ACCESSION: MSBNK-UFZ-WANA223613D9F1PH
RECORD_TITLE: Cyproterone; LC-ESI-ITFT; MS2; CE: 50%; 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$MASS_SPECTROMETRY: COLLISION_ENERGY 50 % (nominal)
AC$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$SPLASH: splash10-004i-1891000000-00265419ead390ff7ff7
PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm)
55.0176 C3H3O+ 1 55.0178 -3.73
55.0541 C4H7+ 1 55.0542 -2.22
59.0491 C3H7O+ 1 59.0491 -1.5
61.0282 C2H5O2+ 1 61.0284 -2.63
67.0541 C5H7+ 1 67.0542 -1.68
69.0334 C4H5O+ 1 69.0335 -1.39
69.0699 C5H9+ 1 69.0699 0.03
79.0544 C6H7+ 1 79.0542 1.61
81.07 C6H9+ 1 81.0699 1.61
83.0492 C5H7O+ 1 83.0491 1.16
85.0649 C5H9O+ 1 85.0648 1.24
87.0442 C4H7O2+ 1 87.0441 1.5
91.0543 C7H7+ 1 91.0542 0.87
93.0701 C7H9+ 1 93.0699 2.15
95.0494 C6H7O+ 1 95.0491 2.48
95.0857 C7H11+ 1 95.0855 1.51
97.0651 C6H9O+ 1 97.0648 2.72
105.07 C8H9+ 1 105.0699 1.32
107.0857 C8H11+ 1 107.0855 1.28
109.065 C7H9O+ 1 109.0648 1.61
109.1013 C8H13+ 1 109.1012 1.46
111.0806 C7H11O+ 1 111.0804 1.38
117.0702 C9H9+ 1 117.0699 2.99
119.0857 C9H11+ 1 119.0855 1.66
121.065 C8H9O+ 1 121.0648 1.51
121.1014 C9H13+ 1 121.1012 1.69
123.0805 C8H11O+ 1 123.0804 0.54
129.0702 C10H9+ 1 129.0699 2.62
131.0857 C10H11+ 1 131.0855 1.65
133.1014 C10H13+ 1 133.1012 1.4
135.0805 C9H11O+ 1 135.0804 0.77
135.1172 C10H15+ 1 135.1168 2.62
137.0961 C9H13O+ 1 137.0961 0.08
141.0471 C8H10Cl+ 1 141.0466 4.14
141.0701 C11H9+ 1 141.0699 1.38
142.0778 C11H10+ 1 142.0777 0.94
143.0858 C11H11+ 1 143.0855 1.57
145.065 C10H9O+ 1 145.0648 1.19
145.1014 C11H13+ 1 145.1012 1.34
147.0805 C10H11O+ 1 147.0804 0.54
147.117 C11H15+ 1 147.1168 1.21
149.0961 C10H13O+ 1 149.0961 0.23
151.1119 C10H15O+ 1 151.1117 0.92
155.026 C8H8ClO+ 1 155.0258 1.39
155.0857 C12H11+ 1 155.0855 0.89
157.1014 C12H13+ 1 157.1012 1.16
159.0807 C11H11O+ 1 159.0804 1.38
159.1169 C12H15+ 1 159.1168 0.65
161.096 C11H13O+ 1 161.0961 -0.73
163.1122 C11H15O+ 1 163.1117 2.63
165.0462 C10H10Cl+ 1 165.0466 -1.96
167.0259 C9H8ClO+ 1 167.0258 0.76
167.0854 C13H11+ 1 167.0855 -0.61
169.0421 C9H10ClO+ 1 169.0415 3.74
169.1012 C13H13+ 1 169.1012 0.13
