#METABOLOMICS WORKBENCH mkuboniwa_20160416_184048 DATATRACK_ID:597 VERSION 1 CREATED_ON November 16, 2016, 9:28 am #PROJECT PR:PROJECT_TITLE Metabolomic profiles in P. gingivalis cells treated with pABA PR:PROJECT_SUMMARY Metabolomics data for Porphyromonas gingivalis in the presence or absence of 4 PR:PROJECT_SUMMARY aminobenzoate/para-amino benzoic acid (pABA) PR:INSTITUTE Osaka University PR:LAST_NAME Kuboniwa PR:FIRST_NAME Masae PR:ADDRESS 1-8 Yamadaoka, Suita, Osaka, 565-0871, Japan PR:EMAIL kuboniwa@dent.osaka-u.ac.jp PR:PHONE +81-6-6879-2922 #STUDY ST:STUDY_TITLE Metabolomic profiles in P. gingivalis cells treated with pABA ST:STUDY_SUMMARY Many human infections are polymicrobial in origin, and synergistic interactions ST:STUDY_SUMMARY among community inhabitants control colonization and pathogenic potential ST:STUDY_SUMMARY (Murray et al., 2014). However, few interspecies interactions have been ST:STUDY_SUMMARY functionally dissected at the molecular level or characterized on a systems ST:STUDY_SUMMARY level. Periodontitis, which is the sixth most prevalent infectious disease ST:STUDY_SUMMARY worldwide (Kassebaum et al., 2014), is associated with a dysbiotic microbial ST:STUDY_SUMMARY community, and the keystone pathogen Porphyromonas gingivalis forms synergistic ST:STUDY_SUMMARY communities with the accessory pathogen Streptococcus gordonii (Lamont and ST:STUDY_SUMMARY Hajishengallis, 2015). P. gingivalis and S. gordonii communicate through ST:STUDY_SUMMARY co-adhesion and metabolite perception, and close association between P. ST:STUDY_SUMMARY gingivalis and S. gordonii results in significant changes in the expressed ST:STUDY_SUMMARY proteomes of both organisms (Kuboniwa et al., 2012, Hendrickson et al., 2012). ST:STUDY_SUMMARY Here we show that streptococcal 4 aminobenzoate/para-amino benzoic acid (pABA) ST:STUDY_SUMMARY is required for maximal accumulation of P. gingivalis in communities with S. ST:STUDY_SUMMARY gordonii. Exogenous pABA upregulates production of fimbrial interspecies ST:STUDY_SUMMARY adhesins and of a tyrosine phosphorylation-dependent signaling system in P. ST:STUDY_SUMMARY gingivalis. Consequently, fimbrial-dependent attachment and invasion of ST:STUDY_SUMMARY epithelial cells by P. gingivalis is also increased by pABA. Moreover, ST:STUDY_SUMMARY trans-omics studies performed by proteomics and metabolomics showed that pABA ST:STUDY_SUMMARY induces metabolic shifts within P. gingivalis, predominantly folate derivative ST:STUDY_SUMMARY biosynthesis. In a murine oral infection model, pABA increased colonization and ST:STUDY_SUMMARY survival of P. gingivalis, but did not increase virulence. The results establish ST:STUDY_SUMMARY streptococcal pABA as a major component of the interspecies S. gordonii-P. ST:STUDY_SUMMARY gingivalis interaction which regulates distinct aspects of polymicrobial ST:STUDY_SUMMARY synergy. ST:INSTITUTE Osaka University Graduate School of Dentistry ST:LAST_NAME Kuboniwa ST:FIRST_NAME Masae ST:ADDRESS 1-8 Yamadaoka, Suita, Osaka, 565-0871, Japan ST:EMAIL kuboniwa@dent.osaka-u.ac.jp ST:PHONE +81-6-6879-2922 #SUBJECT SU:SUBJECT_TYPE Bacteria SU:SUBJECT_SPECIES Porphyromonas gingivalis ATCC 33277 SU:TAXONOMY_ID 431947 #SUBJECT_SAMPLE_FACTORS: SUBJECT(optional)[tab]SAMPLE[tab]FACTORS(NAME:VALUE pairs separated by |)[tab]Additional sample data SUBJECT_SAMPLE_FACTORS - PBS-1 Treatment:- SUBJECT_SAMPLE_FACTORS - PBS-2 Treatment:- SUBJECT_SAMPLE_FACTORS - PBS-3 Treatment:- SUBJECT_SAMPLE_FACTORS - pABA-1 Treatment:pABA (1 mg/ml) SUBJECT_SAMPLE_FACTORS - pABA-2 Treatment:pABA (1 mg/ml) SUBJECT_SAMPLE_FACTORS - pABA-3 Treatment:pABA (1 mg/ml) #COLLECTION CO:COLLECTION_SUMMARY Cells were collected and washed with Milli-Q water by centrifugation. #TREATMENT TR:TREATMENT_SUMMARY P. gingivalis cells were incubated anaerobically with PBS in the presence or TR:TREATMENT_SUMMARY absence of 1 mg/ml of pABA at 37°C for 2 h. #SAMPLEPREP SP:SAMPLEPREP_SUMMARY Bacterial pellets (5E+09 cfu) were immediately fixed by adding 5 µM internal SP:SAMPLEPREP_SUMMARY standard-containing methanol. #CHROMATOGRAPHY CH:CHROMATOGRAPHY_TYPE Reversed phase CH:INSTRUMENT_NAME Agilent CE CH:COLUMN_NAME Fused silica capillary i.d. 50 µm ×80 cm #ANALYSIS AN:ANALYSIS_TYPE MS #MS MS:MS_COMMENTS - MS:INSTRUMENT_NAME Agilent CE-TOFMS MS:INSTRUMENT_TYPE TOF MS:MS_TYPE ESI MS:ION_MODE UNSPECIFIED #MS_METABOLITE_DATA MS_METABOLITE_DATA:UNITS Relative Area MS_METABOLITE_DATA_START Samples PBS-1 PBS-2 PBS-3 pABA-1 pABA-2 pABA-3 Factors Treatment:- Treatment:- Treatment:- Treatment:pABA (1 mg/ml) Treatment:pABA (1 mg/ml) Treatment:pABA (1 mg/ml) 3-Acetylacrylic acid N N N N 0.00032324 0.000132573 Maleic acid N N N N 0.001148199 0.000555068 5-Oxo-2-tetrahydrofurancarboxylic acid N N N N 0.000479447 N Pimelic acid N N N N 0.002269178 N 3-Hydroxymethylglutaric acid N N N 0.000257304 0.006848364 0.000269329 Vanillic acid N N N N 0.000339325 N 2-Isopropylmalic acid N N N N 0.000633798 N Biotin N N N N 0.002169267 N Fructose 1,6-diphosphate N N N 0.000794314 0.000762785 0.000516776 CoA_divalent N N N 0.001863723 0.000496151 0.000167647 p-Aminobenzoic acid N N N 0.004518772 0.004111756 0.003134658 Tyramine N N N 0.00024809 0.000277309 N 2-(Methylamino)benzoic acid N N N N 0.001050753 0.000372695 N6-acetyllysine N N N N 0.000379814 0.000147883 N-6-trimethyllysine N N N 0.000358184 0.000495814 0.000400314 Deoxyadenosine/5-Deoxyadenosine N N N 0.000643977 0.000474928 0.000470216 Deoxyguanosine N N N 0.001378065 0.000706929 0.001177756 dCMP 0.000200458 0.00020137 0.000197952 0.003198013 0.003590597 0.003714611 dAMP 0.000385047 0.000340211 0.000375397 0.003239195 0.00351172 0.003644142 GDP-mannose/GDP-galactose 0.000350245 0.000365478 0.000393056 0.003327489 0.003649677 0.002738014 Citramalic acid 0.000937142 0.000625804 0.000673037 0.000959371 0.008912153 0.001197981 Glutaric acid 0.000680166 0.000572208 0.000636864 0.00128586 0.005962469 0.001250753 Glucose 6-phosphate 0.006874046 0.006308067 0.006372058 0.028237532 0.029079563 0.025985225 3-Phosphoglyceric acid 0.00109194 0.001057385 0.001137583 0.005179681 0.004720236 0.003543747 dTMP 0.001226414 0.000284317 0.000389923 0.002238313 0.002591181 0.002763112 Fructose 6-phosphate 0.002776903 0.002836282 0.002536348 0.009765356 0.01004272 0.008318619 Glucose 1-phosphate 0.000370848 0.000346591 0.000322989 0.001353398 0.00112933 0.001079567 Adipic acid 0.000235538 0.000153133 N 0.000207227 0.001077983 N Sedoheptulose 