Supplementary Information for the Article
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- Πρόκρις Μιχαηλίδης
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1 Supplementary Information for the Article Separation and quantitation of water soluble cellular metabolites by hydrophilic interaction chromatography tandem spectrometry Sunil U. Bajad a, Wenyun Lu a, Elizabeth H. Kimball a, Jie Yuan a, Celeste Peterson b, and Joshua D. Rabinowitz a * a LewisSigler Institute for Integrative Genomics and Department of Chemistry Princeton University, Princeton, NJ 08544, USA b Department of Molecular Biology Princeton University, Princeton, NJ 08544, USA The main manuscript text focuses on the metabolome as a whole and, to a lesser extent, on compounds of specific interest. Here, in the Supplementary Information, we provide comprehensive results for every individual compound studied, in the form of three tables: Table S1: Known isomers of the metabolites investigated here (begins on Page S2) Table S2: MS/MS parameters and LCMS/MS method performance for compound standards (begins on Page S4) Table S3: Performance of different chromatography conditions for distinct cellular metabolites (begins on Page S12) Bajad et al., 2006 Supplementary Materials Page S1 of 17
2 Table S1: Known isomers of the metabolites investigated here *. The table is limited to those isomers that are known components of metabolism, as indicated by their being contained in the Ecocyc database ( Metabolite ion formula Isomers Alanine C 3 H 8 NO 2 90 βalanine, DAlanine, Sarcosine Acetoacetate C 4 H 5 O Oxobutanoate, Succinate semialdehyde Serine C 3 H 8 NO DSerine Fumarate C 4 H 3 O Maleate Succinate C 4 H 5 O Methylmalonate Threonine a C 4 H 8 NO LAllothreonine, Homoserine, DThreonine Valine C 5 H 12 NO Betaine Homoserine a C 4 H 10 NO LThreonine, Allothreonine, LAllothreonine, DThreonine Cysteine C 3 H 8 NO 2 S 122 DCysteine Nicotinate C 6 H 4 NO Picolinate Aspartate C 4 H 6 NO DAspartate (Iso)leucine* C 6 H 14 NO LIsoleucine, LLeucine Malate C 4 H 5 O (R)Malate paminobenzoate/anthranilate* C 7 H 6 NO paminobenzoate, Anthranilate phydroxybenzoate C 7 H 5 O Salicylate Acetylphosphate C 2 H 4 O 5 P 139 Phosphonoacetate Glutamine C 5 H 11 N 2 O Glutamide Glutamate C 5 H 10 NO OAcetylLserine, Dglutamate Carnitine C 7 H 16 NO DCarnitine Phenylpyruvate C 9 H 7 O Coumarate Dihydroxyacetonephosphate C 3 H 6 O 6 P 169 DGlyceraldehyde3phosphate Aconitate* C 6 H 5 O cisaconitate, transaconitate myoinositol C 6 H 11 O Mannose, αdgalactose, 2Deoxygluconate, DAllose, Fructose, βdglucose, βdgalactose 3Phosphoglycerate C 3 H 6 O 7 P 185 2Phosphoglycerate Citrate C 6 