171.0805 C12H11O+ 1 171.0804 0.28
171.1173 C13H15+ 1 171.1168 2.72
173.0964 C12H13O+ 1 173.0961 1.78
173.1331 C13H17+ 1 173.1325 3.5
175.1119 C12H15O+ 1 175.1117 0.99
177.0467 C11H10Cl+ 1 177.0466 0.97
177.1276 C12H17O+ 1 177.1274 1.25
179.0261 C10H8ClO+ 1 179.0258 1.71
179.0853 C14H11+ 1 179.0855 -1.28
181.0417 C10H10ClO+ 1 181.0415 1.28
181.0782 C11H14Cl+ 1 181.0779 2.08
181.1015 C14H13+ 1 181.1012 1.96
182.1081 C14H14+ 1 182.109 -5
183.0578 C10H12ClO+ 1 183.0571 3.62
183.0806 C13H11O+ 1 183.0804 1
183.117 C14H15+ 1 183.1168 0.96
184.0885 C13H12O+ 1 184.0883 1.42
185.0963 C13H13O+ 1 185.0961 1.34
185.1332 C14H17+ 1 185.1325 4.1
187.112 C13H15O+ 1 187.1117 1.6
189.0461 C12H10Cl+ 1 189.0466 -2.61
189.1276 C13H17O+ 1 189.1274 1.2
191.026 C11H8ClO+ 1 191.0258 0.84
191.0622 C12H12Cl+ 1 191.0622 -0.01
193.0417 C11H10ClO+ 1 193.0415 1.33
193.1016 C15H13+ 1 193.1012 2.43
195.0574 C11H12ClO+ 1 195.0571 1.26
195.1172 C15H15+ 1 195.1168 1.81
196.125 C15H16+ 1 196.1247 1.65
197.0964 C14H13O+ 1 197.0961 1.62
197.1329 C15H17+ 1 197.1325 2.2
199.1115 C14H15O+ 1 199.1117 -0.98
201.0461 C13H10Cl+ 1 201.0466 -2.41
201.128 C14H17O+ 1 201.1274 3.07
203.0626 C13H12Cl+ 1 203.0622 1.77
205.0416 C12H10ClO+ 1 205.0415 0.41
205.0777 C13H14Cl+ 1 205.0779 -0.52
205.1014 C16H13+ 1 205.1012 0.93
207.0575 C12H12ClO+ 1 207.0571 1.98
207.117 C16H15+ 1 207.1168 1.02
209.0958 C15H13O+ 1 209.0961 -1.26
209.1326 C16H17+ 1 209.1325 0.67
211.1121 C15H15O+ 1 211.1117 1.67
211.1486 C16H19+ 1 211.1481 2.35
215.0621 C14H12Cl+ 1 215.0622 -0.68
217.0781 C14H14Cl+ 1 217.0779 1.11
217.1007 C17H13+ 1 217.1012 -2.16
218.1088 C17H14+ 1 218.109 -1.02
219.0573 C13H12ClO+ 1 219.0571 0.67
219.1169 C17H15+ 1 219.1168 0.39
220.1252 C17H16+ 1 220.1247 2.27
221.0735 C13H14ClO+ 1 221.0728 3.17
221.0966 C16H13O+ 1 221.0961 2.38
221.1328 C17H17+ 1 221.1325 1.44
222.1034 C16H14O+ 1 222.1039 -2.16
223.112 C16H15O+ 1 223.1117 1.07
223.1484 C17H19+ 1 223.1481 1.03
224.12 C16H16O+ 1 224.1196 2.1
225.1278 C16H17O+ 1 225.1274 1.69
229.078 C15H14Cl+ 1 229.0779 0.48
231.0933 C15H16Cl+ 1 231.0935 -0.7
231.1175 C18H15+ 1 231.1168 2.83
232.1251 C18H16+ 1 232.1247 2.04