7-phosphate 0.007129352 0.007083687 0.00701234 0.022633843 0.022248212 0.020099252 Malonic acid 0.003588759 0.002676513 0.002902346 0.003945545 0.016481853 0.005603451 5-Oxohexanoic acid 0.002619321 0.00300626 0.002961874 0.004494746 0.016198824 0.003103876 UDP N N 8.48772E-05 0.000192401 0.000269109 N Suberic acid 0.000297068 0.000174572 0.000143266 0.000112344 0.001355753 0.000143191 Leucinic acid 0.000249181 0.000245524 0.000187129 0.000327807 0.000777942 N Cyclohexylamine 0.000185627 0.000255116 0.000187629 0.000602126 0.000405841 N 2-Hydroxyisobutyric acid 0.000494742 0.000374921 0.000551132 0.000695808 0.001639091 0.000812169 Sebacic acid 0.000120553 N N N 0.000263851 N Guanine N 0.000188446 0.000211246 0.000259401 0.000546906 0.00046135 N-Acetyl-Glucosamine 6-Phosphate 0.000180134 0.000179932 0.000172318 0.00039271 0.000382939 0.000321779 Guanosine 0.000224059 0.000219784 0.000217493 0.00040192 N 0.000391108 GDP 0.001342513 0.001633676 0.001798657 0.003227335 0.003061967 0.002267252 2-Phosphoglyceric acid 0.000887863 0.000662812 0.000848772 0.001452894 0.001646824 0.001073131 CMP 0.000418178 0.000208261 0.000206212 0.000442128 0.000458414 0.000545093 Citraconic acid 0.001188272 0.000789146 0.000704082 0.001187024 0.001845408 0.00147085 beta-hydroxybutyric acid 0.000931574 0.000725596 0.000929092 0.000860864 0.002324856 0.001044815 Succinic acid 0.00743338 0.00551841 0.006080969 0.007771169 0.014989689 0.007882287 Hydroxypropionic acid 0.000427923 0.000393552 0.000647402 0.00054953 0.001220271 0.000594969 dTDP N 0.000176869 0.000228998 0.00030804 0.000338088 0.000291531 Cytosine 0.00022293 0.000212829 0.000223172 0.000380806 0.000305265 0.00031575 m-Toluic acid 0.026149773 0.036785404 0.034824443 0.071924824 0.039816399 0.035670437 Phosphoserine 0.006546352 0.006128391 0.006485987 0.010292483 0.009804853 0.008049934 His-Glu 0.000121605 0.000103805 0.000143644 N N 0.000174681 Phosphoenolpyruvic acid 0.002195017 0.001651286 0.001996609 0.002844179 0.002952468 0.002448413 Benzoic acid 0.009037046 0.008229379 0.008076723 0.011560223 0.0140509 0.009231826 Lysine 0.408963167 0.35510206 0.38878675 0.440019779 0.485551256 0.621006078 Levulinic acid 0.001642644 0.001398106 0.001612383 0.001492758 0.003297051 0.001396841 Glycolic acid 0.010000359 0.007144175 0.008304012 0.010333006 0.007070456 0.014734561 AMP 0.004768121 0.003496797 0.00366795 0.004835072 0.005135345 0.005083779 Threonine 0.01367577 0.008475869 0.010768462 0.01582343 0.011978268 0.011654805 Glutamine 0.004433486 0.004241551 0.005411205 0.006794182 0.005220992 0.00478263 Quinic acid 0.00027396 0.000246289 0.000219883 0.000418407 0.000154042 0.000309551 ADP-glucose/GDP-fucose 0.001252029 0.001018846 0.00113445 0.00134615 0.001517837 0.001191224 β-Ala-Lys 0.00160425 0.001597467 0.001623532 0.00183918 0.001808774 0.002068404 2-Carboxybenzaldehyde 0.000298738 0.000373135 0.000265455 0.000534045 0.00034613 0.000227176 Cyclohexanecarboxylic acid 0.000140321 0.000156451 0.000202794 8.69759E-05 0.000213741 0.000269329 Ketoleucine/3-Methyl-2-oxovaleric acid 0.000509776 0.000604111 0.000666486 0.000705362 0.000609362 0.000710487 Mannosamine 0.000353584 0.00025456 0.000330783 0.000288055 0.000328722 0.000446688 Thiamine 