ACCESSION: MSBNK-IPB_Halle-PB011901
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$CHROMATOGRAPHY: RETENTION_TIME 10.538 min
AC$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$SPLASH: splash10-01t9-0291000000-92338fb9fa58f976baa9
PK$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
117.06 C5H9O3+ 1 117.0546 45.96
119.05 C8H7O+ 1 119.0491 7.21
120.06 C8H8O+ 1 120.057 25.27
121.06 C8H9O+ 1 121.0648 -39.58
122.06 C4H10O4+ 1 122.0574 21.63
123.04 C7H7O2+ 1 123.0441 -32.96
123.13 C2H19O5+ 1 123.1227 59.29
125.01 C5H3NO3+ 1 125.0107 -5.95
128.06 C10H8+ 1 128.0621 -16.02
132.05 C9H8O+ 1 132.057 -52.75
133.02 C4H5O5+ 1 133.0131 51.5
133.07 C9H9O+ 1 133.0648 39.14
133.12 C7H17O2+ 1 133.1223 -17.32
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
139.04 C7H7O3+ 1 139.039 7.4
141.07 C11H9+ 2 141.0699 0.87
143.08 C11H11+ 1 143.0855 -38.63
145.06 C10H9O+ 1 145.0648 -33.03
147.04 C9H7O2+ 1 147.0441 -27.58
148.04 C5H8O5+ 1 148.0366 22.8
151.04 C8H7O3+ 1 151.039 6.82
151.1 C6H15O4+ 1 151.0965 23.26
152.06 C12H8+ 2 152.0621 -13.49
153.07 C12H9+ 2 153.0699 0.81
155.08 C12H11+ 1 155.0855 -35.64
157.09 C8H13O3+ 1 157.0859 25.97
158.07 C11H10O+ 1 158.0726 -16.55
161.06 C10H9O2+ 1 161.0597 1.83
163.07 C10H11O2+ 1 163.0754 -32.84
165.07 C13H9+ 2 165.0699 0.75
166.07 C9H10O3+ 2 166.0624 45.49
167.09 C6H15O5+ 2 167.0914 -8.38
168.09 C13H12+ 2 168.0934 -19.94
168.15 C11H20O+ 1 168.1509 -5.15
169.07 C12H9O+ 1 169.0648 30.81
171.03 C7H7O5+ 2 171.0288 7.02
171.08 C12H11O+ 1 171.0804 -2.58
172.09 C12H12O+ 1 172.0883 10.07
173.06 C11H9O2+ 1 173.0597 1.7
177.07 C14H9+ 2 177.0699 0.7
178.08 C14H10+ 2 178.0777 12.91
179.09 C7H15O5+ 2 179.0914 -7.82
180.1 C7H16O5+ 2 180.0992 4.3
181.06 C13H9O+ 2 181.0648 -26.46
182.07 C13H10O+ 1 182.0726 -14.37
183.08 C13H11O+ 1 183.0804 -2.41
184.09 C13H12O+ 1 184.0883 9.42
185.1 C13H13O+ 1 185.0961 21.12
186.09 C9H14O4+ 1 186.0887 7.2
187.07 C12H11O2+ 2 187.0754 -28.63
189.08 C8H13O5+ 2 189.0757 22.48
190.08 C15H10+ 2 190.0777 12.09
192.08 C11H12O3+ 1 192.0781 9.91
193.07 C14H9O+ 1 193.0648 26.98
194.08 C14H10O+ 1 194.0726 38.05
195.08 C14H11O+ 1 195.0804 -2.26
196.09 C14H12O+ 1 196.0883 8.84
197.06 C13H9O2+ 1 197.0597 1.49
198.07 C13H10O2+ 1 198.0675 12.47
199.08 C13H11O2+ 1 199.0754 23.33
200.08 C13H12O2+ 1 200.0832 -15.9
201.09 C13H13O2+ 1 201.091 -5
203.09 C9H15O5+ 2 203.0914 -6.89
205.09 C12H13O3+ 2 205.0859 19.89
206.08 C15H10O+ 1 206.0726 35.83
207.08 C15H11O+ 1 207.0804 -2.13
207.16 C10H23O4+ 1 207.1591 4.41
208.09 C15H12O+ 1 208.0883 8.33
209.08 C11H13O4+ 1 209.0808 -4
210.07 C14H10O2+ 1 210.0675 11.75
211.08 C14H11O2+ 1 211.0754 22
212.08 C14H12O2+ 2 212.0832 -15
212.97 C11HO5+ 1 212.9818 -55.64
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
217.1 C17H13+ 2 217.1012 -5.42
219.07 C12H11O4+ 2 219.0652 21.98
219.17 C15H23O+ 2 219.1743 -19.81
220.11 C13H16O3+ 1 220.1094 2.75
221.09 C16H13O+ 2 221.0961 -27.55
222.09 C12H14O4+ 1 222.0887 6.03
223.08 C15H11O2+ 1 223.0754 20.82
223.16 C10H23O5+ 2 223.154 26.89
224.08 C15H12O2+ 2 224.0832 -14.2
225.09 C15H13O2+ 1 225.091 -4.47
226.07 C14H10O3+ 2 226.0624 33.42
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
235.08 C16H11O2+ 1 235.0754 19.76
235.13 C14H19O3+ 1 235.1329 -12.21
