ACCESSION: MSBNK-NaToxAq-NA003152
RECORD_TITLE: Protopin; LC-ESI-ITFT; MS2; CE: 75%; 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 75% (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-d0b117c4076694dd4338
PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm)
77.0388 C6H5+ 1 77.0386 3.24
79.0542 C6H7+ 1 79.0542 0.02
91.0542 C7H7+ 1 91.0542 -0.39
93.0699 C7H9+ 1 93.0699 0.33
103.0541 C8H7+ 1 103.0542 -0.84
107.0491 C7H7O+ 1 107.0491 -0.42
109.0648 C7H9O+ 1 109.0648 0.16
115.0542 C9H7+ 1 115.0542 -0.34
117.0698 C9H9+ 1 117.0699 -1.03
118.065 C8H8N+ 1 118.0651 -0.98
119.0491 C8H7O+ 1 119.0491 -0.28
120.0807 C8H10N+ 1 120.0808 -0.56
121.0647 C8H9O+ 1 121.0648 -0.75
130.0651 C9H8N+ 1 130.0651 -0.38
131.0491 C9H7O+ 1 131.0491 -0.21
131.0729 C9H9N+ 1 131.073 -0.37
132.0808 C9H10N+ 1 132.0808 0.56
135.0441 C8H7O2+ 1 135.0441 -0.03
137.0599 C8H9O2+ 1 137.0597 1.2
143.0493 C10H7O+ 1 143.0491 1.25
144.0808 C10H10N+ 1 144.0808 0.02
146.0601 C9H8NO+ 1 146.06 0.48
147.0441 C9H7O2+ 1 147.0441 -0.01
148.0517 C9H8O2+ 1 148.0519 -1.36
148.0761 C9H10NO+ 1 148.0757 2.93
149.0597 C9H9O2+ 1 149.0597 -0.33
159.044 C10H7O2+ 1 159.0441 -0.09
159.0678 C10H9NO+ 1 159.0679 -0.23
160.0516 C10H8O2+ 1 160.0519 -1.91
160.0757 C10H10NO+ 1 160.0757 -0.23
161.0596 C10H9O2+ 1 161.0597 -0.57
161.0831 C10H11NO+ 1 161.0835 -2.41
163.0389 C9H7O3+ 1 163.039 -0.33
165.0546 C9H9O3+ 1 165.0546 0.04
165.0697 C13H9+ 1 165.0699 -1.05
167.0855 C13H11+ 1 167.0855 -0.22
173.0599 C11H9O2+ 1 173.0597 1.3
174.055 C10H8NO2+ 1 174.055 0.18
175.0389 C10H7O3+ 1 175.039 -0.39
176.0706 C10H10NO2+ 1 176.0706 -0.07
177.0699 C14H9+ 1 177.0699 -0.11
177.0784 C10H11NO2+ 1 177.0784 -0.16
178.0773 C14H10+ 1 178.0777 -2.41
178.0863 C10H12NO2+ 1 178.0863 0.11
179.0855 C14H11+ 1 179.0855 0.07
181.0651 C13H9O+ 1 181.0648 1.48
187.0396 C11H7O3+ 1 187.039 3.36
188.0706 C11H10NO2+ 1 188.0706 -0.26
189.0694 C15H9+ 1 189.0699 -2.47
189.0784 C11H11NO2+ 1 189.0784 -0.25
190.086 C11H12NO2+ 1 190.0863 -1.29
191.0852 C15H11+ 1 191.0855 -1.71
193.0647 C14H9O+ 1 193.0648 -0.38
195.0804 C14H11O+ 1 195.0804 -0.37
204.065 C11H10NO3+ 1 204.0655 -2.36
205.0646 C15H9O+ 1 205.0648 -0.97
206.0811 C11H12NO3+ 1 206.0812 -0.42
207.0803 C15H11O+ 1 207.0804 -0.53
209.0596 C14H9O2+ 1 209.0597 -0.63
217.0647 C16H9O+ 1 217.0648 -0.47
219.0803 C16H11O+ 1 219.0804 -0.55
220.1128 C16H14N+ 1 220.1121 3.24
221.059 C15H9O2+ 1 221.0597 -3.34
222.0673 C15H10O2+ 1 222.0675 -1.19
223.0753 C15H11O2+ 1 223.0754 -0.16
225.0908 C15H13O2+ 1 225.091 -0.85
233.0594 C16H9O2+ 1 233.0597 -1.22
233.083 C16H11NO+ 1 233.0835 -2.42
235.0753 C16H11O2+ 1 235.0754 -0.43
237.0544 C15H9O3+ 1 237.0546 -1.02
237.0908 C16H13O2+ 1 237.091 -1.06
245.0597 C17H9O2+ 1 245.0597 -0.11
246.0675 C17H10O2+ 1 246.0675 0.03
