#METABOLOMICS WORKBENCH Ghizal_20221004_164454 DATATRACK_ID:3491 STUDY_ID:ST002309 ANALYSIS_ID:AN003772 PROJECT_ID:PR001480 VERSION 1 CREATED_ON October 7, 2022, 7:41 am #PROJECT PR:PROJECT_TITLE Targeting malaria parasites with novel derivatives of azithromycin PR:PROJECT_SUMMARY The spread of artemisinin resistant Plasmodium falciparum parasites is of global PR:PROJECT_SUMMARY concern and highlights the need to identify new antimalarials for future PR:PROJECT_SUMMARY treatments. Azithromycin, a macrolide antibiotic used clinically against PR:PROJECT_SUMMARY malaria, kills parasites via two mechanisms: ‘delayed death’ by inhibiting PR:PROJECT_SUMMARY the bacterium-like ribosomes of the apicoplast, and ‘quick-killing’ that PR:PROJECT_SUMMARY kills rapidly across the entire blood stage development. Here, 22 azithromycin PR:PROJECT_SUMMARY analogues were explored for delayed death and quick-killing activities against PR:PROJECT_SUMMARY P. falciparum (the most virulent human malaria) and P. knowlesi (a monkey PR:PROJECT_SUMMARY parasite that frequently infects humans). Seventeen analogues showed improved PR:PROJECT_SUMMARY quick-killing against both Plasmodium species, with up to 38 to 20-fold higher PR:PROJECT_SUMMARY potency over azithromycin after less than 48 or 28 hours of treatment for P. PR:PROJECT_SUMMARY falciparum and P. knowlesi, respectively. Lead analogues had limited activity PR:PROJECT_SUMMARY against the related parasite Toxoplasma gondii and were >5-fold more selective PR:PROJECT_SUMMARY against malaria than human cells. Quick-killing analogues maintained activity PR:PROJECT_SUMMARY throughout the blood stage lifecycle including ring stages of P. falciparum PR:PROJECT_SUMMARY parasites (<12 hrs treatment). Isopentenyl pyrophosphate supplemented parasites PR:PROJECT_SUMMARY that lacked an apicoplast were equally sensitive to quick-killing analogues, PR:PROJECT_SUMMARY confirming that the quick killing activity of these drugs was not directed at PR:PROJECT_SUMMARY the apicoplast. Metabolomic profiling of parasites subjected to the lead PR:PROJECT_SUMMARY analogue revealed a similar profile to chloroquine treatment, suggesting that PR:PROJECT_SUMMARY the food-vacuole is a likely target of this drugs activity. The azithromycin PR:PROJECT_SUMMARY analogues characterised in this study expanded the structural diversity over PR:PROJECT_SUMMARY previously reported quick-killing compounds and provide new starting points to PR:PROJECT_SUMMARY develop azithromycin analogues with quick-killing antimalarial activity. PR:INSTITUTE Monash University PR:LAST_NAME Siddiqui PR:FIRST_NAME Ghizal PR:ADDRESS 381 Royal Parade, Parkville, Melbourne, Victoria, 3052, Australia PR:EMAIL ghizal.siddiqui@monash.edu PR:PHONE 99039282 #STUDY ST:STUDY_TITLE Targeting malaria parasites with novel derivatives of azithromycin ST:STUDY_SUMMARY The spread of artemisinin resistant Plasmodium falciparum parasites is of global ST:STUDY_SUMMARY concern and highlights the need to identify new antimalarials for future ST:STUDY_SUMMARY treatments. Azithromycin, a macrolide antibiotic used clinically against ST:STUDY_SUMMARY malaria, kills parasites via two mechanisms: ‘delayed death’ by inhibiting ST:STUDY_SUMMARY the bacterium-like ribosomes of the apicoplast, and ‘quick-killing’ that ST:STUDY_SUMMARY kills rapidly across the entire blood stage development. Here, 22 azithromycin ST:STUDY_SUMMARY analogues were explored for delayed death and quick-killing activities against ST:STUDY_SUMMARY P. falciparum (the most virulent human malaria) and P. knowlesi (a monkey ST:STUDY_SUMMARY parasite that frequently infects humans). Seventeen analogues showed improved ST:STUDY_SUMMARY quick-killing against both Plasmodium species, with up to 38 to 20-fold higher ST:STUDY_SUMMARY potency over azithromycin after less than 48 or 28 hours of treatment for P. ST:STUDY_SUMMARY falciparum and P. knowlesi, respectively. Lead analogues had limited activity ST:STUDY_SUMMARY against the related parasite Toxoplasma gondii and were >5-fold more selective ST:STUDY_SUMMARY against malaria than human cells. Quick-killing analogues maintained activity ST:STUDY_SUMMARY throughout the blood stage lifecycle including ring stages of P. falciparum ST:STUDY_SUMMARY parasites (<12 hrs treatment). Isopentenyl pyrophosphate supplemented parasites ST:STUDY_SUMMARY that lacked an apicoplast were equally sensitive to quick-killing analogues, ST:STUDY_SUMMARY confirming that the quick killing activity of these drugs was not directed at ST:STUDY_SUMMARY the apicoplast. Metabolomic profiling of parasites subjected to the lead ST:STUDY_SUMMARY analogue revealed a similar profile to chloroquine treatment, suggesting that ST:STUDY_SUMMARY the food-vacuole is a likely target of this drugs activity. The azithromycin ST:STUDY_SUMMARY analogues characterised in this study expanded the structural diversity over ST:STUDY_SUMMARY previously reported quick-killing compounds and provide new starting points to ST:STUDY_SUMMARY