ACCESSION: MSBNK-IPB_Halle-PB011601
RECORD_TITLE: (20S)-14-oxapentacyclo[20.2.2.210,13.115,19.02,7]nonacosa-1(24),2(7),3,5,10(29),11,13(28),15,17,19(27),22,25-dodecaene-5,16,20,24-tetrol; LC-ESI-QTOF; MS2; CE: 30.58772; [M+H]+
DATE: 2019.06.20
AUTHORS: Stefanie Doell, Kristian Peters, Hendrik Treutler, Dept. Biochemistry of Plant Interactions, Leibniz Institute of Plant Biochemistry, Germany
LICENSE: CC BY
COPYRIGHT: Copyright (C) Stefanie Doell, Kristian Peters, Hendrik Treutler, Dept. Biochemistry of Plant Interactions, Leibniz Institute of Plant Biochemistry, Germany
COMMENT: CONFIDENCE Predicted
CH$NAME: (20S)-14-oxapentacyclo[20.2.2.210,13.115,19.02,7]nonacosa-1(24),2(7),3,5,10(29),11,13(28),15,17,19(27),22,25-dodecaene-5,16,20,24-tetrol
CH$NAME: Maruchantin E
CH$COMPOUND_CLASS: Lignane
CH$FORMULA: C28H24O5
CH$EXACT_MASS: 440.162
CH$SMILES: C1CC2=C(C=CC(=C2)O)C3=C(C=C(C[C@@H](C4=CC(=C(C=C4)O)OC5=CC=C1C=C5)O)C=C3)O
CH$IUPAC: InChI=1S/C28H24O5/c29-21-7-11-23-19(15-21)5-1-17-2-8-22(9-3-17)33-28-16-20(6-12-25(28)30)26(31)13-18-4-10-24(23)27(32)14-18/h2-4,6-12,14-16,26,29-32H,1,5,13H2/t26-/m0/s1
CH$LINK: PUBCHEM
CID:101549217
CH$LINK: INCHIKEY
BTGPMKAMOFOWKF-SANMLTNESA-N
SP$SAMPLE: Marchantia polymorpha
AC$INSTRUMENT: Bruker MicrOTOF-Q
AC$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: CAPILLARY_TEMPERATURE 190 C
AC$MASS_SPECTROMETRY: CAPILLARY_VOLTAGE 5000V
AC$MASS_SPECTROMETRY: COLLISION_ENERGY 30.58772
AC$MASS_SPECTROMETRY: FRAGMENTATION_MODE CID
AC$MASS_SPECTROMETRY: FUNNEL1_RF 200Vpp
AC$MASS_SPECTROMETRY: FUNNEL2_RF 300VPP
AC$MASS_SPECTROMETRY: HEXAPOLE RF 100VPP
AC$MASS_SPECTROMETRY: COLLISION_CELL_RF 400VPP
AC$MASS_SPECTROMETRY: TRANSFER_TIME 70µs
AC$MASS_SPECTROMETRY: PREPULSE_STORAGE_TIME 5µs
AC$CHROMATOGRAPHY: COLUMN_NAME ACQUITY UPLC HSS T3 Column
AC$CHROMATOGRAPHY: RETENTION_TIME 10.273 min
AC$CHROMATOGRAPHY: FLOW_GRADIENT 0 to 1 min, isocratic 95% A , 5% B; 1 to 18 min, linear from 5% to 95% B, delay 18 to 20 min, 95% A isocratic
AC$CHROMATOGRAPHY: FLOW_RATE 0.15 ml/min
AC$CHROMATOGRAPHY: SOLVENT A water with 0.1% formic acid
AC$CHROMATOGRAPHY: SOLVENT B acetonitrile with 0.1% formic acid
MS$FOCUSED_ION: BASE_PEAK 441.1697
MS$FOCUSED_ION: PRECURSOR_M/Z 441.1697
MS$FOCUSED_ION: PRECURSOR_TYPE [M+H]+
MS$DATA_PROCESSING: REANALYZE Peaks with additional N2/O included
