ACCESSION: MSBNK-Athens_Univ-AU280005
RECORD_TITLE: Norgestimate; LC-ESI-QTOF; MS2; CE: 50 eV; R=35000; [M+H]+
DATE: 2019.05.31
AUTHORS: Nikiforos Alygizakis, Katerina Galani, Nikolaos Thomaidis, University of Athens
LICENSE: CC BY
COPYRIGHT: Copyright (C) 2019 Department of Chemistry, University of Athens
COMMENT: CONFIDENCE standard compound
COMMENT: INTERNAL_ID 2800
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$EXACT_MASS: 369.2303939
CH$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$INSTRUMENT: Bruker maXis Impact
AC$INSTRUMENT_TYPE: LC-ESI-QTOF
AC$MASS_SPECTROMETRY: MS_TYPE MS2
AC$MASS_SPECTROMETRY: ION_MODE POSITIVE
AC$MASS_SPECTROMETRY: IONIZATION ESI
AC$MASS_SPECTROMETRY: FRAGMENTATION_MODE CID
AC$MASS_SPECTROMETRY: COLLISION_ENERGY 50 eV
AC$MASS_SPECTROMETRY: RESOLUTION 35000
AC$CHROMATOGRAPHY: COLUMN_NAME Acclaim RSLC C18 2.2um, 2.1x100mm, Thermo
AC$CHROMATOGRAPHY: FLOW_GRADIENT 99/1 at 0-1 min, 61/39 at 3 min, 0.1/99.9 at 14-16 min, 99/1 at 16.1-20 min
AC$CHROMATOGRAPHY: FLOW_RATE 200 uL/min at 0-3 min, 400 uL/min at 14 min, 480 uL/min at 16-19 min, 200 uL/min at 19.1-20 min
AC$CHROMATOGRAPHY: RETENTION_TIME 11.947 min
AC$CHROMATOGRAPHY: SOLVENT A 90:10 water:methanol with 0.01% formic acid and 5mM ammonium formate
AC$CHROMATOGRAPHY: SOLVENT B methanol with 0.01% formic acid and 5mM ammonium formate
MS$FOCUSED_ION: BASE_PEAK 370.238
MS$FOCUSED_ION: PRECURSOR_M/Z 370.2377
MS$FOCUSED_ION: PRECURSOR_TYPE [M+H]+
MS$DATA_PROCESSING: RECALIBRATE identity on assigned fragments and MS1
MS$DATA_PROCESSING: WHOLE RMassBank 2.10.1
PK$SPLASH: splash10-05i3-0910000000-f6815ebba24e724dc87e
PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm)
115.0537 C9H7+ 1 115.0542 -4.97
116.0605 C9H8+ 1 116.0621 -13.62
117.0559 C5H9O3+ 2 117.0546 11.34
117.0688 C9H9+ 1 117.0699 -9.33
119.0845 C9H11+ 1 119.0855 -8.32
120.0806 C8H10N+ 2 120.0808 -1.75
121.0879 C8H11N+ 2 121.0886 -6.16
121.0991 C9H13+ 1 121.1012 -17.23
122.0598 C7H8NO+ 1 122.06 -1.77
122.0963 C8H12N+ 2 122.0964 -0.83
123.0791 C8H11O+ 1 123.0804 -11.09
124.0751 C7H10NO+ 1 124.0757 -5.03
125.078 C6[13]CH10NO+ 1 125.0796 -12.59
127.0549 C10H7+ 1 127.0542 5.28
128.061 C10H8+ 1 128.0621 -8.49
129.0686 C10H9+ 1 129.0699 -10.18
130.0752 C10H10+ 1 130.0777 -19.16
131.0728 C9H9N+ 2 131.073 -0.86
131.0844 C10H11+ 1 131.0855 -8.7
