ACCESSION: MSBNK-RIKEN-PR300149
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$SPLASH: splash10-05fr-0962000000-ffd06268ff80d13ec654
PK$NUM_PEAK: 391
PK$PEAK: m/z int. rel.int.
  68.03838 5.0 5
  79.04565 8.0 8
  79.05254 24.0 24
  80.05087 20.0 20
  80.05846 6.0 6
  82.06435 9.0 9
  84.04006 6.0 6
  91.05373 59.0 59
  91.06332 7.0 7
  93.02737 6.0 6
  93.05402 7.0 7
  93.05806 7.0 7
  93.06848 71.0 71
  94.06509 22.0 22
  96.08085 30.0 30
  96.17473 6.0 6
  98.06383 7.0 7
  98.98429 6.0 6
  102.6756 10.0 10
  103.05434 163.0 163
  104.05793 9.0 9
  105.05804 37.0 37
  106.0425 10.0 10
  106.06483 419.0 419
  107.0668 10.0 10
  107.07243 7.0 7
  108.08076 16.0 16
  108.08572 13.0 13
  109.0619 6.0 6
  109.09982 8.0 8
  110.05823 7.0 7
  110.07008 5.0 5
  110.08517 6.0 6
  110.09638 105.0 105
  111.09592 8.0 8
  112.84808 7.0 7
  113.51183 5.0 5
  115.82677 6.0 6
  117.05893 6.0 6
  118.04166 6.0 6
  118.06255 37.0 37
  118.06848 58.0 58
  119.06648 8.0 8
  119.07627 13.0 13
  119.99979 6.0 6
  120.05588 10.0 10
  120.07977 802.0 801
  121.08467 120.0 120
  122.39546 5.0 5
  124.06166 6.0 6
  124.07449 43.0 43
  124.08935 6.0 6
  126.09028 10.0 10
  127.05533 6.0 6
  128.09709 7.0 7
  129.06264 8.0 8
  130.0665 24.0 24
  130.07578 10.0 10
  131.07175 31.0 31
  132.04292 6.0 6
  132.07738 8.0 8
  133.05367 8.0 8
  133.28621 11.0 11
  134.10266 6.0 6
  135.07756 8.0 8
  136.04889 13.0 13
  136.07565 320.0 320
  137.07719 71.0 71
  137.0862 14.0 14
  138.07095 6.0 6
  138.09169 241.0 241
  139.08617 6.0 6
  139.09421 26.0 26
  139.15927 6.0 6
  143.0699 24.0 24
  143.07869 11.0 11
  144.0648 8.0 8
  144.0759 10.0 10
  144.0845 38.0 38
  145.08932 30.0 30
  145.09981 5.0 5
  146.05826 8.0 8
  146.10725 7.0 7
  147.05275 9.0 9
  147.06523 49.0 49
  147.07974 11.0 11
  148.07574 76.0 76
  149.64452 6.0 6
  150.06079 9.0 9
  150.06885 5.0 5
  150.08147 10.0 10
  150.09044 45.0 45
  150.0968 21.0 21
  154.06294 13.0 13
  154.07576 6.0 6
  154.0834 5.0 5
  154.48262 8.0 8
  155.06612 7.0 7
  155.07848 6.0 6
  156.07628 5.0 5
  156.27856 5.0 5
  157.08636 8.0 8
  158.05907 228.0 228
  158.73438 6.0 6
  159.05536 30.0 30
  159.06546 47.0 47
  160.05991 10.0 10
  160.0773 182.0 182
  160.11842 8.0 8
  161.08269 26.0 26
  162.08957 103.0 103
  163.0997 11.0 11
  164.08864 8.0 8
  164.10794 31.0 31
  165.1013 5.0 5
  165.11234 7.0 7
  166.06152 6.0 6
  166.07056 7.0 7
  166.08456 27.0 27
  167.08485 9.0 9
  169.09225 10.0 10
  171.07066 6.0 6
  172.08144 33.0 33
  173.04898 10.0 10
  173.06004 7.0 7
