ACCESSION: MSBNK-Athens_Univ-AU280606
RECORD_TITLE: Norgestrel; LC-ESI-QTOF; MS2; CE: Ramp 21.9-32.8 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 2806
CH$NAME: Norgestrel
CH$NAME: (8R,9S,10R,13S,14S)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
CH$COMPOUND_CLASS: N/A; Environmental Standard
CH$FORMULA: C21H28O2
CH$EXACT_MASS: 312.2089301
CH$SMILES: [H][C@@]12CCC(O)(C#C)[C@@]1(CC)CC[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H]
CH$IUPAC: InChI=1S/C21H28O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,13,16-19,23H,3,5-12H2,1H3/t16-,17+,18+,19-,20-,21?/m0/s1
CH$LINK: PUBCHEM
CID:16051930
CH$LINK: INCHIKEY
WWYNJERNGUHSAO-CULCCENASA-N
CH$LINK: CHEMSPIDER
10481953
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$MASS_SPECTROMETRY: COLLISION_ENERGY Ramp 21.9-32.8 eV
AC$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 10.151 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$FOCUSED_ION: BASE_PEAK 313.216
MS$FOCUSED_ION: PRECURSOR_M/Z 313.2162
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: splash10-03dj-2942000000-001d2b1ad1aaf65fdb04
PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm)
53.0383 C4H5+ 1 53.0386 -4.49
55.0171 C3H3O+ 1 55.0178 -14.17
55.0535 C4H7+ 1 55.0542 -13.33
57.0327 C3H5O+ 1 57.0335 -14.33
57.0689 C4H9+ 1 57.0699 -16.55
65.0384 C5H5+ 1 65.0386 -2.21
67.0536 C5H7+ 1 67.0542 -9.85
68.0572 C4[13]CH7+ 1 68.0581 -14.22
69.0692 C5H9+ 1 69.0699 -9.71
71.0486 C4H7O+ 1 71.0491 -7.24
79.0537 C6H7+ 1 79.0542 -6.13
80.0571 C5[13]CH7+ 1 80.0581 -13.21
81.033 C5H5O+ 1 81.0335 -5.82
81.0694 C6H9+ 1 81.0699 -5.35
82.0727 C5[13]CH9+ 1 82.0738 -13.62
83.0487 C5H7O+ 1 83.0491 -5.38
84.0523 C4[13]CH7O+ 1 84.053 -9.44
91.0544 C7H7+ 1 91.0542 2.23
92.0579 C6[13]CH7+ 1 92.0581 -2.44
93.0701 C7H9+ 1 93.0699 2.45
94.0735 C6[13]CH9+ 1 94.0738 -2.55
95.0492 C6H7O+ 1 95.0491 0.4
95.0857 C7H11+ 1 95.0855 2.24
96.0893 C6[13]CH11+ 1 96.0894 -1.19
97.0645 C6H9O+ 1 97.0648 -3.21
97.1013 C7H13+ 1 97.1012 1.39
103.0545 C8H7+ 1 103.0542 2.18
105.0706 C8H9+ 1 105.0699 6.9
106.0735 C7[13]CH9+ 1 106.0738 -2.59
107.0502 C7H7O+ 1 107.0491 10.03
107.0862 C8H11+ 1 107.0855 6.7
108.0536 C6[13]CH7O+ 1 108.053 4.76
108.0892 C7[13]CH11+ 1 108.0894 -2.25
109.0659 C7H9O+ 1 109.0648 10.58
109.1023 C8H13+ 1 109.1012 10.64
110.0685 C6[13]CH9O+ 1 110.0687 -1.97
110.1056 C7[13]CH13+ 1 110.1051 4.54
111.0816 C7H11O+ 1 111.0804 10.38
115.0538 C9H7+ 1 115.0542 -3.68
116.0606 C9H8+ 1 116.0621 -12.17
117.0696 C9H9+ 1 117.0699 -2.57