H 7 O ,5DiketoDgluconate, 5Keto4deoxyDglucarate, Isocitrate, 2,3DiketoLgulonate 2DehydroDgluconate C 6 H 9 O Ketogluconate, Galacturonate, DTagaturonate, Fructuronate, Glucuronate, 3KetoLgulonate, 2 KetoLgulonate Gluconate C 6 H 11 O DMannonate, LIdonate, DGalactonate, DAltronate DGlucarate C 6 H 9 O DGalactarate Deoxyribosephosphate* C 5 H 10 O 7 P 213 Deoxyribose1phosphate, Deoxyribose5phosphate, 1DeoxyDxylulose 5phosphate Prephenate C 10 H 9 O Chorismate, Isochorismate Bajad et al., 2006 Supplementary Materials Page S2 of 17
3 ion formula Metabolite Isomers DRibulose5phosphate, DRibose5phosphate, DRibulose1phosphate, Ribose1phosphate, DRib(ul)ose5phosphate* C 5 H 10 O 8 P 229 DArabinose5phosphate, Xylulose5phosphate, LRibulose5phosphate, LXylulose5phosphate Deoxyadenosine C 10 H 14 N 5 O 'Deoxyadenosine αdglucose1phosphate, DFructose6phosphate, Mannose6phosphate, Mannose1 phosphate, αdgalactose1phosphate, αdglucose6phosphate, βdglucose6phosphate, β DGlucose 1phosphate, Fructose1phosphate, 1LmyoInositol 1phosphate, 1DmyoInositol 1 DHexosephosphate C 6 H 12 O 9 P 259 phosphate, Tagatose6phosphate, DAllose6phosphate Glucosamine1P b C 6 H 15 NO 8 P 260 Glucosamine6P Glucosamine6P b C 6 H 15 NO 8 P 260 Glucosamine1P Adenosine c C 10 H 14 N 5 O Deoxyguanosine Deoxyguanosine c C 10 H 14 N 5 O Adenosine NAcetylglucosamine1 phosphate C 8 H 15 NO 9 P 300 NAcetylDglucosamine6phosphate, NAcetylDmannosamine6phosphate Fructose1,6bisphosphate C 6 H 13 O 12 P Glucose1,6bisphosphate, Tagatose1,6bisphosphate Trehalose C 12 H 21 O Sucrose, Lactose, Maltose, Cellobiose, Melibiose AMP d C 10 H 15 N 5 O 7 P 348 dgmp dgmp d C 10 H 15 N 5 O 7 P 348 AMP ADP e C 10 H 14 N 5 O 10 P ',5'ADP, dgdp dgdp e C 10 H 14 N 5 O 10 P ADP, 3',5'ADP ATP f C 10 H 15 N 5 O 13 P dgtp dgtp f C 10 H 15 N 5 O 13 P ATP UDPDglucose C 15 H 23 N 2 O 17 P UDPgalactose, UDPDgalacto1,4furanose ADPDglucose C 16 H 24 N 5 O 15 P Guanosine diphosphate fucose UDPNacetylDglucosamine C 17 H 26 N 3 O 17 P UDPNacetylDmannosamine SuccinylCoA C 25 H 41 N 7 O 19 P 3 S 868 LMethylmalonylCoA, DMethylmalonylCoA * Collective name assigned to describe isomers that were explicitly studied and could not be differentiated by product ion or retention time; the studied compounds are marked in bold in the isomer column a Compounds form distinct product ions b Compounds form distinct products and have different retention times c Compounds form distinct products and have different retention times d Compounds form distinct product ions e Compounds have different retention times f Compounds have different retention times Bajad et al., 2006 Supplementary Materials Page S3 of 17