0.004159479 0.004940408 0.005288262 0.006721414 0.004454616 0.00484844 Tiglic acid 0.000605551 0.000373645 0.000504991 N 0.000385723 0.000697616 Hydrocinnamic acid 0.00270897 0.002369226 0.002707527 0.002899857 0.002774917 0.00279529 DL-2-hydroxy valeric acid 0.001097509 0.000860098 0.000878679 0.000825942 0.001037462 0.001185754 trans-Ferlic acid 0.000352751 0.000331789 0.000259758 0.00042862 0.000299732 0.000271581 Undecylic acid 0.001128969 0.000951723 0.001128753 0.000834508 0.00105231 0.001436098 PGE2 0.001828346 0.000831513 0.000847348 0.001090823 0.001123763 0.001401346 ADP 0.001370076 0.001277386 0.001450603 0.001496382 0.00148041 0.001206348 Riboflavin 0.002594172 0.003037747 0.002853248 0.00262002 0.003409004 0.002477925 Glycerol 3-phosphate 0.000274516 0.000222043 0.000182002 0.00012091 0.000287978 0.000254205 NAD+ 0.042857129 0.044455846 0.044638871 0.043795683 0.043707037 0.041068594 Acetyl CoA_divalent 0.000371405 0.000396105 0.000336091 0.000403582 0.000476045 0.000193711 Thiamine phosphate 0.000647344 0.000649615 0.000781669 0.00068809 0.000535981 0.000697993 FAD_divalent 0.004068745 0.003860999 0.003780739 0.003462565 0.004173048 0.002785315 Lauric acid 0.026516166 0.021325075 0.025642322 0.016816338 0.019651463 0.028627349 Azelaic acid 0.001138436 0.000360884 0.000340648 0.000442128 0.000731544 0.00045403 Capric acid 0.01338142 0.01055343 0.011750654 0.007518807 0.010304406 0.013556208 Pelargonic acid 0.012402795 0.009393191 0.011279272 0.006554165 0.009613074 0.012708643 Ala-Ala 0.002228172 0.002944548 0.003450076 0.002366652 0.002512811 0.002616364 Malic acid 0.000890647 0.000633716 0.000688417 0.000509336 0.000772065 0.00058982 NADP+ 0.001484783 0.001298825 0.001386518 0.001306286 0.001352041 0.000856253 Caprylic acid 0.00676268 0.005248641 0.005978148 0.003155514 0.005059252 0.006832645 Lactic acid 0.094337023 0.072145648 0.083354281 0.061496606 0.077114618 0.069837847 Heptylic acid 0.004296488 0.003169092 0.003747985 0.001737542 0.002855341 0.004717273 Diethanolamine 0.002477627 0.003376604 0.00234018 0.001976043 0.0017715 0.003042252 Pyridoxamine 0.002384787 0.002156386 0.002436433 0.001784133 0.001577737 0.00223685 Caproic acid 0.00938562 0.006387441 0.007317955 0.002725905 0.00550189 0.009858007 Glyceric acid 0.001510118 0.000971375 0.00147111 0.000896116 0.00088342 0.00130449 Propionic acid 0.003629686 0.001778897 0.003070106 0.001034157 0.00152557 0.003923124 Tyr-Glu 0.000512457 0.000495766 0.000645665 0.000421903 0.000396844 0.000441573 5-Oxoproline 0.00204189 0.001449406 0.001637447 0.001237101 0.001688892 0.000871376 Arginine 0.015485171 0.01413127 0.015053587 0.008681999 0.010856822 0.013402685 2,6-diaminopimelic acid 0.001082763 0.001073324 0.001089453 0.000842298 0.000695361 0.000813586 Ribulose-5-phosphate 0.001026791 0.001001236 0.000985772 0.000837802 0.000712675 0.000562791 Gly-Leu 0.011949896 0.014349385 0.017227098 0.009727141 0.009813781 0.010683685 Urea 0.037624663 0.02442439 0.047040401 0.024148376 0.026185612 0.024795615 ppGpp_divalent 0.000245004 0.000437451 0.000392201 0.000398969 0.000249313 8.17317E-05 Adenine 0.002068452 0.001528194 0.001408594 0.00089282 0.001163541 0.00130051 Butyric acid 0.005848647 0.002774263 0.003998914 