Lipid Blast In silico created MSMS libraries for

Lipid. Blast - In silico created MS/MS libraries for lipid profiling Supplement of covered structures The structure drawing files (*. mrv) Marvin. Sketch can be found under: http: //fiehnlab. ucdavis. edu/projects/Lipid. Blast Tobias Kind, Oliver Fiehn. Lab – Metabolomics UC Davis Genome Center, Davis, USA Created: FEB 2014; Kind/Fiehn. Lab

Covered structures and MS/MS spectra in Lipid. Blast Number 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 Total Lipid. Class Phosphatidylcholines Lysophosphatidylcholines Plasmenylphosphatidylcholines Phosphatidylethanolamines Lysophosphatidylethanolamines Plasmenylphosphatidylethanolamines Phosphatidylserines Sphingomyelines Phosphatidic acids Lyso phosphatidic acids Phosphatidylinositols Phosphatidylglycerols Cardiolipins Ceramide-1 -phosphates N-acylsphingosines (ceramides) Sulfatides Gangliosides Cholesteryl esters Monoacylglycerols Diacylglycerols Triacylglycerols Monogalactosyldiacylglycerols Digalactosyldiacylglycerols Sulfoquinovosyldiacylglycerols Diacylated phosphatidylinositol monomannoside Diacylated phosphatidylinositol dimannoside Triacylated phosphatidylinositol dimannoside Tetraacylated phosphatidylinositol dimannoside Diphosphorylated hexaacyl Lipid A All libraries Short Number compounds PC 5476 lyso. PC 80 plasmenyl-PC 222 PE 5476 lyso. PE 80 plasmenyl-PE 222 PS 5123 SM 168 PA 5476 lyso. PA 80 PI 5476 PG 5476 CL 25426 Cer. P 168 Cer-d 28 ST 168 [glycan]-Cer 880 CE 33 MG 74 DG 1764 TG 2640 MGDG 5476 DGDG 5476 SQDG 5476 Ac 2 PIM 1 144 Ac 2 PIM 2 144 Ac 3 PIM 2 1728 Ac 4 PIM 2 20736 Lipid. A-PP 15625 119341 Number MS/MS spectra Number with different adducts MS/MS LIBS 10952 2 160 2 444 2 16428 3 240 3 666 3 15369 3 336 2 16428 3 80 1 5476 1 50852 2 336 2 56 2 168 1 880 1 33 1 148 2 3528 2 7920 3 21904 4 10952 2 5476 1 144 1 1728 1 20736 1 15625 1 212685 54

Abbreviation Systematic Name Formula Mass TG(16: 0/18: 1(11 E)/20: 0) 1 -hexadecanoyl-2 -(11 E-octadecenoyl)-3 -eicosanoyl-sn-glycerol C 57 H 108 O 6 888. 81 Abbreviation Systematic Name Formula Mass DG(16: 0/18: 1(11 E)/0: 0) 1 -hexadecanoyl-2 -(11 E-octadecenoyl)-sn-glycerol C 37 H 70 O 5 594. 52 Abbreviation Systematic Name Formula Mass MG(16: 0/0: 0) 1 -hexadecanoyl-sn-glycerol C 19 H 38 O 4 330. 28 Abbreviation Systematic Name Formula Mass PA(16: 0/18: 1(11 E)) 1 -hexadecanoyl-2 -(11 E-octadecenoyl)-sn-glycero-3 -phosphate C 37 H 71 O 8 P 674. 49 Abbreviation Systematic Name Formula Mass PC(16: 0/18: 1(11 E)) 1 -hexadecanoyl-2 -(11 E-octadecenoyl)-sn-glycero-3 -phosphocholine C 42 H 82 NO 8 P 759. 58 Abbreviation PE(16: 0/18: 1(11 E)) Systematic Name 1 -hexadecanoyl-2 -(11 E-octadecenoyl)-sn-glycero-3 phosphoethanolamine Formula C 39 H 76 NO 8 P Mass 717. 53 Abbreviation Systematic Name glycerol) Formula Mass PG(16: 0/18: 1(11 E)) 1 -hexadecanoyl-2 -(11 E-octadecenoyl)-sn-glycero-3 -phospho-(1'-sn. C 40 H 77 O 10 P 748. 53 Abbreviation Systematic Name inositol) Formula Mass PI(16: 0/18: 1(11 E)) 1 -hexadecanoyl-2 -(11 E-octadecenoyl)-sn-glycero-3 -phospho-(1'-myo. C 43 H 81 O 13 P 836. 54

