MassBank Record: MSBNK-RIKEN-PR310626
ACCESSION: MSBNK-RIKEN-PR310626
RECORD_TITLE: Karakoline; LC-ESI-QTOF; MS2
DATE: 2019.03.28
AUTHORS: Tetsuya Mori, Center for Sustainable Resource Science, RIKEN
LICENSE: CC BY-NC-SA
PUBLICATION: Tsugawa H., Nakabayashi R., Mori T., Yamada Y., Takahashi M., Rai A., Sugiyama R., Yamamoto H., Nakaya T., Yamazaki M., Kooke R., Bac-Molenaar JA., Oztolan-Erol N., Keurentjes JJB., Arita M., Saito K. (2019) "A cheminformatics approach to characterize metabolomes in stable-isotope-labeled organisms" Nature Methods 16(4):295-298. [doi:10.1038/s41592-019-0358-2]
COMMENT: Annotation level-1
CH$NAME: Karakoline
CH$COMPOUND_CLASS: Alkaloids
CH$FORMULA: C22H35NO4
CH$EXACT_MASS: 377.525
CH$SMILES: CCN1CC2(C)CCC(O)C34C5CC6C(O)C5C(O)(CC6OC)C(CC23)C14
CH$IUPAC: InChI=1S/C22H35NO4/c1-4-23-10-20(2)6-5-16(24)22-12-7-11-14(27-3)9-21(26,17(12)18(11)25)13(19(22)23)8-15(20)22/h11-19,24-26H,4-10H2,1-3H3
CH$LINK: INCHIKEY
HKQZUYOVMYOFIT-UHFFFAOYSA-N
AC$INSTRUMENT: LC, Waters Acquity UPLC System; MS, Waters Xevo G2 Q-Tof
AC$INSTRUMENT_TYPE: LC-ESI-QTOF
AC$MASS_SPECTROMETRY: MS_TYPE MS2
AC$MASS_SPECTROMETRY: ION_MODE POSITIVE
AC$MASS_SPECTROMETRY: COLLISION_ENERGY 6V
AC$MASS_SPECTROMETRY: DESOLVATION_GAS_FLOW 800/h
AC$MASS_SPECTROMETRY: DESOLVATION_TEMPERATURE 450 C
AC$MASS_SPECTROMETRY: IONIZATION ESI
AC$CHROMATOGRAPHY: CAPILLARY_VOLTAGE +3.00 kV
AC$CHROMATOGRAPHY: COLUMN_NAME Acquity bridged ethyl hybrid C18 (1.7 um, 2.1 mm * 100 mm, Waters)
AC$CHROMATOGRAPHY: COLUMN_TEMPERATURE 40 C
AC$CHROMATOGRAPHY: FLOW_GRADIENT A/B = (99.5%/0.5% at 0 min, 99.5%/0.5% at 0.1 min, 20%/80% at 10 min, 0.5%/99.5% at 10.1 min, 0.5%/99.5% at 12.0 min, 99.5%/0.5% at 12.1 min, 99.5%/0.5% at 15.0 min)
AC$CHROMATOGRAPHY: FLOW_RATE 0.3 ml/min at 0 min, 0.3 ml/min at 10 min, 0.4 ml/min at 10.1 min, 0.4 ml/min at 14.4 min, 0.3 ml/min at 14.5 min
AC$CHROMATOGRAPHY: RETENTION_TIME 2.89
AC$CHROMATOGRAPHY: SOLVENT A water including 0.1% formic acid
AC$CHROMATOGRAPHY: SOLVENT B acetonitrile including 0.1% formic acid
MS$FOCUSED_ION: PRECURSOR_TYPE [M+H]+
MS$FOCUSED_ION: PRECURSOR_M/Z 378.26389
PK$SPLASH: splash10-004i-0009000000-0fbf310df2df8129d392
PK$NUM_PEAK: 405
PK$PEAK: m/z int. rel.int.