0.000958712 0.00197192 0.005454468 Gly-Gly 0.000579336 0.000659074 0.000737375 N 0.000405841 N Isovaleric acid 0.006880171 0.00347204 0.004537229 0.00115935 0.002493126 0.005405236 Triethanolamine 0.001412925 0.001290048 0.000980138 0.000492409 0.000940215 0.000801311 Proline 0.012680486 0.008161772 0.010326662 0.007842718 0.005490589 0.005395377 Ornithine 0.095489116 0.059927557 0.069274098 0.03920831 0.040937934 0.050088725 Gly-Asp 0.000602758 0.000609831 0.000799557 0.000280891 0.000338041 0.000545573 Pyridoxamine 5-phosphate 0.011732328 0.012046661 0.011641274 0.007531286 0.00610144 0.006411848 Gluconic acid 0.000605272 0.000721257 0.000686423 0.00040424 0.000409541 0.000318239 5-hydroxylysine 0.000781102 0.000661021 0.000631752 0.000346119 0.000329043 0.000473626 Homoserinelactone 0.001538217 0.001698735 0.001218359 0.000725794 0.000669654 0.001061822 Niacinamide 0.028044598 0.01201272 0.015408788 0.005636305 0.008373573 0.016193632 Carboxymethyllysine 0.002701122 0.002811286 0.002724342 0.001541699 0.001514435 0.001403487 Ribose-5-phosphate 0.000864198 0.000770515 0.000957859 0.000524162 0.000453155 0.000409624 Histidine 0.008237406 0.003274502 0.003693691 0.003770356 0.001989041 0.002291407 Citrulline 0.009027255 0.008314508 0.011690394 0.005752809 0.004281097 0.005222498 Pyridoxine 0.000488753 0.000421206 0.00043669 0.000238538 0.000194358 0.000264603 IMP 0.000346347 0.000315199 0.000274284 0.000179553 0.000162084 0.000138687 Glu-Glu 0.000406354 0.000326337 0.00034356 0.00015128 0.000173782 0.000212396 Thr-Asp 0.000599089 0.000730295 0.000837036 0.000365725 0.000316511 0.000399291 N-Acetylornithine 0.00202697 0.001731563 0.002753871 0.000819298 0.001116305 0.001301874 Aspartic acid 0.008116628 0.003093111 0.003595734 0.002410012 0.002480357 0.002263446 UMP 0.001260659 0.000604111 0.000724305 0.000382167 0.000408613 0.000426357 ADP-ribose 0.001632342 0.000996387 0.001102834 0.000391392 0.000632252 0.000701155 GMP 0.000499475 0.000391511 0.000413278 0.000201956 0.000188376 0.000208512 Ser-Glu 0.000852214 0.000833788 0.001089169 N 0.000345431 0.000496472 S-Adenosylmethionine 0.010782759 0.01087346 0.011641558 0.003950579 0.004674086 0.006399913 Methionine sulfoxide 0.002130252 0.001368503 0.001654197 0.000381183 0.001149402 0.00074232 Leucine 0.0195789 0.012153771 0.016719709 0.00898325 0.006167312 0.006197369 Methyl sulfate 0.003362686 0.001830452 0.00151184 0.001202508 0.000972195 0.000767442 Asparagine 0.004520682 0.003468969 0.00386973 0.001781493 0.001535 0.001700483 Phenylalanine 0.010744099 0.008461958 0.011364439 0.004951985 0.003669604 0.00427968 Glutamic acid 0.009956507 0.006976052 0.008768719 0.004490494 0.003097956 0.003020088 Isobutyryl CoA_divalent 0.002094788 0.001470334 0.001520954 0.000738966 0.000885586 0.000466579 Spermidine 0.003144724 0.001406339 0.001783386 0.001017242 0.001215275 0.000323934 5-Methylthioadenosine 0.001749295 0.001117003 0.001506835 0.000487884 0.000475249 0.000762779 Valine 0.013470053 0.006071322 0.009300242 0.004421873 0.00332353 0.003547248 Isoleucine 0.011327103 0.005640934 0.007683525 0.004309517 0.002491282 0.002468718 Pyridoxal 0.000788721 0.000652675 0.000982126 0.000381183 0.000216173 0.000292222 Glycine 0.012872093 0.005502387 