233.0731 C14H14ClO+ 1 233.0728 1.39
233.1326 C18H17+ 1 233.1325 0.47
234.1406 C18H18+ 1 234.1403 1.26
235.0876 C14H16ClO+ 1 235.0884 -3.54
235.1114 C17H15O+ 1 235.1117 -1.43
235.1485 C18H19+ 1 235.1481 1.45
236.1196 C17H16O+ 1 236.1196 0.14
237.1275 C17H17O+ 1 237.1274 0.66
237.164 C18H21+ 1 237.1638 1.01
238.135 C17H18O+ 1 238.1352 -0.74
239.1433 C17H19O+ 1 239.143 1.18
241.0771 C16H14Cl+ 1 241.0779 -3.26
243.0943 C16H16Cl+ 1 243.0935 3.13
245.0732 C15H14ClO+ 1 245.0728 1.91
245.1095 C16H18Cl+ 1 245.1092 1.38
245.1331 C19H17+ 1 245.1325 2.66
246.1403 C19H18+ 1 246.1403 -0.07
247.1478 C19H19+ 1 247.1481 -1.42
248.1196 C18H16O+ 1 248.1196 -0.02
249.1282 C18H17O+ 1 249.1274 3.17
249.164 C19H21+ 1 249.1638 0.99
250.1354 C18H18O+ 1 250.1352 0.91
250.1722 C19H22+ 1 250.1716 2.4
251.1435 C18H19O+ 1 251.143 1.88
251.18 C19H23+ 1 251.1794 2.27
253.1585 C18H21O+ 1 253.1587 -0.95
257.1087 C17H18Cl+ 1 257.1092 -1.75
259.0881 C16H16ClO+ 1 259.0884 -1.34
259.1489 C20H19+ 1 259.1481 3.08
260.1559 C20H20+ 1 260.156 -0.15
261.1286 C19H17O+ 1 261.1274 4.51
261.1637 C20H21+ 1 261.1638 -0.44
262.1352 C19H18O+ 1 262.1352 -0.22
263.1432 C19H19O+ 1 263.143 0.66
264.1515 C19H20O+ 1 264.1509 2.34
265.1587 C19H21O+ 1 265.1587 0.21
269.1092 C18H18Cl+ 1 269.1092 0.22
270.1409 C21H18+ 1 270.1403 2.06
273.104 C17H18ClO+ 1 273.1041 -0.18
275.142 C20H19O+ 2 275.143 -3.63
275.1801 C21H23+ 1 275.1794 2.44
277.1591 C20H21O+ 1 277.1587 1.48
278.1669 C20H22O+ 1 278.1665 1.2
279.1744 C20H23O+ 1 279.1743 0.28
281.1094 C19H18Cl+ 1 281.1092 1.03
285.1045 C18H18ClO+ 1 285.1041 1.39
287.1201 C18H20ClO+ 1 287.1197 1.28
288.1512 C21H20O+ 1 288.1509 1.21
293.1535 C20H21O2+ 1 293.1536 -0.48
293.1904 C21H25O+ 1 293.19 1.26
299.1197 C19H20ClO+ 1 299.1197 -0.16
303.1741 C22H23O+ 1 303.1743 -0.87
306.1606 C21H22O2+ 1 306.1614 -2.57
313.1355 C20H22ClO+ 1 313.1354 0.47
314.1436 C20H23ClO+ 1 314.1432 1.21
315.1514 C20H24ClO+ 1 315.151 1.35
321.185 C22H25O2+ 1 321.1849 0.21
329.1677 C21H26ClO+ 1 329.1667 3.01
357.1612 C22H26ClO2+ 1 357.1616 -1.13
375.1715 C22H28ClO3+ 1 375.1721 -1.63
PK$NUM_PEAK: 178
PK$PEAK: m/z int. rel.int.
