#METABOLOMICS WORKBENCH Ghizal_20221004_164454 DATATRACK_ID:3491 STUDY_ID:ST002309 ANALYSIS_ID:AN003771 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 POSITIVE 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 5-Hydroxyconiferaldehyde 0 0 0 0 115969 0 Adenosine 190048 168887 240072 74116 96800 62261 Nicotine 132339 179783 120638 142605 144723 144342 dAMP 59424 69176 96993 33821 51551 51676 AMP 3377075 3629125 4700868 1591543 1666570 1262838 formycin A 244443 166974 177969 115575 115900 126171 dihydrothymidine 11184338 11080848 10542589 8073096 7143003 6214704 GammaGlutamylglutamicacid 58148 46032 33095 11292 0 0 Ala-Gly-Pro 545166 548675 522904 623564 360857 286353 Dethiobiotin 824537 861775 882275 465334 555788 537538 9-mercaptodethiobiotin 176066 182012 228568 216036 145701 150633 N2-Succinyl-L-arginine 171142 181728 159024 296772 172206 90351 Ile-Asn 205073 191126 184296 185217 141753 109753 Lys-Asn 20555 14827 17345 42378 80493 43863 Gly-Gly-Arg 66556 64342 89164 66716 30766 38555 Lys-Thr 267226 251567 229212 143022 138808 84675 Thr-Arg 178482 154209 157492 136837 118700 75099 L-Tryptophan 269656 253545 182589 163784 90711 96179 Nicotinamide D-ribonucleotide 338101 287558 495897 154436 150097 92927 5'-Methylthioadenosine 284092 393682 619675 102438 147961 249554 Heliamine 242186 258576 267917 254706 259792 235920 Pro-His 292582 256641 284813 182071 203735 128511 L-isoleucyl-L-proline 363376 559659 627521 642291 713214 546558 Lys-Pro 2017367 1869594 1795617 1016870 995545 700386 Epsilon-(gamma-Glutamyl)-lysine 422973 422955 274796 106033 92578 69531 Pro-Arg 152732 134827 143843 97827 78790 61575 Glu-Arg 108332 150077 141654 50871 30578 49258 Lys-Val 1069397 924461 489539 515999 438258 290283 Val-Arg 146594 160575 163771 190804 148503 114806 Thiamin 174524 168503 150481 141436 136886 133277 Thiamin diphosphate 135738 98577 107283 34993 14323 18685 Ala-Asp-Pro 836291 901535 782264 251731 226479 218273 Slaframine 45983 49547 49152 127246 106648 117936 His-Leu 821981 771550 710967 307707 365375 338571 Thr-Ala-Pro 217461 209776 173694 106429 101200 76738 psicoselysine 850252 847007 643602 174457 266333 182024 Ile-Arg 201711 163684 161506 139013 113724 87765 Darlingine 0 0 0 214774 167637 154243 6,7-Dimethyl-8-(1-D-ribityl)lumazine 2054896 1839752 1997694 444044 400186 390405 Glu-Ala-Pro 464032 561860 534448 121477 123835 109009 Glu-Ala-Val 281461 280101 271380 75384 67427 74752 Succinyladenosine 712929 450932 600470 150469 127686 380738 Hypaphorine 49102 56530 47758 207397 196709 171717 Pro-Tyr 55930 69868 56352 67017 53633 31036 S-Inosyl-L-homocysteine 109218 92473 101037 0 0 0 S-Adenosyl-L-homocysteine 4451555 3978219 3741868 722707 660939 579974 Ala-Asp-Gly-Pro 511334 506576 458509 265065 266864 235641 Ala-Ala-Ala-Pro 483375 489280 437233 238456 206636 213129 N-Acetyllactosamine 81710 102438 59058 58088 51230 40324 CDP-choline 790177 811406 650705 279004 260210 177999 Trp-Asn 341002 273663 277160 60430 71533 59006 S-Adenosyl-L-methionine 391644 547449 460985 610000 1115380 548681 Glu-Glu-Pro 1034990 1031880 1024063 357109 271322 318497 L-Tyrosyl-L-arginine 497064 401359 326009 86089 44541 36180 Ala-Val-Gly-Pro 1007825 1126038 1110679 