develop azithromycin analogues with quick-killing antimalarial activity. ST:INSTITUTE Monash University ST:LAST_NAME Siddiqui ST:FIRST_NAME Ghizal ST:ADDRESS 381 Royal Parade, Parkville, Melbourne, Victoria, 3052, Australia ST:EMAIL ghizal.siddiqui@monash.edu ST:PHONE 99039282 #SUBJECT SU:SUBJECT_TYPE Cultured cells SU:SUBJECT_SPECIES Plasmodium falciparum SU:TAXONOMY_ID 5833 #SUBJECT_SAMPLE_FACTORS: SUBJECT(optional)[tab]SAMPLE[tab]FACTORS(NAME:VALUE pairs separated by |)[tab]Raw file names and additional sample data SUBJECT_SAMPLE_FACTORS - MaC1_E1_1 treatment:C1 | Experiment:1 RAW_FILE_NAME=MaC1_E1_1 SUBJECT_SAMPLE_FACTORS - MaC1_E1_2 treatment:C1 | Experiment:1 RAW_FILE_NAME=MaC1_E1_2 SUBJECT_SAMPLE_FACTORS - MaC1_E1_3 treatment:C1 | Experiment:1 RAW_FILE_NAME=MaC1_E1_3 SUBJECT_SAMPLE_FACTORS - MaC1_E2_1 treatment:C1 | Experiment:2 RAW_FILE_NAME=MaC1_E2_1 SUBJECT_SAMPLE_FACTORS - MaC1_E2_2 treatment:C1 | Experiment:2 RAW_FILE_NAME=MaC1_E2_2 SUBJECT_SAMPLE_FACTORS - MaC1_E2_3 treatment:C1 | Experiment:2 RAW_FILE_NAME=MaC1_E2_3 #COLLECTION CO:COLLECTION_SUMMARY For metabolomics experiments, two 150 mL flasks at 6% haematocrit containing CO:COLLECTION_SUMMARY tightly synchronised parasites 28-34 hrs post-invasion (5-6 hrs rupture window), CO:COLLECTION_SUMMARY were harvested via magnet purification (Miltenyi Biotech). Infected RBC density CO:COLLECTION_SUMMARY was quantitated by flow cytometry (Tham et al., 2010) and 2 mL of 3x 107 CO:COLLECTION_SUMMARY parasites were added into the wells of 24 well microtiter plates. Parasites were CO:COLLECTION_SUMMARY incubated for 1 hrs at 37o C to stabilise the culture. Following this initial CO:COLLECTION_SUMMARY incubation, 5x IC50 of the azithromycin analogue C1 and control drugs CO:COLLECTION_SUMMARY chloroquine, dihydroartemisinin (DHA) and azithromycin were added and incubated CO:COLLECTION_SUMMARY for 2 hrs. Supernatant was removed and parasites washed twice with 800 L CO:COLLECTION_SUMMARY ice-cold 1 x PBS, with cells pelleted via centrifugation at 400 x g for 5 mins CO:COLLECTION_SUMMARY at 0o C. Cell pellets were resuspended in 200 L of ice-cold extraction buffer CO:COLLECTION_SUMMARY (CHCl3/MeOH/water (1:3:1 v/v)) containing 1 µM internal standards, CHAPS and CO:COLLECTION_SUMMARY PIPES, and then incubated on ice for 1 hrs with shaking at 200 rpm. Cell debris CO:COLLECTION_SUMMARY was pelleted with centrifugation at 14800 x g for 10 mins at 0 oC. The resulting CO:COLLECTION_SUMMARY supernatant (180 µL) was transferred to Eppendorf tubes and the remaining ~20 CO:COLLECTION_SUMMARY µL were combined to make a pooled QC sample. Extraction blank samples (without CO:COLLECTION_SUMMARY cells) were prepared alongside and samples were stored at -80 ºC until CO:COLLECTION_SUMMARY analysis. CO:SAMPLE_TYPE Blood (whole) #TREATMENT TR:TREATMENT_SUMMARY For metabolomics experiments, two 150 mL flasks at 6% haematocrit containing TR:TREATMENT_SUMMARY tightly synchronised parasites 28-34 hrs post-invasion (5-6 hrs rupture window), TR:TREATMENT_SUMMARY were harvested via magnet purification (Miltenyi Biotech). Infected RBC density TR:TREATMENT_SUMMARY was quantitated by flow cytometry (Tham et al., 2010) and 2 mL of 3x 107 TR:TREATMENT_SUMMARY parasites were added into the wells of 24 well microtiter plates. Parasites were TR:TREATMENT_SUMMARY incubated for 1 hrs at 37o C to stabilise the culture. Following this initial TR:TREATMENT_SUMMARY incubation, 5x IC50 of the azithromycin analogue C1 and control drugs TR:TREATMENT_SUMMARY chloroquine, dihydroartemisinin (DHA) and azithromycin were added and incubated TR:TREATMENT_SUMMARY for 2 hrs. #SAMPLEPREP SP:SAMPLEPREP_SUMMARY Supernatant was removed and parasites washed twice with 800 L ice-cold 1 x SP:SAMPLEPREP_SUMMARY PBS, with cells pelleted via centrifugation at 400 x g for 5 mins at 0o C. Cell SP:SAMPLEPREP_SUMMARY pellets were resuspended in 200 L of ice-cold extraction buffer SP:SAMPLEPREP_SUMMARY (CHCl3/MeOH/water (1:3:1 v/v)) containing 1 µM internal standards, CHAPS and SP:SAMPLEPREP_SUMMARY PIPES, and then incubated on ice for 1 hrs with shaking at 200 rpm. Cell debris SP:SAMPLEPREP_SUMMARY was pelleted with centrifugation at 14800 x g for 10 mins at 0 oC. The resulting SP:SAMPLEPREP_SUMMARY supernatant (180 µL) was transferred to Eppendorf tubes and the remaining ~20 SP:SAMPLEPREP_SUMMARY µL were combined to make a pooled QC sample. Extraction blank samples (without SP:SAMPLEPREP_SUMMARY cells) were prepared alongside and samples were stored at -80 ºC until SP:SAMPLEPREP_SUMMARY analysis. #CHROMATOGRAPHY CH:CHROMATOGRAPHY_TYPE HILIC CH:INSTRUMENT_NAME Thermo Dionex Ultimate 3000 CH:COLUMN_NAME SeQuant ZIC-pHILIC (150 x 4.6 mm, 5µm) #ANALYSIS AN:ANALYSIS_TYPE MS #MS MS:INSTRUMENT_NAME Thermo Q Exactive Orbitrap MS:INSTRUMENT_TYPE Orbitrap MS:MS_TYPE ESI MS:ION_MODE NEGATIVE MS:MS_COMMENTS Liquid chromatography-mass spectrometry (LC-MS) data was acquired on a MS:MS_COMMENTS Q-Exactive Orbitrap mass spectrometer (Thermo Scientific) coupled with MS:MS_COMMENTS