58.05909 25.0 0
58.06698 197.0 3
61.03249 36.0 1
67.0524 27.0 0
71.05069 22.0 0
71.73367 24.0 0
72.0481 18.0 0
72.05457 20.0 0
72.07905 17.0 0
72.08376 23.0 0
79.05724 29.0 1
82.00949 17.0 0
82.06694 17.0 0
84.06813 17.0 0
84.07558 22.0 0
84.08316 22.0 0
85.34259 21.0 0
91.05773 72.0 1
93.06999 41.0 1
95.0941 20.0 0
97.0802 23.0 0
98.0854 26.0 0
98.09673 244.0 4
99.08619 17.0 0
100.05314 25.0 0
103.03979 20.0 0
105.07068 53.0 1
106.07168 22.0 0
107.04937 23.0 0
108.08486 20.0 0
110.10014 100.0 2
111.10467 54.0 1
112.11224 24.0 0
113.05932 17.0 0
117.056 20.0 0
117.07078 58.0 1
119.05027 73.0 1
119.09175 24.0 0
120.03929 21.0 0
120.05032 27.0 0
121.07204 27.0 0
121.10438 19.0 0
122.0974 101.0 2
123.04218 23.0 0
124.11002 335.0 6
125.11945 40.0 1
126.12537 88.0 2
127.07194 37.0 1
128.06454 18.0 0
129.05405 18.0 0
129.07341 76.0 1
131.08528 47.0 1
132.08824 20.0 0
133.06795 18.0 0
133.08678 18.0 0
133.10243 173.0 3
134.1019 30.0 1
135.04065 30.0 1
135.08015 29.0 1
135.11827 26.0 0
136.11887 17.0 0
137.05984 130.0 2
137.0925 19.0 0
137.11819 23.0 0
137.54234 25.0 0
138.12704 52.0 1
140.10364 19.0 0
141.6676 19.0 0
142.06859 20.0 0
142.08479 41.0 1
142.11613 17.0 0
142.13138 21.0 0
143.08075 22.0 0
143.0876 102.0 2
144.07669 25.0 0
145.04857 21.0 0
145.09818 35.0 1
145.10545 106.0 2
146.06816 23.0 0
146.10866 29.0 1
147.10889 20.0 0
147.11844 81.0 1
148.11191 39.0 1
149.05608 20.0 0
150.11652 21.0 0
150.13426 43.0 1
151.59222 20.0 0
153.07236 21.0 0
153.09531 28.0 0
153.16246 45.0 1
154.06395 27.0 0
154.08736 21.0 0
155.07909 73.0 1
155.09122 87.0 2
156.09215 20.0 0
156.10983 20.0 0
157.10007 160.0 3
157.78026 20.0 0
159.07454 21.0 0
159.08487 17.0 0
159.11168 36.0 1
159.12669 18.0 0
160.09554 17.0 0
160.118 18.0 0
161.12993 104.0 2
163.07643 21.0 0
163.1102 23.0 0
164.08229 43.0 1
167.0723 22.0 0
167.0864 79.0 1
168.06322 25.0 0
168.0871 17.0 0
169.0648 20.0 0
169.1064 55.0 1
171.11642 85.0 2
171.1311 25.0 0
172.11417 26.0 0
173.08734 25.0 0
173.10066 22.0 0
173.13374 65.0 1
174.14125 20.0 0
175.14984 39.0 1
176.12617 19.0 0
176.1478 42.0 1
177.09427 17.0 0
177.12878 25.0 0
179.08615 43.0 1
180.07805 20.0 0
180.09303 47.0 1
181.0706 22.0 0
181.09793 38.0 1
181.10538 50.0 1
182.11809 25.0 0
183.08054 17.0 0
183.10533 27.0 0
183.11914 92.0 2
184.13261 20.0 0
185.13231 83.0 1
185.14355 22.0 0
187.10579 17.0 0
187.11438 21.0 0
188.15128 20.0 0
189.10344 21.0 0
189.15472 24.0 0
189.95471 18.0 0
190.16861 21.0 0
191.16528 40.0 1
192.09285 19.0 0
193.09305 22.0 0
195.08826 17.0 0
195.11444 29.0 1
195.1243 54.0 1
195.79044 40.0 1
196.13213 51.0 1
197.09906 42.0 1
197.13074 194.0 3
197.14029 30.0 1
197.72356 17.0 0
198.09755 33.0 1
199.11569 29.0 1
199.14592 106.0 2
199.15451 104.0 2
199.1691 24.0 0
199.8159 21.0 0
200.13326 20.0 0
200.14545 44.0 1
200.15308 39.0 1
201.12828 18.0 0
201.14415 24.0 0
202.16779 19.0 0
202.55695 18.0 0
203.13557 18.0 0
205.11938 37.0 1
206.07425 18.0 0
206.11023 45.0 1
207.11607 36.0 1
208.38435 24.0 0
209.12186 20.0 0
209.13541 52.0 1
209.14558 17.0 0
210.14108 69.0 1
211.00896 18.0 0
211.10622 20.0 0
211.13593 19.0 0
211.1487 116.0 2
212.12125 20.0 0
213.08282 71.0 1
213.12471 37.0 1
214.12265 20.0 0
214.1709 17.0 0
215.11493 25.0 0
215.40594 20.0 0
215.83818 18.0 0
216.16898 18.0 0
217.11868 25.0 0
219.5072 34.0 1
219.5219 20.0 0
220.12889 21.0 0
221.13606 48.0 1
222.13727 38.0 1
222.90295 31.0 1
223.11708 41.0 1
223.14935 55.0 1
224.01703 27.0 0
