ACCESSION: MSBNK-NaToxAq-NA003153
RECORD_TITLE: Protopin; LC-ESI-ITFT; MS2; CE: 80%; 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 80% (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-a7f51d188661035a7499
PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm)
77.0387 C6H5+ 1 77.0386 1.66
79.0542 C6H7+ 1 79.0542 0.12
91.0542 C7H7+ 1 91.0542 0.03
93.0698 C7H9+ 1 93.0699 -0.74
103.0541 C8H7+ 1 103.0542 -0.84
107.0491 C7H7O+ 1 107.0491 -0.2
109.0649 C7H9O+ 1 109.0648 1.07
115.0542 C9H7+ 1 115.0542 -0.08
118.065 C8H8N+ 1 118.0651 -0.66
119.0492 C8H7O+ 1 119.0491 0.11
120.0809 C8H10N+ 1 120.0808 1.34
121.0648 C8H9O+ 1 121.0648 -0.19
130.0652 C9H8N+ 1 130.0651 0.56
131.0491 C9H7O+ 1 131.0491 -0.68
131.0729 C9H9N+ 1 131.073 -0.14
132.0806 C9H10N+ 1 132.0808 -1.29
135.0441 C8H7O2+ 1 135.0441 0.43
143.0489 C10H7O+ 1 143.0491 -1.95
144.0808 C10H10N+ 1 144.0808 0.13
146.06 C9H8NO+ 1 146.06 -0.04
147.0441 C9H7O2+ 1 147.0441 0.1
148.0516 C9H8O2+ 1 148.0519 -1.56
148.0754 C9H10NO+ 1 148.0757 -1.71
149.0597 C9H9O2+ 1 149.0597 -0.13
158.0601 C10H8NO+ 1 158.06 0.55
159.0441 C10H7O2+ 1 159.0441 0.48
159.0679 C10H9NO+ 1 159.0679 0.06
160.0524 C10H8O2+ 1 160.0519 3.14
160.0757 C10H10NO+ 1 160.0757 0.25
161.0595 C10H9O2+ 1 161.0597 -1.24
161.0828 C10H11NO+ 1 161.0835 -4.49
163.0391 C9H7O3+ 1 163.039 0.51
165.0548 C9H9O3+ 1 165.0546 1.06
165.07 C13H9+ 1 165.0699 0.89
167.0855 C13H11+ 1 167.0855 -0.13
173.06 C11H9O2+ 1 173.0597 1.57
174.055 C10H8NO2+ 1 174.055 0.26
175.0389 C10H7O3+ 1 175.039 -0.13
176.0708 C10H10NO2+ 1 176.0706 1.05
177.0701 C14H9+ 1 177.0699 1.1
177.0787 C10H11NO2+ 1 177.0784 1.48
178.0778 C14H10+ 1 178.0777 0.41
178.0863 C10H12NO2+ 1 178.0863 0.19
179.0856 C14H11+ 1 179.0855 0.16
181.0647 C13H9O+ 1 181.0648 -0.63
187.0398 C11H7O3+ 1 187.039 4.58
188.0706 C11H10NO2+ 1 188.0706 -0.01
189.0696 C15H9+ 1 189.0699 -1.26
189.0784 C11H11NO2+ 1 189.0784 -0.09
190.0866 C11H12NO2+ 1 190.0863 1.68
191.0855 C15H11+ 1 191.0855 -0.36
193.0647 C14H9O+ 1 193.0648 -0.3
195.0804 C14H11O+ 1 195.0804 -0.06
204.0651 C11H10NO3+ 1 204.0655 -2.21
205.0647 C15H9O+ 1 205.0648 -0.6
206.0811 C11H12NO3+ 1 206.0812 -0.5
207.0803 C15H11O+ 1 207.0804 -0.45
209.0596 C14H9O2+ 1 209.0597 -0.49
217.0647 C16H9O+ 1 217.0648 -0.26
219.0805 C16H11O+ 1 219.0804 0.08
220.1122 C16H14N+ 1 220.1121 0.75
222.0675 C15H10O2+ 1 222.0675 -0.09
223.0755 C15H11O2+ 1 223.0754 0.52
225.0914 C15H13O2+ 1 225.091 1.59
233.0599 C16H9O2+ 1 233.0597 1.01
233.0841 C16H11NO+ 1 233.0835 2.36
235.0753 C16H11O2+ 1 235.0754 -0.3
237.0545 C15H9O3+ 1 237.0546 -0.38
237.0909 C16H13O2+ 1 237.091 -0.61
245.0598 C17H9O2+ 1 245.0597 0.2
246.0672 C17H10O2+ 1 246.0675 -1.28
