ACCESSION: MSBNK-RIKEN-PR306066
RECORD_TITLE: Procyanidin B1; 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$NAME: Procyanidin B1
CH$NAME: cis,trans''-4,8''-Bi-(3,3',4',5,7-pentahydroxyflavane)
CH$NAME: (-)-Epicatechin-(4-beta-8)-(+)-catechin
CH$COMPOUND_CLASS: Biflavonoids and polyflavonoids
CH$FORMULA: C₃₀H₂₆O₁₂
CH$EXACT_MASS: 578.14243
CH$SMILES: C1[C@@H]([C@H](OC2=C1C(=CC(=C2[C@@H]3[C@H]([C@H](OC4=CC(=CC(=C34)O)O)C5=CC(=C(C=C5)O)O)O)O)O)C6=CC(=C(C=C6)O)O)O
CH$IUPAC: InChI=1S/C30H26O12/c31-13-7-20(37)24-23(8-13)41-29(12-2-4-16(33)19(36)6-12)27(40)26(24)25-21(38)10-17(34)14-9-22(39)28(42-30(14)25)11-1-3-15(32)18(35)5-11/h1-8,10,22,26-29,31-40H,9H2/t22-,26+,27+,28+,29+/m0/s1
CH$LINK: CAS 20315-25-7
CH$LINK: CHEMSPIDER 9425166
CH$LINK: INCHIKEY XFZJEEAOWLFHDH-UKWJTHFESA-N
CH$LINK: KNAPSACK C00009075
CH$LINK: PUBCHEM CID:11250133

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 2.8429
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 577.13514984783

PK$SPLASH: splash10-0570-0891200000-34e666d6d5de48af67b8
PK$NUM_PEAK: 115
PK$PEAK: m/z int. rel.int.
  109.02724 50.0 50
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  123.04828 34.0 34
  125.02402 1000.0 999
  126.03351 53.0 53
  127.02477 23.0 23
  133.03065 36.0 36
  133.68933 42.0 42
  137.01613 65.0 65
  137.02144 174.0 174
  138.01779 38.0 38
  149.02371 70.0 70
  151.0349 61.0 61
  151.04181 76.0 76
  154.69031 23.0 23
  161.02245 317.0 317
  161.03578 53.0 53
  161.06451 56.0 56
  162.02853 67.0 67
  163.02727 27.0 27
  163.04628 31.0 31
  165.01257 24.0 24
  165.01828 40.0 40
  167.03107 22.0 22
  175.04044 47.0 47
  177.01694 23.0 23
  177.0576 28.0 28
  178.02744 53.0 53
  179.03287 89.0 89
  180.03896 57.0 57
  187.03976 117.0 117
  188.04318 107.0 107
  191.02969 25.0 25
  194.05836 22.0 22
  201.06017 24.0 24
  203.03113 28.0 28
  203.06764 192.0 192
  204.06975 56.0 56
  205.05023 203.0 203
  206.05133 68.0 68
  212.92644 31.0 31
  214.05777 22.0 22
  215.04045 33.0 33
  217.00534 44.0 44
  217.08534 68.0 68
  221.07607 27.0 27
  222.07681 39.0 39
  229.0081 30.0 30
  229.04387 23.0 23
  229.0515 69.0 69
  229.09601 22.0 22
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  241.0527 23.0 23
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  245.04317 56.0 56
  245.08241 255.0 255
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  247.06233 55.0 55
  256.03455 83.0 83
  256.0498 32.0 32
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  257.04263 49.0 49
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  273.04935 34.0 34
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  283.03802 25.0 25
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  287.04996 23.0 23
  289.06976 665.0 664
  290.07251 43.0 43
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  313.0257 27.0 27
  337.10733 22.0 22
  339.05911 36.0 36
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  340.08307 33.0 33
  341.06097 38.0 38
  341.0802 24.0 24
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  381.09375 23.0 23
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  407.0802 552.0 551
  407.10394 49.0 49
  408.0816 217.0 217
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  409.07266 33.0 33
  409.09293 66.0 66
  422.11496 24.0 24
  423.11606 23.0 23
  425.0816 23.0 23
//