224.12862 32.0 1
224.14867 22.0 0
224.81091 20.0 0
225.14987 20.0 0
225.16872 26.0 0
226.15123 27.0 0
226.16873 34.0 1
227.14159 92.0 2
227.18843 17.0 0
227.41017 31.0 1
228.13109 20.0 0
228.1393 26.0 0
228.15797 26.0 0
230.72136 28.0 0
231.17395 30.0 1
231.48119 18.0 0
232.01637 31.0 1
232.12509 23.0 0
233.14745 38.0 1
235.14645 20.0 0
236.58905 17.0 0
236.81119 24.0 0
236.87486 23.0 0
237.11826 17.0 0
237.13388 23.0 0
237.16154 77.0 1
238.93321 17.0 0
239.13696 78.0 1
239.17088 38.0 1
240.15298 30.0 1
240.18127 29.0 1
241.80467 19.0 0
243.18098 39.0 1
244.16104 23.0 0
245.32649 25.0 0
246.14523 23.0 0
246.17351 17.0 0
247.14532 43.0 1
248.16508 21.0 0
249.15913 20.0 0
249.27837 21.0 0
251.13951 17.0 0
252.07593 24.0 0
252.20441 19.0 0
253.14429 31.0 1
253.16629 47.0 1
253.21574 17.0 0
254.02571 20.0 0
254.12431 18.0 0
254.17427 18.0 0
254.19337 25.0 0
255.16733 74.0 1
255.18634 17.0 0
256.31354 25.0 0
256.64352 20.0 0
257.17599 38.0 1
257.85327 27.0 0
258.34851 25.0 0
258.79797 17.0 0
259.14713 17.0 0
259.17191 59.0 1
260.1423 34.0 1
262.15341 36.0 1
262.95245 19.0 0
263.55289 36.0 1
265.15955 91.0 2
265.95392 17.0 0
266.1489 25.0 0
266.17093 17.0 0
266.18448 17.0 0
266.35703 18.0 0
266.53073 18.0 0
267.14682 17.0 0
267.17462 52.0 1
269.19464 83.0 1
273.12286 32.0 1
273.19714 17.0 0
273.21329 18.0 0
273.22418 17.0 0
275.51312 24.0 0
280.82928 24.0 0
281.16528 22.0 0
281.18753 39.0 1
282.16833 19.0 0
282.42938 17.0 0
283.17587 53.0 1
283.55609 27.0 0
283.81003 23.0 0
284.05496 23.0 0
284.18323 22.0 0
284.20572 18.0 0
284.2308 23.0 0
285.2529 17.0 0
286.18924 18.0 0
287.18634 24.0 0
287.20889 21.0 0
297.17865 68.0 1
297.18988 17.0 0
299.20898 37.0 1
300.2088 45.0 1
300.228 57.0 1
300.92798 19.0 0
306.43085 22.0 0
308.21185 18.0 0
308.68097 18.0 0
310.06219 17.0 0
310.18427 23.0 0
310.1918 49.0 1
310.20764 120.0 2
310.22562 102.0 2
310.24582 50.0 1
311.22174 62.0 1
311.23431 17.0 0
314.04172 17.0 0
314.21143 90.0 2
314.22617 47.0 1
314.26678 33.0 1
315.24738 27.0 0
317.44064 18.0 0
317.55432 17.0 0
323.76572 23.0 0
324.2197 29.0 1
326.21011 23.0 0
327.80569 17.0 0
327.90219 17.0 0
328.2272 765.0 14
328.25076 41.0 1
328.48495 22.0 0
329.22073 40.0 1
329.23578 128.0 2
329.26627 18.0 0
330.22488 18.0 0
331.46161 17.0 0
331.8519 23.0 0
332.16202 19.0 0
332.22656 128.0 2
332.25784 63.0 1
333.21451 20.0 0
333.24045 23.0 0
339.02487 21.0 0
341.8299 18.0 0
342.23599 369.0 7
342.2489 329.0 6
342.58908 18.0 0
343.23279 92.0 2
343.25815 126.0 2
343.80179 21.0 0
346.09409 25.0 0
347.48349 17.0 0
347.71207 20.0 0
352.15454 24.0 0
357.37909 20.0 0
358.24597 28.0 0
359.85165 26.0 0
359.88306 18.0 0
360.14584 64.0 1
360.18533 73.0 1
360.21286 166.0 3
360.25412 8142.0 144
360.29773 22.0 0
360.32639 41.0 1
360.38675 17.0 0
360.68158 28.0 0
360.71695 17.0 0
360.81836 20.0 0
360.98483 20.0 0
361.05518 22.0 0
361.13925 61.0 1
361.17108 53.0 1
361.17966 22.0 0
361.20563 37.0 1
361.25836 2285.0 40
361.3613 21.0 0
362.10059 20.0 0
362.24542 61.0 1
362.2623 314.0 6
363.06061 17.0 0
363.24744 25.0 0
363.66595 21.0 0
363.79578 20.0 0
365.63828 19.0 0
366.8772 29.0 1
367.93411 25.0 0
369.43951 19.0 0
371.09302 24.0 0
373.24313 20.0 0
375.93393 22.0 0
376.06873 22.0 0
376.28308 20.0 0
376.664 20.0 0
376.84686 19.0 0
377.29956 21.0 0
377.44299 17.0 0
377.54419 20.0 0
378.01163 34.0 1
378.12781 18.0 0
378.17542 115.0 2
378.21387 237.0 4
378.26474 56383.0 999
378.32095 1506.0 27
378.40939 17.0 0
//