247.0753 C17H11O2+ 1 247.0754 -0.03
248.1071 C17H14NO+ 1 248.107 0.27
249.0913 C17H13O2+ 1 249.091 1.28
250.0622 C16H10O3+ 1 250.0624 -1.06
262.0617 C17H10O3+ 1 262.0624 -2.67
262.0864 C17H12NO2+ 1 262.0863 0.69
263.0705 C17H11O3+ 1 263.0703 0.77
263.0943 C17H13NO2+ 1 263.0941 0.98
265.0859 C17H13O3+ 1 265.0859 -0.13
266.0574 C16H10O4+ 1 266.0574 0.08
267.065 C16H11O4+ 1 267.0652 -0.54
275.0703 C18H11O3+ 1 275.0703 0.17
276.102 C18H14NO2+ 1 276.1019 0.21
278.1174 C18H16NO2+ 1 278.1176 -0.65
280.0733 C17H12O4+ 1 280.073 1.17
290.0817 C18H12NO3+ 1 290.0812 1.71
291.0876 C18H13NO3+ 1 291.089 -4.73
292.0728 C18H12O4+ 1 292.073 -0.77
293.0808 C18H13O4+ 1 293.0808 -0.19
304.0975 C19H14NO3+ 1 304.0968 2.34
320.0916 C19H14NO4+ 1 320.0917 -0.3
334.1076 C20H16NO4+ 1 334.1074 0.64
PK$NUM_PEAK: 93
PK$PEAK: m/z int. rel.int.
77.0387 3837.1 10
79.0542 10507.7 29
91.0542 37506.1 106
93.0698 3146.1 8
103.0541 6234.7 17
107.0491 37792.4 107
109.0649 3207.4 9
115.0542 2470 7
118.065 4262.7 12
119.0492 29046.2 82
120.0809 2412 6
121.0648 1378.2 3
130.0652 7417.4 21
131.0491 9410.7 26
131.0729 25175.3 71
132.0806 4442 12
135.0441 47798.1 136
143.0489 2106.1 6
144.0808 7859.9 22
146.06 7171.7 20
147.0441 40997.6 116
148.0516 1671.3 4
148.0754 2581.5 7
149.0597 112484.8 320
158.0601 1414.5 4
159.0441 12005.8 34
159.0679 52923.6 150
160.0524 1568.2 4
160.0757 28958.7 82
161.0595 5898.3 16
161.0828 1885.8 5
163.0391 27892.8 79
165.0548 11730.1 33
165.07 7402 21
167.0855 29307.5 83
173.06 3563.8 10
174.055 17034.7 48
175.0389 12987.6 37
176.0708 6282.5 17
177.0701 12457.8 35
177.0787 6087.2 17
178.0778 8449.7 24
178.0863 2160.8 6
179.0856 49019.9 139
181.0647 2145.6 6
187.0398 1372.7 3
188.0706 350214.2 999
189.0696 72000.2 205
189.0784 172323.1 491
190.0866 7093.1 20
191.0855 11238.1 32
193.0647 3886.5 11
195.0804 27690.7 78
204.0651 2280.5 6
205.0647 19562.9 55
206.0811 22441.3 64
207.0803 48493.9 138
209.0596 48577.1 138
217.0647 49564.2 141
219.0805 14848.3 42
220.1122 1854 5
222.0675 6776.6 19
223.0755 9183.1 26
225.0914 1853.2 5
233.0599 4159.5 11
233.0841 1522.2 4
235.0753 38326.5 109
237.0545 12105.2 34
237.0909 16577 47
245.0598 3596.9 10
246.0672 3414.4 9
247.0753 62220.5 177
248.1071 3347.8 9
249.0913 1180.4 3
250.0622 1889.1 5
262.0617 1398.9 3
262.0864 1631.4 4
263.0705 9412.5 26
263.0943 2980 8
265.0859 9801.2 27
266.0574 2886.7 8
267.065 2504.1 7
275.0703 23368.5 66
276.102 2701.4 7
278.1174 4888.4 13
280.0733 1726.6 4
290.0817 1442.6 4
291.0876 1597.4 4
292.0728 1604.2 4
293.0808 3663.2 10
304.0975 1266.8 3
320.0916 15059.2 42
334.1076 2662.5 7
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