MS$DATA_PROCESSING: WHOLE RMassBank 2.9.1
PK$SPLASH: splash10-01t9-0291000000-80af9ea6bfb64c9d3a39
PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm)
107.04 C3H7O4+ 1 107.0339 57.13
115.05 C9H7+ 1 115.0542 -36.74
117.07 C9H9+ 2 117.0699 1.05
119.05 C8H7O+ 1 119.0491 7.21
120.05 C8H8O+ 1 120.057 -58.02
121.06 C8H9O+ 1 121.0648 -39.58
122.07 C8H10O+ 1 122.0726 -21.43
123.04 C7H7O2+ 1 123.0441 -32.96
124.04 C3H8O5+ 1 124.0366 27.21
125.02 C6H5O3+ 1 125.0233 -26.56
128.06 C10H8+ 1 128.0621 -16.02
129.07 C10H9+ 2 129.0699 0.96
130.07 C6H10O3+ 2 130.0624 58.08
131.05 C9H7O+ 1 131.0491 6.55
131.08 C10H11+ 1 131.0855 -42.16
132.05 C9H8O+ 1 132.057 -52.75
133.06 C9H9O+ 1 133.0648 -36.01
134.07 C9H10O+ 1 134.0726 -19.51
135.04 C8H7O2+ 1 135.0441 -30.03
136.05 C8H8O2+ 1 136.0519 -13.82
137.06 C8H9O2+ 1 137.0597 2.15
138.06 C8H10O2+ 2 138.0675 -54.55
139.03 C9H3N2+ 1 139.0291 6.66
141.07 C11H9+ 2 141.0699 0.87
142.07 C7H10O3+ 2 142.0624 53.18
144.06 C10H8O+ 1 144.057 21.06
145.06 C10H9O+ 1 145.0648 -33.03
146.07 C10H10O+ 1 146.0726 -17.91
147.05 C9H7O2+ 1 147.0441 40.42
149.06 C9H9O2+ 1 149.0597 1.97
151.05 C12H7+ 1 151.0542 -27.98
152.06 C12H8+ 2 152.0621 -13.49
153.07 C12H9+ 2 153.0699 0.81
154.07 C8H10O3+ 2 154.0624 49.03
155.08 C12H11+ 1 155.0855 -35.64
157.06 C11H9O+ 1 157.0648 -30.51
158.07 C11H10O+ 1 158.0726 -16.55
159.08 C11H11O+ 1 159.0804 -2.77
161.06 C10H9O2+ 1 161.0597 1.83
162.06 C10H10O2+ 2 162.0675 -46.47
163.05 C13H7+ 1 163.0542 -25.92
164.06 C13H8+ 2 164.0621 -12.51
165.07 C13H9+ 2 165.0699 0.75
166.08 C13H10+ 2 166.0777 13.84
167.08 C13H11+ 2 167.0855 -33.08
168.06 C12H8O+ 1 168.057 18.05
169.06 C12H9O+ 1 169.0648 -28.34
170.07 C12H10O+ 1 170.0726 -15.38
171.08 C12H11O+ 1 171.0804 -2.58
172.08 C8H12O4+ 2 172.073 40.62
173.06 C11H9O2+ 1 173.0597 1.7
173.09 C12H13O+ 2 173.0961 -35.19
176.06 C14H8+ 2 176.0621 -11.65
177.07 C14H9+ 2 177.0699 0.7
178.08 C14H10+ 2 178.0777 12.91
179.08 C14H11+ 2 179.0855 -30.86
180.09 C14H12+ 2 180.0934 -18.61
181.07 C13H9O+ 1 181.0648 28.77
182.07 C13H10O+ 1 182.0726 -14.37
183.08 C13H11O+ 1 183.0804 -2.41
184.08 C9H12O4+ 2 184.073 37.97
185.09 C13H13O+ 2 185.0961 -32.91
186.08 C9H14O4+ 1 186.0887 -46.54
187.07 C12H11O2+ 2 187.0754 -28.63
188.08 C12H12O2+ 1 188.0832 -16.91
189.06 C11H9O3+ 2 189.0546 28.45
191.08 C15H11+ 3 191.0855 -28.92
192.09 C15H12+ 2 192.0934 -17.45
