ACCESSION: MSBNK-RIKEN-PR306054
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$SPLASH: splash10-004r-0590520000-de9907aa8773101516ce
PK$NUM_PEAK: 119
PK$PEAK: m/z int. rel.int.
  98.02945 20.0 20
  109.02999 24.0 24
  121.02608 20.0 20
  124.70187 25.0 25
  125.02153 592.0 591
  129.26637 20.0 20
  133.03482 25.0 25
  137.02217 60.0 60
  139.03856 21.0 21
  139.07892 25.0 25
  143.04265 18.0 18
  145.03075 20.0 20
  146.03384 26.0 26
  149.02202 33.0 33
  150.02638 20.0 20
  152.03499 20.0 20
  161.02097 109.0 109
  161.0291 105.0 105
  162.02635 20.0 20
  162.0331 31.0 31
  162.06987 50.0 50
  163.03844 41.0 41
  164.00471 28.0 28
  165.02628 21.0 21
  166.01903 22.0 22
  166.02676 34.0 34
  168.03894 24.0 24
  173.05927 34.0 34
  174.02586 21.0 21
  175.03592 129.0 129
  176.05005 21.0 21
  177.01981 39.0 39
  178.21735 22.0 22
  179.0341 71.0 71
  180.03397 44.0 44
  187.03845 38.0 38
  189.01617 21.0 21
  202.01839 25.0 25
  202.06749 30.0 30
  203.06239 26.0 26
  203.07259 63.0 63
  203.87303 39.0 39
  205.00656 24.0 24
  205.01939 25.0 25
  205.05421 18.0 18
  206.04619 20.0 20
  211.07785 19.0 19
  212.05005 20.0 20
  219.04918 23.0 23
  227.06442 26.0 26
  229.03969 22.0 22
  230.04671 25.0 25
  230.06033 57.0 57
  240.07983 24.0 24
  243.02617 47.0 47
  245.03432 33.0 33
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  245.08147 245.0 245
  246.08041 46.0 46
  246.0898 25.0 25
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  281.04889 56.0 56
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  287.06454 20.0 20
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  289.04855 54.0 54
  289.07083 1000.0 999
  290.05994 26.0 26
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  299.0578 114.0 114
  325.073 18.0 18
  339.08221 93.0 93
  339.09567 55.0 55
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  407.07715 644.0 643
  407.38708 21.0 21
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  408.07394 147.0 147
  411.10519 20.0 20
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  418.06476 27.0 27
  425.08499 377.0 377
  425.10172 134.0 134
  427.08676 18.0 18
  433.08789 34.0 34
  434.08734 21.0 21
  450.91638 27.0 27
  451.09418 100.0 100
  451.1113 78.0 78
  452.08496 47.0 47
  452.10495 24.0 24
  453.10791 21.0 21
  454.08722 18.0 18
  473.12244 19.0 19
  559.11218 20.0 20
  559.1413 20.0 20
  576.10028 18.0 18
  577.13409 758.0 757
//