high-performance liquid chromatography system (HPLC, Dionex Ultimate® 3000 RS, MS:MS_COMMENTS Thermo Scientific) as per previously described 49. Briefly, chromatographic MS:MS_COMMENTS separation was performed on a ZIC-pHILIC column equipped with a guard (5 µm, MS:MS_COMMENTS 4.6 × 150 mm, SeQuant®, Merck). The mobile phase (A) was 20 mM ammonium MS:MS_COMMENTS carbonate (Sigma Aldrich), (B) acetonitrile (Burdick and Jackson) and needle MS:MS_COMMENTS wash solution was 50% isopropanol. The column flow rate was maintained at 0.3 MS:MS_COMMENTS ml/min with temperature at 25 ºC and the gradient program was as follows: 80% B MS:MS_COMMENTS decreasing to 50% B over 15 min, then to 5% B at 18 min until 21 min, increasing MS:MS_COMMENTS to 80% B at 24 min until 32 min. Total run time was 32 min with an injection MS:MS_COMMENTS volume of 10 µL. Mass spectrometer was operated in full scan mode with positive MS:MS_COMMENTS and negative polarity switching at 35k resolution at 200 m/z, with detection MS:MS_COMMENTS range of 85 to 1275 m/z, AGC target was 1e6 ions with a maximum injection time MS:MS_COMMENTS of 50 ms. Electro-spray ionization source (HESI) was set to 4.0 kV voltage for MS:MS_COMMENTS positive and negative mode, sheath gas was set to 50, aux gas to 20 and sweep MS:MS_COMMENTS gas to 2 arbitrary units, capillary temperature 300 °C, probe heater MS:MS_COMMENTS temperature 120 °C. The samples were analyzed as a single batch to avoid MS:MS_COMMENTS batch-to-batch variation and randomized to account for LCMS system drift over MS:MS_COMMENTS time. Repeated analysis of pooled quality control samples was performed MS:MS_COMMENTS throughout the batch to confirm signal reproducibility #MS_METABOLITE_DATA MS_METABOLITE_DATA:UNITS relative intensity MS_METABOLITE_DATA_START Samples MaC1_E1_1 MaC1_E1_2 MaC1_E1_3 MaC1_E2_1 MaC1_E2_2 MaC1_E2_3 Factors treatment:C1 | Experiment:1 treatment:C1 | Experiment:1 treatment:C1 | Experiment:1 treatment:C1 | Experiment:2 treatment:C1 | Experiment:2 treatment:C1 | Experiment:2 4-Amino-4-deoxychorismate 95843 66547 38932 38521 10287 9264 IMP 450965 462308 525152 314665 220194 234340 Guanosine 64036 57026 0 11246 0 0 GMP 155408 194471 245079 38762 37540 37996 dGDP 2446953 1710504 2793378 283704 43643 105920 GDP 59560 25691 65843 0 0 0 FA dioxo(10:0) 114934 42438 68428 101162 96129 122510 Norophthalmicacid 111990 114482 108750 45702 34399 40295 Glutathione 88243504 89417712 74687696 16947962 3740643 4750862 L-beta-aspartyl-L-leucine 177188 151025 146782 96100 94803 69613 Gammaglutamylornithine 563582 477065 481889 107007 146212 136267 Val-Val 433224 441922 569515 94486 0 0 Ile-Thr 1029922 991545 874069 1001740 732133 686114 FA hydroxy(10:0) 198441 200028 239776 149989 173934 141649 beta-Citryl-L-glutamic acid 201025 132431 177263 0 0 0 N-Acetyl-aspartyl-glutamate 56931 54179 52489 13890 5642 14364 [FA hydroxy(11:2/11:2)] 2R,9R-dihydroxy-3S,4S,7S,8S-diepoxy-5E,10-undecadien-1-ol 66249 69336 95075 90126 105337 104675 2,7-Anhydro-alpha-N-acetylneuraminic acid 108706 90419 84797 96111 81464 65178 L-gamma-glutamyl-L-isoleucine 592878 590882 552562 301396 270726 295808 CMP-2-aminoethylphosphonate 480530 494315 446001 202828 152317 110735 CDP-ethanolamine 2155258 2086903 2036239 636087 377794 447770 Met-Cys-Cys 240377 235710 167588 203302 130132 126312 Ile-Val 1003748 608948 669521 1552281 1444445 1377566 [FA (11:0)] undecanoic acid 303092 370945 358117 332475 371554 401105 p-aminobenzoyl glutamate 92216 81892 82901 44304 27943 55261 4-Hexyloxyphenol 239900 422707 291892 281390 424372 763767 furaneol glucopyranoside 0 21367 0 62259 52640 9440 ferric dicitrate 58735 59697 0 0 0 0 Ile-Lys 141297 115573 155691 145095 105115 0 sodium dodecyl sulfate 730935 430895 450081 688426 593774 583130 Trp-Gly 94588 85293 99799 0 0 0 (R)-S-Lactoylglutathione 106079 87941 72242 13817 0 0 Asp-Cys-Cys-Ser 66958 84685 100167 12616 6496 0 Gamma-Glutamyltyrosine 57294 67597 66341 107003 46173 30628 Sinalbin 128856 108849 84327 36157 27096 27480 Rishitin 790592 702836 798754 640329 676476 1411566 Glu-Asp-Val 107512 86976 106999 54010 36886 34655 CMP-N-trimethyl-2-aminoethylphosphonate 334284 294649 221584 194313 89518 77637 Zinnimidine 175545 145589 278146 264629 155203 178657 Cyclic ADP-ribose 3264257 3350812 2783820 1455632 790948 795395 Mukaadial 0 144939 166646 0 0 0 Lys-Tyr 35692 32632 37876 57502 26368 11069 UDP-glucose 915807 796916 886959 257493 71873 103049 Pro-Thr-Ser-Ser 154629 120312 122004 51072 33614 0 GDP-mannose 278602 191476 270355 31895 6017 6149 Dihydrozeatin-O-glucoside 1262014 1185191 1020569 316028 373472 240952 Ala-Leu-Thr-Ala 310153 305884 234100 255249 186194 144960 FA hydroxy(16:0)] hexadecanoic acid 97605 156735 238090 74401 214421 246319 Phytuberin 11299359 11055069 13323772 12599064 12390186 25186234 UDP-N-acetyl-D-galactosamine 1180503 1182618 1145493 353609 139575 192918 Asp-Met-Pro-Ser 63972 70268 29388 33315 32792 0 Kinobscurinone 122845 92954 89924 40618 15562 12308 Ala-Asp-Gly-Tyr 321424 179506 294942 60223 