55.0176 1029 29
55.0541 1174.7 33
59.0491 1798.7 51
61.0282 2343.1 67
67.0541 2897.5 82
69.0334 2031 58
69.0699 1474.7 42
79.0544 1899.9 54
81.07 5526 158
83.0492 4534.8 129
85.0649 4733.2 135
87.0442 12932.5 369
91.0543 2874.9 82
93.0701 8255.9 236
95.0494 3869.8 110
95.0857 5644.7 161
97.0651 3805.9 108
105.07 9978 285
107.0857 10782.2 308
109.065 7976.1 228
109.1013 3786.4 108
111.0806 9497.7 271
117.0702 2628.4 75
119.0857 12114.9 346
121.065 8432.6 241
121.1014 8311.2 237
123.0805 5204 148
129.0702 3315.4 94
131.0857 10046.5 287
133.1014 26103.7 746
135.0805 4093.5 117
135.1172 2866.3 81
137.0961 1699.3 48
141.0471 1202.3 34
141.0701 1266.2 36
142.0778 1418.6 40
143.0858 7710.5 220
145.065 5930 169
145.1014 13481.2 385
147.0805 7346 210
147.117 25756.3 736
149.0961 4075 116
151.1119 3655.1 104
155.026 3186.8 91
155.0857 7013.1 200
157.1014 12675.3 362
159.0807 9093.2 260
159.1169 7294.3 208
161.096 3994.5 114
163.1122 4669.6 133
165.0462 2286.8 65
167.0259 1553.1 44
167.0854 2683.7 76
169.0421 2623.1 75
169.1012 7033.7 201
171.0805 4847.1 138
171.1173 6751.9 193
173.0964 2965.3 84
173.1331 999.7 28
175.1119 16048.4 459
177.0467 7862.3 224
177.1276 2499.2 71
179.0261 2152.2 61
179.0853 1956.8 55
181.0417 11681.5 334
181.0782 1536.2 43
181.1015 5041.8 144
182.1081 1065.5 30
183.0578 1978.9 56
183.0806 3503.6 100
183.117 8181.9 234
184.0885 2998.9 85
185.0963 13724.2 392
185.1332 2737.8 78
187.112 3508.7 100
189.0461 2443.9 69
189.1276 2167.2 62
191.026 3632.8 103
191.0622 5381.1 153
193.0417 5347.7 152
193.1016 7111.8 203
195.0574 3427.6 98
195.1172 12141.7 347
196.125 2060.2 58
197.0964 2671.2 76
197.1329 5185.4 148
199.1115 3348.5 95
201.0461 1402.5 40
201.128 2911.4 83
203.0626 4296.1 122
205.0416 5507.5 157
205.0777 1318.7 37
205.1014 4471.4 127
207.0575 4189.6 119
207.117 9636.5 275
209.0958 4688.1 134
209.1326 7966.1 227
211.1121 4916.5 140
211.1486 2092.3 59
215.0621 1801 51
217.0781 3703.8 105
217.1007 1679.9 48
218.1088 1431 40
219.0573 33128.9 947
219.1169 6929.4 198
220.1252 1614.3 46
221.0735 3886.3 111
221.0966 2702.8 77
221.1328 7513.7 214
222.1034 1446.6 41
223.112 6027.1 172
223.1484 5841.2 167
224.12 1268.5 36
225.1278 3025.4 86
229.078 2256.1 64
231.0933 3240.3 92
231.1175 2015.7 57
232.1251 1863.5 53
233.0731 1517.8 43
233.1326 9114.9 260
234.1406 1470.7 42
235.0876 2221.4 63
235.1114 5257.3 150
235.1485 10723.6 306
236.1196 3257 93
237.1275 8429.5 241
237.164 3630.1 103
238.135 2832.2 81
239.1433 3642.2 104
241.0771 1011 28
243.0943 1829.7 52
245.0732 5337.2 152
245.1095 2360.1 67
245.1331 3251.4 93
246.1403 3110.4 88
247.1478 5499.1 157
248.1196 1482.3 42
249.1282 4781.6 136
249.164 6322.2 180
250.1354 2903.2 83
250.1722 3509.9 100
251.1435 11576.6 331
251.18 4465.5 127
253.1585 3467.1 99
257.1087 1365 39
259.0881 2529.6 72
259.1489 3881 111
260.1559 2937.3 84
261.1286 2029.2 58
261.1637 9645.3 275
262.1352 3026.6 86
263.1432 21395.8 612
264.1515 2906.4 83
265.1587 3930.6 112
269.1092 1922.9 55
270.1409 1191.1 34
273.104 3015.2 86
275.142 1204.4 34
275.1801 4585.6 131
277.1591 19476.5 557
278.1669 14703 420
279.1744 34919.6 999
281.1094 1038.3 29
285.1045 2405.3 68
287.1201 3127.5 89
288.1512 1849.6 52
293.1535 11109.1 317
293.1904 3747.5 107
299.1197 4171.5 119
303.1741 7259.6 207
306.1606 4244.5 121
313.1355 11302.6 323
314.1436 8230.1 235
315.1514 4165.8 119
321.185 19758.7 565
329.1677 1133.1 32
357.1612 2462 70
375.1715 4475.9 128
//