118.0734 C8[13]CH9+ 1 118.0738 -3.37
119.0853 C9H11+ 1 119.0855 -1.83
120.0885 C8[13]CH11+ 1 120.0894 -7.56
121.0643 C8H9O+ 1 121.0648 -3.8
121.1011 C9H13+ 1 121.1012 -0.23
122.1043 C8[13]CH13+ 1 122.1051 -6.22
123.0802 C8H11O+ 1 123.0804 -2.27
123.1168 C9H15+ 1 123.1168 -0.34
124.0843 C7[13]CH11O+ 1 124.0843 -0.53
125.0954 C8H13O+ 1 125.0961 -5.82
128.0611 C10H8+ 1 128.0621 -7.41
129.0689 C10H9+ 1 129.0699 -7.69
130.0748 C10H10+ 1 130.0777 -22.44
131.0847 C10H11+ 1 131.0855 -6.07
132.0886 C9[13]CH11+ 1 132.0894 -6.57
133.0641 C9H9O+ 1 133.0648 -5.56
133.1005 C10H13+ 1 133.1012 -4.89
134.1039 C9[13]CH13+ 1 134.1051 -8.47
135.0796 C9H11O+ 1 135.0804 -5.97
135.1159 C10H15+ 1 135.1168 -6.65
136.0827 C8[13]CH11O+ 1 136.0843 -12.19
136.1183 C9[13]CH15+ 1 136.1207 -17.54
137.0954 C9H13O+ 1 137.0961 -4.96
137.1321 C10H17+ 1 137.1325 -2.67
141.0687 C11H9+ 1 141.0699 -8.69
142.076 C11H10+ 1 142.0777 -12.26
143.0844 C11H11+ 1 143.0855 -7.88
144.0901 C10[13]CH11+ 1 144.0894 4.56
145.0629 C10H9O+ 1 145.0648 -13.1
145.1 C11H13+ 1 145.1012 -8.14
146.1038 C10[13]CH13+ 1 146.1051 -8.84
147.0793 C10H11O+ 1 147.0804 -7.68
147.1155 C11H15+ 1 147.1168 -9.07
148.0836 C9[13]CH11O+ 1 148.0843 -5.18
148.1188 C10[13]CH15+ 1 148.1207 -12.9
149.0948 C10H13O+ 1 149.0961 -8.57
149.1309 C11H17+ 1 149.1325 -10.5
150.0977 C9[13]CH13O+ 1 150.1 -15.46
151.1103 C10H15O+ 1 151.1117 -9.57
153.0691 C12H9+ 1 153.0699 -5.29
154.0751 C12H10+ 1 154.0777 -17.12
155.0839 C12H11+ 1 155.0855 -10.31
156.0903 C12H12+ 1 156.0934 -19.38
157.0634 C11H9O+ 1 157.0648 -8.93
157.0998 C12H13+ 1 157.1012 -8.97
158.1045 C11[13]CH13+ 1 158.1051 -3.49
159.0792 C11H11O+ 1 159.0804 -7.69
159.1154 C12H15+ 1 159.1168 -8.97
160.0841 C10[13]CH11O+ 1 160.0843 -1.53
160.119 C11[13]CH15+ 1 160.1207 -10.62
161.0948 C11H13O+ 1 161.0961 -8.08
161.1309 C12H17+ 1 161.1325 -9.79
162.1001 C11H14O+ 1 162.1039 -23.71
163.1104 C11H15O+ 1 163.1117 -8.18
163.1477 C12H19+ 1 163.1481 -2.74
164.1143 C10[13]CH15O+ 1 164.1156 -8.25
165.0674 C13H9+ 1 165.0699 -15.19
166.077 C13H10+ 1 166.0777 -4.34
167.0841 C13H11+ 1 167.0855 -8.5
168.0919 C13H12+ 1 168.0934 -8.39
169.0995 C13H13+ 1 169.1012 -10.08
170.1058 C13H14+ 1 170.109 -19.1
171.1154 C13H15+ 1 171.1168 -8.22
172.1196 C12[13]CH15+ 1 172.1207 -6.32
173.0953 C12H13O+ 1 173.0961 -4.31
173.131 C13H17+ 1 173.1325 -8.65
174.1004 C12H14O+ 1 174.1039 -20.4
174.1349 C12[13]CH17+ 1 174.1364 -8.33
175.1101 C12H15O+ 1 175.1117 -9.37
175.147 C13H19+ 1 175.1481 -6.57
176.1144 C11[13]CH15O+ 1 176.1156 -7.06
