ACCESSION: MSBNK-RIKEN-PR300134
RECORD_TITLE: Hydroxygardnutine; 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$NAME: Hydroxygardnutine
CH$COMPOUND_CLASS: Macroline alkaloids
CH$FORMULA: C₂₀H₂₂N₂O₃
CH$EXACT_MASS: 338.407
CH$SMILES: COC1=CC2=C(C=C1)C1=C(N2)[C@@H]2C[C@@H]3[C@@H]4CO[C@H]1[C@@H]4N2C\C3=C\CO
CH$IUPAC: InChI=1S/C20H22N2O3/c1-24-11-2-3-12-15(6-11)21-18-16-7-13-10(4-5-23)8-22(16)19-14(13)9-25-20(19)17(12)18/h2-4,6,13-14,16,19-21,23H,5,7-9H2,1H3/b10-4-/t13-,14-,16-,19+,20+/m0/s1
CH$LINK: INCHIKEY OUONWRIEOZGMSQ-NUUNSNFRSA-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 3.602583
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 339.170319

PK$SPLASH: splash10-0a4i-0930000000-e9fb182eeca67c990f82
PK$NUM_PEAK: 364
PK$PEAK: m/z int. rel.int.
  65.03734 11.0 11
  65.0425 13.0 13
  67.05646 9.0 9
  77.03961 85.0 85
  78.03006 9.0 9
  79.0538 62.0 62
  79.73885 6.0 6
  80.0364 16.0 16
  80.0493 39.0 39
  81.03357 6.0 6
  81.05571 21.0 21
  82.0642 7.0 7
  86.31937 9.0 9
  90.04244 6.0 6
  91.04878 29.0 29
  91.05436 54.0 54
  91.05925 34.0 34
  92.04848 11.0 11
  92.05899 13.0 13
  93.05772 35.0 35
  93.06947 23.0 23
  93.07561 16.0 16
  94.0627 12.0 12
  94.06728 11.0 11
  94.07475 8.0 8
  95.0656 9.0 9
  95.09313 8.0 8
  95.39268 5.0 5
  96.07971 12.0 12
  101.42999 7.0 7
  103.05353 144.0 144
  104.05995 14.0 14
  105.04482 13.0 13
  105.051 8.0 8
  105.05862 19.0 19
  105.0698 6.0 6
  106.06584 385.0 385
  107.05278 5.0 5
  107.06683 10.0 10
  107.07459 26.0 26
  107.38763 6.0 6
  108.04687 11.0 11
  108.05666 11.0 11
  108.0827 47.0 47
  109.05424 9.0 9
  109.09064 6.0 6
  110.08897 11.0 11
  110.09743 16.0 16
  115.05329 31.0 31
  116.05706 14.0 14
  116.06381 11.0 11
  117.04305 11.0 11
  117.05746 103.0 103
  118.03454 13.0 13
  118.04922 7.0 7
  118.05611 39.0 39
  118.06614 87.0 87
  119.05405 7.0 7
  119.07617 11.0 11
  120.06743 7.0 7
  120.08181 110.0 110
  121.05848 7.0 7
  121.08469 17.0 17
  121.09216 7.0 7
  122.06546 7.0 7
  122.6655 8.0 8
  123.063 8.0 8
  124.05541 10.0 10
  127.05675 6.0 6
  128.04951 18.0 18
  128.51933 9.0 9
  129.06422 9.0 9
  129.07358 8.0 8
  129.37366 7.0 7
  130.04463 8.0 8
  130.05284 29.0 29
  130.06189 168.0 168
  130.06891 210.0 210
  131.06454 43.0 43
  131.06989 30.0 30
  131.07814 29.0 29
  131.08763 5.0 5
  132.0466 73.0 73
  132.05927 6.0 6
  132.06871 6.0 6
  132.0782 8.0 8
  132.08397 9.0 9
  132.09821 6.0 6
  133.05775 8.0 8
  134.07738 11.0 11
  135.06847 6.0 6
  136.06537 12.0 12
  136.07568 30.0 30
  136.08093 19.0 19
  138.08704 11.0 11