4 Table S2: MS/MS parameters and LCMS/MS method performance for compound standards. Metabolite ion formula* Collision energy (ev) ion Stability LOD formula (ng/ml) RT (min) R 2 Intraday %RSD Interday % RSD Glycine C 2 H 6 NO CH 4 N Putrescine C 4 H 13 N C 4 H 10 N >2000 n/a n/a n/a n/a Alanine C 3 H 8 NO C 2 H 6 N Acetoacetate C 4 H 5 O C 3 H 5 O n/a n/a n/a Choline C 5 H 14 NO C 3 H 10 N Glycerate C 3 H 5 O C 2 H 3 O Serine C 3 H 8 NO C 2 H 6 NO Cytosine C 4 H 6 N 3 O C 4 H 3 N 2 O Uracil C 4 H 5 N 2 O C 3 H 4 NO >2000 n/a n/a n/a n/a Fumarate C 4 H 3 O C 3 H 3 O Proline C 5 H 10 NO C 4 H 8 N Succinate C 4 H 5 O C 3 H 5 O n/a 5 10 Threonine C 4 H 8 NO C 2 H 4 NO Valine C 5 H 12 NO C 4 H Homoserine C 4 H 10 NO C 2 H 6 N Cysteine C 3 H 8 NO 2 S C 2 H 3 S >2000 n/a n/a n/a n/a Nicotinate C 6 H 4 NO C 5 H 4 N Nicotinamide C 6 H 7 N 2 O C 5 H 6 N b 26 b 10 b Taurine C 2 H 6 NO 3 S SO Thymine C 5 H 7 N 2 O C 5 H 4 NO Agmatine C 5 H 15 N C 4 H 10 N >2000 n/a n/a n/a n/a Oxaloacetate C 4 H 3 O C 3 H 3 O n/a n/a n/a Bajad et al., 2006 Supplementary Materials Page S4 of 17
5 Metabolite ion formula* Collision energy (ev) ion Stability LOD formula (ng/ml) RT (min) R 2 Intraday %RSD Interday % RSD Aspartate C 4 H 6 NO 4 (Iso)leucine C 6 H 14 NO 2 Asparagine C 4 H 9 N 2 O 3 Malate C 4 H 5 O 5 Ornithine C 5 H 13 N 2 O 2 Adenine C 5 H 6 N C 3 H 6 NO C 5 H 12 N C 2 H 4 NO C 4 H 3 O C 4 H 8 N C 5 H 3 N Homocysteine C 4 H 10 NO 2 S C 3 H 8 N paminobenzoate/ Anthranilate C 7 H 6 NO C 6 H 6 N b 21 b 10 b Hypoxanthine C 5 H 5 N 4 O C 4 H 4 N 3 O phydroxybenzoate C 7 H 5 O 3 Acetylphosphate C 2 H 4 O 5 P PO 3 Carbamoylphosphate CH 3 NO 5 P PO C 6 H 5 O b 7 b 11 b Histidinol C 6 H 12 N 3 O C 5 H 7 N 2 αketoglutarate C 5 H 5 O 5 Spermidine C 7 H 20 N 3 Glutamine C 5 H 11 N 2 O 3 Lysine C 6 H 15 N 2 O 2 Glutamate C 5 H 10 NO C 4 H 5 O n/a n/a n/a n/a n/a n/a C 7 H 14 N >2000 n/a n/a n/a n/a C 4 H 6 NO C 5 H 10 N C 4 H 6 NO Methionine C 5 H 12 NO 2 S C 5 H 9 O 2 S Guanine C 5 H 6 N 5 O C 4 H 4 N 3 O ,3Dihydroxybenzoate C 7 H 5 O C 6 H 5 O Xanthine C 5 H 5 N 4 O C 4 H 4 N 3 O >2000 n/a n/a n/a n/a Orotate C 5 H 3 N 2 O C 4 H 3 N 2 O Histidine C 6 H 10 N 3 O C 5 H 8 N Bajad et al., 2006 Supplementary Materials Page S5 of 17
6 Metabolite ion formula* Collision energy (ev) ion Stability LOD formula (ng/ml) RT (min) R 2 Intraday %RSD Interday % RSD Dihydroorotate C 5 H 5 N 2 O C 4 H 5 N 2 O Allantoin C 4 H 7 N 4 O C 3 H 3 N 2 O 2 >2000 n/a n/a n/a n/a Carnitine C 7 H 16 NO C 4 H 7 O Phenylpyruvate C 9 H 7 O C 7 H Phenylalanine C 9 H 12 NO C 8 H Quinolinate C 7 H 4 NO C 6 H 4 NO Phosphoenolpyruvate C 3 H 4 O 6 P PO Dihydroxyacetonephosphate C 3 H 6 O 6 P PO n/a n/a n/a