247.0753 C17H11O2+ 1 247.0754 -0.33
248.1071 C17H14NO+ 1 248.107 0.39
249.0909 C17H13O2+ 1 249.091 -0.38
250.0627 C16H10O3+ 1 250.0624 1.01
251.0695 C16H11O3+ 1 251.0703 -3.06
262.0622 C17H10O3+ 1 262.0624 -0.8
262.0863 C17H12NO2+ 1 262.0863 0.11
263.0703 C17H11O3+ 1 263.0703 -0.04
263.094 C17H13NO2+ 1 263.0941 -0.17
265.0859 C17H13O3+ 1 265.0859 -0.25
266.0571 C16H10O4+ 1 266.0574 -0.95
267.0649 C16H11O4+ 1 267.0652 -1
275.0702 C18H11O3+ 1 275.0703 -0.27
276.1018 C18H14NO2+ 1 276.1019 -0.45
278.0568 C17H10O4+ 1 278.0574 -2.13
278.1173 C18H16NO2+ 1 278.1176 -0.76
280.0728 C17H12O4+ 1 280.073 -0.79
290.0824 C18H12NO3+ 1 290.0812 4.24
292.0728 C18H12O4+ 1 292.073 -0.67
293.0809 C18H13O4+ 1 293.0808 0.33
306.1119 C19H16NO3+ 1 306.1125 -1.85
320.0917 C19H14NO4+ 1 320.0917 -0.21
334.1065 C20H16NO4+ 1 334.1074 -2.74
PK$NUM_PEAK: 96
PK$PEAK: m/z int. rel.int.
77.0388 2555.5 7
79.0542 9230.5 25
91.0542 31312.1 86
93.0699 2458.2 6
103.0541 4681.2 12
107.0491 32477.6 89
109.0648 4706.4 12
115.0542 1255.2 3
117.0698 1082.4 2
118.065 4756.6 13
119.0491 31306.7 85
120.0807 2793.6 7
121.0647 1566.3 4
130.0651 4494.8 12
131.0491 8221.4 22
131.0729 16070.2 44
132.0808 3790.8 10
135.0441 52098.9 143
137.0599 2147.3 5
143.0493 2226.4 6
144.0808 10389.3 28
146.0601 5334.1 14
147.0441 38676.5 106
148.0517 1946.9 5
148.0761 1664.9 4
149.0597 129912.4 356
159.044 13347.8 36
159.0678 45407.9 124
160.0516 2184.8 6
160.0757 22801.3 62
161.0596 7162.6 19
161.0831 3016.3 8
163.0389 30294.4 83
165.0546 20301 55
165.0697 3179.5 8
167.0855 26366 72
173.0599 4846.1 13
174.055 14005.8 38
175.0389 18539.6 50
176.0706 9052 24
177.0699 8357 22
177.0784 9383.9 25
178.0773 3411.6 9
178.0863 5481.8 15
179.0855 37950.9 104
181.0651 3289.1 9
187.0396 2370.9 6
188.0706 363720.7 999
189.0694 47190.7 129
189.0784 246515.6 677
190.086 9572.9 26
191.0852 10600.6 29
193.0647 4201.6 11
195.0804 36139 99
204.065 2506.4 6
205.0646 21746.6 59
206.0811 37278 102
207.0803 55359.2 152
209.0596 43734.3 120
217.0647 51334.7 140
219.0803 14753.2 40
220.1128 2239.2 6
221.059 2120.3 5
222.0673 6041.1 16
223.0753 9526 26
225.0908 4135 11
233.0594 4230.6 11
233.083 1159.7 3
235.0753 51046 140
237.0544 15559.9 42
237.0908 22239.4 61
245.0597 5126.9 14
246.0675 2915.1 8
247.0753 81238.2 223
248.1071 3065.8 8
249.0909 3363 9
250.0627 2894.6 7
251.0695 2469.1 6
262.0622 1234.5 3
262.0863 1405.2 3
263.0703 12457.5 34
263.094 3371.2 9
265.0859 17776.5 48
266.0571 4399.1 12
267.0649 5159.3 14
275.0702 37476.7 102
276.1018 1903.3 5
278.0568 1209 3
278.1173 5851.3 16
280.0728 2852.9 7
290.0824 2534.2 6
292.0728 1749 4
293.0809 6094.9 16
306.1119 2811 7
320.0917 19330.7 53
334.1065 5285.5 14
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