ACCESSION: MSBNK-UFZ-WANA2236155BE0PH
RECORD_TITLE: Cyproterone; LC-ESI-ITFT; MS2; CE: 60%; R=15000; [M+H]+
DATE: 2023.08.12
AUTHORS: Tobias Schulze, Martin Krauss, Department of Effect-Directed Analysis, Helmholtz Centre for Environmental Research - UFZ, Leipzig, Germany
LICENSE: CC0
COPYRIGHT: Copyright (C) 2023
COMMENT: CONFIDENCE Reference Standard (Level 1)
CH$NAME: Cyproterone
CH$NAME: (1S,2S,3S,5R,11R,12S,15R,16S)-15-acetyl-9-chloro-15-hydroxy-2,16-dimethylpentacyclo[9.7.0.02,8.03,5.012,16]octadeca-7,9-dien-6-one
CH$COMPOUND_CLASS: N/A; Environmental Standard
CH$FORMULA: C22H27ClO3
CH$EXACT_MASS: 374.164872404
CH$SMILES: CC(=O)[C@@]1(O)CC[C@H]2[C@@H]3C=C(Cl)C4=CC(=O)[C@@H]5C[C@@H]5[C@]4(C)[C@H]3CC[C@]12C
CH$IUPAC: InChI=1S/C22H27ClO3/c1-11(24)22(26)7-5-14-12-9-18(23)17-10-19(25)13-8-16(13)21(17,3)15(12)4-6-20(14,22)2/h9-10,12-16,26H,4-8H2,1-3H3/t12-,13+,14-,15-,16-,20-,21-,22-/m0/s1
CH$LINK: CAS
2098-66-0
CH$LINK: CHEBI
50742
CH$LINK: KEGG
D07766
CH$LINK: PUBCHEM
CID:5284537
CH$LINK: INCHIKEY
DUSHUSLJJMDGTE-ZJPMUUANSA-N
CH$LINK: CHEMSPIDER
4447594
CH$LINK: COMPTOX
DTXSID3022873
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$MASS_SPECTROMETRY: COLLISION_ENERGY 60 % (nominal)
AC$MASS_SPECTROMETRY: RESOLUTION 15000
AC$MASS_SPECTROMETRY: MASS_RANGE_M/Z 50-390
AC$CHROMATOGRAPHY: COLUMN_NAME Kinetex Evo C18 2.6 um 50 x 2.1 mm
AC$CHROMATOGRAPHY: FLOW_GRADIENT 95/5 at 0 min, 95/5 at 1 min, 0/100 at 13 min, 0/100 at 24 min, 95/5 at 24.3 min, 95/5 at 32 min
AC$CHROMATOGRAPHY: FLOW_RATE 300 uL/min
AC$CHROMATOGRAPHY: RETENTION_TIME 11.744 min
MS$FOCUSED_ION: BASE_PEAK 303.232
MS$FOCUSED_ION: PRECURSOR_M/Z 375.1721
MS$FOCUSED_ION: PRECURSOR_TYPE [M+H]+
MS$FOCUSED_ION: PRECURSOR_INTENSITY 9443394
MS$DATA_PROCESSING: RECALIBRATE loess on assigned fragments and MS1
MS$DATA_PROCESSING: REANALYZE Peaks with additional N2/O included
MS$DATA_PROCESSING: WHOLE RMassBank 3.11.2
PK$SPLASH: splash10-07eb-1960000000-d8f17a6eca17c3ddbcad
PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm)
55.0179 C3H3O+ 1 55.0178 0.99
55.0543 C4H7+ 1 55.0542 0.49
59.0489 C3H7O+ 1 59.0491 -3.57
61.0283 C2H5O2+ 1 61.0284 -1
67.0542 C5H7+ 1 67.0542 -0.54
69.0699 C5H9+ 1 69.0699 0.14
79.0543 C6H7+ 1 79.0542 1.42
81.07 C6H9+ 1 81.0699 1.33
83.0492 C5H7O+ 1 83.0491 0.97
85.0647 C5H9O+ 1 85.0648 -0.82
87.0442 C4H7O2+ 1 87.0441 1.41
91.0543 C7H7+ 1 91.0542 0.54
93.07 C7H9+ 1 93.0699 1.16
95.0492 C6H7O+ 1 95.0491 0.32
95.0857 C7H11+ 1 95.0855 1.43
97.0649 C6H9O+ 1 97.0648 1.07
105.07 C8H9+ 1 105.0699 1.46
107.0857 C8H11+ 1 107.0855 1.21
109.0649 C7H9O+ 1 109.0648 0.56
109.1011 C8H13+ 1 109.1012 -0.85
111.0806 C7H11O+ 1 111.0804 1.31
117.07 C9H9+ 1 117.0699 1.36
119.0857 C9H11+ 1 119.0855 1.85
121.0651 C8H9O+ 1 121.0648 2.58
121.1015 C9H13+ 1 121.1012 2.7
123.0805 C8H11O+ 1 123.0804 0.48
129.07 C10H9+ 1 129.0699 1.08
131.0857 C10H11+ 1 131.0855 1.31
133.0653 C9H9O+ 1 133.0648 3.53
133.1014 C10H13+ 1 133.1012 1.86
135.0808 C9H11O+ 1 135.0804 2.35
141.0697 C11H9+ 1 141.0699 -1.54
142.0779 C11H10+ 1 142.0777 1.37
143.0856 C11H11+ 1 143.0855 0.72
145.0649 C10H9O+ 1 145.0648 1.08
145.1015 C11H13+ 1 145.1012 2.18
147.0806 C10H11O+ 1 147.0804 1.06
147.117 C11H15+ 1 147.1168 1