193.09 C11H13O3+ 2 193.0859 21.13
194.07 C14H10O+ 1 194.0726 -13.48
195.08 C14H11O+ 1 195.0804 -2.26
196.06 C13H8O2+ 1 196.0519 41.41
197.06 C13H9O2+ 1 197.0597 1.49
198.07 C13H10O2+ 1 198.0675 12.47
199.07 C13H11O2+ 2 199.0754 -26.9
200.08 C13H12O2+ 1 200.0832 -15.9
201.09 C13H13O2+ 1 201.091 -5
202.09 C9H14O5+ 2 202.0836 31.79
203.08 C16H11+ 3 203.0855 -27.21
204.09 C16H12+ 3 204.0934 -16.42
205.07 C15H9O+ 1 205.0648 25.4
206.08 C15H10O+ 1 206.0726 35.83
207.08 C15H11O+ 1 207.0804 -2.13
208.09 C15H12O+ 1 208.0883 8.33
209.07 C14H9O2+ 2 209.0597 49.24
210.07 C14H10O2+ 1 210.0675 11.75
211.08 C14H11O2+ 1 211.0754 22
212.08 C14H12O2+ 2 212.0832 -15
213.09 C14H13O2+ 1 213.091 -4.72
214.09 C10H14O5+ 2 214.0836 30.01
215.07 C13H11O3+ 1 215.0703 -1.26
216.07 C13H12O3+ 1 216.0781 -37.47
217.08 C13H13O3+ 1 217.0859 -27.27
219.08 C16H11O+ 1 219.0804 -2.01
220.09 C16H12O+ 1 220.0883 7.88
221.1 C16H13O+ 1 221.0961 17.68
222.09 C12H14O4+ 1 222.0887 6.03
223.08 C15H11O2+ 1 223.0754 20.82
224.08 C15H12O2+ 2 224.0832 -14.2
225.09 C15H13O2+ 1 225.091 -4.47
226.09 C11H14O5+ 2 226.0836 28.42
227.07 C14H11O3+ 1 227.0703 -1.19
228.08 C14H12O3+ 2 228.0781 8.35
229.08 C14H13O3+ 1 229.0859 -25.84
230.09 C14H14O3+ 1 230.0937 -16.28
231.09 C17H11O+ 2 231.0804 41.36
234.08 C13H14O4+ 2 234.0887 -37
235.08 C16H11O2+ 1 235.0754 19.76
236.08 C16H12O2+ 2 236.0832 -13.47
237.09 C16H13O2+ 1 237.091 -4.24
238.1 C16H14O2+ 1 238.0988 4.91
239.11 C16H15O2+ 1 239.1067 13.98
240.09 C19H12+ 3 240.0934 -13.96
241.09 C15H13O3+ 2 241.0859 16.92
242.09 C15H14O3+ 1 242.0937 -15.47
243.08 C18H11O+ 1 243.0804 -1.82
244.08 C14H12O4+ 2 244.073 28.64
245.09 C18H13O+ 2 245.0961 -24.85
247.07 C17H11O2+ 2 247.0754 -21.68
249.09 C17H13O2+ 2 249.091 -4.04
251.1 C17H15O2+ 2 251.1067 -26.51
253.08 C16H13O3+ 1 253.0859 -23.39
254.09 C16H14O3+ 1 254.0937 -14.74
255.1 C16H15O3+ 1 255.1016 -6.16
256.1 C16H16O3+ 2 256.1094 -36.69
257.1 C19H13O+ 1 257.0961 15.2
258.1 C19H14O+ 2 258.1039 -15.17
259.1 C15H15O4+ 2 259.0965 13.56
260.1 C15H16O4+ 1 260.1043 -16.57
261.09 C18H13O2+ 2 261.091 -3.85
262.1 C18H14O2+ 1 262.0988 4.46
263.1 C18H15O2+ 2 263.1067 -25.3
265.1 C21H13+ 3 265.1012 -4.44
268.09 C20H12O+ 1 268.0883 6.47
269.09 C20H13O+ 2 269.0961 -22.64
270.1 C20H14O+ 2 270.1039 -14.5
271.11 C20H15O+ 2 271.1117 -6.42
272.09 C19H12O2+ 2 272.0832 25.06