40911 26531 [FA (18:1)] 9Z-octadecenoic acid 10730851 12979087 10519912 7112092 7947475 8555232 Ala-Ala-Asp-Tyr 163544 171798 88176 99890 90611 0 FA (19:1) 116400 156266 106517 54011 116454 62916 Cys-Phe-Cys-Gln 18406 41173 0 19997 0 0 Glutathione disulfide 933686 564022 860714 77536 62071 77431 FA (20:4) 435182 530525 425664 292837 304902 344682 Icosatrienoic acid 226475 314141 210612 203710 225005 212695 Asp-Leu-Lys-Asp 403523 392839 314403 115279 78704 74442 Deamino-NAD+ 268750 272285 188491 100341 38127 62468 NADP+ 511464 328271 524270 38788 0 10714 Ala-Met-Asp-Tyr 5474747 5669772 2275698 1113952 665681 1337457 Glu-Glu-Gln-His 103554 87636 113924 28530 6170 11664 Cys-Leu-Cys-Tyr 596524 630123 301205 103479 126857 107396 Glu-Glu-Lys-Pro 134405 123506 139801 80189 56111 66118 Ala-Ile-Ile-Lys 493018 447475 396426 261128 200492 305294 [FA (22:5)] 7Z,10Z,13Z,16Z,19Z-docosapentaenoic acid 261637 299213 219807 243048 246540 253861 Lys-Lys-Val-Val 60921 79299 126203 61240 124090 119120 Lys-Lys-Met-Val 280882 366032 471479 472651 458137 567011 [PG (16:0)] 1-hexadecanoyl-sn-glycero-3-phospho-(1'-sn-glycerol) 1430957 1413942 1642357 564395 571523 498343 Ala-Leu-Trp-Ser 9975905 8946483 8722624 2541743 2999338 3067487 Bile salt 616081 596625 575259 144892 169561 201070 [PG (18:1)] 1-(9E-octadecenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol) 1003210 736418 895753 456140 423521 351733 [PG (18:0)] 1-octadecanoyl-sn-glycero-3-phospho-(1'-sn-glycerol) 1483173 1507971 1705253 849136 943452 769201 Ala-Lys-Met-Trp 762530 841605 823109 586491 426226 463375 LysoPE(20:4) 283440 229847 315241 112129 311433 48407 Chenodeoxyglycocholate 173937 189945 202287 0 0 0 PS(O-20:0/0:0) 1056485 921393 1058270 921079 1073668 985551 Cholesterolsulfate 776678 719416 493435 598660 575232 523676 [PI(18:0)] 1-octadecanoyl-sn-glycero-3-phospho-(1'-myo-inositol) 689808 872506 882431 746827 669991 582292 [ST (12:0) homo-seco-cholestatrien-tetrol 3880323 2762448 3584505 3376927 2807210 3670023 Oxalate 187040 193430 156150 126590 184411 129614 2-phosphono-3-sulfoproprionate 139288 85855 62830 17143 4344 0 Ethanolamine phosphate 4113283 3762568 4089037 452452 400833 331033 [SP (16:0)] N-(hexadecanoyl)-sphing-4-enine 79375 261905 71336 511600 671290 447048 PA(32:0) 0 0 0 263260 298432 246659 PE(31:4) 0 0 0 281674 327893 295657 DG(34:3) 160600 173210 60201 137861 61380 69483 PA(34:2) 428857 644426 187511 399993 436375 344447 DG(34:1) 0 0 0 233657 248652 220793 PA(34:1) 472772 1028175 223107 1576084 1755487 1418443 PE(32:1) 419644 531025 416142 438934 405988 409416 PG(32:1) 945924 847630 706300 245165 217738 237777 DG(36:3) 366868 539008 149335 347120 386413 360819 PE(34:3) 900608 888652 836449 648117 626458 620943 PG(33:1) 558562 690310 442749 238357 229756 222142 PE(34:1) 1559561 2870453 1174945 4755179 4844059 4350547 Hydroxypyruvate 133975 141358 146334 107719 127305 122959 Phosphoenolpyruvate 126505 108763 103316 24428 10445 5874 (S)-Lactate 1370936 1416630 1309366 1251331 819901 1756460 L-Serine 1496555 1342054 1480880 952299 810213 880641 Glycerone phosphate 108723 91749 89031 52934 30919 26959 2-Phospho-D-glycerate 239025 140264 168703 42284 4608 12465 O-Phospho-L-serine 128917 107246 120507 9064 6604 8361 sn-Glycerol 3-phosphate 904101 833812 739430 716349 485058 442059 PG(34:2) 10269659 8754422 6562165 2584478 2624400 2220666 PG(34:1) 19827172 22565646 12845138 10434793 10377992 8838333 PE(36:5) 1227195 1213408 1109269 1057509 986409 957803 PE(36:4) 2183314 2341525 1828157 1903492 1890408 1882682 PE(36:3) 1165503 1590636 1104959 1227281 1307440 1168085 PE(36:2) 939396 1387739 662616 1134386 1215084 1200315 PE(36:1) 312233 425434 176124 943320 974248 926555 PS(36:2) 8047473 12017595 4606596 10077807 10086879 8926661 PG(36:2) 17368104 17768588 10862784 8284107 7972458 6979055 PG(36:1) 5334963 7610428 2970933 6329503 6151608 5550535 PS(O-36:1) 13279198 11440578 12393700 7504119 7893328 7233795 PE(38:6) 696637 725084 637144 719709 682488 572317 PE(38:5) 1255976 1496708 1174154 1679257 1616791 1611688 PE(O-38:5) 391560 504979 258584 693902 750075 733358 PI(34:1) 1753080 2721004 950907 3084153 3262674 2783854 PS(38:7) 120316 80794 120560 0 57958 66362 PS(38:6) 1250399 1260054 832824 782684 789216 773520 PG(38:5) 4019715 3626615 2831317 1829382 1777278 1661517 PS(38:4) 6760506 10786120 3777882 13689218 14091836 11873856 PG(38:4) 2396598 2624158 1631292 1460617 1448635 1213999 PI(36:4) 474858 442133 324835 302244 313677 394523 PI(36:3) 540503 822235 345256 499108 598543 541228 PA(P-42:4) 1655001 701343 1697403 1639183 1709505 1536189 PI(36:2) 1025119 1981719 519195 1689671 1666898 1419261 PI(36:1) 481661 1253474 223888 4159221 4486793 3298039 PS(40:7) 1086987 1109715 665420 842825 844338 1169622 PS(40:6) 2199802 3721869 1412743 4041091 4288546 3497711 PS(40:5) 1547433 2689612 809155 4894344 5235218 4058393 PG(40:5) 658321 677856 378627 636194 657944 551505 PI(38:5) 367689 640238 307833 441996 472702 441550 PI(38:4) 520162 1041499 357071 1110680 1312548 1027025 PG(41:2) 5184820 