ACCESSION: MSBNK-AAFC-AC000755
RECORD_TITLE: Verruculogen; LC-ESI-ITFT; MS2; CE: 40; R=17500; [M+H]+
DATE: 2017.07.07
AUTHORS: Megan J. Kelman, Justin B. Renaud, Mark W. Sumarah, Agriculture and Agri-Food Canada
LICENSE: CC BY-SA
COPYRIGHT: Copyright (C) 2017
COMMENT: CONFIDENCE Penicillium amphipolaria

CH$NAME: Verruculogen
CH$NAME: TR toxin
CH$NAME: (5R,10S,10aR,14aS,15bS)-10,10a-dihydroxy-6-methoxy-2,2-dimethyl-5-(2-methylprop-1-en-1-yl)-1,10,10a,14,14a,15b-hexahydro-12H-3,4-dioxa-5a,11a,15a-triazacycloocta[1,2,3-lm]indeno[5,6-b]fluorene-11,15(2H,13H)-dione
CH$COMPOUND_CLASS: Natural Product; Fungal metabolite
CH$FORMULA: C₂₇H₃₃N₃O₇
CH$EXACT_MASS: 511.23184
CH$SMILES: CC(=C[C@@H]1N2C3=C(C=CC(=C3)OC)C4=C2[C@H](CC(OO1)(C)C)N5C(=O)[C@@H]6CCCN6C(=O)[C@@]5([C@H]4O)O)C
CH$IUPAC: InChI=1S/C27H33N3O7/c1-14(2)11-20-29-18-12-15(35-5)8-9-16(18)21-22(29)19(13-26(3,4)37-36-20)30-24(32)17-7-6-10-28(17)25(33)27(30,34)23(21)31/h8-9,11-12,17,19-20,23,31,34H,6-7,10,13H2,1-5H3/t17-,19-,20+,23-,27+/m0/s1
CH$LINK: INCHIKEY LRXYHMMJJCTUMY-GWXUGYLUSA-N
CH$LINK: PUBCHEM CID:13887805
CH$LINK: CHEMSPIDER 10405461
CH$LINK: KNAPSACK C00011299
CH$LINK: COMPTOX DTXSID30894030

AC$INSTRUMENT: Q-Exactive Orbitrap Thermo Scientific
AC$INSTRUMENT_TYPE: LC-ESI-ITFT
AC$MASS_SPECTROMETRY: MS_TYPE MS2
AC$MASS_SPECTROMETRY: ION_MODE POSITIVE
AC$MASS_SPECTROMETRY: IONIZATION ESI
AC$MASS_SPECTROMETRY: IONIZATION_VOLTAGE 3.9 kV
AC$MASS_SPECTROMETRY: FRAGMENTATION_MODE HCD
AC$MASS_SPECTROMETRY: COLLISION_ENERGY 40(NCE)
AC$MASS_SPECTROMETRY: RESOLUTION 17500
AC$CHROMATOGRAPHY: COLUMN_NAME Agilent RRHD Eclipse 50 x 2 mm, 1.8 uM
AC$CHROMATOGRAPHY: FLOW_GRADIENT 100:0 at 0 min, 100:0 at 0.5 min, 0:100 at 3.5 min, 0:100 at 5.5 min, 100:0 at 7 min
AC$CHROMATOGRAPHY: FLOW_RATE 0.3 mL min-1
AC$CHROMATOGRAPHY: RETENTION_TIME 3.77
AC$CHROMATOGRAPHY: NAPS_RTI 1288
AC$CHROMATOGRAPHY: SOLVENT A H2O 0.1% FA
AC$CHROMATOGRAPHY: SOLVENT B ACN 0.1% FA

MS$FOCUSED_ION: BASE_PEAK 70.0658
MS$FOCUSED_ION: PRECURSOR_M/Z 512.2386
MS$FOCUSED_ION: PRECURSOR_TYPE [M+H]+
MS$DATA_PROCESSING: DEPROFILE Proteowizard
MS$DATA_PROCESSING: RECALIBRATE based on Fragment ion formula determination
MS$DATA_PROCESSING: INTENSITY CUTOFF 0.05 Base Peak