  138.09532 20.0 20
  141.05638 12.0 12
  142.05421 9.0 9
  142.0621 16.0 16
  143.03458 5.0 5
  143.05321 20.0 20
  143.05803 8.0 8
  143.07602 67.0 67
  144.04488 10.0 10
  144.05676 55.0 55
  144.0782 31.0 31
  144.08571 81.0 81
  145.05151 98.0 98
  145.07224 12.0 12
  145.0863 18.0 18
  145.09445 13.0 13
  146.05911 17.0 17
  146.09689 6.0 6
  147.06816 20.0 20
  147.08289 7.0 7
  148.07697 14.0 14
  150.05853 6.0 6
  153.05037 5.0 5
  153.0713 9.0 9
  154.05844 37.0 37
  154.0661 64.0 64
  155.048 5.0 5
  155.06201 18.0 18
  155.07167 50.0 50
  155.08051 28.0 28
  155.98303 11.0 11
  156.04704 6.0 6
  156.06676 13.0 13
  156.07625 14.0 14
  157.0462 7.0 7
  157.0569 12.0 12
  157.08488 8.0 8
  157.09315 5.0 5
  158.03264 5.0 5
  158.06091 1000.0 999
  158.09137 14.0 14
  159.06538 247.0 247
  159.08896 7.0 7
  160.07555 75.0 75
  160.08675 21.0 21
  161.08232 5.0 5
  162.0968 11.0 11
  163.09251 9.0 9
  166.06581 5.0 5
  166.07712 7.0 7
  167.05556 6.0 6
  167.07347 99.0 99
  168.06825 13.0 13
  168.08052 44.0 44
  169.05278 6.0 6
  169.07974 30.0 30
  170.04872 5.0 5
  170.06168 39.0 39
  170.08395 19.0 19
  171.05884 5.0 5
  171.06981 21.0 21
  172.05086 13.0 13
  172.0762 93.0 93
  173.04128 6.0 6
  173.0527 32.0 32
  173.06943 18.0 18
  173.08403 126.0 126
  173.09084 33.0 33
  174.04842 7.0 7
  174.07677 23.0 23
  174.08989 40.0 40
  175.09985 11.0 11
  178.06235 7.0 7
  178.07732 6.0 6
  179.07452 24.0 24
  180.05324 7.0 7
  180.08241 119.0 119
  181.06848 12.0 12
  181.07819 17.0 17
  181.08864 30.0 30
  181.09807 24.0 24
  181.27859 8.0 8
  182.05746 50.0 50
  182.0961 11.0 11
  183.06619 29.0 29
  184.04768 8.0 8
  184.05687 24.0 24
  184.07385 31.0 31
  185.04785 6.0 6
  185.07167 19.0 19
  185.62064 5.0 5
  186.07759 9.0 9
  186.09021 30.0 30
  186.10109 11.0 11
  187.08107 10.0 10
  187.10529 6.0 6
  188.05746 12.0 12
  189.06358 12.0 12
  189.07443 9.0 9
  189.11325 13.0 13
  191.07053 38.0 38
  191.08305 19.0 19
  192.06128 5.0 5
  192.06883 11.0 11
  192.08327 54.0 54
  193.07465 16.0 16
  193.08965 121.0 121
  194.06592 11.0 11
  194.09743 28.0 28
  195.05627 14.0 14
  195.07031 10.0 10
  195.07845 6.0 6
  195.09048 5.0 5
  195.10461 6.0 6
  196.07426 5.0 5
  196.08488 18.0 18
  196.11145 8.0 8
  197.07681 71.0 71
  197.09248 14.0 14
  198.08977 56.0 56
  199.05499 7.0 7
  199.08379 38.0 38
  199.09503 28.0 28
  200.0744 8.0 8
  200.10252 6.0 6
  204.06067 7.0 7
  204.07921 24.0 24
  205.07158 9.0 9
  205.08159 27.0 27
  205.09183 31.0 31
  206.05312 6.0 6
  206.07428 30.0 30
  206.09457 32.0 32