132.0813 C9H10N+ 2 132.0808 4.25
133.0647 C9H9O+ 1 133.0648 -0.61
133.0867 C6H13O3+ 2 133.0859 5.66
133.1006 C10H13+ 1 133.1012 -4.51
134.0953 C9H12N+ 2 134.0964 -8.55
135.0822 C9H11O+ 1 135.0804 12.66
135.0994 C8[13]CH12N+ 1 135.1003 -6.76
136.0752 C8H10NO+ 1 136.0757 -3.68
138.0905 C8H12NO+ 1 138.0913 -5.85
141.0692 C11H9+ 1 141.0699 -4.83
142.0762 C11H10+ 1 142.0777 -10.83
143.0844 C11H11+ 1 143.0855 -8.04
144.0804 C10H10N+ 2 144.0808 -2.31
145.0635 C10H9O+ 1 145.0648 -8.69
145.1002 C11H13+ 1 145.1012 -6.64
146.0952 C10H12N+ 2 146.0964 -8.63
147.1035 C10H13N+ 2 147.1043 -5.19
147.1157 C11H15+ 1 147.1168 -7.52
148.0744 C9H10NO+ 1 148.0757 -8.97
148.1114 C10H14N+ 2 148.1121 -4.35
149.0952 C10H13O+ 1 149.0961 -5.72
150.0905 C9H12NO+ 1 150.0913 -5.82
151.0981 C8[13]CH12NO+ 1 151.0952 18.99
152.0609 C12H8+ 1 152.0621 -7.58
153.0689 C12H9+ 1 153.0699 -6.56
154.0759 C12H10+ 1 154.0777 -11.54
155.0592 C7H9NO3+ 1 155.0577 9.8
155.0841 C12H11+ 1 155.0855 -9.41
156.0906 C12H12+ 1 156.0934 -17.85
157.1005 C12H13+ 1 157.1012 -4.49
158.0955 C11H12N+ 2 158.0964 -5.68
159.0787 C11H11O+ 1 159.0804 -10.7
159.1069 C11H13N+ 1 159.1043 16.5
159.1144 C12H15+ 1 159.1168 -15.2
160.1108 C11H14N+ 2 160.1121 -7.96
161.0964 C11H13O+ 1 161.0961 1.91
161.118 C8H17O3+ 2 161.1172 5.03
161.132 C12H17+ 1 161.1325 -3.22
162.091 C10H12NO+ 1 162.0913 -2.26
162.1261 C8H18O3+ 2 162.125 6.56
163.111 C11H15O+ 1 163.1117 -4.27
164.1052 C10H14NO+ 1 164.107 -10.7
165.0684 C13H9+ 1 165.0699 -8.68
165.1099 C9[13]CH14NO+ 1 165.1109 -5.85
166.0753 C13H10+ 1 166.0777 -14.48
167.084 C13H11+ 1 167.0855 -8.96
168.0928 C13H12+ 1 168.0934 -3.51
169.0998 C13H13+ 1 169.1012 -7.88
170.1066 C13H14+ 1 170.109 -14.26
171.1157 C13H15+ 1 171.1168 -6.49
172.113 C12H14N+ 2 172.1121 5.64
173.0955 C12H13O+ 1 173.0961 -3.32
173.1315 C13H17+ 1 173.1325 -5.63
174.0895 C11H12NO+ 1 174.0913 -10.6
174.128 C12H16N+ 2 174.1277 1.61
175.1123 C12H15O+ 1 175.1117 3.1
175.1458 C13H19+ 1 175.1481 -13.23
176.1058 C11H14NO+ 1 176.107 -6.5
177.1113 C10[13]CH14NO+ 1 177.1109 2.12
178.0772 C14H10+ 1 178.0777 -2.8
178.1218 C11H16NO+ 1 178.1226 -4.82
179.0844 C14H11+ 1 179.0855 -6.37
179.1268 C11H17NO+ 1 179.1305 -20.39
180.091 C14H12+ 1 180.0934 -13.32
181.0999 C14H13+ 1 181.1012 -7.02
183.1156 C14H15+ 1 183.1168 -6.48
184.1123 C13H14N+ 2 184.1121 0.96
185.1314 C14H17+ 1 185.1325 -5.73