Pyridoxine C 8 H 12 NO C 8 H 8 NO Glycerol3phosphate C 3 H 8 O 6 P PO Arginine C 6 H 13 N 4 O C 5 H 11 N 2 O Shikimate C 7 H 9 O C 6 H 5 O Aconitate C 6 H 5 O 6 Citrulline C 6 H 12 N 3 O 3 Allantoate C 4 H 7 N 4 O 4 CarbamoylLaspartate C 5 H 7 N 2 O 5 NαAcetylornithine C 7 H 15 N 2 O 3 Hydroxyphenylpyruvate C 9 H 7 O 4 myoinositol C 6 H 11 O 6 Glucosamine C 6 H 14 NO C 5 H 5 O C 5 H 11 N 2 O C 3 H 6 N 3 O C 4 H 6 NO C 5 H 9 NO 2 a a C 7 H 7 O C 6 H 9 O C 6 H 12 NO 4 Homocysteic acid C 4 H 8 NO 5 S SO 3 Tyrosine C 9 H 12 NO C 6 H 5 3Phosphoglycerate C 3 H 6 O 7 P H 2 PO 4 3Phosphoserine C 3 H 9 NO 6 P C 3 H 6 NO >2000 n/a n/a n/a n/a Bajad et al., 2006 Supplementary Materials Page S6 of 17
7 Metabolite ion formula* Collision energy (ev) ion Stability LOD formula (ng/ml) RT (min) R 2 Intraday %RSD Interday % RSD Citrate C 6 H 7 O C 5 H 3 O DehydroDgluconate C 6 H 9 O C 4 H 7 O Gluconate C 6 H 11 O C 5 H 5 O 4 a Erythrose4phosphate C 4 H 8 O 7 P H 2 PO n/a n/a n/a Tryptophan C 11 H 13 N 2 O C 9 H 8 NO DGlucarate C 6 H 9 O C 4 H 5 O Deoxyribosephosphate C 5 H 10 O 7 P PO n/a n/a n/a Pantothenate C 9 H 16 NO C 7 H 16 NO Cystathionine C 7 H 15 N 2 O 4 S C 4 H 8 NO 2 S Prephenate C 10 H 9 O C 6 H 3 O n/a n/a n/a Deoxyuridine C 9 H 13 N 2 O C 4 H 5 N 2 O DRib(ul)ose5phosphate C 5 H 10 O 8 P PO 3 a Thymidine C 10 H 13 N 2 O C 5 H 5 N 2 O Uridine C 9 H 11 N 2 O C 8 H 10 NO Cytidine C 9 H 14 N 3 O C 4 H 6 N 3 O Biotin C 10 H 17 N 2 O 3 S C 10 H 15 N 2 O 2 S Deoxyadenosine C 10 H 14 N 5 O C 5 H 6 N 5 < Deoxyinosine C 10 H 13 N 4 O C 5 H 5 N 4 O DHexosephosphate C 6 H 12 O 9 P PO Glucosamine1P C 6 H 15 NO 8 P C 6 H 12 NO Glucosamine6P C 6 H 15 NO 8 P C 6 H 8 NO Thiamine C 12 H 17 N 4 OS C 6 H 8 N Adenosine C 10 H 14 N 5 O C 5 H 6 N Deoxyguanosine C 10 H 14 N 5 O C 5 H 6 N 5 O Bajad et al., 2006 Supplementary Materials Page S7 of 17
8 Metabolite ion formula* Collision energy (ev) ion Stability LOD formula (ng/ml) RT (min) R 2 Intraday %RSD Interday % RSD Inosine C 10 H 13 N 4 O 5 6PhosphoDgluconate C 6 H 12 O 10 P H 2 PO 4 Guanosine C 10 H 14 N 5 O C 5 H 5 N 4 O C 5 H 3 N 4 O Xanthosine C 10 H 13 N 4 O C 5 H 5 N 4 O 2 NAcetylglucosamine1 phosphate C 8 H 15 NO 9 P PO dump C 9 H 12 N 2 O 8 P C 5 H 8 O 6 P dcmp C 9 H 15 N 3 O 7 P C 4 H 6 N 3 O Reduced glutathione C 10 H 18 N 3 O 6 S C 5 H 8 NO 3 S GeranylPP C 10 H 19 O 7 P PO 3 a dtmp C 10 H 16 N 2 O 8 P C 5 H 5 O CMP C 9 H 15 N 3 O 8 P C 4 H 6 N 3 O UMP C 9 H 14 N 2 O 9 P C 5 H 5 O cyclicamp C 10 H 11 N 5 O 6 P C 5 H 4 N damp C 10 H 15 N 5 O 6 P C 5 H 6 N Fructose1,6bisphosphate C 6 H 13 O 12 P H 2 PO Trehalose C 12 H 21 O C 6 H 11 O Thiaminephosphate C 12 H 18 N 4 O 4 PS C 6 H 8 N AMP C 10 H 15 N 5 O 7 P C 5 H 6 N dgmp C 10 H 15 N 5 O 7 P C 5 H 3 N 4 O IMP C 10 H 14 N 4 O 8 P C 5 H 5 N 4 O GMP C 10 H 15 N 5 O 8 P C 5 H 6 N 5 O Xanthosine5phosphate C 10 H 14 N 4 O 9 P C 5 H 5 O Orotidinephosphate C 10 H 12 N 2 O 11 P C 9 H 12 N 2 O 9 P Riboflavin C 17 H 21 N 4 O C 12 H 12 N 4 O Bajad et al., 2006 Supplementary Materials Page S8 of 17
