ACCESSION: MSBNK-UFZ-WANA223611C9CFPH
RECORD_TITLE: Cyproterone; LC-ESI-ITFT; MS2; CE: 40%; 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$MASS_SPECTROMETRY: COLLISION_ENERGY 40 % (nominal)
AC$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$SPLASH: splash10-004i-0694000000-5774c94fc6f0d75484b2
PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm)
61.0283 C2H5O2+ 1 61.0284 -2.5
69.0334 C4H5O+ 1 69.0335 -0.73
69.0696 C5H9+ 1 69.0699 -3.5
79.0542 C6H7+ 1 79.0542 -0.8
81.0696 C6H9+ 1 81.0699 -3.37
83.0488 C5H7O+ 1 83.0491 -3.99
85.0646 C5H9O+ 1 85.0648 -2.08
87.0438 C4H7O2+ 1 87.0441 -2.8
91.054 C7H7+ 1 91.0542 -2.98
93.0697 C7H9+ 1 93.0699 -1.87
95.0488 C6H7O+ 1 95.0491 -3.3
95.0854 C7H11+ 1 95.0855 -1.54
97.0646 C6H9O+ 1 97.0648 -1.68
105.0696 C8H9+ 1 105.0699 -2.75
107.0852 C8H11+ 1 107.0855 -3.42
109.0645 C7H9O+ 1 109.0648 -2.94
109.1008 C8H13+ 1 109.1012 -3.3
111.0802 C7H11O+ 1 111.0804 -2.13
119.0852 C9H11+ 1 119.0855 -3.09
121.0645 C8H9O+ 1 121.0648 -2.65
121.101 C9H13+ 1 121.1012 -1.71
123.0801 C8H11O+ 1 123.0804 -3.05
131.0854 C10H11+ 1 131.0855 -1.02
133.0646 C9H9O+ 1 133.0648 -1.4
133.1008 C10H13+ 1 133.1012 -2.5
135.0805 C9H11O+ 1 135.0804 0.77
135.1165 C10H15+ 1 135.1168 -2.12
137.0956 C9H13O+ 1 137.0961 -3.48
141.0468 C8H10Cl+ 1 141.0466 1.43
143.0851 C11H11+ 1 143.0855 -3.12
145.0643 C10H9O+ 1 145.0648 -3.34
145.1008 C11H13+ 1 145.1012 -2.55
147.08 C10H11O+ 1 147.0804 -2.88
147.1164 C11H15+ 1 147.1168 -3.14
149.0956 C10H13O+ 1 149.0961 -3.46
151.1113 C10H15O+ 1 151.1117 -2.61
155.0257 C8H8ClO+ 1 155.0258 -0.78
155.0851 C12H11+ 1 155.0855 -2.55
157.1008 C12H13+ 1 157.1012 -2.14
159.08 C11H11O+ 1 159.0804 -2.75
159.1164 C12H15+ 1 159.1168 -2.9
161.0957 C11H13O+ 1 161.0961 -2.63
163.1114 C11H15O+ 1 163.1117 -2.04
167.0252 C9H8ClO+ 1 167.0258 -3.71
169.0415 C9H10ClO+ 1 169.0415 0.13
169.1009 C13H13+ 1 169.1012 -1.86
171.0802 C12H11O+ 1 171.0804 -1.33
171.1164 C13H15+ 1 171.1168 -2.36
173.0959 C12H13O+ 1 173.0961 -1.12
173.1321 C13H17+ 1 173.1325 -2.06
175.1113 C12H15O+ 1 175.1117 -2.58
177.0461 C11H10Cl+ 1 177.0466 -2.82
177.1271 C12H17O+ 1 177.1274 -1.85
179.0621 C11H12Cl+ 1 179.0622 -0.64
181.041 C10H10ClO+ 1 181.0415 -2.85
181.0773 C11H14Cl+ 1 181.0779 -3.31
181.101 C14H13+ 1 181.1012 -1.16
183.0568 C10H12ClO+ 1 183.0571 -1.71
183.1163 C14H15+ 1 183.1168 -2.63
185.0956 C13H13O+ 1 185.0961 -2.61
185.1325 C14H17+ 1 185.1325 0.14
187.1112 C13H15O+ 1 187.1117 -3.05
189.046 C12H10Cl+ 1 189.0466 -3.1
189.127 C13H17O+ 1 189.1274 -1.95
191.0258 C11H8ClO+ 1 191.0258 0.04
191.0617 C12H12Cl+ 1 191.0622 -2.72
193.0408 C11H10ClO+ 1 193.0415 -3.65
195.0566 C11H12ClO+ 1 195.0571 -2.49
195.1164 C15H15+ 1 195.1168 -2.34
196.1237 C15H16+ 1 196.1247 -4.73
197.0954 C14H13O+ 1 197.0961 -3.72
197.1326 C15H17+ 1 197.1325 0.42
199.1113 C14H15O+ 1 199.1117 -2.13
201.0464 C13H10Cl+ 1 201.0466 -0.89
201.1269 C14H17O+ 1 201.1274 -2.62