186.1289 C13H16N+ 2 186.1277 6.08
187.1459 C14H19+ 1 187.1481 -11.86
190.1217 C12H16NO+ 1 190.1226 -4.83
191.0849 C15H11+ 1 191.0855 -3.32
192.0923 C15H12+ 1 192.0934 -5.7
193.1002 C15H13+ 1 193.1012 -5.08
194.1059 C15H14+ 1 194.109 -15.73
195.115 C15H15+ 1 195.1168 -9.48
196.1145 C14H14N+ 1 196.1121 12.47
197.129 C15H17+ 1 197.1325 -17.4
198.1313 C14H16N+ 1 198.1277 18.27
199.147 C15H19+ 1 199.1481 -5.86
200.1475 C14H18N+ 1 200.1434 20.51
203.0848 C16H11+ 1 203.0855 -3.47
204.0917 C16H12+ 1 204.0934 -8.27
205.1006 C16H13+ 1 205.1012 -2.85
206.106 C16H14+ 1 206.109 -14.76
207.1164 C16H15+ 1 207.1168 -1.96
208.1209 C16H16+ 1 208.1247 -18.14
209.1319 C16H17+ 1 209.1325 -2.82
210.1294 C15H16N+ 2 210.1277 8.09
211.1466 C16H19+ 1 211.1481 -7.3
212.1443 C15H18N+ 2 212.1434 4.48
213.1265 C15H17O+ 1 213.1274 -4
213.1596 C16H21+ 1 213.1638 -19.5
214.1587 C15H20N+ 2 214.159 -1.57
217.1 C17H13+ 1 217.1012 -5.4
218.107 C17H14+ 1 218.109 -9.4
219.1165 C17H15+ 1 219.1168 -1.72
220.1164 C16H14N+ 1 220.1121 19.62
221.1312 C17H17+ 1 221.1325 -5.72
222.1306 C16H16N+ 1 222.1277 12.96
223.1471 C17H19+ 1 223.1481 -4.43
224.1448 C16H18N+ 2 224.1434 6.23
225.1607 C17H21+ 1 225.1638 -13.71
226.1203 C15H16NO+ 1 226.1226 -10.23
226.1617 C16H20N+ 2 226.159 11.94
233.1313 C18H17+ 1 233.1325 -5.1
234.1275 C17H16N+ 2 234.1277 -0.95
235.1358 C17H17N+ 2 235.1356 0.88
235.1496 C18H19+ 1 235.1481 6.2
236.1424 C17H18N+ 2 236.1434 -4.22
237.1506 C17H19N+ 2 237.1512 -2.66
237.1621 C18H21+ 1 237.1638 -7.03
238.1589 C17H20N+ 2 238.159 -0.53
239.1777 C18H23+ 1 239.1794 -7.1
247.1472 C19H19+ 1 247.1481 -3.78
248.1455 C18H18N+ 2 248.1434 8.61
249.1635 C19H21+ 1 249.1638 -1.11
250.1624 C18H20N+ 2 250.159 13.29
251.1764 C19H23+ 1 251.1794 -12.24
253.1863 C18H23N+ 1 253.1825 15.07
260.1983 C17H26NO+ 1 260.2009 -9.88
261.1655 C20H21+ 1 261.1638 6.68
262.1604 C19H20N+ 2 262.159 5.35
264.1733 C16H24O3+ 2 264.172 5.11
265.1763 C15[13]CH24O3+ 1 265.1759 1.35
266.1631 C19H22O+ 1 266.1665 -12.87
266.1906 C19H24N+ 2 266.1903 0.98
278.1891 C20H24N+ 2 278.1903 -4.35
282.185 C19H24NO+ 1 282.1852 -0.9
283.1897 C18[13]CH24NO+ 1 283.1891 2.13
292.2043 C18H28O3+ 2 292.2033 3.54
310.2176 C21H28NO+ 1 310.2165 3.49
311.2199 C20[13]CH28NO+ 1 311.2204 -1.9
370.2345 C23H32NO3+ 1 370.2377 -8.66
PK$NUM_PEAK: 153
PK$PEAK: m/z int. rel.int.
