ACCESSION: MSBNK-RIKEN-PR306019
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$SPLASH: splash10-0a70-0791200000-bae41cb5587d93b56003
PK$NUM_PEAK: 141
PK$PEAK: m/z int. rel.int.
  75.95211 19.0 19
  109.02543 68.0 68
  109.03218 56.0 56
  110.03278 25.0 25
  121.02158 23.0 23
  121.02882 52.0 52
  122.03607 18.0 18
  122.04243 30.0 30
  123.04289 50.0 50
  125.02293 1000.0 999
  126.02223 40.0 40
  126.0282 43.0 43
  133.02544 22.0 22
  137.02008 174.0 174
  137.02713 125.0 125
  138.02347 33.0 33
  147.10019 33.0 33
  151.03519 52.0 52
  151.04309 45.0 45
  161.02135 441.0 441
  161.05522 25.0 25
  162.02544 18.0 18
  162.03545 49.0 49
  163.00287 21.0 21
  163.03723 53.0 53
  163.04681 31.0 31
  164.00362 57.0 57
  164.01178 43.0 43
  165.02399 36.0 36
  175.03841 93.0 93
  176.04703 27.0 27
  177.0098 21.0 21
  177.01923 113.0 113
  178.02042 20.0 20
  179.04158 41.0 41
  180.04297 19.0 19
  187.03549 23.0 23
  188.04126 60.0 60
  189.04688 21.0 21
  191.02968 18.0 18
  199.04115 23.0 23
  203.04604 22.0 22
  203.06929 46.0 46
  204.06863 19.0 19
  204.07903 61.0 61
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  205.04587 246.0 246
  205.0589 33.0 33
  206.04282 29.0 29
  206.05171 22.0 22
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  211.8183 18.0 18
  212.09998 29.0 29
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  289.0723 540.0 539
  290.06879 61.0 61
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  313.10947 19.0 19
  315.08508 18.0 18
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  328.09995 25.0 25
  339.08655 133.0 133
  339.09845 36.0 36
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  346.26065 20.0 20
  363.10382 21.0 21
  364.11017 30.0 30
  381.08261 18.0 18
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  407.07709 660.0 659
  407.11459 49.0 49
  408.0784 263.0 263
  409.07404 19.0 19
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  431.13205 24.0 24
  449.09543 27.0 27
  458.75278 24.0 24
//