9 Metabolite ion formula* Collision energy (ev) ion Stability LOD formula (ng/ml) RT (min) R 2 Intraday %RSD Interday % RSD trans, transfarnesyl diphosphate C 15 H 27 O 7 P PO 3 SAdenosylLhomocysteine C 14 H 21 N 6 O 5 S C 5 H 6 N 5 dcdp C 9 H 14 N 3 O 10 P 2 PRPP C 5 H 12 O 14 P HO 6 P C 5 H 9 O 10 P 2 SAdenosylLmethionine C 15 H 23 N 6 O 5 S C 10 H 12 N 5 O 3 dtdp C 10 H 15 N 2 O 11 P 2 CDP C 9 H 14 N 3 O 11 P 2 UDP C 9 H 13 N 2 O 12 P 2 ADP C 10 H 14 N 5 O 10 P HO 6 P HO 6 P 2 a a C 9 H 10 N 2 O 8 P C 5 H 4 N APS C 10 H 13 N 5 O 10 PS C 10 H 13 N 5 O 7 P a dgdp C 10 H 14 N 5 O 10 P HO 6 P IDP C 10 H 13 N 4 O 11 P HO 6 P n/a n/a n/a Folate C 19 H 20 N 7 O C 14 H 11 N 6 O GDP C 10 H 14 N 5 O 11 P 2 7,8Dihydrofolate C 19 H 22 N 7 O HO 6 P b 8 b 9 b C 7 H 8 N 5 O n/a n/a n/a FMN C 17 H 20 N 4 O 9 P C 5 H 10 O 7 P MethylTHF C 20 H 26 N 7 O C 15 H 17 N 6 O 2 a dctp C 9 H 15 N 3 O 13 P HO 6 P dutp C 9 H 14 N 2 O 14 P HO 6 P TTP C 10 H 16 N 2 O 14 P HO 6 P CTP C 9 H 15 N 3 O 14 P HO 6 P UTP C 9 H 14 N 2 O 15 P HO 6 P datp C 10 H 15 N 5 O 12 P HO 6 P Bajad et al., 2006 Supplementary Materials Page S9 of 17
10 Metabolite ion formula* Collision energy (ev) ion Stability LOD formula (ng/ml) RT (min) R 2 Intraday %RSD Interday % RSD ATP C 10 H 15 N 5 O 13 P 3 dgtp C 10 H 15 N 5 O 13 P 3 ITP C 10 H 14 N 4 O 14 P 3 GTP C 10 H 15 N 5 O 14 P 3 UDPDglucose C 15 H 23 N 2 O 17 P 2 UDPDglucuronate C 15 H 21 N 2 O 18 P 2 ADPDglucose C 16 H 24 N 5 O 15 P 2 Guanosine 5'diphosphate,3' diphosphate C 10 H 16 N 5 O 17 P 4 UDPNacetylDglucosamine C 17 H 26 N 3 O 17 P 2 Oxidized glutathione C 20 H 33 N 6 O 12 S 2 NAD C 21 H 26 N 7 O 14 P 2 NADH C 21 H 28 N 7 O 14 P C 10 H 12 N 5 O 9 P HO 6 P C 10 H 11 N 4 O 10 P C 10 H 12 N 5 O 10 P b 6 b 30 b C 9 H 12 N 2 O 9 P H 13 N 2 O 12 P C 10 H 13 N 5 O 7 P C 10 H 13 N 5 O 13 P C 9 H 11 N 2 O 11 P C 8 H 11 N 2 O 2 S C 15 H 20 N 5 O 13 P C 10 H 12 N 5 O 9 P n/a n/a n/a a DephosphoCoA C 21 H 36 N 7 O 13 P 2 S C 10 H 15 N 5 O 7 P NADP C 21 H 27 N 7 O 17 P C 15 H 20 N 5 O 16 P NAD C 21 H 29 N 7 O 17 P C 10 H 12 N 5 O 9 P n/a n/a n/a CoA C 21 H 37 N 7 O 16 P 3 S C 11 H 21 N 2 O 3 S FAD C 27 H 34 N 9 O 15 P C 10 H 15 N 5 O 7 P AcetylCoA C 23 H 39 N 7 O 17 P 3 S C 13 H 23 N 2 O 4 S b 2 b 13 b PropionylCoA C 24 H 41 N 7 O 17 P 3 S C 14 H 25 N 2 O 4 S AcetoacetylCoA C 25 H 41 N 7 O 18 P 3 S C 15 H 15 N 2 O 5 S b 6 b 17 b MalonylCoA C 24 H 39 N 7 O 19 P 3 S C 14 H 23 N 2 O 6 S a SuccinylCoA C 25 H 41 N 7 O 19 P 3 S C 15 H 25 N 2 O 6 S Hydroxy3 methylglutarylcoa C 27 H 43 N 7 O 20 P 3 S C 10 H 12 N 5 O 9 P Bajad et al., 2006 Supplementary Materials Page S10 of 17