176.1507 C12[13]CH19+ 1 176.152 -7.71
177.1269 C12H17O+ 1 177.1274 -2.7
179.0838 C14H11+ 1 179.0855 -9.84
180.091 C14H12+ 1 180.0934 -12.84
181.0999 C14H13+ 1 181.1012 -7.04
182.1058 C14H14+ 1 182.109 -17.37
183.1158 C14H15+ 1 183.1168 -5.49
184.1208 C13[13]CH15+ 1 184.1207 0.55
185.0947 C13H13O+ 1 185.0961 -7.6
185.1314 C14H17+ 1 185.1325 -5.67
186.1001 C13H14O+ 1 186.1039 -20.47
186.1348 C13[13]CH17+ 1 186.1364 -8.74
187.1103 C13H15O+ 1 187.1117 -7.74
187.1472 C14H19+ 1 187.1481 -5.17
188.117 C13H16O+ 1 188.1196 -13.85
188.1514 C13[13]CH19+ 1 188.152 -3.56
189.126 C13H17O+ 1 189.1274 -7.18
190.1297 C12[13]CH17O+ 1 190.1313 -8.52
191.1417 C13H19O+ 1 191.143 -7.19
192.0922 C15H12+ 1 192.0934 -6
193.101 C15H13+ 1 193.1012 -0.92
194.1072 C15H14+ 1 194.109 -9.23
195.1153 C15H15+ 1 195.1168 -7.7
196.1221 C15H16+ 1 196.1247 -13.19
197.0941 C14H13O+ 1 197.0961 -10.06
197.1313 C15H17+ 1 197.1325 -6.12
198.136 C14[13]CH17+ 1 198.1364 -1.77
199.11 C14H15O+ 1 199.1117 -8.55
199.1474 C15H19+ 1 199.1481 -3.62
200.1159 C13[13]CH15O+ 1 200.1156 1.23
200.1522 C14[13]CH19+ 1 200.152 1
201.1267 C14H17O+ 1 201.1274 -3.43
201.1614 C15H21+ 1 201.1638 -11.89
202.1319 C13[13]CH17O+ 1 202.1313 3.11
203.142 C14H19O+ 1 203.143 -5.07
203.1783 C15H23+ 1 203.1794 -5.78
204.1465 C13[13]CH19O+ 1 204.1469 -2.3
205.1009 C16H13+ 1 205.1012 -1.33
206.1053 C16H14+ 1 206.109 -18.12
207.1164 C16H15+ 1 207.1168 -2.22
208.1221 C16H16+ 1 208.1247 -12.22
209.1313 C16H17+ 1 209.1325 -5.48
210.1369 C16H18+ 1 210.1403 -16.36
211.111 C15H15O+ 1 211.1117 -3.67
211.1476 C16H19+ 1 211.1481 -2.29
212.1501 C15[13]CH19+ 1 212.152 -9.02
213.1261 C15H17O+ 1 213.1274 -5.87
213.1627 C16H21+ 1 213.1638 -4.85
214.1327 C15H18O+ 1 214.1352 -11.93
214.1665 C15[13]CH21+ 1 214.1677 -5.54
215.1429 C15H19O+ 1 215.143 -0.75
215.1784 C16H23+ 1 215.1794 -4.98
216.1461 C14[13]CH19O+ 1 216.1469 -4.08
217.1557 C15H21O+ 1 217.1587 -13.77
219.1145 C17H15+ 1 219.1168 -10.41
220.1252 C17H16+ 1 220.1247 2.36
221.1317 C17H17+ 1 221.1325 -3.61
222.1369 C17H18+ 1 222.1403 -15.35
223.1474 C17H19+ 1 223.1481 -3.47
224.1529 C16[13]CH19+ 1 224.152 4.06
225.1268 C16H17O+ 1 225.1274 -2.71
225.1633 C17H21+ 1 225.1638 -2.3
226.1324 C15[13]CH17O+ 1 226.1313 4.96
226.167 C16[13]CH21+ 1 226.1677 -2.91
227.1407 C16H19O+ 1 227.143 -10.23
227.1788 C17H23+ 1 227.1794 -2.72
228.1816 C16[13]CH23+ 1 228.1833 -7.67
229.1589 C16H21O+ 1 229.1587 0.99
230.1639 C16H22O+ 1 230.1665 -11.34
231.1723 C16H23O+ 1 231.1743 -8.92
