ACCESSION: MSBNK-RIKEN-PR308725
RECORD_TITLE: Icariin; 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$NAME: Icariin
CH$NAME: 3-[(6-Deoxy-alpha-L-mannopyranosyl)oxy]-7-(beta-D-glucopyranosyloxy)-5-hydroxy-2-(4-methoxyphenyl)-8-(3-methyl-2-buten-1-yl)-4H-1-benzopyran-4-one
CH$COMPOUND_CLASS: Prenylated flavonols
CH$FORMULA: C₃₃H₄₀O₁₅
CH$EXACT_MASS: 676.236721
CH$SMILES: C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC2=C(OC3=C(C2=O)C(=CC(=C3CC=C(C)C)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)C5=CC=C(C=C5)OC)O)O)O
CH$IUPAC: InChI=1S/C33H40O15/c1-13(2)5-10-17-19(45-33-28(42)26(40)23(37)20(12-34)46-33)11-18(35)21-24(38)31(48-32-27(41)25(39)22(36)14(3)44-32)29(47-30(17)21)15-6-8-16(43-4)9-7-15/h5-9,11,14,20,22-23,25-28,32-37,39-42H,10,12H2,1-4H3/t14-,20+,22-,23+,25+,26-,27+,28+,32-,33+/m0/s1
CH$LINK: CAS 489-32-7
CH$LINK: CHEMSPIDER 4477421
CH$LINK: COMPTOX DTXSID00964133
CH$LINK: INCHIKEY TZJALUIVHRYQQB-XLRXWWTNSA-N
CH$LINK: NIKKAJI J15.942E
CH$LINK: PUBCHEM CID:5318997
CH$LINK: ZINC ZINC03960893

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 NEGATIVE
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 5.43
AC$CHROMATOGRAPHY: SOLVENT A water including 0.1% formic acid
AC$CHROMATOGRAPHY: SOLVENT B acetonitrile including 0.1% formic acid

MS$FOCUSED_ION: PRECURSOR_TYPE [M+HCOO]-
MS$FOCUSED_ION: PRECURSOR_M/Z 721.23492

PK$SPLASH: splash10-03xr-0005090100-b5af25a2cb25f47f5861
PK$NUM_PEAK: 72
PK$PEAK: m/z int. rel.int.
  64.92299 25.0 3
  115.25178 19.0 2
  187.07193 20.0 3
  187.10641 36.0 5
  193.08118 20.0 3
  201.84583 20.0 3
  217.09541 21.0 3
  218.05319 21.0 3
  245.89868 20.0 3
  273.08078 23.0 3
  275.89539 26.0 3
  277.98792 20.0 3
  279.1218 18.0 2
  283.06506 19.0 2
  294.12247 18.0 2
  298.71426 18.0 2
  302.61166 19.0 2
  312.06226 38.0 5
  323.04929 23.0 3
  324.06241 22.0 3
  327.04767 18.0 2
  338.1423 18.0 2
  343.73712 28.0 4
  346.74762 27.0 3
  351.0791 19.0 2
  352.0925 78.0 10
  353.14783 18.0 2
  364.08829 21.0 3
  366.10938 758.0 96
  367.07758 37.0 5
  367.11722 4615.0 583
  367.17548 20.0 3
  368.12164 1121.0 142
  368.27527 24.0 3
  369.11887 101.0 13
  369.13461 51.0 6
  381.12646 38.0 5
  394.10962 24.0 3
  409.1265 531.0 67
  410.12643 96.0 12
  410.14633 39.0 5
  411.09106 18.0 2
  411.13242 40.0 5
  414.04791 21.0 3
  433.11844 18.0 2
  456.44724 30.0 4
  510.11749 18.0 2
  513.1756 7909.0 999
  513.21997 63.0 8
  513.25397 22.0 3
  514.17615 2152.0 272
  515.17938 244.0 31
  516.1759 59.0 7
  517.21912 23.0 3
  529.07202 22.0 3
  529.16919 1063.0 134
  530.1698 210.0 27
  530.19415 115.0 15
  530.87366 21.0 3
  531.16956 46.0 6
  532.1864 19.0 2
  535.18787 33.0 4
  539.94635 18.0 2
  553.14435 18.0 2
  555.19324 89.0 11
  556.18451 20.0 3
  557.19714 43.0 5
  588.62091 20.0 3
  598.19641 25.0 3
  617.22406 21.0 3
  675.22931 73.0 9
  721.23267 2517.0 318
//