ACCESSION: MSBNK-NaToxAq-NA003150
RECORD_TITLE: Protopin; LC-ESI-ITFT; MS2; CE: 65%; 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 65% (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-0940000000-038866df9c6feb611abf
PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm)
79.0542 C6H7+ 1 79.0542 -0.36
91.0542 C7H7+ 1 91.0542 -0.39
93.0703 C7H9+ 1 93.0699 4.02
103.0543 C8H7+ 1 103.0542 0.28
107.0491 C7H7O+ 1 107.0491 -0.13
109.0647 C7H9O+ 1 109.0648 -0.89
118.065 C8H8N+ 1 118.0651 -1.24
119.0491 C8H7O+ 1 119.0491 -0.4
120.0809 C8H10N+ 1 120.0808 1.09
121.0649 C8H9O+ 1 121.0648 1.14
131.0491 C9H7O+ 1 131.0491 0.02
131.0727 C9H9N+ 1 131.073 -1.65
132.0808 C9H10N+ 1 132.0808 0.21
135.0441 C8H7O2+ 1 135.0441 -0.03
137.0597 C8H9O2+ 1 137.0597 -0.25
143.0494 C10H7O+ 1 143.0491 2.1
144.0808 C10H10N+ 1 144.0808 0.13
146.0603 C9H8NO+ 1 146.06 1.95
147.0441 C9H7O2+ 1 147.0441 0.1
149.0597 C9H9O2+ 1 149.0597 -0.13
159.0443 C10H7O2+ 1 159.0441 1.25
159.0679 C10H9NO+ 1 159.0679 -0.03
160.0521 C10H8O2+ 1 160.0519 1.33
160.0756 C10H10NO+ 1 160.0757 -0.42
161.0598 C10H9O2+ 1 161.0597 0.37
161.0832 C10H11NO+ 1 161.0835 -2.13
163.039 C9H7O3+ 1 163.039 0.04
165.0547 C9H9O3+ 1 165.0546 0.23
167.0855 C13H11+ 1 167.0855 -0.22
173.0599 C11H9O2+ 1 173.0597 1.04
174.0549 C10H8NO2+ 1 174.055 -0.44
175.039 C10H7O3+ 1 175.039 -0.05
176.0706 C10H10NO2+ 1 176.0706 0.01
177.0545 C10H9O3+ 1 177.0546 -0.64
177.0785 C10H11NO2+ 1 177.0784 0.45
178.0863 C10H12NO2+ 1 178.0863 0.37
179.0854 C14H11+ 1 179.0855 -0.44
181.0652 C13H9O+ 1 181.0648 2.07
187.039 C11H7O3+ 1 187.039 0.09
188.0706 C11H10NO2+ 1 188.0706 -0.01
189.0784 C11H11NO2+ 1 189.0784 -0.01
191.0848 C15H11+ 1 191.0855 -3.71
193.0647 C14H9O+ 1 193.0648 -0.7
195.0804 C14H11O+ 1 195.0804 -0.37
201.0784 C12H11NO2+ 1 201.0784 -0.24
204.0656 C11H10NO3+ 1 204.0655 0.18
205.0645 C15H9O+ 1 205.0648 -1.35
206.0811 C11H12NO3+ 1 206.0812 -0.35
207.0801 C15H11O+ 1 207.0804 -1.41
209.0596 C14H9O2+ 1 209.0597 -0.56
211.0756 C14H11O2+ 1 211.0754 0.96
212.1285 C11H18NO3+ 1 212.1281 1.8
217.0647 C16H9O+ 1 217.0648 -0.33
219.0804 C16H11O+ 1 219.0804 -0.34
221.0594 C15H9O2+ 1 221.0597 -1.33
222.0678 C15H10O2+ 1 222.0675 1.08
223.0754 C15H11O2+ 1 223.0754 0.25
225.091 C15H13O2+ 1 225.091 -0.24
233.059 C16H9O2+ 1 233.0597 -2.92
235.0752 C16H11O2+ 1 235.0754 -0.69
237.0544 C15H9O3+ 1 237.0546 -0.76
237.0909 C16H13O2+ 1 237.091 -0.35
245.0595 C17H9O2+ 1 245.0597 -0.73
247.0753 C17H11O2+ 1 247.0754 -0.09
248.1069 C17H14NO+ 1 248.107 -0.41
249.091 C17H13O2+ 1 249.091 -0.13
250.0629 C16H10O3+ 1 250.0624 1.8
251.0704 C16H11O3+ 1 251.0703 0.59
253.0863 C16H13O3+ 1 253.0859 1.33
262.0618 C17H10O3+ 1 262.0624 -2.55
263.0702 C17H11O3+ 1 263.0703 -0.15
