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. 2020 Oct 16;9:e61886. doi: 10.7554/eLife.61886

Appendix 1—table 1. MS2 data of glo-1-dependent features presented in this manuscript.

Representative MS/MS spectra of modular glucosides.
Formula RT [min.] Compound number SMID m/z (M+H) m/z (M-H) ms/ms fragments, positive ionization mode ms/ms fragments, negative ionization mode Substituents on glucose Stable isotope labeling
C26H26N3O12P 9.30 angl#10 604.13381 602.11813 105.03366 (C7 H5 O+) 120.04469 (C7 H6 O N+) 96.96870 (H2 O4 P-) 121.02911 (C7 H5 O2-) 136.03983 (C7 H6 O2 N-) anthranilic acid, nicotinic acid
C20H22N2O7 8.67 SI-5 angl#3 403.14998 401.13542 120.04459 (C7 H6 O N+) 138.05496 (C7 H8 O2 N+) anthranilic acid, anthranilic acid
C20H23N2O11P 9.26 25 angl#4 499.11235 497.09667 120.04463 (C7H6ON+) 96.96868 (H2 O4 P-) 78.95800 (O3 P-) 136.03999 (C7 H6 O2 N-) 223.00078 (C6 H8 O7 P-) anthranilic acid, anthranilic acid
C19H21N2O9P 9.59 22 iglu#10 453.10574 451.09119 94.02916 (C5 H4 O N+) 118.06535 (C8 H8 N+) C14 H12 O2 N (C14 H12 O2 N+) 78.95802 (O3 P-) 96.96867 (H2 O4 P-) 110.02444 (C5 H4 O2 N-) 116.05042 (C8 H6 N-) indole, nicotinic acid
C21H22NO9P 10.79 23 iglu#12 464.11049 462.09594 105.03382 (C7 H5 O+) 118.06538 (C8 H8 N+) 226.08620 (C14 H12 O2 N+) 348.12271 (C21 H18 O4 N+) 78.95801 (O3 P-) 96.96865 (H2 O4 P-) indole, benzoic acid
C14H18NO8P 6.05 16 iglu#2 360.08541 358.06973 98.98453 (H4 O4 P+) 118.06536 (C8 H8 N+) 244.09660 (C14 H14 O3 N+) 78.95802 (O3 P-) 96.96869 (H2 O4 P-) indole
C21H22N2O6 10.69 34 iglu#3 399.15506 397.13938 116.05032 (C8 H6 N-) 136.04002 (C7 H6 O2 N-) 215.09431 (C13 H13 O2 N-) indole, anthranilic acid
C21H23N2O9P 10.29 19 iglu#4 479.12252 477.10684 118.06536 (C8 H8 N+) 120.04456 (C7 H6 O N+) 138.05490 (C7 H8 O2 N+) 226.08612 (C14 H12 O2 N+) 78.95801 (O3 P-) 96.96867 (H2 O4 P-) 116.05042 (C8 H6 N-) 136.03970 (C7 H6 O2 N-) 358.06805 (C14 H17 O8 N P-) indole, anthranilic acid
C27H26N3O10P 10.49 41 iglu#41 584.14398 582.1283 96.04494 (C5 H6 O N+) 120.04456 (C7 H6 O N+) 124.03937 (C6 H6 O2 N+) 166.04985 (C8 H8 O3 N+) 228.06477 (C13 H10 O3 N+) 330.03705 (C12 H13 O8 N P+) 78.95801 (O3 P-) 96.96867 (H2 O4 P-) 122.02431 (C6 H4 O2 N-) 136.04013 (C7 H6 O2 N-) indole, anthranilic acid, nicotinic acid
C26H29N2O10P 10.48 20 iglu#42 561.16439 559.14871 83.04974 (C5 H7 O+) 118.06553 (C8 H8 N+) 120.04465 (C7 H6 O N+) 202.08635 (C12 H12 O2 N+) 78.95805 (O3 P-) 96.96868 (H2 O4 P-)136.03995 (C7 H6 O2 N-) indole, antranilic acid, tiglic acid
C20H20N2O6 8.93 SI-2 iglu#5 385.13941 383.12373 106.02911 (C6 H4 O N+) 118.06535 (C8 H8 N+) 124.03936 (C6 H6 O2 N+) 268.08124 (C12 H14 O6 N+) indole, nicotinic acid
C20H21N2O9P 8.29 20 iglu#6 465.10687 463.09119 106.02907 (C6 H4 O N+) 118.06532 (C8 H8 N+) 124.03942 (C6 H6 O2 N+) 226.08630 (C14 H12 O2 N+) 250.07079 (C12 H12 O5 N+) 78.95802 (O3 P-) 96.96868 (H2 O4 P-) 122.02421 (C6 H4 O2 N-) 340.05878 (C14 H15 O7 N P-) indole, nicotinic acid
C19H23NO6 11.24 SI-3 iglu#7 362.15981 360.14413 83.04967 (C5 H7 O+) 101.06001 (C5 H9 O2+) 118.06536 (C8 H8 N+) 198.09097 (C13 H12 O N+) 226.08626 (C14 H12 O2 N+) indole, tiglic acid
C19H24NO9P 10.48 21 iglu#8 442.12727 440.11159 83.04967 (C5 H7 O+) 101.06020 (C5 H9 O2+) 118.06538 (C8 H8 N+) 226.08621 (C14 H12 O2 N+) 78.95798 (O3 P-) 96.96864 (H2 O4 P-) 116.05011 (C8 H6 N-) indole, tiglic acid