  173.08321 757.0 756
  174.08029 68.0 68
  174.09161 291.0 291
  175.09744 40.0 40
  175.11737 5.0 5
  176.09644 7.0 7
  176.10539 5.0 5
  177.08815 5.0 5
  181.08057 7.0 7
  181.08667 18.0 18
  182.05975 13.0 13
  183.06496 7.0 7
  184.06357 6.0 6
  185.08719 8.0 8
  186.0663 7.0 7
  186.07742 24.0 24
  186.09129 112.0 112
  187.09673 17.0 17
  188.06705 57.0 57
  188.07497 35.0 35
  188.08362 27.0 27
  188.10663 131.0 131
  189.07222 6.0 6
  189.10347 20.0 20
  189.11894 14.0 14
  192.07126 12.0 12
  192.0782 13.0 13
  192.99138 5.0 5
  193.07826 10.0 10
  193.08797 38.0 38
  194.08951 5.0 5
  194.10318 9.0 9
  195.09546 7.0 7
  196.07599 13.0 13
  197.0778 57.0 57
  197.0898 7.0 7
  197.23608 5.0 5
  198.0802 13.0 13
  198.09332 82.0 82
  199.08926 89.0 89
  200.06195 10.0 10
  200.07031 13.0 13
  200.09134 18.0 18
  200.10669 41.0 41
  201.06943 9.0 9
  202.07054 7.0 7
  202.08662 103.0 103
  202.34018 6.0 6
  203.08464 11.0 11
  204.09126 12.0 12
  207.10623 5.0 5
  208.06775 11.0 11
  209.06735 11.0 11
  209.08449 61.0 61
  210.04407 6.0 6
  210.0874 73.0 73
  210.09958 21.0 21
  211.06212 10.0 10
  211.07558 9.0 9
  211.08488 8.0 8
  211.09703 8.0 8
  212.04588 8.0 8
  212.05745 8.0 8
  212.08076 14.0 14
  212.10542 69.0 69
  212.11653 23.0 23
  212.12701 5.0 5
  213.06496 11.0 11
  213.08514 19.0 19
  213.10461 27.0 27
  213.22885 5.0 5
  214.06845 11.0 11
  215.08011 50.0 50
  215.1118 6.0 6
  215.12941 6.0 6
  216.02521 8.0 8
  216.08185 8.0 8
  216.10422 25.0 25
  216.11102 8.0 8
  216.24205 8.0 8
  216.26465 6.0 6
  218.09135 19.0 19
  219.10498 7.0 7
  220.10754 7.0 7
  222.08226 8.0 8
  222.10608 8.0 8
  223.08876 8.0 8
  223.10753 25.0 25
  223.16205 6.0 6
  224.06093 6.0 6
  224.10701 231.0 231
  224.12944 6.0 6
  225.1115 17.0 17
  225.12212 8.0 8
  226.09056 6.0 6
  226.1261 7.0 7
  227.07997 22.0 22
  227.09132 19.0 19
  227.10539 5.0 5
  227.12157 8.0 8
  227.64064 6.0 6
  228.0798 21.0 21
  228.09781 22.0 22
  228.12236 8.0 8
  229.10017 6.0 6
  230.10242 10.0 10
  230.11298 6.0 6
  232.09663 7.0 7
  232.10971 6.0 6
  233.07845 10.0 10
  233.12349 12.0 12
  234.08762 33.0 33
  234.09836 8.0 8
  235.07991 6.0 6
  235.09497 23.0 23
  235.10902 5.0 5
  235.14217 6.0 6
  236.07726 5.0 5
  236.08694 7.0 7
  236.10078 22.0 22
  236.11824 10.0 10
  237.09233 5.0 5
  237.10515 20.0 20
  237.11696 25.0 25
  238.07208 5.0 5
  238.09062 12.0 12
  238.11462 24.0 24
  238.12714 34.0 34
  239.07343 5.0 5
  239.11115 17.0 17
  239.1257 16.0 16
  240.11356 19.0 19
  241.0891 5.0 5
  241.10684 9.0 9