236.08 C16H12O2+ 2 236.0832 -13.47
237.09 C16H13O2+ 1 237.091 -4.24
237.17 C11H25O5+ 2 237.1697 1.47
238 C17H2O2+ 2 238.0049 -20.72
238.09 C12H14O5+ 2 238.0836 26.99
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
242.17 C17H22O+ 1 242.1665 14.38
243.08 C18H11O+ 1 243.0804 -1.82
243.97 C15O4+ 1 243.9791 -37.34
244.07 C14H12O4+ 1 244.073 -12.33
245.08 C14H13O4+ 1 245.0808 -3.41
247.07 C17H11O2+ 2 247.0754 -21.68
247.15 C19H19+ 2 247.1481 7.58
249.09 C17H13O2+ 2 249.091 -4.04
250.08 C20H10+ 2 250.0777 9.19
251.11 C17H15O2+ 1 251.1067 13.32
252.09 C20H12+ 3 252.0934 -13.3
253.08 C16H13O3+ 1 253.0859 -23.39
254.09 C16H14O3+ 1 254.0937 -14.74
255.1 C16H15O3+ 1 255.1016 -6.16
256.11 C16H16O3+ 2 256.1094 2.36
257.11 C16H17O3+ 2 257.1172 -28.08
259.11 C19H15O+ 2 259.1117 -6.72
260.11 C15H16O4+ 2 260.1043 21.87
261.09 C18H13O2+ 2 261.091 -3.85
263.09 C14H15O5+ 2 263.0914 -5.32
264.12 C18H16O2+ 2 264.1145 20.9
268.09 C20H12O+ 1 268.0883 6.47
269.12 C17H17O3+ 2 269.1172 10.33
270.1 C20H14O+ 2 270.1039 -14.5
271.1 C16H15O4+ 2 271.0965 12.96
273.08 C15H13O5+ 2 273.0757 15.56
274.08 C22H10+ 2 274.0777 8.39
275.1 C19H15O2+ 2 275.1067 -24.19
276.11 C19H16O2+ 2 276.1145 -16.23
277.11 C15H17O5+ 2 277.1071 10.65
281.15 C19H21O2+ 2 281.1536 -12.83
283.11 C21H15O+ 2 283.1117 -6.15
284.11 C17H16O4+ 2 284.1043 20.03
286 C21H2O2+ 2 286.0049 -17.24
286.13 C21H18O+ 2 286.1352 -18.23
287.1 C20H15O2+ 2 287.1067 -23.18
287.19 C18H25NO2+ 1 287.188 7.03
288.12 C20H16O2+ 2 288.1145 19.15
289.13 C20H17O2+ 2 289.1223 26.61
291.1 C19H15O3+ 2 291.1016 -5.4
297.09 C21H13O2+ 2 297.091 -3.39
299.11 C21H15O2+ 2 299.1067 11.18
301.12 C21H17O2+ 2 301.1223 -7.66
302.12 C17H18O5+ 2 302.1149 16.96
303.14 C21H19O2+ 2 303.138 6.74
304.11 C20H16O3+ 2 304.1094 1.99
304.2 C22H24O+ 1 304.1822 58.63
306.13 C20H18O3+ 3 306.125 16.18
307.14 C20H19O3+ 3 307.1329 23.21
311.14 C23H19O+ 2 311.143 -9.78
312.11 C22H16O2+ 2 312.1145 -14.36
313.11 C18H17O5+ 2 313.1071 9.42
314.13 C22H18O2+ 2 314.1301 -0.42
315.1 C21H15O3+ 2 315.1016 -4.98
316.15 C22H20O2+ 2 316.1458 13.34
317.12 C21H17O3+ 3 317.1172 8.76
318.13 C21H18O3+ 3 318.125 15.57
319.13 C21H19O3+ 3 319.1329 -9
320.14 C21H20O3+ 2 320.1407 -2.17
321.13 C24H17O+ 3 321.1274 8.12
322.13 C24H18O+ 2 322.1352 -16.19
323.12 C20H19O4+ 2 323.1278 -24.09
329.13 C26H17+ 3 329.1325 -7.53
330.12 C22H18O3+ 2 330.125 -15.28
331.11 C25H15O+ 2 331.1117 -5.26
331.97 C21O5+ 2 331.974 -12.12
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
337.13 C24H17O2+ 2 337.1223 22.82
338.13 C24H18O2+ 2 338.1301 -0.39
344.14 C23H20O3+ 3 344.1407 -2.02
345.05 C24H9O3+ 3 345.0546 -13.39
346.11 C22H18O4+ 2 346.12 -28.78
347.13 C22H19O4+ 2 347.1278 6.38
348.13 C22H20O4+ 3 348.1356 -16.12
349.12 C25H17O2+ 2 349.1223 -6.61
350.07 C27H10O+ 2 350.0726 -7.47
366.16 C26H22O2+ 2 366.1614 -3.91
373.19 C25H25O3+ 1 373.1798 27.28
381.15 C26H21O3+ 2 381.1485 3.88
395.16 C27H23O3+ 1 395.1642 -10.56
410.04 C28H10O4+ 2 410.0574 -42.34
423.16 C28H23O4+ 1 423.1591 2.16
424.17 C28H24O4+ 1 424.1669 7.28
439.16 C28H23O5+ 1 439.154 13.66
440.16 C28H24O5+ 1 440.1618 -4.15
441.17 C28H25O5+ 1 441.1697 0.79
443.16 C26H23N2O5+ 1 443.1601 -0.33
PK$NUM_PEAK: 200
PK$PEAK: m/z int. rel.int.