PK$SPLASH: splash10-006t-2790000000-00c07a02bed9340e8d69
PK$ANNOTATION: m/z tentative_formula mass_error(ppm)
  70.0658 C4H8N1+ 9.53
  98.0605 C5H8N1O1+ 4.67
  125.071 C6H9N2O1+ 0.5
  126.0549 C6H8N1O2+ -0.41
  141.0655 C6H9N2O2+ -2.47
  148.0755 C9H10N1O1+ -1.31
  153.0656 C7H9N2O2+ -1.62
  158.06 C10H8N1O1+ -0.27
  160.0755 C10H10N1O1+ -1.21
  172.0754 C11H10N1O1+ -1.71
  174.0912 C11H12N1O1+ -0.84
  176.0701 C10H10N1O2+ -2.86
  183.0674 C12H9N1O1+ -2.56
  184.0757 C12H10N1O1+ 0.03
  186.0547 C11H8N1O2+ -1.35
  188.0702 C11H10N1O2+ -2.15
  189.1018 C11H13N2O1+ -2.34
  191.0576 C10H9N1O3+ -0.46
  197.0838 C13H11N1O1+ 1.42
  198.0912 C13H12N1O1+ -0.74
  199.0861 C12H11N2O1+ -2.46
  200.0704 C12H10N1O2+ -1.02
  200.1071 C13H14N1O1+ 0.51
  202.0499 C11H8N1O3+ 0.19
  202.0862 C12H12N1O2+ -0.28
  202.1223 C13H16N1O1+ -1.73
  209.0699 C13H9N2O1+ -4.96
  210.0915 C14H12N1O1+ 0.73
  211.0849 C10H13N1O4+ 4.73
  212.1078 C14H14N1O1+ 3.78
  213.0647 C12H9N2O2+ -5.39
  215.0794 C9H13N1O5+ 2.73
  217.0969 C12H13N2O2+ -1.16
  227.0808 C13H11N2O2+ -3.08
  228.1032 C14H14N1O2+ 5.66
  230.1171 C14H16N1O2+ -2.0
  231.076 C12H11N2O3+ -1.77
  239.0802 C14H11N2O2+ -5.44
  240.1016 C15H14N1O2+ -1.28
  241.0599 C13H9N2O3+ -3.56
  243.0767 C13H11N2O3+ 1.19
  245.0917 C13H13N2O3+ -1.48
  252.0893 C15H12N2O2+ -0.1
  253.0953 C12H15N1O5+ 3.3
  255.0761 C14H11N2O3+ -1.22
  259.0709 C13H11N2O4+ -1.62
  267.1124 C16H15N2O2+ -1.51
  279.112 C17H15N2O2+ -2.88
  283.0595 C16H11O5+ -2.08
  295.1346 C22H17N1+ -3.27
  296.1387 C17H18N3O2+ -2.2
  310.1183 C17H16N3O3+ -1.0
  322.1113 C22H14N2O1+ 3.82
  323.1261 C18H17N3O3+ -1.04
  324.1324 C15H20N2O6+ 2.55
  352.1301 C21H20O5+ -1.2
  379.0443 C18H9N3O7+ 2.19
PK$NUM_PEAK: 57
PK$PEAK: m/z int. rel.int.
  70.0651 1171716.0 999
  98.06 44476.671875 36
  125.0709 53326.234375 44
  126.055 60052.85546875 50
  141.0658 78905.1953125 66
  148.0757 93078.25 78
  153.0658 91157.6953125 76
  158.06 48630.27734375 40
  160.0757 136139.5 115
  172.0757 176542.5625 149
  174.0913 172042.359375 145
  176.0706 101882.421875 85
  183.0679 67201.296875 56
  184.0757 114130.546875 96
  186.055 58826.265625 49
  188.0706 119559.40625 101
  189.1022 64291.41015625 53
  191.0577 51916.03125 43
  197.0835 79568.2265625 66
  198.0913 866562.0625 738
  199.0866 800160.875 681
  200.0706 116683.4921875 98
  200.107 67249.671875 56
  202.0499 38596.30078125 31
  202.0863 121556.8828125 102
  202.1226 210597.828125 178
  209.0709 59569.26953125 49
  210.0913 77896.2578125 65
  211.0839 78703.7421875 66
  212.107 52594.3046875 43
  213.0658 232721.609375 197
  215.0788 60591.62890625 50
  217.0972 86518.390625 72
  227.0815 660501.875 562
  228.1019 57607.4296875 48
  230.1176 157955.34375 133
  231.0764 117818.5703125 99
  239.0815 46893.23046875 39
  240.1019 209265.3125 177
  241.0608 87167.703125 73
  243.0764 40001.37890625 33
  245.0921 90052.03125 75
  252.0893 68964.5 57
  253.0945 77041.8125 64
  255.0764 443403.03125 377
  259.0713 175514.8125 148
  267.1128 127967.21875 108
  279.1128 50548.91796875 42
  283.0601 56781.25 47
  295.1356 48020.5234375 39
  296.1394 51955.51953125 43
  310.1186 113640.0234375 95
  322.1101 45972.0234375 38
  323.1264 79527.828125 66
  324.1316 59193.09765625 49
  352.1305 44691.75390625 37
  379.0435 45450.1953125 37
//