  243.09734 9.0 9
  245.10988 7.0 7
  245.11978 7.0 7
  246.10025 10.0 10
  247.08099 8.0 8
  247.09587 11.0 11
  247.10454 17.0 17
  247.1198 15.0 15
  248.10635 47.0 47
  249.09851 49.0 49
  249.11284 69.0 69
  250.10698 43.0 43
  250.12999 38.0 38
  251.09129 10.0 10
  251.11693 21.0 21
  251.13379 40.0 40
  252.09442 31.0 31
  252.10519 22.0 22
  252.13039 27.0 27
  252.14444 7.0 7
  253.09029 6.0 6
  253.10367 20.0 20
  253.12914 10.0 10
  253.13721 9.0 9
  254.1169 34.0 34
  254.14665 7.0 7
  255.11618 27.0 27
  255.1272 6.0 6
  255.15157 6.0 6
  256.12488 8.0 8
  256.13248 19.0 19
  258.10831 6.0 6
  259.09738 16.0 16
  260.01926 7.0 7
  260.10596 25.0 25
  260.11969 12.0 12
  261.10199 23.0 23
  261.12198 12.0 12
  261.13242 6.0 6
  261.42288 6.0 6
  262.11438 40.0 40
  262.14496 7.0 7
  263.09018 19.0 19
  263.11234 43.0 43
  263.12332 98.0 98
  263.14413 10.0 10
  264.09308 10.0 10
  264.10623 16.0 16
  264.13446 53.0 53
  265.09528 32.0 32
  265.10483 21.0 21
  265.11557 11.0 11
  265.13583 35.0 35
  265.84531 6.0 6
  266.11441 24.0 24
  266.13742 40.0 40
  267.10403 5.0 5
  267.13675 8.0 8
  268.12506 33.0 33
  268.13196 13.0 13
  269.13525 5.0 5
  270.09561 6.0 6
  270.13913 8.0 8
  273.11081 7.0 7
  274.13614 14.0 14
  275.11414 35.0 35
  275.13739 13.0 13
  276.10107 11.0 11
  276.11557 8.0 8
  276.12598 18.0 18
  276.13632 17.0 17
  277.06754 5.0 5
  277.13306 220.0 220
  277.15219 31.0 31
  278.1167 35.0 35
  278.14316 98.0 98
  278.31494 7.0 7
  279.11636 94.0 94
  279.14371 47.0 47
  280.09799 6.0 6
  280.11957 48.0 48
  280.13309 59.0 59
  280.15979 8.0 8
  281.11008 12.0 12
  281.13181 10.0 10
  282.13953 9.0 9
  282.15701 9.0 9
  283.15158 9.0 9
  284.10318 12.0 12
  284.16367 5.0 5
  288.11557 6.0 6
  289.12076 8.0 8
  290.12213 8.0 8
  291.13126 5.0 5
  291.15005 23.0 23
  292.09872 7.0 7
  292.1377 16.0 16
  292.15479 20.0 20
  293.12842 199.0 199
  293.16565 7.0 7
  293.1813 6.0 6
  294.09003 12.0 12
  294.12018 52.0 52
  294.13614 252.0 252
  294.16711 6.0 6
  295.13889 67.0 67
  295.43222 7.0 7
  300.31451 6.0 6
  304.13315 11.0 11
  304.68915 6.0 6
  305.11188 7.0 7
  305.12631 13.0 13
  306.14188 8.0 8
  307.10425 5.0 5
  307.14203 22.0 22
  307.17917 19.0 19
  308.10941 5.0 5
  308.13345 7.0 7
  308.14731 19.0 19
  309.11639 17.0 17
  309.16098 1000.0 999
  310.16367 297.0 297
  311.14328 7.0 7
  311.16791 51.0 51
  321.15436 37.0 37
  321.16467 43.0 43
  321.17773 9.0 9
  322.13965 8.0 8
  322.15726 17.0 17
  333.68106 6.0 6
  339.1167 7.0 7
  339.17557 72.0 72
//