C19H20N2O6 6.33 SI-4 iglu#9 373.13941 371.12486 110.02437 (C5 H4 O2 N-) 116.05027 (C8 H6 N-) indole, nicotinic acid
C21H27N2O11P 4.31 oglu#4 515.14365 513.12797 120.04459 (C7 H6 O N+) 136.07550 (C8 H10 O N+) 138.05511 (C7 H8 O2 N+) 216.06795 (C12 H10 O3 N+) 78.95781 (O3 P-) 96.96854 (H2 O4 P-) 136.03995 (C7 H6 O2 N-) 223.00067 (C6 H8 O7 P-) 376.07953 (C14 H19 O9 N P-) octopamine, anthranilic acid d1 from d2-L-Tyrosine
C18H24N2O7 4.79 sgnl#1 381.16563 379.14995 217.09767 (C12 H13 O2 N2-) n-acetylserotonin
C25H29N3O8 7.34 sgnl#3 500.20274 498.18706 120.04427 (C7H6NO+) 160.07555 (C10H10NO+) n-acetylserotonin, anthranilic acid
C25H30N3O11P 7.89 sgnl#4 580.1702 578.15452 120.04459 (C7 H6 O N+) 138.05498 (C7 H8 O2 N+) 160.07590 (C10 H10 O N+) 219.11266 (C12 H15 O2 N2+) (O3 P-) 96.96865 (H2 O4 P-) 136.04048 (C7 H6 O2 N-) 223.00072 (C6 H8 O7 P-) n-acetylserotonin, anthranilic acid
C29H33N2O11P 8.22 tyglu#12 617.1906 615.17492 120.04458 (C7 H6 O N+) 238.08728 (C15 H12 O2 N+) 78.95803 (O3 P-) 96.96867 (H2 O4 P-) 136.04008 (C7 H6 O2 N-) 135.04503 (C8 H7 O2-) 360.08469 (C14 H19 O8 N P-) 478.12738 (C29 H20 O6 N-) tyramine, anthranilic acid, phenylacetic acid d2 from d2-L-Tyrosine
C26H35N2O11P 7.92 tyglu#14 583.20625 581.19057 109.02870 (C6 H5 O2+) 120.04459 (C7 H6 O N+) 138.05489 (C7 H8 O2 N+) 204.10226 (C12 H14 O2 N+) 257.12808 (C15 H17 O2 N2+) 348.14429 (C18 H22 O6 N+) 78.95802 (O3 P-) 96.96866 (H2 O4 P-) 101.05991 (C5 H9 O2-) 136.04047 (C7 H6 O2 N-) 444.14252 (C19 H27 O9 N P-) tyramine, anthranilic acid, (iso)valeric acid
C28H31N2O11P 7.97 tyglu#16 603.17495 601.15927 105.03380 (C7 H5 O+) 120.04455 (C7 H6 O N+) 138.05487 (C7 H8 O2 N+) 224.07047 (C14 H10 O2 N+) 257.12775 (C15 H17 O2 N2+) 368.11160 (C20 H18 O6 N+) 78.95805 (O3 P-)96.96869 (H2 O4 P-) 121.02914 (C7 H5 O2-) 136.03978 (C7 H6 O2 N-) 464.11099 (C21 H23 O9 N P-) tyramine, anthranilic acid, carboxy-benzyl d2 from d2-L-Tyrosine
C21H27N2O10P 5.40 tyglu#2 499.14874 497.13306 120.04459 (C7 H6 O N+) 138.05487 (C7 H8 O2 N+) 138.09137 (C8 H12 O N+) 257.12814 (C15 H17 O2 N2+) 264.08633 (C13 H14 O5 N+) 78.95802 (O3 P-) 96.96870 (H2 O4 P-) 136.04005 (C7 H6 O2 N-) 223.00053 (C6 H8 O7 P-) 360.08472 (C14 H19 O8 N P-) tyramine,anthranilic acid d2 from d2-L-Tyrosine
C28H32N3O11P 7.65 26 tyglu#4 618.18585 616.17017 120.04459 (C7 H6 O N+) 138.09137 (C8 H12 O N+)  78.95802 (O3 P-) 96.96867 (H2 O4 P-) 136.03989 (C7 H6 O2 N-) 479.12198 (C21 H24 O9 N2 P-) tyramine, anthranilic acid (x2)
C27H30N3O11P 6.55 tyglu#6 604.1702 602.15452 106.02901 (C6 H4 O N+) 120.04460 (C7 H6 O N+) 124.03939 (C6 H6 O2 N+) 138.05513 (C7 H8 O2 N+) 166.04988 (C8 H8 O3 N+) 257.12781 (C15 H17 O2 N2+) 78.95781 (O3 P-) 96.96851 (H2 O4 P-) 223.00017 (C6 H8 O7 P-) 381.09375 (C16 H17 O9 N2-) 534.17279 (C22 H33 O12 N P-) tyramine, anthranilic acid, nicotinic acid d2 from d2-L-Tyrosine
C26H33N2O11P 7.67 tyglu#8 581.1906 579.17492 83.04968 (C5 H7 O+) 120.04460 (C7 H6 O N+) 138.05479 (C7 H8 O2 N+) 257.12848 (C15 H17 O2 N2+) 78.95779 (O3 P-) 96.96852 (H2 O4 P-) 99.04408 (C5 H7 O2-) 136.03972 (C7 H6 O2 N-) 442.12637 (C19 H25 O9 N P-) tyramine, anthranilic acid, tiglic acid d2 from d2-L-Tyrosine