334903 282199 304504 Ala-Thr-Ala-Gln 75741 68050 75910 16840 13505 0 Ala-Asp-Gly-Arg 105625 96449 97028 32304 13892 0 Ala-Lys-Ala-Ala 1176134 1151019 577250 237327 62371 31832 Febrifugine 2083215 2129876 2169891 751569 893341 866852 Glu-Glu-His 110465 99463 98651 56197 42376 31763 dTDP-3-amino-2,3,6-trideoxy-D-threo-hexopyranos-4-ulose 80978 96137 97208 74559 74238 0 Ala-Leu-Asn-Ser 165343 202568 140469 72859 66716 44630 Ala-Asp-Ser-Arg 86384 75420 64319 0 0 0 Lys-Trp 43063 46292 71267 100859 71014 52965 Asp-Val-Pro-Ser 2650795 2406434 2567881 1306674 1193363 1053057 Asn-Lys-Gly-Pro 296726 240769 187470 98868 79278 39189 Ile-Lys-Pro 425917 438021 402322 350644 337128 301583 14-Methyl-8Z-hexadecen-1-ol 69087 58608 49400 137607 212779 132698 Prekinamycin 458872 427825 425326 129613 71578 95492 Ala-Leu-Asn-Pro 739363 663256 735728 309451 294197 262133 Ala-Lys-Asp-Pro 1877700 1800890 1632755 1154972 1166241 1114538 [SP amino(18:0/2:0)] 2S-aminooctadecane-1,3R-diol 27677 80931 43394 166886 206898 113824 Ala-Phe-Thr-Ser 0 0 0 0 0 0 Ala-Glu-Glu-His 4635724 3720221 4629156 782019 497864 753117 Glu-Glu-Pro-Thr 102778 101693 87585 24646 0 0 Ala-Leu-Met-Val 44474 37847 51523 42765 26181 0 Ala-Lys-Lys-Asp 1006344 881209 374372 136787 44686 31263 FA methyl(18:0) 576941 541595 472438 2602198 2093396 2148827 Thr-Trp-Pro 252175 240337 252901 85662 87063 91619 Asn-Leu-Pro-Pro 2464218 1967148 2127961 863744 727969 575592 NAD+ 25797878 23732836 20236538 8325903 4509634 4137578 Glu-Ile-Gln-Lys 68272 51836 28558 61984 41168 0 Arg-Leu-Lys-Asp 54428 53238 111005 104629 56165 39159 3Z,6Z,9Z,12Z,15Z-Tricosapentaene 461202 313124 288834 302804 225228 241757 LysoPE(18:1) 344197 453628 410279 264926 275456 201618 Bis(2-ethylhexyl)phthalate 380464 478567 496732 882868 467404 448489 LysoPC(O-16:1) 364436 300547 358513 226992 260137 270526 LysoPC(16:0) 1355136 1798253 1759391 1420788 1975793 1543801 Pro-Thr-Trp-Pro 0 0 145530 0 0 398012 Gln-Thr-Trp-Pro 400364 433016 520764 197464 202346 186282 Erythrophleguine 433474 631712 701213 0 0 0 3-oxohexacosanoic acid 0 0 0 788726 540794 534968 LysoPC(18:1) 795102 1170790 1307741 604461 1063508 538442 LysoPC(18:0) 2154879 1652612 1681629 1911399 2232291 1778868 [ST (3:0)] cholest-5Z,7Z,24-trien-3beta-ol 92216 102853 111641 126329 116437 115403 [ST] (5Z,7E)-9,10-seco-5,7,10(19)-cholestatriene 200617 170988 492385 241207 195390 220070 5beta-cholestan-3alpha,4alpha,11beta,12beta,21-pentol-3,21-disulphate 408697 368333 232736 182700 141621 61201 PD 123177 0 0 442589 0 111012 1511306 (24R,24'R)-Fucosterol epoxide 453255 457739 552655 333301 363199 316717 Phosphonoacetaldehyde 144643 160714 114088 31059 12272 20044 DG(32:0) 0 0 0 2018852 2435564 1926213 PE(32:0) 178038 264730 141174 380410 466991 276152 SM(d32:1) 695427 663888 522396 715796 738021 647277 PC(30:0) 1903657 2515057 1671582 1392198 1602059 1245928 SM(d33:1) 497768 438586 492360 491315 524806 422959 DG(36:2) 4036195 8157877 2073830 6121310 6727085 5209336 SM(d34:2) 572188 596019 689383 729769 767583 553915 SM(d34:1) 4212293 4016930 4235759 5613939 5771447 4271528 L-Alanine 266361 249911 200974 231963 190255 160981 PS(34:1) 986042 1337390 676731 1373613 1325645 1072555 