233.1323 C18H17+ 1 233.1325 -0.84
234.1381 C18H18+ 1 234.1403 -9.38
235.147 C18H19+ 1 235.1481 -4.65
236.1517 C18H20+ 1 236.156 -17.87
237.1627 C18H21+ 1 237.1638 -4.37
238.1678 C17[13]CH21+ 1 238.1677 0.34
239.1414 C17H19O+ 1 239.143 -6.78
239.1774 C18H23+ 1 239.1794 -8.43
240.1473 C16[13]CH19O+ 1 240.1469 1.59
241.1583 C17H21O+ 1 241.1587 -1.52
243.1733 C17H23O+ 1 243.1743 -4.28
245.1897 C17H25O+ 1 245.19 -1.27
246.193 C16[13]CH25O+ 1 246.1939 -3.57
247.1967 C15[13]C2H25O+ 1 247.1973 -2.26
248.1549 C19H20+ 1 248.156 -4.35
249.1618 C19H21+ 1 249.1638 -7.89
250.1671 C18[13]CH21+ 1 250.1677 -2.24
251.1424 C18H19O+ 1 251.143 -2.71
251.1791 C19H23+ 1 251.1794 -1.21
253.1587 C18H21O+ 1 253.1587 -0.02
253.1954 C19H25+ 1 253.1951 1.2
255.1742 C18H23O+ 1 255.1743 -0.59
257.1873 C18H25O+ 1 257.19 -10.51
266.1664 C19H22O+ 1 266.1665 -0.47
267.1723 C19H23O+ 1 267.1743 -7.78
267.2092 C20H27+ 1 267.2107 -5.82
268.1788 C18[13]CH23O+ 1 268.1782 2.14
269.1904 C19H25O+ 1 269.19 1.45
277.1947 C21H25+ 1 277.1951 -1.37
278.1982 C20[13]CH25+ 1 278.199 -2.76
284.1772 C19H24O2+ 1 284.1771 0.52
295.2051 C21H27O+ 1 295.2056 -1.88
296.2087 C20[13]CH27O+ 1 296.2095 -2.92
313.2164 C21H29O2+ 1 313.2162 0.7
314.2194 C20[13]CH29O2+ 1 314.2201 -2.4
315.2221 C19[13]C2H29O2+ 1 315.2235 -4.39
PK$NUM_PEAK: 218
PK$PEAK: m/z int. rel.int.
53.0383 1000 5
55.0171 2060 12
55.0535 6920 40
57.0327 3224 18
57.0689 908 5
65.0384 972 5
67.0536 18652 109
68.0572 1612 9
69.0692 5148 30
71.0486 996 5
79.0537 29548 174
80.0571 1848 10
81.033 3288 19
81.0694 29984 176
82.0727 2308 13
83.0487 51388 302
84.0523 2632 15
91.0544 29448 173
92.0579 2148 12
93.0701 28104 165
94.0735 2228 13
95.0492 3912 23
95.0857 18624 109
96.0893 1412 8
97.0645 4536 26
97.1013 852 5
103.0545 1068 6
105.0706 18756 110
106.0735 1788 10
107.0502 14224 83
107.0862 13484 79
108.0536 980 5
108.0892 1220 7
109.0659 56092 330
109.1023 6968 41
110.0685 4912 28
110.1056 856 5
111.0816 1424 8
115.0538 4212 24
116.0606 1676 9
117.0696 14548 85
118.0734 1876 11
119.0853 16704 98
120.0885 2080 12
121.0643 5648 33
121.1011 8276 48
122.1043 1196 7
123.0802 10932 64
123.1168 6812 40
124.0843 1308 7
125.0954 4128 24
128.0611 4244 25
129.0689 15088 88
130.0748 3376 19
131.0847 27244 160
132.0886 3448 20
133.0641 4536 26
133.1005 25956 152
134.1039 4092 24
135.0796 21828 128
135.1159 9988 58
136.0827 2628 15
136.1183 1448 8
137.0954 3640 21
137.1321 3188 18
141.0687 4504 26
142.076 3640 21
143.0844 19104 112
144.0901 3320 19
145.0629 2212 13