0.009199162 0.003497759 0.003477127 0.002955983 Urocanic acid 0.006295375 0.000937003 0.002251593 0.001252889 0.001141369 0.00090531 Inosine 0.003069944 0.003029679 0.003561662 0.000825708 0.001087385 0.001252431 Tyrosine 0.013972916 0.0123883 0.015777333 0.004675995 0.004030459 0.004807181 UDP-glucuronic acid 0.002691987 0.002807442 0.002914878 0.001005165 0.001018594 0.000652889 Xanthosine 0.000309597 0.000309074 0.000352611 N 9.80547E-05 N Methionine 0.006150611 0.005080903 0.006812417 0.002110645 0.001476196 0.001868247 Tryptophan 0.014241561 0.012297605 0.014215415 0.004215258 0.003183108 0.003589189 Serine 0.057730977 0.032660443 0.040986086 0.013736161 0.010749497 0.009594244 Alanine 0.036752132 0.027385073 0.037571218 0.009634391 0.008816047 0.007827269 N8-Acetylspermidine 0.000383214 0.000118178 0.000142455 N 5.00769E-05 N β-Alanine 0.002552408 0.002378674 0.003076136 0.000648501 0.000481997 0.000641048 Adenosine 0.003427479 0.003700716 0.004228338 0.000621355 0.000473964 0.000542163 Pantothenic acid 0.000947722 0.000965505 0.001053845 N 0.000115995 N Phthalic acid 0.002397146 N N N 0.000214978 N Choline 0.014350486 0.011543384 0.011472334 0.000746908 0.000871129 0.000887579 Fumaric acid 0.000612511 N N N N N XMP 0.000295119 0.000186823 N N N N 1-Aminocyclopropanecarboxylic acid 0.000330444 0.000450418 0.000360028 N N N Gamma-Aminobutyric acid 0.000924454 0.000694406 0.000720623 N N N Creatinine 0.000150775 N N N N N Agmatine 0.00244066 0.000602876 0.001038345 N N N Creatine 0.000203177 N N N N N Hypoxanthine 0.001992543 0.001561022 0.001752154 N N N Methylimidazoleacetic acid 0.001183787 N 0.000429308 N N N sn-glycero-3-phosphocholine 0.000577078 0.000427605 0.000462812 N N N MS_METABOLITE_DATA_END #METABOLITES METABOLITES_START metabolite_name KEGG ID HMDB ID 3-Acetylacrylic acid C07091 Maleic acid C01384 176 5-Oxo-2-tetrahydrofurancarboxylic acid Pimelic acid C02656 857 3-Hydroxymethylglutaric acid C03761 Vanillic acid C06672 484 2-Isopropylmalic acid C02504 402 Biotin C00120 30 Fructose 1,6-diphosphate C00354 1058 CoA_divalent C00010 1423 p-Aminobenzoic acid C00568 1392 Tyramine C00483 306 2-(Methylamino)benzoic acid C03005 N6-acetyllysine C02727 206 N-6-trimethyllysine C03793 1325 Deoxyadenosine/5-Deoxyadenosine C00559/C05198 00101/01983 Deoxyguanosine C00330 85 dCMP C00239 1202 dAMP C00360 905 GDP-mannose/GDP-galactose C00096/C02280 01163/ Citramalic acid C02612,C02614 426 Glutaric acid C00489 661 Glucose 6-phosphate C00668,C01172,C00092 1401 3-Phosphoglyceric acid C00197 807 dTMP C00364 1227 Fructose 6-phosphate C00085 124 Glucose 1-phosphate C00103 1586 Adipic acid C06104 448 Sedoheptulose 7-phosphate C05382 1068 Malonic acid C00383 691 5-Oxohexanoic acid C02129 UDP C00015 295 Suberic acid C08278 893 Leucinic acid C03264 624 Cyclohexylamine C00571 2-Hydroxyisobutyric acid 729 Sebacic acid C08277 792 Guanine C00242 132 N-Acetyl-Glucosamine 6-Phosphate C00357 1062 Guanosine C00387 133 GDP C00035 1201 2-Phosphoglyceric acid C00631 3391 CMP C00055 95 Citraconic acid C02226 634 beta-hydroxybutyric acid C01089,C03197 110,035,700,442 Succinic acid C00042 254 Hydroxypropionic acid C01013 700 dTDP C00363 1274 Cytosine C00380 630 m-Toluic acid C07211 Phosphoserine C01005 