149.0967 C10H13O+ 1 149.0961 4.32
155.0263 C8H8ClO+ 1 155.0258 2.96
155.0857 C12H11+ 1 155.0855 1.19
157.1014 C12H13+ 1 157.1012 1.35
159.0805 C11H11O+ 1 159.0804 0.23
159.1169 C12H15+ 1 159.1168 0.46
163.1116 C11H15O+ 1 163.1117 -0.83
165.0466 C10H10Cl+ 1 165.0466 0.26
167.0861 C13H11+ 1 167.0855 3.5
169.1015 C13H13+ 1 169.1012 2.2
171.0807 C12H11O+ 1 171.0804 1.26
171.1171 C13H15+ 1 171.1168 1.74
173.096 C12H13O+ 1 173.0961 -0.77
175.1121 C12H15O+ 1 175.1117 1.95
177.0466 C11H10Cl+ 1 177.0466 0.46
179.0252 C10H8ClO+ 1 179.0258 -3.66
179.0622 C11H12Cl+ 1 179.0622 -0.13
179.0855 C14H11+ 1 179.0855 0.09
181.042 C10H10ClO+ 1 181.0415 2.89
181.1013 C14H13+ 1 181.1012 0.52
182.1091 C14H14+ 1 182.109 0.78
183.0812 C13H11O+ 1 183.0804 3.92
183.1171 C14H15+ 1 183.1168 1.37
184.0884 C13H12O+ 1 184.0883 0.68
185.0963 C13H13O+ 1 185.0961 0.93
189.0469 C12H10Cl+ 1 189.0466 1.91
191.0256 C11H8ClO+ 1 191.0258 -1.4
191.0628 C12H12Cl+ 1 191.0622 3.35
193.0417 C11H10ClO+ 1 193.0415 1.01
193.1014 C15H13+ 1 193.1012 0.93
195.1171 C15H15+ 1 195.1168 1.42
197.0962 C14H13O+ 1 197.0961 0.77
197.1325 C15H17+ 1 197.1325 0.03
199.1114 C14H15O+ 1 199.1117 -1.51
201.1276 C14H17O+ 1 201.1274 1.25
203.0623 C13H12Cl+ 1 203.0622 0.42
205.0417 C12H10ClO+ 1 205.0415 1.23
205.1014 C16H13+ 1 205.1012 0.93
207.0573 C12H12ClO+ 1 207.0571 1.1
207.1171 C16H15+ 1 207.1168 1.39
209.0971 C15H13O+ 1 209.0961 4.8
209.1324 C16H17+ 1 209.1325 -0.2
211.1124 C15H15O+ 1 211.1117 2.97
217.0784 C14H14Cl+ 1 217.0779 2.58
217.1018 C17H13+ 1 217.1012 2.83
218.1093 C17H14+ 1 218.109 1.57
219.0573 C13H12ClO+ 1 219.0571 0.88
219.1171 C17H15+ 1 219.1168 1.37
220.1249 C17H16+ 1 220.1247 1.3
221.1325 C17H17+ 1 221.1325 0.13
222.1041 C16H14O+ 1 222.1039 0.86
223.1123 C16H15O+ 1 223.1117 2.71
223.1485 C17H19+ 1 223.1481 1.86
224.1197 C16H16O+ 1 224.1196 0.53
225.1277 C16H17O+ 1 225.1274 1.42
229.0785 C15H14Cl+ 1 229.0779 2.67
231.1166 C18H15+ 1 231.1168 -1.13
232.1249 C18H16+ 1 232.1247 1.12
233.133 C18H17+ 1 233.1325 2.04
234.1409 C18H18+ 1 234.1403 2.56
235.1127 C17H15O+ 1 235.1117 3.89
235.1483 C18H19+ 1 235.1481 0.74
236.12 C17H16O+ 1 236.1196 1.69
237.1274 C17H17O+ 1 237.1274 0.02
237.1638 C18H21+ 1 237.1638 0.3
239.1426 C17H19O+ 1 239.143 -2.01
245.0725 C15H14ClO+ 1 245.0728 -1.02
245.1093 C16H18Cl+ 1 245.1092 0.75
245.1325 C19H17+ 1 245.1325 0.23
246.1405 C19H18+ 1 246.1403 0.67
247.1118 C18H15O+ 1 247.1117 0.15
247.1482 C19H19+ 1 247.1481 0.3
248.1199 C18H16O+ 1 248.1196 1.39
249.1271 C18H17O+ 1 249.1274 -1.3
249.1643 C19H21+ 1 249.1638 2.09
250.1349 C18H18O+ 1 250.1352 -1.35
250.1724 C19H22+ 1 250.1716 3.37
251.1436 C18H19O+ 1 251.143 2.37
259.1485 C20H19+ 1 259.1481 1.43
260.1568 C20H20+ 1 260.156 3.25
261.1637 C20H21+ 1 261.1638 -0.44
262.1351 C19H18O+ 1 262.1352 -0.57
263.1432 C19H19O+ 1 263.143 0.54
264.1509 C19H20O+ 1 264.1509 0.26
277.1592 C20H21O+ 1 277.1587 1.7
278.1672 C20H22O+ 1 278.1665 2.63
279.1744 C20H23O+ 1 279.1743 0.28
293.1534 C20H21O2+ 1 293.1536 -0.8
293.1892 C21H25O+ 1 293.19 -2.6
299.1187 C19H20ClO+ 1 299.1197 -3.53
313.1357 C20H22ClO+ 1 313.1354 0.96
314.1422 C20H23ClO+ 1 314.1432 -3.17
321.1849 C22H25O2+ 1 321.1849 0.12
PK$NUM_PEAK: 131
PK$PEAK: m/z int. rel.int.