4943832 5847199 3086818 3636805 3359913 SM(d18:0/24:1(15Z)(OH)) 222662 284092 170382 365915 394777 338846 PI(40:5) 179540 288635 86582 529524 610085 456199 demethyl-phosphinothricin 69221 60138 111336 243515 20937 55025 fosmidomycin 269423 149821 346550 0 0 0 Fumarate 620996 596910 651340 209769 148055 155928 Succinate 375718 367047 428235 197534 203961 195577 (S)-Malate 11936991 12135719 12926971 3587622 2635898 2514050 (R,R)-Tartaric acid 419744 447051 416119 328681 464772 370447 L-Aspartate 20665494 19875102 18880756 16540180 14308114 9960398 L-Asparagine 4495295 4671821 4322136 3586428 3033642 2688948 D-Erythrose 41895 81535 36620 33737 37188 212496 [FA trihydroxy(4:0)] 2,3,4-trihydroxy-butanoic acid 353288 365258 233695 198706 145840 103047 L-Threonine 4142766 3259917 2913813 464736 698420 339910 Gly-Ser 140172 103990 139348 69227 56691 58716 2-Deoxy-D-ribose 5-phosphate 560907 428322 267193 132139 64421 28667 D-Ribose 5-phosphate 222116 200660 190769 152773 90956 80016 2-C-Methyl-D-erythritol 4-phosphate 6015417 21427446 5296951 5981032 864036 21332194 sn-glycero-3-Phosphoethanolamine 159995 116334 95058 32177 40667 37480 Orotate 144112 75216 0 147142 54169 0 (S)-Dihydroorotate 142090 87138 85624 174166 116057 0 2-Hydroxy-2,4-pentadienoate 54084 106953 37369 55170 36595 243787 2-Oxoglutarate 599316 664567 686918 260088 314006 302107 5-Oxoproline 705591 975125 758402 348722 288672 901792 N-Carbamoyl-L-aspartate 771386 536463 416815 391722 255632 257346 5-Valerolactone 0 0 0 0 0 0 (R)-2-Hydroxyglutarate 392726 351061 397019 359183 351566 321231 L-Glutamate 41430432 39685624 37038488 22809202 18899076 13857910 phosphinomethylisomalate 117074 109389 106146 68762 64431 49481 TG(61:11) 0 75273 0 602843 653580 406651 Asp-Gly 226298 144781 118038 44183 39880 44814 (S)-2-Aceto-2-hydroxybutanoate 136768 117333 144528 78222 65092 59187 D-myo-Inositol 1,2-cyclic phosphate 175769 162053 138383 124491 105755 90192 N-gamma-Acetyldiaminobutyrate 215636 183572 222591 72919 87333 0 N5-formyl-N5-hydroxy-L-ornithine 237146 225338 174355 91965 92140 0 L-Cystine 45679 115784 29144 68156 27748 132153 D-Galactose 96724 94242 83163 131892 109346 84456 D-Gluconic acid 3119724 3561456 3077947 2261887 638174 1125318 D-Glucose 6-phosphate 1673454 1312522 776021 829257 275977 447922 Glycerophosphoglycerol 264400 283964 161600 77669 55333 29930 D-Mannitol 1-phosphate 680681 616144 627162 895602 645652 669726 Hydantoin-5-propionate 863438 745962 694457 178387 197409 170081 Citrate 646002 565889 614848 60276 73040 37460 (S)-AMPA 151563 136546 125827 15662 32301 23109 N-Acetyl-L-glutamate 996026 1312085 895752 142918 82265 110778 FA oxo(7:0) 480656 407201 649197 576645 546557 623809 3-Propylmalate 113594 108679 119083 115676 73604 73649 N-Acetylornithine 418338 373142 412372 165373 240418 238194 N-hydroxy DAP 286508 235676 190873 274091 142025 88288 D-Sedoheptulose 7-phosphate 626979 513959 425490 268629 154448 146810 6-formyl-H2-pterin 55130 77644 70038 48590 0 0 N-Acetyl-D-mannosaminolactone 635366 664866 573951 201259 91288 122373 Glutamylalanine 97704 100500 73660 37040 34876 24299 gamma-L-Glutamyl-L-cysteine 603416 604797 501975 430670 53612 68435 Glu-Ser 287872 259850 254711 81305 64440 55296 N-Acetyl-L-citrulline 71116 98952 66748 88429 57608 0 Gln-Ser 272371 244001 166390 258589 220734 118290 N6-Acetyl-N6-hydroxy-L-lysine 172334 160789 164362 144071 116632 142737 3-[4-amino-3-hydroxybutyl]-hydroxy-carbamoyl-propanoate 73837 81040 0 91397 84636 0 Lys-Gly 503238 481963 523138 411281 289107 245970 5-Pyridoxolactone 427182 407732 436603 359943 283313 244109 UMP 747907 968729 1058766 197043 276876 191255 2'-azido-2'-deoxyuridine-5'-diphosphate 186950 150817 167435 31617 6227 14434 N-Succinyl-L-glutamate 4810990 4211503 3469864 522344 257425 245527 UDP 251051 162218 260420 24758 0 6543 5-6-Dihydrouridine 961238 937743 824309 462945 387880 323666 CMP 122882 161363 193869 37991 62549 42307 CDP 82712 42496 80250 6627 0 0 Ala-Ala-Ala 136923 149146 170015 172926 136904 101217 N-α-acetyl lysine methyl ester 217311 210677 138766 33688 16936 0 D-4'-Phosphopantothenate 759927 738619 767270 230023 172738 179168 Lys-Ser 244041 235288 226867 228590 247488 232130 Adrenochrome 121275 144003 173228 125357 142588 169298 Hydroxymethylphosphonate 674796 253269 594489 48819 37053 47538 Sulfate 651503 731432 566732 489353 0 528127 MS_METABOLITE_DATA_END #METABOLITES METABOLITES_START metabolite_name retention time Mass KEGGid Lmid InchiKEY HMDBID 4-Amino-4-deoxychorismate 13.7471187 225.0639609 C11355 OIUJHGOLFKDBSU-HTQZYQBOSA-N IMP 15.43778303 348.0475223 C00130 GRSZFWQUAKGDAV-KQYNXXCUSA-N HMDB00175 Guanosine 12.2839458 283.0919726 C00387 NYHBQMYGNKIUIF-UUOKFMHZSA-N HMDB00133 GMP 16.85579165 363.0583517 C00144 RQFCJASXJCIDSX-UUOKFMHZSA-N HMDB01397 dGDP 15.57558617 427.029878 C00361 CIKGWCTVFSRMJU-KVQBGUIXSA-N HMDB00960 GDP 19.3100055 443.0248826 C00035 QGWNDRXFNXRZMB-UUOKFMHZSA-N HMDB01201 FA dioxo(10:0) 4.639510151 200.1051045 LMFA01060079 AEVOBXGBFZDZTC-UHFFFAOYSA-N Norophthalmicacid 