  207.04314 16.0 16
  207.0639 8.0 8
  207.08974 6.0 6
  207.10329 8.0 8
  208.05772 14.0 14
  208.07509 34.0 34
  208.08533 30.0 30
  208.10327 8.0 8
  209.05275 12.0 12
  209.07812 21.0 21
  209.0898 7.0 7
  210.09602 35.0 35
  211.07243 17.0 17
  211.08255 11.0 11
  211.74573 7.0 7
  212.09601 14.0 14
  213.65784 8.0 8
  216.08244 14.0 14
  217.05087 6.0 6
  217.07875 15.0 15
  217.09073 18.0 18
  218.09584 68.0 68
  218.32176 7.0 7
  219.02084 8.0 8
  219.09215 34.0 34
  219.10138 41.0 41
  220.06718 6.0 6
  220.07967 21.0 21
  220.09807 39.0 39
  221.0787 7.0 7
  221.09036 17.0 17
  222.06894 6.0 6
  222.08609 39.0 39
  222.09946 6.0 6
  222.1172 15.0 15
  223.10214 28.0 28
  224.07892 6.0 6
  224.09309 7.0 7
  224.10448 14.0 14
  225.05309 7.0 7
  225.06114 6.0 6
  225.09859 13.0 13
  226.08943 6.0 6
  227.06848 6.0 6
  228.08766 21.0 21
  228.12868 6.0 6
  230.08806 7.0 7
  230.11136 5.0 5
  231.08907 35.0 35
  232.10371 39.0 39
  233.08737 5.0 5
  233.10986 14.0 14
  234.05634 14.0 14
  234.08926 32.0 32
  234.10869 14.0 14
  234.12061 15.0 15
  235.08432 13.0 13
  235.10056 29.0 29
  235.12872 19.0 19
  235.14185 7.0 7
  236.10667 25.0 25
  237.09688 11.0 11
  237.27512 5.0 5
  238.0748 19.0 19
  239.11261 5.0 5
  239.12065 9.0 9
  242.08554 6.0 6
  242.10835 6.0 6
  244.10825 13.0 13
  245.07623 9.0 9
  245.09796 6.0 6
  245.11578 8.0 8
  245.6313 7.0 7
  246.08875 14.0 14
  246.09775 17.0 17
  246.11685 19.0 19
  247.07384 12.0 12
  247.09296 64.0 64
  247.1154 6.0 6
  247.12874 7.0 7
  248.06325 12.0 12
  248.08162 9.0 9
  248.09258 16.0 16
  248.10294 33.0 33
  248.12892 13.0 13
  249.06691 7.0 7
  249.10309 41.0 41
  249.12181 11.0 11
  250.10477 9.0 9
  250.11346 25.0 25
  250.1245 6.0 6
  251.06995 11.0 11
  251.1162 35.0 35
  252.1084 6.0 6
  252.12462 6.0 6
  254.09531 7.0 7
  257.08499 6.0 6
  258.05655 6.0 6
  259.09946 13.0 13
  259.11328 6.0 6
  259.13589 7.0 7
  260.10123 14.0 14
  261.10596 6.0 6
  262.10361 26.0 26
  262.11298 22.0 22
  262.1221 11.0 11
  262.55106 7.0 7
  263.08856 9.0 9
  263.11429 56.0 56
  265.09637 5.0 5
  265.13345 16.0 16
  269.10867 5.0 5
  273.11685 6.0 6
  274.12982 8.0 8
  275.10107 7.0 7
  275.11911 16.0 16
  277.10602 7.0 7
  277.1283 28.0 28
  277.14026 12.0 12
  277.41577 5.0 5
  278.09662 17.0 17
  278.12112 30.0 30
  279.11398 20.0 20
  279.13675 9.0 9
  280.12466 11.0 11
  283.18814 9.0 9
  285.80096 6.0 6
  287.12189 13.0 13
  293.07742 5.0 5
  293.11688 6.0 6
  293.13794 11.0 11
  294.13544 7.0 7
  294.14505 8.0 8
  301.73706 5.0 5
  307.15579 6.0 6
  310.14297 9.0 9
//