203.0621 C13H12Cl+ 1 203.0622 -0.55
205.0408 C12H10ClO+ 1 205.0415 -3.31
205.0773 C13H14Cl+ 1 205.0779 -2.83
207.0566 C12H12ClO+ 1 207.0571 -2.74
207.1165 C16H15+ 1 207.1168 -1.63
209.0957 C15H13O+ 1 209.0961 -1.99
209.1318 C16H17+ 1 209.1325 -3.12
211.1116 C15H15O+ 1 211.1117 -0.64
213.127 C15H17O+ 1 213.1274 -1.76
215.0612 C14H12Cl+ 1 215.0622 -4.65
217.0773 C14H14Cl+ 1 217.0779 -2.76
217.1014 C17H13+ 1 217.1012 1.15
219.0565 C13H12ClO+ 1 219.0571 -2.67
219.1163 C17H15+ 1 219.1168 -2.46
221.0719 C13H14ClO+ 1 221.0728 -4.01
221.0952 C16H13O+ 1 221.0961 -3.9
221.1318 C17H17+ 1 221.1325 -3.11
223.1112 C16H15O+ 1 223.1117 -2.48
223.1478 C17H19+ 1 223.1481 -1.56
225.1269 C16H17O+ 1 225.1274 -2.24
227.0617 C15H12Cl+ 1 227.0622 -2.36
227.1055 C15H15O2+ 1 227.1067 -4.99
229.0774 C15H14Cl+ 1 229.0779 -2.12
231.0929 C15H16Cl+ 1 231.0935 -2.42
233.0722 C14H14ClO+ 1 233.0728 -2.48
233.1316 C18H17+ 1 233.1325 -3.59
235.1119 C17H15O+ 1 235.1117 0.58
235.1477 C18H19+ 1 235.1481 -1.92
237.1267 C17H17O+ 1 237.1274 -2.75
237.1634 C18H21+ 1 237.1638 -1.76
238.134 C17H18O+ 2 238.1352 -4.97
239.1422 C17H19O+ 1 239.143 -3.41
241.0773 C16H14Cl+ 1 241.0779 -2.5
243.0933 C16H16Cl+ 1 243.0935 -0.7
245.0722 C15H14ClO+ 1 245.0728 -2.32
245.1086 C16H18Cl+ 1 245.1092 -2.17
245.1334 C19H17+ 1 245.1325 3.59
247.1478 C19H19+ 1 247.1481 -1.24
249.1267 C18H17O+ 1 249.1274 -2.77
249.1632 C19H21+ 1 249.1638 -2.26
251.1423 C18H19O+ 1 251.143 -3.1
251.1789 C19H23+ 1 251.1794 -2.04
253.1581 C18H21O+ 1 253.1587 -2.34
255.0939 C17H16Cl+ 1 255.0935 1.51
257.1085 C17H18Cl+ 1 257.1092 -2.7
259.0876 C16H16ClO+ 1 259.0884 -3.22
259.1476 C20H19+ 1 259.1481 -1.98
260.1559 C20H20+ 1 260.156 -0.39
261.1278 C19H17O+ 1 261.1274 1.47
261.1633 C20H21+ 1 261.1638 -1.96
263.1423 C19H19O+ 1 263.143 -2.71
264.1505 C19H20O+ 1 264.1509 -1.48
265.1956 C20H25+ 1 265.1951 1.9
269.1083 C18H18Cl+ 1 269.1092 -3.19
271.0883 C17H16ClO+ 1 271.0884 -0.53
271.1251 C18H20Cl+ 1 271.1248 1.02
273.1036 C17H18ClO+ 1 273.1041 -1.85
275.1196 C17H20ClO+ 1 275.1197 -0.61
275.1789 C21H23+ 1 275.1794 -1.99
277.158 C20H21O+ 1 277.1587 -2.49
278.1663 C20H22O+ 1 278.1665 -0.88
279.1736 C20H23O+ 1 279.1743 -2.68
283.0873 C18H16ClO+ 1 283.0884 -3.79
285.1636 C22H21+ 1 285.1638 -0.7
287.1189 C18H20ClO+ 1 287.1197 -2.76
289.1348 C18H22ClO+ 1 289.1354 -2.1
293.1529 C20H21O2+ 1 293.1536 -2.36
293.1894 C21H25O+ 1 293.19 -1.97
297.1394 C20H22Cl+ 1 297.1405 -3.69
297.1837 C20H25O2+ 1 297.1849 -4.16
299.1195 C19H20ClO+ 1 299.1197 -0.77
303.1736 C22H23O+ 2 303.1743 -2.58
306.1611 C21H22O2+ 1 306.1614 -1.07
313.1345 C20H22ClO+ 1 313.1354 -2.94
314.1425 C20H23ClO+ 1 314.1432 -2.1
315.1502 C20H24ClO+ 1 315.151 -2.52
321.1841 C22H25O2+ 1 321.1849 -2.64
329.1663 C21H26ClO+ 1 329.1667 -1.17
339.1942 C22H27O3+ 1 339.1955 -3.76
357.1606 C22H26ClO2+ 1 357.1616 -2.84
375.171 C22H28ClO3+ 1 375.1721 -3.17
PK$NUM_PEAK: 156
PK$PEAK: m/z int. rel.int.