11 * Charge on the ion indicates ionization mode used for the metabolite The product ion formula is confirmed only for compounds found in Supplementary Table 4; for other compounds, the product ion and formula are best guesses based on available literature Stable ( 20% loss) when stored for 1 week at 4 C at ph 2.8 a Unstable (> 20% loss) when stored for 1 week at 4 C at ph 2.8, but stable ( 20% loss) when stored for 1 week at 4 C at ph 6.8 Unstable (> 20% loss) when stored for 1 week at 4 C at ph 2.8 or ph 6.8. Note that, except for oxaloaceate (at ph 6.8), erythrose4 phosphate (at ph 2.8 and 6.8), deoxyribosephosphate (at ph 2.8), and PRPP (at ph 2.8), t 1/2 for all compounds is > 24 hrs at 4 C Linearity is not reported for unstable metabolites or metabolites with LOD 1000 ng/ml b Reported results are for peak area, not height Intra and interday assay variation is not reported for unstable metabolites or metabolites with LOD > 1000 ng/ml n/a not applicable Bajad et al., 2006 Supplementary Materials Page S11 of 17
12 Table S3: Performance of different chromatography conditions for distinct cellular metabolites. The chromatography columns and conditions employed are described in Table 2 of the main text. The numerical values found in here refer to the overall performance score for the specified metabolite under the stated chromatography conditions as determined in the Methods, with values > 500 considered good, fair, and < 250 poor. Metabolite name ion formula Reverse Phase HILIC ph 2.5 ph 5.8 ph 9 ph 2.8 ph 5.8 ph 9.0 ion Unstable Bajad et al., 2006 Supplementary Materials Page S12 of 17 Glycine C 2 H 6 NO 2 Putrescine C 4 H 13 N 2 Alanine C 3 H 8 NO 2 Acetoacetate C 4 H 5 O 3 Choline C 5 H 14 NO Glycerate C 3 H 5 O Serine C 3 H 8 NO Cytosine C 4 H 6 N 3 O Uracil C 4 H 5 N 2 O Fumarate C 4 H 3 O Proline C 5 H 10 NO Succinate C 4 H 5 O Threonine C 4 H 8 NO Valine C 5 H 12 NO Homoserine C 4 H 10 NO Cysteine C 3 H 8 NO 2 S Nicotinate C 6 H 4 NO Nicotinamide C 6 H 7 N 2 O Taurine C 2 H 6 NO 3 S Thymine C 5 H 7 N 2 O Agmatine C 5 H 15 N Oxaloacetate C 4 H 3 O Unstable Aspartate C 4 H 6 NO (Iso)leucine C 6 H 14 NO Asparagine C 4 H 9 N 2 O