145.1 31196 183
146.1038 3300 19
147.0793 7048 41
147.1155 12224 72
148.0836 924 5
148.1188 1200 7
149.0948 21984 129
149.1309 5356 31
150.0977 2240 13
151.1103 2636 15
153.0691 1364 8
154.0751 1236 7
155.0839 7252 42
156.0903 3524 20
157.0634 2716 16
157.0998 23024 135
158.1045 3428 20
159.0792 6800 40
159.1154 25004 147
160.0841 1292 7
160.119 3892 22
161.0948 15100 88
161.1309 6100 35
162.1001 3468 20
163.1104 12704 74
163.1477 1672 9
164.1143 1712 10
165.0674 1348 7
166.077 912 5
167.0841 3664 21
168.0919 2132 12
169.0995 11072 65
170.1058 3900 22
171.1154 21172 124
172.1196 3492 20
173.0953 3468 20
173.131 11696 68
174.1004 940 5
174.1349 1772 10
175.1101 12728 75
175.147 9792 57
176.1144 1900 11
176.1507 1452 8
177.1269 3040 17
179.0838 2328 13
180.091 1264 7
181.0999 7084 41
182.1058 1988 11
183.1158 16344 96
184.1208 2684 15
185.0947 4656 27
185.1314 31448 185
186.1001 1228 7
186.1348 6312 37
187.1103 6820 40
187.1472 17544 103
188.117 3180 18
188.1514 2224 13
189.126 9624 56
190.1297 1544 9
191.1417 1940 11
192.0922 864 5
193.101 3652 21
194.1072 1268 7
195.1153 7596 44
196.1221 2452 14
197.0941 2284 13
197.1313 8840 52
198.136 1964 11
199.11 3728 21
199.1474 14084 82
200.1159 924 5
200.1522 2644 15
201.1267 6844 40
201.1614 3580 21
202.1319 1468 8
203.142 4656 27
203.1783 892 5
204.1465 916 5
205.1009 968 5
206.1053 1564 9
207.1164 6180 36
208.1221 2624 15
209.1313 6428 37
210.1369 1876 11
211.111 3332 19
211.1476 5132 30
212.1501 948 5
213.1261 3844 22
213.1627 3796 22
214.1327 1188 7
214.1665 976 5
215.1429 3664 21
215.1784 1548 9
216.1461 904 5
217.1557 1536 9
219.1145 976 5
220.1252 1144 6
221.1317 6884 40
222.1369 2828 16
223.1474 5488 32
224.1529 1448 8
225.1268 4368 25
225.1633 10644 62
226.1324 1344 7
226.167 2256 13
227.1407 2400 14
227.1788 25040 147
228.1816 3760 22
229.1589 1784 10
230.1639 1000 5
231.1723 1044 6
233.1323 1428 8
234.1381 1204 7
235.147 5892 34
236.1517 1952 11
237.1627 12424 73
238.1678 3132 18
239.1414 4512 26
239.1774 2472 14
240.1473 1332 7
241.1583 2928 17
243.1733 4636 27
245.1897 100820 594
246.193 22584 133
247.1967 1636 9
248.1549 4072 23
249.1618 5604 33
250.1671 1088 6
251.1424 860 5
251.1791 3188 18
253.1587 2392 14
253.1954 3088 18
255.1742 2396 14
257.1873 856 5
266.1664 4004 23
267.1723 5908 34
267.2092 1692 9
268.1788 1096 6
269.1904 1124 6
277.1947 13160 77
278.1982 2928 17
284.1772 1864 10
295.2051 36944 217
296.2087 9032 53
313.2164 169524 999
314.2194 49664 292
315.2221 4468 26
//