273.12 C20H17O+ 2 273.1274 -27.06
274.13 C20H18O+ 2 274.1352 -19.03
275.11 C19H15O2+ 1 275.1067 12.15
276.11 C19H16O2+ 2 276.1145 -16.23
277.11 C15H17O5+ 2 277.1071 10.65
281.09 C21H13O+ 2 281.0961 -21.67
283.11 C21H15O+ 2 283.1117 -6.15
284.11 C17H16O4+ 2 284.1043 20.03
285.12 C21H17O+ 2 285.1274 -25.92
286.1 C20H14O2+ 2 286.0988 4.09
287.11 C20H15O2+ 1 287.1067 11.65
288.11 C20H16O2+ 2 288.1145 -15.55
289.11 C16H17O5+ 2 289.1071 10.2
290.11 C23H14+ 3 290.109 3.44
291.12 C16H19O5+ 2 291.1227 -9.27
293.1 C22H13O+ 2 293.0961 13.34
294.1 C22H14O+ 2 294.1039 -13.32
295.11 C22H15O+ 2 295.1117 -5.9
296.12 C22H16O+ 2 296.1196 1.46
297.09 C21H13O2+ 2 297.091 -3.39
298.1 C21H14O2+ 2 298.0988 3.92
299.11 C21H15O2+ 2 299.1067 11.18
300.11 C21H16O2+ 2 300.1145 -14.93
301.12 C21H17O2+ 2 301.1223 -7.66
302.13 C21H18O2+ 2 302.1301 -0.43
303.13 C17H19O5+ 2 303.1227 24.08
304.12 C24H16+ 3 304.1247 -15.3
305.11 C20H17O3+ 2 305.1172 -23.67
306.12 C20H18O3+ 2 306.125 -16.48
307.11 C23H15O+ 2 307.1117 -5.67
311.11 C22H15O2+ 3 311.1067 10.75
312.11 C22H16O2+ 2 312.1145 -14.36
313.12 C22H17O2+ 2 313.1223 -7.37
314.11 C25H14+ 3 314.109 3.18
315.1 C21H15O3+ 2 315.1016 -4.98
316.13 C18H20O5+ 3 316.1305 -1.66
317.12 C21H17O3+ 3 317.1172 8.76
318.12 C21H18O3+ 2 318.125 -15.86
319.13 C21H19O3+ 3 319.1329 -9
320.13 C24H16O+ 2 320.1196 32.59
321.13 C24H17O+ 3 321.1274 8.12
322.12 C20H18O4+ 2 322.12 0.12
327.1 C22H15O3+ 3 327.1016 -4.8
329.12 C22H17O3+ 3 329.1172 8.44
330.12 C22H18O3+ 2 330.125 -15.28
331.12 C25H15O+ 2 331.1117 24.94
332.14 C22H20O3+ 2 332.1407 -2.1
333.11 C21H17O4+ 3 333.1121 -6.41
334.11 C21H18O4+ 2 334.12 -29.81
335.13 C21H19O4+ 2 335.1278 6.61
336.13 C21H20O4+ 2 336.1356 -16.69
345.11 C22H17O4+ 3 345.1121 -6.19
346.12 C22H18O4+ 2 346.12 0.11
347.13 C22H19O4+ 2 347.1278 6.38
348.13 C22H20O4+ 3 348.1356 -16.12
349.14 C22H21O4+ 3 349.1434 -9.84
350.14 C25H18O2+ 2 350.1301 28.19
395.17 C27H23O3+ 1 395.1642 14.75
396.16 C27H24O3+ 1 396.172 -30.28
405.15 C28H21O3+ 2 405.1485 3.65
411.15 C27H23O4+ 1 411.1591 -22.1
413.16 C27H25O4+ 2 413.1747 -35.66
423.16 C28H23O4+ 1 423.1591 2.16
424.16 C28H24O4+ 1 424.1669 -16.29
425.13 C27H21O5+ 1 425.1384 -19.64
439.15 C28H23O5+ 1 439.154 -9.11
440.16 C28H24O5+ 1 440.1618 -4.15
441.17 C28H25O5+ 1 441.1697 0.79
443.17 C27H25NO5+ 1 443.1727 -6.15
PK$NUM_PEAK: 207
PK$PEAK: m/z int. rel.int.
