ACCESSION: MSBNK-UFZ-WANA022213D9F1PH
RECORD_TITLE: Norgestimate; 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$NAME: Norgestimate
CH$NAME: [(3E,8R,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-3-hydroxyimino-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl] acetate
CH$COMPOUND_CLASS: N/A; Environmental Standard
CH$FORMULA: C23H31NO3
CH$EXACT_MASS: 369.230393852
CH$SMILES: CC[C@]12CC[C@H]3[C@@H](CCC4=C\C(CC[C@H]34)=N\O)[C@@H]1CC[C@@]2(OC(C)=O)C#C
CH$IUPAC: InChI=1S/C23H31NO3/c1-4-22-12-10-19-18-9-7-17(24-26)14-16(18)6-8-20(19)21(22)11-13-23(22,5-2)27-15(3)25/h2,14,18-21,26H,4,6-13H2,1,3H3/b24-17+/t18-,19+,20+,21-,22-,23-/m0/s1
CH$LINK: CAS
20799-27-3
CH$LINK: CHEBI
50815
CH$LINK: KEGG
D05209
CH$LINK: PUBCHEM
CID:6540478
CH$LINK: INCHIKEY
KIQQMECNKUGGKA-NMYWJIRASA-N
CH$LINK: CHEMSPIDER
5022837
CH$LINK: COMPTOX
DTXSID1046922
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$MASS_SPECTROMETRY: MASS_RANGE_M/Z 50-385
AC$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$CHROMATOGRAPHY: RETENTION_TIME 12.979 min
MS$FOCUSED_ION: BASE_PEAK 65.0595
MS$FOCUSED_ION: PRECURSOR_M/Z 370.2377
MS$FOCUSED_ION: PRECURSOR_TYPE [M+H]+
MS$FOCUSED_ION: PRECURSOR_INTENSITY 2002075.88
MS$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$SPLASH: splash10-00di-2911000000-5d0ef8f0a8ed16ed9209
PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm)
65.0383 C5H5+ 1 65.0386 -3.51
67.054 C5H7+ 1 67.0542 -3.04
69.0697 C5H9+ 1 69.0699 -2.73
70.0649 C4H8N+ 1 70.0651 -3.8
77.0386 C6H5+ 1 77.0386 0.51
79.0541 C6H7+ 1 79.0542 -1.86
80.0493 C5H6N+ 1 80.0495 -1.59
81.0697 C6H9+ 1 81.0699 -1.77
82.065 C5H8N+ 1 82.0651 -1.24
91.0541 C7H7+ 1 91.0542 -1.14
92.0494 C6H6N+ 1 92.0495 -0.61
93.0698 C7H9+ 1 93.0699 -1.13
94.065 C6H8N+ 1 94.0651 -0.94
95.0729 C6H9N+ 1 95.073 -0.55
95.0855 C7H11+ 1 95.0855 -0.74
96.0444 C5H6NO+ 1 96.0444 0.01
96.0808 C6H10N+ 1 96.0808 0.23
98.0599 C5H8NO+ 1 98.06 -1.18
103.0542 C8H7+ 1 103.0542 -0.64
105.0697 C8H9+ 1 105.0699 -1.22
106.065 C7H8N+ 1 106.0651 -1.63
107.0729 C7H9N+ 1 107.073 -0.12
107.0854 C8H11+ 1 107.0855 -1.28
108.0806 C7H10N+ 1 108.0808 -1.18
109.0646 C7H9O+ 1 109.0648 -1.82
109.0885 C7H11N+ 1 109.0886 -1.03
109.1011 C8H13+ 1 109.1012 -0.85
110.0599 C6H8NO+ 1 110.06 -1.29
111.0681 C6H9NO+ 1 111.0679 1.74
112.0756 C6H10NO+ 1 112.0757 -0.66
115.0541 C9H7+ 1 115.0542 -0.68
116.0619 C9H8+ 1 116.0621 -1.33
117.0573 C8H7N+ 1 117.0573 0.14
117.0697 C9H9+ 1 117.0699 -1.12
118.065 C8H8N+ 1 118.0651 -0.96
119.0854 C9H11+ 1 119.0855 -0.97
120.0807 C8H10N+ 1 120.0808 -0.81