272 His-Glu Phosphoenolpyruvic acid C00074 263 Benzoic acid C00180 1870 Lysine C00047,C00739,C16440 18,203,405 Levulinic acid 720 Glycolic acid C00160 115 AMP C00020 45 Threonine C00188,C00820 167 Glutamine C00064,C00303,C00819 64,103,423 Quinic acid C00296 3072 ADP-glucose/GDP-fucose C00498/C00325 06557/01095 β-Ala-Lys C05341 2-Carboxybenzaldehyde C03057 Cyclohexanecarboxylic acid C09822 Ketoleucine/3-Methyl-2-oxovaleric acid C00233/C00671,C03465 00695/00491 Mannosamine C03570 Thiamine C00378 235 Tiglic acid C08279 1470 Hydrocinnamic acid C05629 764 DL-2-hydroxy valeric acid 1863 trans-Ferlic acid C01494 954 Undecylic acid 947 PGE2 C00584 1220 ADP C00008 1341 Riboflavin C00255 244 Glycerol 3-phosphate C00093 126 NAD+ C00003 902 Acetyl CoA_divalent C00024 1206 Thiamine phosphate C01081 2666 FAD_divalent C00016 1248 Lauric acid C02679 638 Azelaic acid C08261 784 Capric acid C01571 511 Pelargonic acid C01601 847 Ala-Ala C00993 3459 Malic acid C00149,C00497,C00711 15,600,744 NADP+ C00006 217 Caprylic acid C06423 482 Lactic acid C00186,C00256,C01432 19,001,311 Heptylic acid 666 Diethanolamine C06772 4437 Pyridoxamine C00534 1431 Caproic acid C01585 535 Glyceric acid C00258 13,906,372 Propionic acid C00163 237 Tyr-Glu 5-Oxoproline C01879 267 Arginine C00062,C00792 51,703,416 2,6-diaminopimelic acid C00666 1370 Ribulose-5-phosphate C00199,C01101 618 Gly-Leu C02155 759 Urea C00086 294 ppGpp_divalent C01228 Adenine C00147 34 Butyric acid C00246 39 Gly-Gly C02037 11733 Isovaleric acid C08262 718 Triethanolamine C06771 Proline C00148,C00763,C16435 16,203,411 Ornithine C00077,C00515,C01602 21,403,374 Gly-Asp Pyridoxamine 5-phosphate C00647 1555 Gluconic acid C00257 625 5-hydroxylysine C16741 450 Homoserinelactone Niacinamide C00153 1406 Carboxymethyllysine Ribose-5-phosphate C00117 1548 Histidine C00135,C00768,C06419 177 Citrulline C00327 904 Pyridoxine C00314 239 IMP C00130 175 Glu-Glu C01425 Thr-Asp N-Acetylornithine C00437 3357 Aspartic acid C00049,C00402,C16433 19,106,483 UMP C00105 288 ADP-ribose C00301 1178 GMP C00144 1397 Ser-Glu S-Adenosylmethionine C00019 1185 Methionine sulfoxide C02989 2005 Leucine C00123,C01570,C16439 687 Methyl sulfate C02704 Asparagine C00152,C01905,C16438 168 Phenylalanine C00079,C02057,C02265 159 Glutamic acid C00025,C00217,C00302 14,803,339 Isobutyryl CoA_divalent C00630 1243 Spermidine C00315 1257 5-Methylthioadenosine C00170 1173 Valine C00183,C06417,C16436 883 Isoleucine C00407,C06418,C16434 172 Pyridoxal C00250 1545 Glycine C00037 123 Urocanic acid C00785 301 Inosine C00294 195 Tyrosine C00082,C01536,C06420 158 UDP-glucuronic acid C00167 935 Xanthosine C01762 299 Methionine C00073,C00855,C01733 696 Tryptophan C00078,C00525,C00806 929 Serine C00065,C00716,C00740 18,703,406 Alanine C00041,C00133,C01401 16,101,310 N8-Acetylspermidine C01029 2189 β-Alanine C00099 56 Adenosine C00212 50 Pantothenic acid C00864 210 Phthalic acid C01606 2107 Choline C00114 97 Fumaric acid C00122 134 XMP C00655 1554 1-Aminocyclopropanecarboxylic acid C01234 Gamma-Aminobutyric acid C00334 112 Creatinine C00791 562 Agmatine C00179 1432 Creatine C00300 64 Hypoxanthine C00262 157 Methylimidazoleacetic acid C05828 2820 sn-glycero-3-phosphocholine C00670 86 METABOLITES_END #END