15.33573931 275.1122798 RPVCUZZJCXVVDW-WDSKDSINSA-N HMDB05766 Glutathione 14.2552441 307.0840306 C00051 RWSXRVCMGQZWBV-WDSKDSINSA-N HMDB00125 L-beta-aspartyl-L-leucine 12.16411384 246.1215989 IYJILWQAFPUBHP-UHFFFAOYSA-N HMDB11166 Gammaglutamylornithine 16.35356131 261.1325535 FCQBDQYWNGUTPD-BQBZGAKWSA-N HMDB02248 Val-Val 7.508760661 216.147377 KRNYOVHEKOBTEF-HTQZYQBOSA-N Ile-Thr 7.516994907 232.1424189 FA hydroxy(10:0) 4.562127404 188.1413005 LMFA01050029 GHPVDCPCKSNJDR-UHFFFAOYSA-N beta-Citryl-L-glutamic acid 20.74445696 321.070098 GAQNUGISBQJMKO-YFKPBYRVSA-N HMDB13220 N-Acetyl-aspartyl-glutamate 17.43444453 304.0912662 C12270 OPVPGKGADVGKTG-UHFFFAOYSA-N HMDB01067 [FA hydroxy(11:2/11:2)] 2R,9R-dihydroxy-3S,4S,7S,8S-diepoxy-5E,10-undecadien-1-ol 4.643160744 228.1000864 LMFA05000013 WWAQOPQUSWZTHG-SHEFQFEDSA-N 2,7-Anhydro-alpha-N-acetylneuraminic acid 13.1558109 291.0957105 C04521 NCMJSVDTRDLWJE-GSQQXRCOSA-N L-gamma-glutamyl-L-isoleucine 10.54917687 260.1369943 SNCKGJWJABDZHI-UHFFFAOYSA-N HMDB11170 CMP-2-aminoethylphosphonate 15.01941225 430.0655746 C05673 FBADRUOBFLBKJQ-PEBGCTIMSA-N CDP-ethanolamine 16.19360914 446.0606259 C00570 WVIMUEUQJFPNDK-PEBGCTIMSA-N HMDB01564 Met-Cys-Cys 18.64894033 355.0689784 Ile-Val 7.484544881 230.1630074 BCXBIONYYJCSDF-CIUDSAMLSA-N [FA (11:0)] undecanoic acid 4.013721077 186.1621059 LMFA01010011 ZDPHROOEEOARMN-UHFFFAOYSA-N HMDB00947 p-aminobenzoyl glutamate 14.82253017 266.0901464 GADGMZDHLQLZRI-UHFFFAOYSA-L 4-Hexyloxyphenol 3.876357182 240.1362731 C14305 XIIIHRLCKLSYNH-UHFFFAOYSA-N furaneol glucopyranoside 14.5332688 352.1012852 VIVUUBYKBXDNAJ-QPLYKKBVSA-N ferric dicitrate 14.47284449 446.03702 C06229 ISOHCBXAFHMIHK-UHFFFAOYSA-N Ile-Lys 12.07901314 259.18972 sodium dodecyl sulfate 3.697253734 266.155243 MOTZDAYCYVMXPC-UHFFFAOYSA-M Trp-Gly 8.290646023 261.1113853 UYKREHOKELZSPB-JTQLQIEISA-N (R)-S-Lactoylglutathione 13.91546615 379.1050484 C03451 VDYDCVUWILIYQF-CSMHCCOUSA-N HMDB01066 Asp-Cys-Cys-Ser 17.06926455 426.0886181 Gamma-Glutamyltyrosine 14.01863096 310.1169232 VVLXCWVSSLFQDS-QWRGUYRKSA-N HMDB11741 Sinalbin 14.6132407 424.0374694 C08426 WWBNBPSEKLOHJU-LPUQOGTASA-N Rishitin 3.892659755 222.1621515 C09715 XSCYYIVXGBKTOC-GZZJDILISA-N Glu-Asp-Val 16.37168611 361.1483905 CMP-N-trimethyl-2-aminoethylphosphonate 13.94148865 508.0895093 C05674 RNUGPSIGKYHQNQ-OJAKKHQRSA-O Zinnimidine 7.471805936 261.1367734 C10626 DSOITGJEUKHAJN-UHFFFAOYSA-N Cyclic ADP-ribose 13.61537103 541.0599561 C13050 BQOHYSXSASDCEA-KEOHHSTQSA-N Mukaadial 4.587661099 302.1288019 C09702 AMHCJQBKGMEAAJ-NZBPQXDJSA-N Lys-Tyr 13.89465003 309.1693521 UDP-glucose 16.70176572 566.0554874 C00029 HSCJRCZFDFQWRP-JZMIEXBBSA-N HMDB00286 Pro-Thr-Ser-Ser 12.57095719 390.1751984 GDP-mannose 18.63463612 605.0778412 C00096 MVMSCBBUIHUTGJ-GDJBGNAASA-N HMDB01163 Dihydrozeatin-O-glucoside 10.92459651 383.1807177 C16448 QRZHDHJUYBONQQ-UFZVAZPKSA-N HMDB12214 Ala-Leu-Thr-Ala 13.96023585 374.2167967 FA hydroxy(16:0)] hexadecanoic acid 3.901541675 272.2350644 LMFA01050047 JGHSBPIZNUXPLA-UHFFFAOYSA-N Phytuberin 3.90081461 294.1833162 C09709 YARAJYKHRCCDLG-XLNGHYISSA-N UDP-N-acetyl-D-galactosamine 15.27670626 607.0822214 C00203 LMSL01010002 LFTYTUAZOPRMMI-UHFFFAOYSA-N HMDB00304 Asp-Met-Pro-Ser 14.74140304 484.1391316 Kinobscurinone 13.90630288 306.0526621 C12391 KESQQXMHWJFEFV-UHFFFAOYSA-N Ala-Asp-Gly-Tyr 14.48248949 424.1597764 [FA (18:1)] 9Z-octadecenoic acid 3.762589654 282.2560531 C00712 LMFA01030002 ZQPPMHVWECSIRJ-KTKRTIGZSA-N HMDB00207 Ala-Ala-Asp-Tyr 11.22542438 438.1755508 FA (19:1) 3.751943269 296.2715322 LMFA01030083 INKQLYSQWHBEGS-ISLYRVAYSA-N Cys-Phe-Cys-Gln 14.5877284 499.1547287 Glutathione disulfide 17.51530808 612.1525413 C00127 YPZRWBKMTBYPTK-BJDJZHNGSA-N HMDB03337 FA (20:4) 3.773755452 304.2406714 C00219 LMFA01030001 YZXBAPSDXZZRGB-DOFZRALJSA-N HMDB01043 Icosatrienoic acid 3.754733333 306.2562962 C16522 LMFA01030378 AHANXAKGNAKFSK-PDBXOOCHSA-N Asp-Leu-Lys-Asp 13.90784998 489.2445165 Deamino-NAD+ 14.21418111 664.093965 C00857 SENPVEZBRZQVST-HISDBWNOSA-O HMDB01179 NADP+ 17.02982668 743.0765117 C00006 XJLXINKUBYWONI-NNYOXOHSSA-O HMDB00217 Ala-Met-Asp-Tyr 10.45781868 498.1797248 Glu-Glu-Gln-His 16.3252507 541.2135916 Cys-Leu-Cys-Tyr 10.46346488 500.1772861 Glu-Glu-Lys-Pro 16.37258405 501.2439647 Ala-Ile-Ile-Lys 14.98725146 489.3166463 [FA (22:5)] 7Z,10Z,13Z,16Z,19Z-docosapentaenoic acid 3.748513456 330.2565886 C16513 LMFA04000044 YUFFSWGQGVEMMI-JLNKQSITSA-N HMDB06528 Lys-Lys-Val-Val 27.8078017 518.3420274 Lys-Lys-Met-Val 27.74410934 550.3134996 [PG (16:0)] 1-hexadecanoyl-sn-glycero-3-phospho-(1'-sn-glycerol) 3.815521691 484.280313 LMGP04050008 BVJSKAUUFXBDOB-LEWJYISDSA-N Ala-Leu-Trp-Ser 7.517128337 475.2432729 Bile salt 4.636894775 408.2876713 C01558 BHQCQFFYRZLCQQ-UMZBRFQRSA-N [PG (18:1)] 1-(9E-octadecenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol) 3.784301575 510.2958925 LMGP04050003 FQQQKGAFQIIGLQ-XRDMFJJNSA-N [PG (18:0)] 1-octadecanoyl-sn-glycero-3-phospho-(1'-sn-glycerol) 3.753881135 512.311551 LMGP04050009 HFJVKBVEKQHVTO-XZOQPEGZSA-N