121.0884 C8H11N+ 1 121.0886 -1.38
121.101 C9H13+ 1 121.1012 -1.21
122.0599 C7H8NO+ 1 122.06 -1.42
122.0963 C8H12N+ 1 122.0964 -0.81
123.0801 C8H11O+ 1 123.0804 -2.49
123.1165 C9H15+ 1 123.1168 -3
124.0755 C7H10NO+ 1 124.0757 -1.16
128.0618 C10H8+ 1 128.0621 -2.01
129.0697 C10H9+ 1 129.0699 -1.16
130.065 C9H8N+ 1 130.0651 -1.25
130.0776 C10H10+ 1 130.0777 -0.8
131.0853 C10H11+ 1 131.0855 -1.37
132.0806 C9H10N+ 1 132.0808 -1.68
133.101 C10H13+ 1 133.1012 -1.12
134.0964 C9H12N+ 1 134.0964 -0.29
135.0804 C9H11O+ 1 135.0804 -0.14
135.1037 C9H13N+ 1 135.1043 -4.13
135.1166 C10H15+ 1 135.1168 -1.56
136.0756 C8H10NO+ 1 136.0757 -0.34
137.096 C9H13O+ 1 137.0961 -0.48
138.0912 C8H12NO+ 1 138.0913 -1.12
141.0698 C11H9+ 1 141.0699 -0.78
142.0775 C11H10+ 1 142.0777 -1.32
143.0853 C11H11+ 1 143.0855 -1.31
144.0807 C10H10N+ 1 144.0808 -0.85
144.0928 C11H12+ 1 144.0934 -3.73
145.088 C10H11N+ 1 145.0886 -4.01
145.101 C11H13+ 1 145.1012 -1.29
146.0963 C10H12N+ 1 146.0964 -1.06
147.0802 C10H11O+ 1 147.0804 -1.32
147.1041 C10H13N+ 1 147.1043 -1.05
147.1167 C11H15+ 1 147.1168 -1.07
148.0754 C9H10NO+ 1 148.0757 -2.12
148.1119 C10H14N+ 1 148.1121 -1.05
149.0959 C10H13O+ 1 149.0961 -1.21
150.0911 C9H12NO+ 1 150.0913 -1.39
152.1068 C9H14NO+ 1 152.107 -0.98
153.0701 C12H9+ 1 153.0699 1.22
154.0776 C12H10+ 1 154.0777 -0.68
155.0854 C12H11+ 1 155.0855 -0.98
156.0807 C11H10N+ 1 156.0808 -0.47
156.0927 C12H12+ 1 156.0934 -4.01
157.0886 C11H11N+ 1 157.0886 -0.18
157.101 C12H13+ 1 157.1012 -1.07
158.0963 C11H12N+ 1 158.0964 -0.67
159.104 C11H13N+ 1 159.1043 -1.82
159.1166 C12H15+ 1 159.1168 -1.36
160.1119 C11H14N+ 1 160.1121 -0.96
161.0962 C11H13O+ 1 161.0961 0.88
161.1195 C11H15N+ 1 161.1199 -2.29
161.1322 C12H17+ 1 161.1325 -1.64
162.0912 C10H12NO+ 1 162.0913 -0.81
162.1274 C11H16N+ 1 162.1277 -2.28
163.1116 C11H15O+ 1 163.1117 -0.64
164.1068 C10H14NO+ 1 164.107 -1.37
165.0701 C13H9+ 1 165.0699 1.42
166.0777 C13H10+ 1 166.0777 0.13
167.0854 C13H11+ 1 167.0855 -0.52
168.0931 C13H12+ 1 168.0934 -1.24
169.101 C13H13+ 1 169.1012 -1.04
170.0963 C12H12N+ 1 170.0964 -0.84
171.1044 C12H13N+ 1 171.1043 1.13
171.1167 C13H15+ 1 171.1168 -0.67
172.1119 C12H14N+ 1 172.1121 -0.9
173.0966 C12H13O+ 1 173.0961 2.67
173.1324 C13H17+ 1 173.1325 -0.73
174.0911 C11H12NO+ 1 174.0913 -1.45
174.1274 C12H16N+ 1 174.1277 -1.85
175.1118 C12H15O+ 1 175.1117 0.21
176.1068 C11H14NO+ 1 176.107 -0.81
178.1226 C11H16NO+ 1 178.1226 -0.44
179.0855 C14H11+ 1 179.0855 -0.25
180.0929 C14H12+ 1 180.0934 -2.53
181.1009 C14H13+ 1 181.1012 -1.41
182.0967 C13H12N+ 1 182.0964 1.55
182.1089 C14H14+ 1 182.109 -0.39