Abbreviation Systematic Name Formula Mass PS(16: 0/18: 1(11 E)) 1 -hexadecanoyl-2 -(11 E-octadecenoyl)-sn-glycero-3 -phoserine C 40 H 76 NO 10 P 761. 52 Abbreviation CL(1'-[14: 0/16: 0], 3'-[14: 0/18: 1(11 E)]) Systematic Name 1'-[1 -tetradecanoyl-2 -hexadecanoyl-sn-glycero-3 -phospho], 3'-[1 tetradecanoyl-2 -(11 E-octadecenoyl)-sn-glycero-3 -phospho]-sn-glycerol Formula C 71 H 136 O 17 P 2 Mass 1322. 93 Common Name Systematic Name Exact Mass Formula PC(16: 0/0: 0)[U] (lyso. PC) 1 -hexadecanoyl-sn-glycero-3 -phosphocholine 495. 33 C 24 H 50 NO 7 P LM ID Common Name Exact Mass Formula LMGP 01030007 (plasmenyl-PC) PC(P-16: 0/18: 1(9 Z))[U] 743. 58 C 42 H 82 NO 7 P LM ID Common Name Exact Mass Formula LMGP 02050003 (lyso. PE) PE(14: 0/0: 0) 425. 25 C 19 H 40 NO 7 P LM ID Common Name Exact Mass Formula LMGP 02030004 (plasmenyl-PE) PE(P-18: 0/18: 1(9 Z)) 729. 57 C 41 H 80 NO 7 P

LM ID Common Name Systematic Name Synonyms Exact Mass Formula LMSP 03010003 SM(d 18: 1/16: 0) N-(hexadecanoyl)-sphing-4 -enine-1 -phosphocholine C 16 Sphingomyelin 702. 57 C 39 H 79 N 2 O 6 P LM ID Common Name Systematic Name Synonyms Exact Mass Formula LMSP 02050002 (Ceramide-phosphate) Cer. P(d 18: 1/16: 0) N-(hexadecanoyl)-sphing-4 -enine-1 -phosphate C 16 Cer. P 617. 48 C 34 H 68 NO 6 P LM ID Common Name Systematic Name Synonyms Exact Mass Formula LMSP 06020002 C 16 Sulfatide (3'-sulfo)Galß-Cer(d 18: 1/16: 0) C 16 Sulfatide 779. 52 C 40 H 77 NO 11 S LM ID Common Name Systematic Name Synonyms Exact Mass Formula LMSP 0601 AJ 01 (GM 3 ganglioside) Neu. Aca 2 -3 Galß 1 -4 Glcß-Cer(d 18: 1/16: 0) 1152. 71 C 57 H 104 N 2 O 21

LM ID Common Name Systematic Name sn-glycerol Synonyms Exact Mass Formula LMGL 05010024 MGDG(18: 2(9 Z, 12 Z)/18: 3(9 Z, 12 Z, 15 Z)) 1 -(9 Z, 12 Z-octadecadienoyl)-2 -(9 Z, 12 Z, 15 Z-octadecatrienoyl)-3 -O-ß-D-galactosyl. Monogalactosyldiacylglycerol(18: 2(9 Z, 12 Z)/18: 3(9 Z, 12 Z, 15 Z)) 776. 54 C 45 H 76 O 10 LM ID LMGL 05010010 Common Name DGDG(18: 5(3 Z, 6 Z, 9 Z, 12 Z, 15 Z)/18: 4(6 Z, 9 Z, 12 Z, 15 Z)) Systematic Name 1 -(3 Z, 6 Z, 9 Z, 12 Z, 15 Z-octadecapentaenoyl)-2 -(6 Z, 9 Z, 12 Z, 15 Z-octadecatetraenoyl)-3 -O-(6'-O-a-D-galactosyl-ß-D-galactosyl)-sn-glycerol Synonyms Digalactosyldiacylglycerol(18: 5(3 Z, 6 Z, 9 Z, 12 Z, 15 Z)/18: 4(6 Z, 9 Z, 12 Z, 15 Z)) Exact Mass 930. 53 Formula C 51 H 78 O 15 LM ID Common Name Systematic Name Synonyms Exact Mass Formula LMGL 05010007 SQDG(16: 0/16: 1(11 Z)) 1 -hexadecanoyl-2 -(11 Z-hexadecenoyl)-3 -(6'-sulfo-a-D-quinovosyl)-sn-glycerol sulfoquinovosyldiacylglycerols; SQDG(16: 0/16: 1) 791. 50 C 41 H 75 O 12 S Diacylated phosphatidylinositol monomannoside Ac 2 PIM 1(16: 0/methyl-18: 0) C 50 H 95 O 18 P 1014. 625603 Ac 2 PIM 1 Diacylated phosphatidylinositol dimannoside Ac 2 PIM 2(16: 0/methyl-18: 0) C 56 H 105 O 23 P Mass: 1176. 678426 Ac 2 PIM 2

Triacylated phosphatidylinositol dimannoside Ac 3 PIM 2(16: 0/methyl-18: 0/16: 0) C 72 H 135 O 24 P 1414. 908092 Tetraacylated phosphatidylinositol dimannoside C 88 H 165 O 25 P 1653. 137757 Ac 4 PIM 2(16: 0/16: 0/methyl-18: 0) Diphosphorylated hexaacyl Lipid A 1825. 250692 C 96 H 182 N 2 O 25 P 2 Lipid. A-PP [14/14/3 O-(14)/3 O-(14)]