13 Metabolite name ion formula Reverse Phase HILIC ph 2.5 ph 5.8 ph 9 ph 2.8 ph 5.8 ph 9.0 ion Malate C 4 H 5 O 5 Ornithine C 5 H 13 N 2 O 2 Adenine C 5 H 6 N 5 Homocysteine C 4 H 10 NO 2 S 136 Added after chromatography optimization paminobenzoate/ C 7 H 6 NO Anthranilate Hypoxanthine C 5 H 5 N 4 O phydroxybenzoate C 7 H 5 O Acetylphosphate C 2 H 4 O 5 P Unstable Carbamoylphosphate CH 3 NO 5 P 140 Added after chromatography optimization and unstable Histidinol C 6 H 12 N 3 O αketoglutarate C 5 H 5 O Spermidine C 7 H 20 N Glutamine C 5 H 11 N 2 O Lysine C 6 H 15 N 2 O Glutamate C 5 H 10 NO Methionine C 5 H 12 NO 2 S Guanine C 5 H 6 N 5 O ,3Dihydroxybenzoate C 7 H 5 O Xanthine C 5 H 5 N 4 O Orotate C 5 H 3 N 2 O Histidine C 6 H 10 N 3 O Dihydroorotate C 5 H 5 N 2 O Allantoin C 4 H 7 N 4 O Carnitine C 7 H 16 NO Phenylpyruvate C 9 H 7 O Phenylalanine C 9 H 12 NO Quinolinate C 7 H 4 NO Phosphoenolpyruvate C 3 H 4 O 6 P Bajad et al., 2006 Supplementary Materials Page S13 of 17
14 Metabolite name ion formula ion Reverse Phase HILIC ph 2.5 ph 5.8 ph 9 ph 2.8 ph 5.8 ph 9.0 Dihydroxyacetonephosphate C 3 H 6 O 6 P 169 Added after chromatography optimization Pyridoxine C 8 H 12 NO Glycerol3phosphate C 3 H 8 O 6 P 171 Added after chromatography optimization Arginine C 6 H 13 N 4 O Shikimate C 7 H 9 O Aconitate C 6 H 5 O Citrulline C 6 H 12 N 3 O Allantoate C 4 H 7 N 4 O CarbamoylLaspartate C 5 H 7 N 2 O Added after chromatography optimization NαAcetylornithine C 7 H 15 N 2 O Hydroxyphenylpyruvate C 9 H 7 O myoinositol C 6 H 11 O Glucosamine C 6 H 14 NO Homocysteic acid C 4 H 8 NO 5 S Tyrosine C 9 H 12 NO Phosphoglycerate C 3 H 6 O 7 P Phosphoserine C 3 H 9 NO 6 P Citrate C 6 H 7 O DehydroDgluconate C 6 H 9 O Gluconate C 6 H 11 O Erythrose4phosphate C 4 H 8 O 7 P 199 Unstable Tryptophan C 11 H 13 N 2 O DGlucarate C 6 H 9 O Added after chromatography optimization Deoxyribosephosphate C 5 H 10 O 7 P 213 Unstable Pantothenate C 9 H 16 NO Cystathionine C 7 H 15 N 2 O 4 S Prephenate C 10 H 9 O Unstable Deoxyuridine C 9 H 13 N 2 O DRib(ul)ose5phosphate C 5 H 10 O 8 P Bajad et al., 2006 Supplementary Materials Page S14 of 17
15 Metabolite name ion formula Reverse Phase HILIC ph 2.5 ph 5.8 ph 9 ph 2.8 ph 5.8 ph 9.0 ion Thymidine C 10 H 13 N 2 O 5 Uridine C 9 H 11 N 2 O 6 Cytidine C 9 H 14 N 3 O 5 Biotin C 10 H 17 N 2 O 3 S Deoxyadenosine C 10 H 14 N 5 O Deoxyinosine C 10 H 13 N 4 O DHexosephosphate C 6 H 12 O 9 P Glucosamine1P C 6 H 15 NO 8 P Glucosamine6P C 6 H 15 NO 8 P Thiamine C 12 H 17 N 4 OS Adenosine C 10 H 14 N 5 O Added after chromatography optimization Deoxyguanosine C 10 H 14 N 5 O Inosine C 10 H 13 N 4 O PhosphoDgluconate C 6 H 12 O 10 P Guanosine C 10 H 14 N 5 O Xanthosine C 10 H 13 N 4 O NAcetylglucosamine1 C 8 H 15 NO 9 P phosphate dump C 9 H 12 N 2 O 8 P dcmp C 9 H 15 N 3 O 7 P Reduced glutathione C 10 H 18 N 3 O 6 S GeranylPP C 10 H 19 O 7 P dtmp C 10 H 16 N 2 O 8 P CMP C 9 H 15 N 3 O 8 P UMP C 9 H 14 N 2 O 9 P cyclicamp C 10 H 11 N 5 O 6 P damp C 10 H 15 N 5 O 6 P Fructose1,6bisphosphate C 6 H 13 O 12 P Added after chromatography optimization Trehalose C 12 H 21 O Thiaminephosphate C 12 H 18 N 4 O 4 PS Bajad et al., 2006 Supplementary Materials Page S15 of 17
