ACCESSION: MSBNK-NaToxAq-NA003151
RECORD_TITLE: Protopin; LC-ESI-ITFT; MS2; CE: 70%; 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 70% (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$CHROMATOGRAPHY: RETENTION_TIME 6.714 min
AC$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-0930000000-be400ed8c7a1d9d792f0
PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm)
77.0384 C6H5+ 1 77.0386 -2.1
79.0543 C6H7+ 1 79.0542 0.41
91.0542 C7H7+ 1 91.0542 -0.05
93.0701 C7H9+ 1 93.0699 2.54
103.0541 C8H7+ 1 103.0542 -0.91
107.0491 C7H7O+ 1 107.0491 -0.34
109.0647 C7H9O+ 1 109.0648 -0.47
115.0542 C9H7+ 1 115.0542 -0.54
118.0652 C8H8N+ 1 118.0651 0.24
119.0492 C8H7O+ 1 119.0491 0.11
120.0807 C8H10N+ 1 120.0808 -1.01
121.0645 C8H9O+ 1 121.0648 -2.08
130.065 C9H8N+ 1 130.0651 -0.73
131.049 C9H7O+ 1 131.0491 -1.38
131.0729 C9H9N+ 1 131.073 -0.49
132.0806 C9H10N+ 1 132.0808 -1.52
135.0441 C8H7O2+ 1 135.0441 0.2
137.0597 C8H9O2+ 1 137.0597 0.2
143.0496 C10H7O+ 1 143.0491 3.38
144.0808 C10H10N+ 1 144.0808 0.02
146.0602 C9H8NO+ 1 146.06 0.8
147.0441 C9H7O2+ 1 147.0441 0.3
148.0758 C9H10NO+ 1 148.0757 0.87
149.0597 C9H9O2+ 1 149.0597 -0.23
158.0607 C10H8NO+ 1 158.06 4.31
159.0441 C10H7O2+ 1 159.0441 0.39
159.0679 C10H9NO+ 1 159.0679 0.35
160.0512 C10H8O2+ 1 160.0519 -4.39
160.0757 C10H10NO+ 1 160.0757 0.34
161.0599 C10H9O2+ 1 161.0597 1.32
161.0838 C10H11NO+ 1 161.0835 1.57
163.039 C9H7O3+ 1 163.039 0.14
165.0547 C9H9O3+ 1 165.0546 0.32
167.0855 C13H11+ 1 167.0855 0.05
173.0599 C11H9O2+ 1 173.0597 1.22
174.055 C10H8NO2+ 1 174.055 0.53
175.039 C10H7O3+ 1 175.039 0.22
176.0705 C10H10NO2+ 1 176.0706 -0.77
177.055 C10H9O3+ 1 177.0546 1.94
177.0699 C14H9+ 1 177.0699 0.24
177.0785 C10H11NO2+ 1 177.0784 0.27
178.077 C14H10+ 1 178.0777 -3.87
178.0862 C10H12NO2+ 1 178.0863 -0.23
179.0855 C14H11+ 1 179.0855 -0.18
181.0655 C13H9O+ 1 181.0648 3.92
187.0394 C11H7O3+ 1 187.039 2.3
188.0706 C11H10NO2+ 1 188.0706 -0.01
189.0693 C15H9+ 1 189.0699 -3.11
189.0784 C11H11NO2+ 1 189.0784 -0.01
191.0853 C15H11+ 1 191.0855 -1.23
193.0643 C14H9O+ 1 193.0648 -2.67
195.0804 C14H11O+ 1 195.0804 -0.14
204.0656 C11H10NO3+ 1 204.0655 0.18
205.0646 C15H9O+ 1 205.0648 -0.97
206.0811 C11H12NO3+ 1 206.0812 -0.35
207.0803 C15H11O+ 1 207.0804 -0.82
209.0595 C14H9O2+ 1 209.0597 -0.78
211.075 C14H11O2+ 1 211.0754 -1.72
217.0647 C16H9O+ 1 217.0648 -0.26
219.0804 C16H11O+ 1 219.0804 -0.41
220.1129 C16H14N+ 1 220.1121 3.59
222.0673 C15H10O2+ 1 222.0675 -0.99
223.0755 C15H11O2+ 1 223.0754 0.45
225.0909 C15H13O2+ 1 225.091 -0.51
233.0597 C16H9O2+ 1 233.0597 -0.17
235.0753 C16H11O2+ 1 235.0754 -0.23
237.0545 C15H9O3+ 1 237.0546 -0.57
237.0908 C16H13O2+ 1 237.091 -0.67
245.0599 C17H9O2+ 1 245.0597 0.95
246.0681 C17H10O2+ 1 246.0675 2.2
247.0754 C17H11O2+ 1 247.0754 0.04
248.1068 C17H14NO+ 1 248.107 -0.6
249.0907 C17H13O2+ 1 249.091 -1.42
250.0621 C16H10O3+ 1 250.0624 -1.37