61.0283 1736 17
69.0334 1972.9 20
69.0696 1784 18
79.0542 2480 25
81.0696 5007.1 51
83.0488 4103.3 42
85.0646 6584.8 67
87.0438 9219.3 95
91.054 1520.8 15
93.0697 6599.3 68
95.0488 3222.7 33
95.0854 5965.6 61
97.0646 4843.2 49
105.0696 6359.5 65
107.0852 10978.1 113
109.0645 8973.7 92
109.1008 5698.3 58
111.0802 12840 132
119.0852 11684.6 120
121.0645 8154.4 84
121.101 7321.6 75
123.0801 4524.4 46
131.0854 5976.5 61
133.0646 2221.9 22
133.1008 27090.1 279
135.0805 3691 38
135.1165 2447.3 25
137.0956 4563.2 47
141.0468 1376 14
143.0851 6780.8 69
145.0643 4782.7 49
145.1008 15614.4 161
147.08 8607.8 88
147.1164 36001.8 371
149.0956 6962.2 71
151.1113 5298.1 54
155.0257 2889.8 29
155.0851 4858.3 50
157.1008 10590.2 109
159.08 6852.8 70
159.1164 6687.9 68
161.0957 3278.5 33
163.1114 8491.9 87
167.0252 2479.3 25
169.0415 5434.4 56
169.1009 6320.5 65
171.0802 2913.8 30
171.1164 6571.8 67
173.0959 3108.2 32
173.1321 1736.6 17
175.1113 23827.1 245
177.0461 8247 85
177.1271 3510.7 36
179.0621 1977.1 20
181.041 14002.5 144
181.0773 2519.2 25
181.101 3665.9 37
183.0568 5460.2 56
183.1163 6812.2 70
185.0956 12067 124
185.1325 3734 38
187.1112 7335.1 75
189.046 3464.8 35
189.127 5224.5 53
191.0258 1601.1 16
191.0617 8843.4 91
193.0408 4371.8 45
195.0566 7181 74
195.1164 12137 125
196.1237 1992.2 20
197.0954 5304.9 54
197.1326 3085.1 31
199.1113 3730.9 38
201.0464 1503.1 15
201.1269 7325.9 75
203.0621 4412.5 45
205.0408 8428.7 86
205.0773 1911.9 19
207.0566 6042 62
207.1165 7878 81
209.0957 3363.2 34
209.1318 10115.2 104
211.1116 4820.3 49
213.127 3949.2 40
215.0612 2747.5 28
217.0773 5489.4 56
217.1014 1742.4 17
219.0565 65688.4 677
219.1163 6768.5 69
221.0719 8812.4 90
221.0952 1825.8 18
221.1318 7661.8 79
223.1112 6498.5 67
223.1478 5355.2 55
225.1269 7194.5 74
227.0617 2311.9 23
227.1055 2016.5 20
229.0774 3132.2 32
231.0929 4848.5 49
233.0722 2479.8 25
233.1316 9379.9 96
235.1119 5226.3 53
235.1477 13196.5 136
237.1267 11985.8 123
237.1634 5723.7 59
238.134 2324.9 23
239.1422 7981.2 82
241.0773 2170.6 22
243.0933 2069.2 21
245.0722 12952.3 133
245.1086 3838.2 39
245.1334 2639.8 27
247.1478 9264.6 95
249.1267 4731.7 48
249.1632 11320.2 116
251.1423 17537.7 180
251.1789 6774.1 69
253.1581 6630.1 68
255.0939 3539 36
257.1085 4398.5 45
259.0876 4678.2 48
259.1476 4854.8 50
260.1559 3536.5 36
261.1278 2645 27
261.1633 14686 151
263.1423 16354.7 168
264.1505 1519.4 15
265.1956 1364.7 14
269.1083 1830.8 18
271.0883 2413.6 24
271.1251 2616.2 26
273.1036 10354.4 106
275.1196 3924.9 40
275.1789 9501.3 97
277.158 25949.1 267
278.1663 20128.8 207
279.1736 61781.9 637
283.0873 1499.6 15
285.1636 2740.2 28
287.1189 7897.5 81
289.1348 3618.9 37
293.1529 22271.3 229
293.1894 12122.5 125
297.1394 4540.7 46
297.1837 2067.1 21
299.1195 6171.6 63
303.1736 20535.4 211
306.1611 7040.9 72
313.1345 25878 266
314.1425 17070.8 176
315.1502 16878.7 174
321.1841 96879.7 999
329.1663 4426.8 45
339.1942 4166.4 42
357.1606 24816.9 255
375.171 83952.1 865
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