107.04 4 4
115.05 4 4
117.07 7 7
119.05 10 10
120.05 10 10
121.06 69 69
122.07 6 6
123.04 38 38
124.04 3 3
125.02 7 7
128.06 5 5
129.07 4 4
130.07 4 4
131.05 8 8
131.08 4 4
132.05 5 5
133.06 33 33
134.07 6 6
135.04 43 43
136.05 24 24
137.06 74 74
138.06 7 7
139.03 3 3
141.07 6 6
142.07 3 3
144.06 3 3
145.06 28 28
146.07 11 11
147.05 6 6
149.06 17 17
151.05 4 4
152.06 7 7
153.07 16 16
154.07 5 5
155.08 16 16
157.06 16 16
158.07 3 3
159.08 6 6
161.06 11 11
162.06 5 5
163.05 3 3
164.06 4 4
165.07 93 93
166.08 32 32
167.08 59 59
168.06 21 21
169.06 32 32
170.07 11 11
171.08 31 31
172.08 5 5
173.06 4 4
173.09 5 5
176.06 6 6
177.07 15 15
178.08 22 22
179.08 35 35
180.09 7 7
181.07 186 186
182.07 55 55
183.08 291 291
184.08 39 39
185.09 56 56
186.08 3 3
187.07 18 18
188.08 3 3
189.06 3 3
191.08 18 18
192.09 9 9
193.09 43 43
194.07 73 73
195.08 178 178
196.06 87 87
197.06 271 271
198.07 96 96
199.07 465 465
200.08 88 88
201.09 33 33
202.09 7 7
203.08 14 14
204.09 3 3
205.07 4 4
206.08 10 10
207.08 64 64
208.09 47 47
209.07 186 186
210.07 191 191
211.08 988 988
212.08 556 556
213.09 808 808
214.09 114 114
215.07 477 477
216.07 63 62
217.08 7 7
219.08 17 17
220.09 12 12
221.1 61 61
222.09 29 29
223.08 159 159
224.08 496 496
225.09 829 829
226.09 321 321
227.07 660 660
228.08 488 488
229.08 837 837
230.09 130 130
231.09 16 16
234.08 3 3
235.08 13 13
236.08 6 6
237.09 98 98
238.1 51 51
239.11 999 999
240.09 274 274
241.09 632 632
242.09 128 128
243.08 29 29
244.08 6 6
245.09 4 4
247.07 3 3
249.09 6 6
251.1 3 3
253.08 28 28
254.09 18 18
255.1 412 412
256.1 84 84
257.1 11 11
258.1 6 6
259.1 6 6
260.1 4 4
261.09 5 5
262.1 5 5
263.1 5 5
265.1 7 7
268.09 4 4
269.09 13 13
270.1 4 4
271.11 5 5
272.09 6 6
273.12 15 15
274.13 4 4
275.11 8 8
276.11 3 3
277.11 5 5
281.09 4 4
283.11 31 31
284.11 9 9
285.12 7 7
286.1 15 15
287.11 24 24
288.11 12 12
289.11 12 12
290.11 3 3
291.12 8 8
293.1 8 8
294.1 5 5
295.11 5 5
296.12 4 4
297.09 8 8
298.1 5 5
299.11 36 36
300.11 12 12
301.12 85 85
302.13 29 29
303.13 31 31
304.12 7 7
305.11 16 16
306.12 6 6
307.11 4 4
311.11 34 34
312.11 16 16
313.12 19 19
314.11 17 17
315.1 56 56
316.13 38 38
317.12 86 86
318.12 24 24
319.13 243 243
320.13 71 71
321.13 12 12
322.12 7 7
327.1 4 4
329.12 63 62
330.12 54 54
331.12 47 47
332.14 38 38
333.11 299 299
334.11 76 76
335.13 119 119
336.13 23 23
345.11 3 3
346.12 4 4
347.13 130 130
348.13 306 306
349.14 77 77
350.14 12 12
395.17 8 8
396.16 3 3
405.15 4 4
411.15 3 3
413.16 4 4
423.16 46 46
424.16 7 7
425.13 3 3
439.15 40 40
440.16 18 18
441.17 86 86
443.17 4 4
//