263.0944 C17H13NO2+ 1 263.0941 1.33
265.0859 C17H13O3+ 1 265.0859 -0.02
266.0574 C16H10O4+ 1 266.0574 0.31
267.0654 C16H11O4+ 1 267.0652 0.72
275.0703 C18H11O3+ 1 275.0703 0.06
276.1017 C18H14NO2+ 1 276.1019 -0.67
277.086 C18H13O3+ 1 277.0859 0.3
278.1173 C18H16NO2+ 1 278.1176 -0.76
279.064 C17H11O4+ 1 279.0652 -4.25
280.0722 C17H12O4+ 1 280.073 -2.75
291.0892 C18H13NO3+ 1 291.089 0.61
292.0739 C18H12O4+ 1 292.073 3.09
293.0807 C18H13O4+ 1 293.0808 -0.29
295.0961 C18H15O4+ 1 295.0965 -1.2
304.0967 C19H14NO3+ 1 304.0968 -0.27
305.0805 C19H13O4+ 1 305.0808 -1.19
306.1125 C19H16NO3+ 1 306.1125 -0.05
311.0902 C18H15O5+ 1 311.0914 -3.74
320.0916 C19H14NO4+ 1 320.0917 -0.49
321.1 C19H15NO4+ 1 321.0996 1.37
323.0908 C19H15O5+ 1 323.0914 -1.72
334.1073 C20H16NO4+ 1 334.1074 -0.27
336.1225 C20H18NO4+ 1 336.123 -1.53
354.1338 C20H20NO5+ 1 354.1336 0.61
PK$NUM_PEAK: 95
PK$PEAK: m/z int. rel.int.
79.0542 5462.3 12
91.0542 19361.7 44
93.0703 1823.6 4
103.0543 2172.7 4
107.0491 27246.6 62
109.0647 4093.6 9
118.065 3508.2 8
119.0491 23905.9 54
120.0809 1813.6 4
121.0649 1457.9 3
131.0491 6181.7 14
131.0727 4197.1 9
132.0808 4171.7 9
135.0441 56735 130
137.0597 1697.5 3
143.0494 1979.2 4
144.0808 21117.5 48
146.0603 4320.7 9
147.0441 28668 65
149.0597 168015.2 385
159.0443 9959.4 22
159.0679 23985.7 54
160.0521 1661.3 3
160.0756 10616.5 24
161.0598 7479.4 17
161.0832 1185.3 2
163.039 29120 66
165.0547 55665.3 127
167.0855 13535.7 31
173.0599 5325.4 12
174.0549 6216.1 14
175.039 31180.3 71
176.0706 12063.7 27
177.0545 2366.6 5
177.0785 14186.7 32
178.0863 10131.5 23
179.0854 15498.3 35
181.0652 2862.1 6
187.039 4551.8 10
188.0706 435715 999
189.0784 377260.8 864
191.0848 3650.5 8
193.0647 2305.2 5
195.0804 44339.3 101
201.0784 2031.5 4
204.0656 4880 11
205.0645 9240.5 21
206.0811 73833 169
207.0801 46460.9 106
209.0596 24406.1 55
211.0756 1458 3
212.1285 1339.2 3
217.0647 36986.6 84
219.0804 10591.5 24
221.0594 1283.6 2
222.0678 2316.7 5
223.0754 15575 35
225.091 9607.6 22
233.059 3756.5 8
235.0752 62474.7 143
237.0544 20566.1 47
237.0909 30780.5 70
245.0595 7147.8 16
247.0753 97673.2 223
248.1069 1211.5 2
249.091 6076.7 13
250.0629 1314.8 3
251.0704 3159.5 7
253.0863 4803.1 11
262.0618 1367.7 3
263.0702 17502.6 40
263.0944 2469.8 5
265.0859 32834.1 75
266.0574 3130.1 7
267.0654 15912.2 36
275.0703 74799 171
276.1017 1232.1 2
277.086 4103 9
278.1173 11682.8 26
279.064 1312.4 3
280.0722 2712.9 6
291.0892 1660.8 3
292.0739 3202.5 7
293.0807 14802.5 33
295.0961 5827.1 13
304.0967 1880.9 4
305.0805 4255.3 9
306.1125 5441.9 12
311.0902 1754.4 4
320.0916 20030.5 45
321.1 7428.4 17
323.0908 1897.5 4
334.1073 7655.5 17
336.1225 7191.4 16
354.1338 9110.6 20
//
