 8513.7 34
116.0494 2945.1 11
117.0336 5742.6 23
117.0573 4167 16
117.0699 3045.1 12
118.0651 12787.9 51
119.0491 35610.1 143
120.0809 2817.8 11
121.065 2340.5 9
130.0651 61713.3 249
131.049 13039.4 52
131.0729 74046.2 299
132.0807 18389.9 74
135.044 33891.2 136
143.0731 3492.5 14
144.0806 8264.1 33
146.0601 6549.6 26
147.044 50896.4 205
148.0758 3382.8 13
149.0596 42744.3 172
151.0542 13410.5 54
152.062 27628.4 111
153.0697 13090.1 52
158.06 7306.3 29
159.0441 7286.7 29
159.0678 36294.7 146
160.0757 48629.4 196
161.0599 2254.3 9
161.0802 1509.6 6
163.039 12270.2 49
164.0619 5432.6 21
165.0698 33732.4 136
166.0775 9811.4 39
167.0494 1658 6
167.0854 23245.8 93
173.0599 1595.4 6
174.0549 24869.9 100
175.0393 2416.3 9
175.0625 1859.1 7
176.062 16574.7 66
177.0699 38896.2 157
178.0776 70142.6 283
179.0488 3253.2 13
179.0855 53838.6 217
180.0565 2469.8 9
181.0648 5516.1 22
186.0553 2314.5 9
187.0637 1492.9 6
188.0705 247181.9 999
189.0697 185102.6 748
189.0786 18913.9 76
190.0862 1988.6 8
191.0853 12977.4 52
192.0567 4920.2 19
193.0647 2798.1 11
194.0727 3071.1 12
195.0806 7014.4 28
202.0775 3456.9 13
204.0578 2051.3 8
204.0808 4528 18
205.0645 19093.8 77
205.0883 2024.5 8
206.0732 5996.4 24
206.0969 1383.5 5
207.0803 17645.9 71
208.052 2709.3 10
209.0595 43635 176
217.0646 18761.6 75
218.0728 6685 27
218.0961 1136.8 4
219.0802 5224.2 21
220.0508 1435.8 5
221.0595 2641.9 10
222.0672 10401.9 42
232.0746 2109.4 8
233.0837 2411.2 9
234.0678 1379 5
234.0907 3777.6 15
235.0751 8517 34
237.0545 1317.8 5
237.0914 1824.9 7
246.0675 5867.6 23
247.0752 8497.5 34
250.0614 1451.7 5
262.0861 5803.1 23
290.0805 3302.9 13
292.0966 2500.3 10
320.0919 1863.9 7
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