183.1035 C13H13N+ 1 183.1043 -3.95
183.1166 C14H15+ 1 183.1168 -1.46
184.1122 C13H14N+ 1 184.1121 0.48
184.1244 C14H16+ 1 184.1247 -1.53
185.1323 C14H17+ 1 185.1325 -0.76
186.1276 C13H16N+ 1 186.1277 -0.57
187.1114 C13H15O+ 1 187.1117 -1.58
187.148 C14H19+ 1 187.1481 -0.73
188.1073 C12H14NO+ 1 188.107 1.45
188.1426 C13H18N+ 1 188.1434 -4.35
190.1224 C12H16NO+ 1 190.1226 -1.11
193.1012 C15H13+ 1 193.1012 0.3
194.0967 C14H12N+ 1 194.0964 1.66
194.1096 C15H14+ 1 194.109 3.06
195.1167 C15H15+ 1 195.1168 -0.77
196.1128 C14H14N+ 1 196.1121 3.69
196.125 C15H16+ 1 196.1247 1.89
197.1207 C14H15N+ 1 197.1199 3.91
197.1323 C15H17+ 1 197.1325 -0.67
198.1279 C14H16N+ 1 198.1277 0.67
198.1411 C15H18+ 1 198.1403 4.05
199.148 C15H19+ 1 199.1481 -0.56
200.1439 C14H18N+ 1 200.1434 2.75
201.1274 C14H17O+ 1 201.1274 0.04
202.1228 C13H16NO+ 1 202.1226 0.59
204.1382 C13H18NO+ 1 204.1383 -0.28
205.1014 C16H13+ 1 205.1012 1.08
207.1169 C16H15+ 1 207.1168 0.28
208.1121 C15H14N+ 1 208.1121 -0.06
208.1249 C16H16+ 1 208.1247 1.4
209.1326 C16H17+ 1 209.1325 0.53
211.1486 C16H19+ 1 211.1481 2.13
212.1435 C15H18N+ 1 212.1434 0.57
213.164 C16H21+ 1 213.1638 1.13
219.1169 C17H15+ 1 219.1168 0.11
220.1248 C17H16+ 1 220.1247 0.47
221.1324 C17H17+ 1 221.1325 -0.35
222.1286 C16H16N+ 1 222.1277 4
222.141 C17H18+ 1 222.1403 3.3
223.1483 C17H19+ 1 223.1481 0.69
224.1443 C16H18N+ 1 224.1434 3.98
225.1637 C17H21+ 1 225.1638 -0.52
227.1438 C16H19O+ 1 227.143 3.24
227.1795 C17H23+ 1 227.1794 0.38
230.1538 C15H20NO+ 1 230.1539 -0.82
231.1176 C18H15+ 1 231.1168 3.16
234.1279 C17H16N+ 1 234.1277 0.94
235.148 C18H19+ 1 235.1481 -0.56
236.1437 C17H18N+ 1 236.1434 1.47
237.164 C18H21+ 1 237.1638 1.01
238.1602 C17H20N+ 1 238.159 4.87
240.1746 C17H22N+ 1 240.1747 -0.43
247.1477 C19H19+ 1 247.1481 -1.55
248.1562 C19H20+ 1 248.156 0.8
249.1639 C19H21+ 1 249.1638 0.56
250.1591 C18H20N+ 1 250.159 0.33
251.1793 C19H23+ 1 251.1794 -0.4
252.1758 C18H22N+ 1 252.1747 4.28
260.2007 C17H26NO+ 1 260.2009 -0.69
261.1637 C20H21+ 1 261.1638 -0.44
262.1596 C19H20N+ 1 262.159 2.09
264.1746 C19H22N+ 1 264.1747 -0.46
268.206 C19H26N+ 1 268.206 0.26
275.1802 C21H23+ 1 275.1794 2.78
277.1949 C21H25+ 1 277.1951 -0.76
278.1907 C20H24N+ 1 278.1903 1.18
282.1854 C19H24NO+ 1 282.1852 0.46
282.2212 C20H28N+ 1 282.2216 -1.52
292.2054 C21H26N+ 1 292.206 -1.95
293.2135 C21H27N+ 1 293.2138 -1.16
310.2162 C21H28NO+ 1 310.2165 -1.26
324.1947 C21H26NO2+ 1 324.1958 -3.49
328.227 C21H30NO2+ 1 328.2271 -0.46
370.2372 C23H32NO3+ 1 370.2377 -1.31
PK$NUM_PEAK: 187
PK$PEAK: m/z int. rel.int.