55.0179 1067.7 58
55.0543 1338.7 72
59.0489 1901.7 103
61.0283 1206.3 65
67.0542 2256.9 123
69.0699 1242.7 67
79.0543 3189.8 173
81.07 3396.7 185
83.0492 3626.6 197
85.0647 1902.8 103
87.0442 7673.9 418
91.0543 4056.1 221
93.07 7836.1 427
95.0492 2074.4 113
95.0857 4292.6 233
97.0649 2501.1 136
105.07 9875.5 538
107.0857 6800 370
109.0649 4414.9 240
109.1011 2462.7 134
111.0806 6818.7 371
117.07 3250.8 177
119.0857 10309.3 561
121.0651 5666.3 308
121.1015 5624.1 306
123.0805 1937.1 105
129.07 3341.5 182
131.0857 7504.7 409
133.0653 1497.3 81
133.1014 15892.7 866
135.0808 2393.7 130
141.0697 1173.6 63
142.0779 2950.7 160
143.0856 7465.6 406
145.0649 5103.8 278
145.1015 9464.1 515
147.0806 2817.8 153
147.117 11377.2 620
149.0967 1509 82
155.0263 1256.2 68
155.0857 7117.3 387
157.1014 8888.1 484
159.0805 4682 255
159.1169 4806.5 261
163.1116 1545.9 84
165.0466 1825.5 99
167.0861 1767.7 96
169.1015 4736.7 258
171.0807 2473.9 134
171.1171 3700 201
173.096 1904.1 103
175.1121 5406.8 294
177.0466 4077.3 222
179.0252 1333.5 72
179.0622 1375.1 74
179.0855 2868.8 156
181.042 3986.2 217
181.1013 6107.2 332
182.1091 2461.9 134
183.0812 3172 172
183.1171 6531.9 356
184.0884 3227.2 175
185.0963 8008 436
189.0469 2902.8 158
191.0256 2136.1 116
191.0628 3117.1 169
193.0417 3231 176
193.1014 4628.2 252
195.1171 7276.4 396
197.0962 1962 106
197.1325 1648.7 89
199.1114 1869.4 101
201.1276 1296 70
203.0623 2511.1 136
205.0417 2177.4 118
205.1014 2546.5 138
207.0573 2199.8 119
207.1171 5587.8 304
209.0971 3234.5 176
209.1324 4553.8 248
211.1124 3529.1 192
217.0784 1629.3 88
217.1018 2166.6 118
218.1093 1507.4 82
219.0573 9230.5 503
219.1171 5193 283
220.1249 2422.4 132
221.1325 4834.6 263
222.1041 1695.7 92
223.1123 4565.4 248
223.1485 2353 128
224.1197 1020.5 55
225.1277 1144.3 62
229.0785 1504.5 82
231.1166 2757 150
232.1249 1276.5 69
233.133 4480.9 244
234.1409 1714.7 93
235.1127 2754.4 150
235.1483 6296.8 343
236.12 2572.5 140
237.1274 5108.6 278
237.1638 1780 97
239.1426 1698.4 92
245.0725 1349.9 73
245.1093 1917.1 104
245.1325 2161.2 117
246.1405 2314.4 126
247.1118 1086.5 59
247.1482 3143.3 171
248.1199 1391.2 75
249.1271 3008.1 163
249.1643 3861.9 210
250.1349 2408.9 131
250.1724 1250.9 68
251.1436 4441.8 242
259.1485 1743.2 95
260.1568 1581 86
261.1637 4268.9 232
262.1351 1278.7 69
263.1432 18327.1 999
264.1509 1836 100
277.1592 5341.8 291
278.1672 4448.8 242
279.1744 12672 690
293.1534 3904.3 212
293.1892 1022.6 55
299.1187 2001.2 109
313.1357 1278 69
314.1422 1535.8 83
321.1849 1970.3 107
//