115.0537 4520 204
116.0605 1388 62
117.0559 872 39
117.0688 4536 205
119.0845 2296 103
120.0806 840 37
121.0879 692 31
121.0991 512 23
122.0598 932 42
122.0963 560 25
123.0791 348 15
124.0751 22092 999
125.078 1888 85
127.0549 424 19
128.061 8236 372
129.0686 12144 549
130.0752 3280 148
131.0728 1140 51
131.0844 10036 453
132.0813 2328 105
133.0647 364 16
133.0867 1168 52
133.1006 3052 138
134.0953 1712 77
135.0822 476 21
135.0994 320 14
136.0752 960 43
138.0905 868 39
141.0692 6284 284
142.0762 5188 234
143.0844 8756 395
144.0804 2368 107
145.0635 1356 61
145.1002 6164 278
146.0952 2440 110
147.1035 1068 48
147.1157 916 41
148.0744 628 28
148.1114 1872 84
149.0952 1360 61
150.0905 1616 73
151.0981 328 14
152.0609 924 41
153.0689 3584 162
154.0759 2624 118
155.0592 1260 56
155.0841 6284 284
156.0906 2760 124
157.1005 6356 287
158.0955 3204 144
159.0787 528 23
159.1069 1672 75
159.1144 3084 139
160.1108 2348 106
161.0964 568 25
161.118 1548 70
161.132 804 36
162.091 664 30
162.1261 1144 51
163.111 372 16
164.1052 1632 73
165.0684 2620 118
165.1099 308 13
166.0753 1408 63
167.084 3276 148
168.0928 1712 77
169.0998 3516 158
170.1066 1972 89
171.1157 3504 158
172.113 1484 67
173.0955 300 13
173.1315 1644 74
174.0895 412 18
174.128 1004 45
175.1123 660 29
175.1458 432 19
176.1058 1336 60
177.1113 308 13
178.0772 1660 75
178.1218 1648 74
179.0844 2292 103
179.1268 340 15
180.091 1652 74
181.0999 2744 124
183.1156 2656 120
184.1123 1296 58
185.1314 2444 110
186.1289 776 35
187.1459 440 19
190.1217 488 22
191.0849 1024 46
192.0923 1164 52
193.1002 2668 120
194.1059 1248 56
195.115 1888 85
196.1145 1020 46
197.129 1416 64
198.1313 864 39
199.147 1060 47
200.1475 492 22
203.0848 440 19
204.0917 464 20
205.1006 1728 78
206.106 1100 49
207.1164 2124 96
208.1209 1104 49
209.1319 1324 59
210.1294 920 41
211.1466 500 22
212.1443 732 33
213.1265 528 23
213.1596 320 14
214.1587 376 17
217.1 440 19
218.107 428 19
219.1165 1288 58
220.1164 724 32
221.1312 1236 55
222.1306 1480 66
223.1471 1124 50
224.1448 572 25
225.1607 424 19
226.1203 332 15
226.1617 424 19
233.1313 868 39
234.1275 760 34
235.1358 456 20
235.1496 748 33
236.1424 1088 49
237.1506 564 25
237.1621 628 28
238.1589 652 29
239.1777 312 14
247.1472 876 39
248.1455 724 32
249.1635 1196 54
250.1624 1096 49
251.1764 360 16
253.1863 332 15
260.1983 420 18
261.1655 520 23
262.1604 748 33
264.1733 2348 106
265.1763 600 27
266.1631 324 14
266.1906 344 15
278.1891 784 35
282.185 3232 146
283.1897 764 34
292.2043 504 22
310.2176 2676 121
311.2199 764 34
370.2345 836 37
//