65.0383 5296.9 5
67.054 53981.8 58
69.0697 14065.7 15
70.0649 6799.5 7
77.0386 8650.5 9
79.0541 121137.5 131
80.0493 15340.1 16
81.0697 77249 83
82.065 34563.6 37
91.0541 202404.8 219
92.0494 22025.8 23
93.0698 151721.6 164
94.065 21025.8 22
95.0729 17975.2 19
95.0855 76643.5 83
96.0444 8220.6 8
96.0808 25628.3 27
98.0599 475508.4 516
103.0542 13361.9 14
105.0697 245813.8 266
106.065 57061.6 61
107.0729 10473.6 11
107.0854 123720.5 134
108.0806 110065.1 119
109.0646 14246 15
109.0885 19098.3 20
109.1011 29324.5 31
110.0599 37754.3 40
111.0681 5261.4 5
112.0756 12152.7 13
115.0541 15971.5 17
116.0619 12530.5 13
117.0573 7794.4 8
117.0697 152927.3 165
118.065 17157.6 18
119.0854 209187.6 227
120.0807 25837.8 28
121.0884 17126.1 18
121.101 55941.5 60
122.0599 44608.4 48
122.0963 23578.6 25
123.0801 11149.2 12
123.1165 8455 9
124.0755 920568.2 999
128.0618 12919 14
129.0697 113512.2 123
130.065 18409.9 19
130.0776 15412.6 16
131.0853 279917.6 303
132.0806 35348.4 38
133.101 206228.6 223
134.0964 29687 32
135.0804 8617.9 9
135.1037 6952 7
135.1166 22150.5 24
136.0756 32519.9 35
137.096 15955.8 17
138.0912 24362.7 26
141.0698 44227 47
142.0775 23431.1 25
143.0853 161722.3 175
144.0807 22645.5 24
144.0928 22330.7 24
145.088 11120.7 12
145.101 200918.9 218
146.0963 39645.7 43
147.0802 7847 8
147.1041 13918.9 15
147.1167 69549.7 75
148.0754 19185.6 20
148.1119 28880.7 31
149.0959 39484 42
150.0911 51136.1 55
152.1068 16895 18
153.0701 7611.9 8
154.0776 9941.4 10
155.0854 75078.8 81
156.0807 11095.8 12
156.0927 22567.2 24
157.0886 10412.5 11
157.101 154597.6 167
158.0963 38546 41
159.104 17860.9 19
159.1166 168951.3 183
160.1119 41773.4 45
161.0962 9974 10
161.1195 20186.4 21
161.1322 43608.4 47
162.0912 30966.2 33
162.1274 28365.1 30
163.1116 12159.7 13
164.1068 40552.1 44
165.0701 7657 8
166.0777 5402.4 5
167.0854 31872.5 34
168.0931 14955.9 16
169.101 78910.5 85
170.0963 13720.7 14
171.1044 8239.8 8
171.1167 94852.7 102
172.1119 22612.7 24
173.0966 7824.2 8
173.1324 61379.8 66
174.0911 24354.2 26
174.1274 22034.2 23
175.1118 15152.8 16
176.1068 90311.5 98
178.1226 56202.9 60
179.0855 15319.3 16
180.0929 9634.9 10
181.1009 47072.9 51
182.0967 11793.6 12
182.1089 14065.4 15
183.1035 6048.9 6
183.1166 90521.5 98
184.1122 14656 15
184.1244 9448.5 10
185.1323 123087.5 133
186.1276 12504 13
187.1114 6966.4 7
187.148 32326.7 35
188.1073 9989.5 10
188.1426 5635.7 6
190.1224 25294.9 27
193.1012 20418.1 22
194.0967 5481.6 5
194.1096 8552.2 9
195.1167 49116.4 53
196.1128 11656.8 12
196.125 12469.7 13
197.1207 6000.6 6
197.1323 49709.1 53
198.1279 16294.3 17
198.1411 6930.5 7
199.148 36124.4 39
200.1439 7606.6 8
201.1274 7687.6 8
202.1228 12106.3 13
204.1382 11059.7 12
205.1014 10140.5 11
207.1169 26261.8 28
208.1121 12170.4 13
208.1249 9986.5 10
209.1326 32458.5 35
211.1486 19185.4 20
212.1435 10180.9 11
213.164 9252.7 10
219.1169 9532.3 10
220.1248 8677.3 9
221.1324 26220.8 28
222.1286 9846.8 10
222.141 7453.6 8
223.1483 32387.3 35
224.1443 12708.8 13
225.1637 32986.7 35
227.1438 3994.8 4
227.1795 5792.8 6
230.1538 6891.6 7
231.1176 6637.1 7
234.1279 6066.6 6
235.148 23876.2 25
236.1437 18886.4 20
237.164 30751.5 33
238.1602 10165.3 11
240.1746 7945.5 8
247.1477 16116.7 17
248.1562 7903.6 8
249.1639 17243.9 18
250.1591 10725.6 11
251.1793 13444.9 14
252.1758 6949.3 7
260.2007 41432 44
261.1637 7139.7 7
262.1596 7464.2 8
264.1746 66323.3 71
268.206 10054.4 10
275.1802 5208.1 5
277.1949 14667.1 15
278.1907 22973.6 24
282.1854 46882.3 50
282.2212 5637.5 6
292.2054 18469.7 20
293.2135 8719.6 9
310.2162 394295.9 427
324.1947 6387 6
328.227 29350.5 31
370.2372 599847.8 650
//