16 Metabolite name ion formula ion Reverse Phase HILIC ph 2.5 ph 5.8 ph 9 ph 2.8 ph 5.8 ph 9.0 AMP C 10 H 15 N 5 O 7 P dgmp C 10 H 15 N 5 O 7 P IMP C 10 H 14 N 4 O 8 P GMP C 10 H 15 N 5 O 8 P Xanthosine5phosphate C 10 H 14 N 4 O 9 P Orotidinephosphate C 10 H 12 N 2 O 11 P 367 Added after chromatography optimization Riboflavin C 17 H 21 N 4 O trans, transfarnesyl diphosphate C 15 H 27 O 7 P SAdenosylLhomocysteine C 14 H 21 N 6 O 5 S dcdp C 9 H 14 N 3 O 10 P PRPP C 5 H 12 O 14 P SAdenosylLmethionine C 15 H 23 N 6 O 5 S dtdp C 10 H 15 N 2 O 11 P CDP C 9 H 14 N 3 O 11 P UDP C 9 H 13 N 2 O 12 P ADP C 10 H 14 N 5 O 10 P APS C 10 H 13 N 5 O 10 PS dgdp C 10 H 14 N 5 O 10 P IDP C 10 H 13 N 4 O 11 P Folate C 19 H 20 N 7 O GDP C 10 H 14 N 5 O 11 P ,8Dihydrofolate C 19 H 22 N 7 O Unstable FMN C 17 H 20 N 4 O 9 P MethylTHF C 20 H 26 N 7 O dctp C 9 H 15 N 3 O 13 P dutp C 9 H 14 N 2 O 14 P TTP C 10 H 16 N 2 O 14 P CTP C 9 H 15 N 3 O 14 P Bajad et al., 2006 Supplementary Materials Page S16 of 17
17 Metabolite name ion formula Reverse Phase HILIC ph 2.5 ph 5.8 ph 9 ph 2.8 ph 5.8 ph 9.0 ion Added after chromatography optimization Added after chromatography optimization and unstable UTP C 9 H 14 N 2 O 15 P 3 datp C 10 H 15 N 5 O 12 P 3 ATP C 10 H 15 N 5 O 13 P 3 dgtp C 10 H 15 N 5 O 13 P 3 ITP C 10 H 14 N 4 O 14 P 3 GTP C 10 H 15 N 5 O 14 P 3 UDPDglucose C 15 H 23 N 2 O 17 P 2 UDPDglucuronate C 15 H 21 N 2 O 18 P 2 ADPDglucose C 16 H 24 N 5 O 15 P 2 Guanosine 5' C 10 H 16 N 5 O 17 P 4 diphosphate,3'diphosphate UDPNacetylDglucosamine C 17 H 26 N 3 O 17 P Oxidized glutathione C 20 H 33 N 6 O 12 S NAD C 21 H 26 N 7 O 14 P NADH C 21 H 28 N 7 O 14 P DephosphoCoA C 21 H 36 N 7 O 13 P 2 S NADP C 21 H 27 N 7 O 17 P NAD C 21 H 29 N 7 O 17 P Unstable CoA C 21 H 37 N 7 O 16 P 3 S FAD C 27 H 34 N 9 O 15 P AcetylCoA C 23 H 39 N 7 O 17 P 3 S PropionylCoA C 24 H 41 N 7 O 17 P 3 S 824 Added after chromatography optimization AcetoacetylCoA C 25 H 41 N 7 O 18 P 3 S MalonylCoA C 24 H 39 N 7 O 19 P 3 S SuccinylCoA C 25 H 41 N 7 O 19 P 3 S 868 Added after chromatography optimization 3Hydroxy3 methylglutarylcoa C 27 H 43 N 7 O 20 P 3 S 910 Added after chromatography optimization Bajad et al., 2006 Supplementary Materials Page S17 of 17
Supporting Information
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