Ala-Lys-Met-Trp 14.5329681 534.2609702 LysoPE(20:4) 4.316896513 501.285778 YWOCITMXHHTBAW-XSQXPFHXSA-N HMDB11487 Chenodeoxyglycocholate 4.37656542 449.3144029 C05462 LMST05030003 GHCZAUBVMUEKKP-AFQLCFGXSA-N HMDB06898 PS(O-20:0/0:0) 4.337564097 585.3643072 LMGP03060001 ZEPUSHULPSPFJG-RPBOFIJWSA-N Cholesterolsulfate 3.608230744 466.3123801 LMST05020016 BHYOQNUELFTYRT-DPAQBDIFSA-N HMDB00653 [PI(18:0)] 1-octadecanoyl-sn-glycero-3-phospho-(1'-myo-inositol) 4.079231389 600.3275796 LMGP06050004 MXAFDFDAIFZFET-HULSJBAWSA-N [ST (12:0) homo-seco-cholestatrien-tetrol 4.226628744 488.3131976 LMST03020315 UKQNCFNXBITWKF-JUOPNIRESA-N Oxalate 19.59099139 89.9954032 C00209 LMFA01170031 MUBZPKHOEPUJKR-UHFFFAOYSA-N HMDB02329 2-phosphono-3-sulfoproprionate 18.49991659 265.9498678 VBVRZFXJOVCTGU-UHFFFAOYSA-K Ethanolamine phosphate 15.66804535 141.0193154 C00346 SUHOOTKUPISOBE-UHFFFAOYSA-N HMDB00224 [SP (16:0)] N-(hexadecanoyl)-sphing-4-enine 3.819700328 537.5125522 C00195 LMSP02010004 YDNKGFDKKRUKPY-TURZORIXSA-N HMDB04949 PA(32:0) 3.644421073 648.4731556 LMGP10010866 PE(31:4) 7.520986774 669.4361342 LMGP02010394 LJRKKSBIPGDNNM-FCDKFIKWSA-N DG(34:3) 3.734192371 636.4969903 PA(34:2) 3.624671794 672.4735659 LMGP10010023 DG(34:1) 3.764182807 640.5267365 LMGL02010004 GSEVZLBSIOIEFK-AAOCECEDSA-N PA(34:1) 3.632760879 674.4887756 LMGP10010007 PE(32:1) 3.974451888 689.4999055 PG(32:1) 3.589767288 720.4943306 DG(36:3) 3.737028856 664.5282947 C00165 LMGL02010056 BLZVZPYMHLXLHG-JOBMVARSSA-N HMDB07219 PE(34:3) 3.944580515 713.4996038 LGHHSOARZMNIGJ-DFCPKGTFSA-N PG(33:1) 3.573405457 734.5096368 LMGP04010254 YBMBGCRCYPZPRW-NYMVISBMSA-N PE(34:1) 3.922817288 717.5310938 DVXMEPWDARXHCX-OTMQOFQLSA-N Hydroxypyruvate 16.24682854 104.0110399 C00168 HHDDCCUIIUWNGJ-UHFFFAOYSA-N HMDB01352 Phosphoenolpyruvate 18.39097376 167.982636 C00074 DTBNBXWJWCWCIK-UHFFFAOYSA-N HMDB00263 (S)-Lactate 9.665195404 90.03171475 C00186 JVTAAEKCZFNVCJ-REOHCLBHSA-N HMDB00190 L-Serine 15.68078771 105.0427119 C00065 MTCFGRXMJLQNBG-REOHCLBHSA-N HMDB00187 Glycerone phosphate 15.51938899 169.9982226 C00111 GNGACRATGGDKBX-UHFFFAOYSA-N HMDB01473 2-Phospho-D-glycerate 17.91446844 185.9931019 C00631 GXIURPTVHJPJLF-UWTATZPHSA-N HMDB03391 O-Phospho-L-serine 16.7259855 185.0091926 C01005 BZQFBWGGLXLEPQ-REOHCLBHSA-N HMDB01721 sn-Glycerol 3-phosphate 15.04343915 172.0138676 C00093 AWUCVROLDVIAJX-GSVOUGTGSA-N HMDB00126 PG(34:2) 3.569141508 746.5104154 LMGP04010485 OKLFBFZTIAAQCG-OPIKARGUSA-N PG(34:1) 3.56800409 748.5257766 LMGP04010457 YIQBSYSBVXVBAC-JYMHUOGFSA-N PE(36:5) 3.835311635 737.4985175 LOVKENPUWMFUJV-XVIXSHTPSA-N PE(36:4) 3.861279858 739.5150953 KUPNWZACJRZMJD-SIOSMUJOSA-N PE(36:3) 3.882256097 741.5300799 FRZXKSQGAKPAPK-XKDWLADFSA-N PE(36:2) 3.885800939 743.5473168 C00350 LMGP02010034 VHHMKXOBDPAFKC-HWQBUQMOSA-N HMDB09026 PE(36:1) 3.892978521 745.5611288 LICSIKXBSOVGBP-VEAYGOGPSA-N PS(36:2) 3.634823263 787.5366964 AGTPCXBHIGMTEU-NREGDSCDSA-N PG(36:2) 3.564507543 774.5411413 CZVJBYZXTBYGJR-XAODMQRJSA-N PG(36:1) 3.568301891 776.5551842 URDBSUCIYKJPCG-INSSKLQOSA-N PS(O-36:1) 3.902707869 821.5785715 LMGP03020012 NHFUOLYNPLVMLN-BFCPHGQOSA-N PE(38:6) 3.782220205 763.5158471 PE(38:5) 3.802780502 765.5299055 PE(O-38:5) 3.861195604 751.5523634 C00350 LMGP02030003 URPXXNCTXCOATD-FXMFQVEGSA-N HMDB05779 PI(34:1) 3.630115077 836.5404847 PS(38:7) 3.637000932 805.4877269 JFVIHLIFBOBUBC-OZMWHMDYSA-N PS(38:6) 3.626272007 807.504382 PWBBJQOVCTWPIM-FAYDGCQZSA-N PG(38:5) 3.562740887 796.5249051 LVQOWSPRPQUBPY-MCQYTGMZSA-N PS(38:4) 3.626400618 811.5364549 IULWELDCBXQXED-DWOSIAKHSA-N PG(38:4) 3.562482069 798.5394819 GGSONEYZZWVXFY-QPQYMHNXSA-N PI(36:4) 3.622968258 858.5246409 QQQIZZJWFPGZFU-XZJTVJSISA-N PI(36:3) 3.628824346 860.5404143 WSWLAMCUBAIQKH-XZMLFBLDSA-N PA(P-42:4) 4.16811761 764.5703282 LMGP10030085 RLYSMZKMLSAVDA-YNURERCLSA-N PI(36:2) 3.632652503 862.5571488 LALGUHSIWLNTNW-SHLWDWSJSA-N PI(36:1) 3.63483942 864.5724955 PONHAMBNZIFEKT-HLQOLDBXSA-N PS(40:7) 3.613255037 833.5190131 PS(40:6) 3.625295593 835.5360758 PS(40:5) 3.618990551 837.5502604 PG(40:5) 3.559087494 824.5560798 PI(38:5) 3.631837503 884.5417879 WMVAOBOFQHVKTL-VEAQMIGASA-N PI(38:4) 3.626237175 886.5569444 KRTOMQDUKGRFDJ-MWZLTEOLSA-N PG(41:2) 4.236059952 844.617296 LMGP04010477 CNTGVCVFGPEWKQ-NQTRGSPBSA-N SM(d18:0/24:1(15Z)(OH)) 4.355294755 874.6789272 C00550 HMDB13469 PI(40:5) 3.626285952 912.5727534 demethyl-phosphinothricin 14.65743234 203.0109563 IDBRULKICVRMNG-VKHMYHEASA-M fosmidomycin 14.5132423 183.0299342 GJXWDTUCERCKIX-UHFFFAOYSA-M Fumarate 16.56009914 116.0110668 C00122 VZCYOOQTPOCHFL-OWOJBTEDSA-N HMDB00134 Succinate 15.58518701 118.0267631 C00042 LMFA01170043 KDYFGRWQOYBRFD-UHFFFAOYSA-N HMDB00254 (S)-Malate 16.5841006 134.0216838 C00149 BJEPYKJPYRNKOW-REOHCLBHSA-N HMDB00156 (R,R)-Tartaric acid 19.09034782 150.0166613 C00898 FEWJPZIEWOKRBE-UHFFFAOYSA-N HMDB00956 L-Aspartate 15.02221725 133.0376561 C00049 CKLJMWTZIZZHCS-REOHCLBHSA-N HMDB00191 L-Asparagine 15.19381325 132.0536538 C00152 DCXYFEDJOCDNAF-REOHCLBHSA-N HMDB00168 D-Erythrose 14.74734481 120.0423714 