107.04 9 9
115.05 10 10
117.06 12 12
119.05 25 25
120.06 14 14
121.06 108 108
122.06 12 12
123.04 38 38
123.13 6 6
125.01 6 6
128.06 12 12
132.05 6 6
133.02 15 15
133.07 18 18
133.12 10 10
134.07 8 8
135.04 75 75
136.05 32 32
137.06 44 44
139.04 7 7
141.07 18 18
143.08 8 8
145.06 10 10
147.04 6 6
148.04 10 10
151.04 15 15
151.1 7 7
152.06 35 35
153.07 28 28
155.08 12 12
157.09 9 9
158.07 7 7
161.06 14 14
163.07 5 5
165.07 63 62
166.07 26 26
167.09 44 44
168.09 30 30
168.15 10 10
169.07 36 36
171.03 7 7
171.08 39 39
172.09 9 9
173.06 15 15
177.07 42 42
178.08 28 28
179.09 25 25
180.1 9 9
181.06 214 214
182.07 59 59
183.08 207 207
184.09 24 24
185.1 65 65
186.09 6 6
187.07 31 31
189.08 6 6
190.08 8 8
192.08 6 6
193.07 55 55
194.08 28 28
195.08 260 260
196.09 227 227
197.06 319 319
198.07 162 162
199.08 472 472
200.08 87 87
201.09 47 47
203.09 15 15
205.09 15 15
206.08 7 7
207.08 55 55
207.16 7 7
208.09 28 28
209.08 187 187
210.07 134 134
211.08 591 591
212.08 336 336
212.97 8 8
213.09 999 999
214.09 199 199
215.07 665 665
216.07 115 115
217.1 7 7
219.07 7 7
219.17 10 10
220.11 11 11
221.09 115 115
222.09 27 27
223.08 54 54
223.16 8 8
224.08 240 240
225.09 714 714
226.07 190 190
227.07 673 673
228.08 579 579
229.08 808 808
230.09 169 169
231.09 16 16
235.08 6 6
235.13 7 7
236.08 10 10
237.09 96 96
237.17 7 7
238 7 7
238.09 30 30
239.11 839 839
240.09 221 221
241.09 890 890
242.09 127 127
242.17 21 21
243.08 24 24
243.97 6 6
244.07 71 71
245.08 17 17
247.07 12 12
247.15 10 10
249.09 18 18
250.08 9 9
251.11 12 12
252.09 10 10
253.08 30 30
254.09 16 16
255.1 591 591
256.11 68 68
257.11 17 17
259.11 26 26
260.11 7 7
261.09 6 6
263.09 9 9
264.12 7 7
268.09 8 8
269.12 6 6
270.1 10 10
271.1 6 6
273.08 15 15
274.08 6 6
275.1 16 16
276.11 6 6
277.11 6 6
281.15 7 7
283.11 31 31
284.11 8 8
286 7 7
286.13 8 8
287.1 26 26
287.19 9 9
288.12 12 12
289.13 22 22
291.1 11 11
297.09 11 11
299.11 40 40
301.12 74 74
302.12 14 14
303.14 57 57
304.11 7 7
304.2 7 7
306.13 19 19
307.14 6 6
311.14 7 7
312.11 17 17
313.11 19 19
314.13 26 26
315.1 48 48
316.15 152 152
317.12 110 110
318.13 24 24
319.13 264 264
320.14 60 60
321.13 14 14
322.13 8 8
323.12 15 15
329.13 21 21
330.12 39 39
331.11 33 33
331.97 8 8
332.14 67 67
333.11 197 197
334.11 38 38
335.13 90 90
336.13 54 54
337.13 8 8
338.13 8 8
344.14 9 9
345.05 6 6
346.11 10 10
347.13 87 87
348.13 85 85
349.12 18 18
350.07 6 6
366.16 8 8
373.19 6 6
381.15 8 8
395.16 13 13
410.04 7 7
423.16 86 86
424.17 36 36
439.16 82 82
440.16 28 28
441.17 196 196
443.16 10 10
//
