ACCESSION: MSBNK-RIKEN-PR305184
RECORD_TITLE: Syrosingopine; 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: registered in RIKEN PlaSMA

CH$NAME: Syrosingopine
CH$COMPOUND_CLASS: Yohimbine alkaloids
CH$FORMULA: C₃₅H₄₂N₂O₁₁
CH$EXACT_MASS: 666.724
CH$SMILES: CCOC(=O)OC1=C(OC)C=C(C=C1OC)C(=O)OC1CC2CN3CCC4=C(NC5=C4C=CC(OC)=C5)C3CC2C(C1OC)C(=O)OC
CH$IUPAC: InChI=1S/C35H42N2O11/c1-7-46-35(40)48-31-26(42-3)12-18(13-27(31)43-4)33(38)47-28-14-19-17-37-11-10-22-21-9-8-20(41-2)15-24(21)36-30(22)25(37)16-23(19)29(32(28)44-5)34(39)45-6/h8-9,12-13,15,19,23,25,28-29,32,36H,7,10-11,14,16-17H2,1-6H3
CH$LINK: INCHIKEY ZCDNRPPFBQDQHR-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 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$CHROMATOGRAPHY: CAPILLARY_VOLTAGE -2.75 kV
AC$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 6.720133
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 665.27158374783

PK$SPLASH: splash10-004i-0791000000-5c6e19df96c56c3e11ba
PK$NUM_PEAK: 137
PK$PEAK: m/z int. rel.int.
  67.05377 10.0 10
  81.03542 24.0 24
  89.02052 26.0 26
  89.02596 71.0 71
  90.00994 26.0 26
  90.02827 33.0 33
  95.04614 12.0 12
  96.01863 15.0 15
  97.03161 11.0 11
  104.99328 10.0 10
  106.00195 10.0 10
  107.01726 12.0 12
  116.04523 10.0 10
  119.77749 10.0 10
  120.02361 23.0 23
  121.028 57.0 57
  121.03547 9.0 9
  122.00347 29.0 29
  123.00855 209.0 209
  123.04498 10.0 10
  125.02073 27.0 27
  126.02235 16.0 16
  135.00063 12.0 12
  137.02357 129.0 129
  138.03131 46.0 46
  138.99843 13.0 13
  139.03165 11.0 11
  146.0573 10.0 10
  151.0042 10.0 10
  152.04294 22.0 22
  152.04893 26.0 26
  153.05455 39.0 39
  160.01756 10.0 10
  163.03023 11.0 11
  164.00911 22.0 22
  165.00952 12.0 12
  165.01828 40.0 40
  166.06226 10.0 10
  166.99211 19.0 19
  167.00288 74.0 74
  167.0377 15.0 15
  167.9966 11.0 11
  168.00175 28.0 28
  168.01007 12.0 12
  169.01636 11.0 11
  169.05548 17.0 17
  170.06325 11.0 11
  175.79256 10.0 10
  181.01494 11.0 11
  181.06268 10.0 10
  183.02739 63.0 63
  183.03998 10.0 10
  183.05887 13.0 13
  184.02881 11.0 11
  184.06769 10.0 10
  194.99316 29.0 29
  195.03079 251.0 251
  196.03455 119.0 119
  196.05501 20.0 20
  197.03636 23.0 23
  198.06335 10.0 10
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  210.05238 198.0 198
  210.07379 16.0 16
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  212.0533 10.0 10
  212.0672 12.0 12
  213.05888 34.0 34
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  222.0773 15.0 15
  223.02954 10.0 10
  225.0768 1000.0 999
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  226.08177 166.0 166
  227.0743 10.0 10
  235.09068 13.0 13
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  263.13254 10.0 10
  269.06259 141.0 141
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  272.10986 18.0 18
  287.11359 10.0 10
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  304.05649 10.0 10
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  337.09872 19.0 19
  337.12192 15.0 15
  349.15619 10.0 10
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  351.09637 13.0 13
  363.16333 16.0 16
  380.1687 75.0 75
  380.18472 39.0 39
  381.18323 31.0 31
  382.02325 11.0 11
  387.21033 10.0 10
  438.16193 13.0 13
  467.17316 15.0 15
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  470.16385 19.0 19
  486.18701 10.0 10
  499.13467 14.0 14
  500.20694 15.0 15
  518.19855 11.0 11
  548.20392 13.0 13
  564.22125 23.0 23
  577.20142 11.0 11
  578.24017 11.0 11
  604.19324 10.0 10
//