C01796 FMAORJIQYMIRHF-HERZVMAMSA-N HMDB02649 [FA trihydroxy(4:0)] 2,3,4-trihydroxy-butanoic acid 12.62940772 136.0373455 C01620 LMFA01050097 JPIJQSOTBSSVTP-UHFFFAOYSA-N HMDB00943 L-Threonine 14.33124598 119.0583725 C00188 AYFVYJQAPQTCCC-GBXIJSLDSA-N HMDB00167 Gly-Ser 14.61933709 162.0640044 WOUIMBGNEUWXQG-UHFFFAOYSA-N 2-Deoxy-D-ribose 5-phosphate 13.89473139 214.0244911 C00673 KKZFLSZAWCYPOC-PYHARJCCSA-N HMDB01031 D-Ribose 5-phosphate 15.83542356 230.01941 C00117 KTVPXOYAKDPRHY-SOOFDHNKSA-N HMDB01548 2-C-Methyl-D-erythritol 4-phosphate 14.20006042 216.0403236 C11434 XMWHRVNVKDKBRG-UHNVWZDZSA-N sn-glycero-3-Phosphoethanolamine 15.35199595 215.0562022 C01233 JZNWSCPGTDBMEW-RXMQYKEDSA-N HMDB00114 Orotate 10.37707854 156.0172158 C00295 PXQPEWDEAKTCGB-UHFFFAOYSA-N HMDB00226 (S)-Dihydroorotate 11.29624513 158.0328221 C00337 UFIVEPVSAGBUSI-REOHCLBHSA-N HMDB00528 2-Hydroxy-2,4-pentadienoate 14.77102235 114.0318197 C00596 VHTQQDXPNUTMNB-ONEGZZNKSA-N 2-Oxoglutarate 16.187983 146.0216608 C00026 KPGXRSRHYNQIFN-UHFFFAOYSA-N HMDB00208 5-Oxoproline 10.18724369 129.0426874 C01879 ODHCTXKNWHHXJC-VKHMYHEASA-N HMDB00267 N-Carbamoyl-L-aspartate 17.31763214 176.0435427 C00438 HLKXYZVTANABHZ-REOHCLBHSA-N HMDB00828 5-Valerolactone 7.505203349 100.0525265 C02240 OZJPLYNZGCXSJM-UHFFFAOYSA-N (R)-2-Hydroxyglutarate 15.62260523 148.0373945 C01087 HWXBTNAVRSUOJR-GSVOUGTGSA-N HMDB00606 L-Glutamate 14.66294996 147.0532993 C00025 WHUUTDBJXJRKMK-VKHMYHEASA-N HMDB00148 phosphinomethylisomalate 15.05513584 212.0088723 TG(61:11) 3.551002423 1012.770567 LMGL03016756 SKHIKGCNPOERGT-WVMNATIMSA-N Asp-Gly 16.88950444 190.05927 JHFNSBBHKSZXKB-VKHMYHEASA-N (S)-2-Aceto-2-hydroxybutanoate 14.35541948 146.058038 C06006 LMFA01050383 VUQLHQFKACOHNZ-LURJTMIESA-N HMDB06900 D-myo-Inositol 1,2-cyclic phosphate 17.36687115 242.0195879 C04299 SXHMVNXROAUURW-FTYOSCRSSA-N HMDB01125 N-gamma-Acetyldiaminobutyrate 11.00505988 160.0848345 C06442 YLZRFVZUZIJABA-YFKPBYRVSA-N N5-formyl-N5-hydroxy-L-ornithine 11.80462182 176.0797288 L-Cystine 16.34610243 240.0241524 C00491 LEVWYRKDKASIDU-UHFFFAOYSA-N HMDB00192 D-Galactose 12.96261325 180.0636019 C00124 WQZGKKKJIJFFOK-SVZMEOIVSA-N HMDB00143 D-Gluconic acid 14.21841839 196.058484 C00257 RGHNJXZEOKUKBD-SQOUGZDYSA-N HMDB00625 D-Glucose 6-phosphate 17.05811954 260.0300132 C00092 NBSCHQHZLSJFNQ-GASJEMHNSA-N HMDB00124 Glycerophosphoglycerol 14.16970581 246.0508344 C03274 LLCSXHMJULHSJN-UHFFFAOYSA-N HMDB01401 D-Mannitol 1-phosphate 15.37684029 262.0456878 C00644 GACTWZZMVMUKNG-UHFFFAOYSA-N Hydantoin-5-propionate 15.57834563 172.048664 C05565 VWFWNXQAMGDPGG-UHFFFAOYSA-N HMDB01530 Citrate 19.36974133 192.0273392 C00158 KRKNYBCHXYNGOX-UHFFFAOYSA-N HMDB01212 (S)-AMPA 14.71092798 186.0642149 C13672 UUDAMDVQRQNNHZ-YFKPBYRVSA-N HMDB00094 N-Acetyl-L-glutamate 14.31900972 189.0639069 C00624 RFMMMVDNIPUKGG-YFKPBYRVSA-N FA oxo(7:0) 7.511774436 144.0787384 LMFA01060011 IDDYNNYMUPHFMO-UHFFFAOYSA-N HMDB01138 3-Propylmalate 14.34357445 176.068642 C02123 LMFA01170064 LOLHYFQEDPGSHZ-AKGZTFGVSA-N N-Acetylornithine 9.149453328 174.1004615 C00437 JRLGPAXAGHMNOL-LURJTMIESA-N N-hydroxy DAP 12.16857804 206.0904622 YCDSWADGJKMVHC-UHFFFAOYSA-M HMDB03357 D-Sedoheptulose 7-phosphate 16.38562048 290.040612 C05382 JDTUMPKOJBQPKX-UHFFFAOYSA-N 6-formyl-H2-pterin 8.962031962 191.0444429 LLJAQDVNMGLRBD-UHFFFAOYSA-N N-Acetyl-D-mannosaminolactone 14.14054909 219.0744576 C03776 NELQYZRSPDCGRQ-XZBKPIIZSA-N Glutamylalanine 14.89403391 218.0903693 JZDHUJAFXGNDSB-UHFFFAOYSA-N gamma-L-Glutamyl-L-cysteine 14.14260129 250.0627028 C00669 RITKHVBHSGLULN-WHFBIAKZSA-N HMDB03764 Glu-Ser 15.70863051 234.0854504 HMDB01049 N-Acetyl-L-citrulline 12.38730004 217.106376 C15532 WMQMIOYQXNRROC-LURJTMIESA-N Gln-Ser 12.81878363 233.1012762 HMDB00856 N6-Acetyl-N6-hydroxy-L-lysine 9.432439618 204.1112103 C03955 YXKGOSZASIKYPU-ZETCQYMHSA-N 3-[4-amino-3-hydroxybutyl]-hydroxy-carbamoyl-propanoate 11.19681018 220.1059097 Lys-Gly 16.76009431 203.1272448 5-Pyridoxolactone 14.40156154 165.0427859 C06052 PPAXBSPBIWBREI-UHFFFAOYSA-N UMP 15.19240285 324.0359475 C00105 DJJCXFVJDGTHFX-XVFCMESISA-N 2'-azido-2'-deoxyuridine-5'-diphosphate 15.5770333 464.9854206 JPDZOZSNEDHGDF-RNMRRNDGSA-K HMDB04291 N-Succinyl-L-glutamate 14.52824404 247.0694766 C05931 JCNBNOQGFSXOML-YFKPBYRVSA-N HMDB00288 UDP 17.33209001 404.0025396 C00015 XCCTYIAWTASOJW-XVFCMESISA-N 5-6-Dihydrouridine 14.04109397 246.0853449 ZPTBLXKRQACLCR-XVFCMESISA-N CMP 15.8480583 323.0520987 C00055 IERHLVCPSMICTF-XVFCMESISA-N HMDB00295 CDP 17.90685176 403.0186277 C00112 ZWIADYZPOWUWEW-XVFCMESISA-N HMDB00497 Ala-Ala-Ala 10.20165765 231.122034 HMDB00095 N-α-acetyl lysine methyl ester 6.441332881 202.1319196 HMDB01546 D-4'-Phosphopantothenate 15.33131543 299.0773851 C03492 XHFVGHPGDLDEQO-ZETCQYMHSA-N Lys-Ser 16.35389504 233.1377583 Adrenochrome 4.624254501 179.0582979 RPHLQSHHTJORHI-UHFFFAOYSA-N HMDB01016 Hydroxymethylphosphonate 14.52648966 111.9926476 C06455 GTTBQSNGUYHPNK-UHFFFAOYSA-N Sulfate 19.66550627 97.96742103 C00059 QAOWNCQODCNURD-UHFFFAOYSA-N HMDB12884 METABOLITES_END #END