ACCESSION: MSBNK-RIKEN-PR308824
RECORD_TITLE: Procyanidin B2; 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: Annotation level-1

CH$NAME: Procyanidin B2
CH$NAME: 4,8'-Bi((+)-epicatechin))
CH$NAME: cis,cis'-4,8'-Bi(3,3',4',5,7-pentahydroxyflavane)
CH$NAME: (-)-Epicatechin-(4-beta-8)-(-)-epicatechin
CH$COMPOUND_CLASS: Biflavonoids
CH$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$IUPAC: InChI=1S/C30H26O12/c31-13-7-20(37)24-23(8-13)41-29(12-2-4-16(33)19(36)6-12)27(40)26(24)25-21(38)10-17(34)14-9-22(39)28(42-30(14)25)11-1-3-15(32)18(35)5-11/h1-8,10,22,26-29,31-40H,9H2/t22-,26-,27-,28-,29-/m1/s1
CH$LINK: CAS 29106-49-8
CH$LINK: CHEMSPIDER 109417
CH$LINK: INCHIKEY XFZJEEAOWLFHDH-NFJBMHMQSA-N
CH$LINK: KNAPSACK C00009077
CH$LINK: PUBCHEM CID:122738

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$CHROMATOGRAPHY: CAPILLARY_VOLTAGE +3.00 kV
AC$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 3.23
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 577.13515

PK$SPLASH: splash10-004r-0490400000-4ca1130831074db1df72
PK$NUM_PEAK: 73
PK$PEAK: m/z int. rel.int.
  109.02116 19.0 35
  122.0342 31.0 58
  123.0408 26.0 48
  125.02094 136.0 253
  125.02618 256.0 475
  126.02538 30.0 56
  146.0397 23.0 43
  161.02388 148.0 275
  162.03505 19.0 35
  165.01132 29.0 54
  173.05789 22.0 41
  175.04111 25.0 46
  179.02451 29.0 54
  179.03209 93.0 173
  187.04369 30.0 56
  200.05444 21.0 39
  201.04811 20.0 37
  203.06931 69.0 128
  205.0162 40.0 74
  212.04474 25.0 46
  215.02161 18.0 33
  221.08661 26.0 48
  229.04463 22.0 41
  229.05519 25.0 46
  230.04976 30.0 56
  243.03351 18.0 33
  244.04114 19.0 35
  245.04831 95.0 176
  245.07025 57.0 106
  245.08234 46.0 85
  246.08052 27.0 50
  247.05496 24.0 45
  256.03091 33.0 61
  256.49298 21.0 39
  257.03497 25.0 46
  257.04691 47.0 87
  259.07758 20.0 37
  263.09241 19.0 35
  269.03607 20.0 37
  273.03879 41.0 76
  281.04492 41.0 76
  281.05893 20.0 37
  284.02188 20.0 37
  287.0531 145.0 269
  288.06299 38.0 71
  289.07327 538.0 999
  290.07428 26.0 48
  296.03497 21.0 39
  297.03879 24.0 45
  297.07581 24.0 45
  299.05106 66.0 123
  310.11411 20.0 37
  324.0636 21.0 39
  327.09195 25.0 46
  339.06631 20.0 37
  389.06247 22.0 41
  389.07394 23.0 43
  407.07156 208.0 386
  407.0874 164.0 305
  408.07892 39.0 72
  408.10727 20.0 37
  409.06158 20.0 37
  409.09937 25.0 46
  425.06647 18.0 33
  425.09613 137.0 254
  426.09177 123.0 228
  426.10318 44.0 82
  451.09415 54.0 100
  451.12332 23.0 43
  452.10522 51.0 95
  559.14172 20.0 37
  577.10486 20.0 37
  577.13751 131.0 243
//