251.0703 C16H11O3+ 1 251.0703 0.1
253.0864 C16H13O3+ 1 253.0859 2.05
263.0702 C17H11O3+ 1 263.0703 -0.15
263.0942 C17H13NO2+ 1 263.0941 0.29
265.0858 C17H13O3+ 1 265.0859 -0.37
266.0568 C16H10O4+ 1 266.0574 -2.22
267.0653 C16H11O4+ 1 267.0652 0.49
275.0703 C18H11O3+ 1 275.0703 -0.05
276.1023 C18H14NO2+ 1 276.1019 1.32
277.085 C18H13O3+ 1 277.0859 -3.23
278.0577 C17H10O4+ 1 278.0574 1.05
278.1175 C18H16NO2+ 1 278.1176 -0.1
279.0661 C17H11O4+ 1 279.0652 3.19
280.0728 C17H12O4+ 1 280.073 -0.9
292.0725 C18H12O4+ 1 292.073 -1.82
293.0809 C18H13O4+ 1 293.0808 0.23
295.0962 C18H15O4+ 1 295.0965 -0.89
304.0981 C19H14NO3+ 1 304.0968 4.05
305.0796 C19H13O4+ 1 305.0808 -4.09
306.1125 C19H16NO3+ 1 306.1125 0.25
311.0919 C18H15O5+ 1 311.0914 1.65
320.0916 C19H14NO4+ 1 320.0917 -0.4
321.0993 C19H15NO4+ 1 321.0996 -0.82
334.1076 C20H16NO4+ 1 334.1074 0.55
336.123 C20H18NO4+ 1 336.123 0.02
354.1343 C20H20NO5+ 1 354.1336 1.9
PK$NUM_PEAK: 100
PK$PEAK: m/z int. rel.int.
77.0384 1461.2 3
79.0543 7104.5 17
91.0542 27393.5 66
93.0701 1872.1 4
103.0541 3939.2 9
107.0491 29201.2 71
109.0647 5627.3 13
115.0542 1698.7 4
118.0652 2800.8 6
119.0492 28054.7 68
120.0807 1929.7 4
121.0645 1556.5 3
130.065 2890.7 7
131.049 6384.1 15
131.0729 8063.8 19
132.0806 3956.9 9
135.0441 59154.5 144
137.0597 2370.5 5
143.0496 1375.5 3
144.0808 13546.2 33
146.0602 7116.8 17
147.0441 33671.2 82
148.0758 1654.4 4
149.0597 144234.8 352
158.0607 1092.2 2
159.0441 10689.4 26
159.0679 37068.8 90
160.0512 1788.3 4
160.0757 16119.4 39
161.0599 8669 21
161.0838 2731.9 6
163.039 29827.1 72
165.0547 32416 79
167.0855 21155 51
173.0599 4917.5 12
174.055 10726.1 26
175.039 22218.2 54
176.0705 9427.5 23
177.055 1532 3
177.0699 4870.2 11
177.0785 10758.8 26
178.077 1840 4
178.0862 7585.2 18
179.0855 26353.1 64
181.0655 1750.2 4
187.0394 3867.5 9
188.0706 409014.6 999
189.0693 29473.5 71
189.0784 308383 753
191.0853 6028.7 14
193.0643 3491.3 8
195.0804 38930.1 95
204.0656 3526.2 8
205.0646 13312.6 32
206.0811 54462.4 133
207.0803 55026.2 134
209.0595 35190.3 85
211.075 1356.6 3
217.0647 43970.5 107
219.0804 11983.8 29
220.1129 1676.6 4
222.0673 3433.5 8
223.0755 12504.9 30
225.0909 6119 14
233.0597 2481.5 6
235.0753 59085.5 144
237.0545 19145.9 46
237.0908 29344 71
245.0599 7208.1 17
246.0681 1531.7 3
247.0754 88639.8 216
248.1068 2370.7 5
249.0907 4446.5 10
250.0621 2578 6
251.0703 2533.6 6
253.0864 1872.7 4
263.0702 16431.8 40
263.0942 3091.1 7
265.0858 21880.1 53
266.0568 3110 7
267.0653 10333 25
275.0703 55478 135
276.1023 1412.6 3
277.085 2102.5 5
278.0577 1747.1 4
278.1175 8389 20
279.0661 1485.3 3
280.0728 2353.8 5
292.0725 3332.4 8
293.0809 10372.3 25
295.0962 2997.4 7
304.0981 2159.8 5
305.0796 2440.5 5
306.1125 3854.9 9
311.0919 1152.5 2
320.0916 19289 47
321.0993 6063.6 14
334.1076 6013.5 14
336.123 2390.2 5
354.1343 1750.7 4
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