PS(34:0) 3410063 3932512 2219990 1335807 1374951 946443 PE(35:1) 3664431 4090141 2844982 2006954 1435717 1398469 PC(32:0) 5666837 8421232 4604459 13235340 14738217 11880359 PS(36:5) 175140 265672 158110 147281 170072 127830 PS(36:4) 728809 880319 479259 535130 524936 513035 PS(36:3) 1889757 2265552 1350030 1217062 1281871 962397 PC(34:2) 34869280 30691790 31658778 17546948 17438454 14762188 [SP (24:0)] N-(15Z-tetracosenoyl)-sphing-4-enine 0 274779 0 712890 704206 541553 PS(36:0) 6703670 8810243 4162233 5102266 4718727 3375296 PC(34:1) 98238056 104370816 83181376 72643640 75690016 62869908 PE(38:1) 2949262 3706089 2402340 3135192 3173729 2551974 PC(36:4) 9291881 8018669 8309420 4963488 5201671 4988650 PE(39:2) 12552851 13223870 9404450 9838776 9141660 8210664 [PI(36:0) 220135 457368 137117 391381 402444 319874 SM(d40:2) 238243 344394 243091 393739 556482 388299 PC(38:6) 3328491 2986126 3323764 1691274 1829423 1590511 PC(38:5) 7621803 7671433 6966919 5786654 6681507 5584584 PC(38:2) 1509389 1782149 1182054 2155003 2144372 1856986 SM(d42:3) 446564 539979 362049 701092 768507 591502 SM(d18:1/24:1(15Z)) 871651 1918565 559473 2514347 2751167 2152105 PC(40:7) 822796 618240 582350 458061 445047 415279 PC(40:6) 1662776 2180987 1451581 1415971 1529098 1266782 Diethanolamine 158912 109501 126391 175550 167782 205829 Phosphodimethylethanolamine 660722 593057 465622 85496 35045 15645 Creatine 599600 510940 476788 2508864 2468313 1752888 4-Aminobutanal 394288 328518 266659 195865 196939 242738 4-Aminobutanoate 6940353 6802113 6785390 2057667 2115715 1612061 PS(52:0) 0 115482 0 316417 327058 182331 L-Glutamine 44764688 52720688 40332100 31376468 26671048 40863568 D-Ribose 53260 60847 61149 17508 13614 0 Piperidine 122493 141152 87950 150718 118667 116037 L-Valine 1270256 1236339 957731 995355 623461 625700 L-Methionine 1203787 1339768 1036811 1876148 882211 886871 L-Ornithine 448684 552915 419723 420775 542693 347180 Choline 206569 201603 172115 141847 172705 178610 Choline phosphate 49527212 54134376 42952752 12293492 9525592 7361908 Hypoxanthine 4193625 6744755 3321877 4323308 2962325 7872239 Adenine 303388 310818 519637 113248 239284 106081 Guanine 796670 831844 799582 285373 259760 131574 5,6-Dihydrothymine 55268 42622 40758 52350 62849 118530 L-Proline 4814782 5424054 4362072 4551635 3675845 3843518 5-Aminolevulinate 1509174 1922284 1290936 1610243 1648030 2364959 D-Glucono-1,5-lactone 51863 53340 39092 63095 28986 15423 L-Pipecolate 1362181 1437109 1202243 539601 356647 246170 O-Acetyl-L-homoserine 293975 238955 162353 148134 90877 50348 FA hydroxy(6:0) 151119 126760 168310 162760 135901 169420 L-Citrulline 54520 43195 32580 71691 76948 59405 L-Ieucine 964556 1150426 686171 978843 607320 1008412 N-hydroxyisoleucine 104962 48045 54721 115084 64950 264980 L-Lysine 4669659 5256410 4149909 1807126 2248907 1456605 L-Arginine 4717908 5362337 4001135 1829380 1947454 2535097 3-deoxy-D-galactose 186920 77154 110755 188657 162582 200301 Mannitol 330086 292917 293726 781908 687842 1010503 Nicotinate 224556 143131 366514 119436 110372 109751 Nicotinamide 456212 530640 886720 442897 264732 820804 2,3-Dimethylmaleate 35171 137632 46471 45298 27201 196342 3-(Pyrazol-1-yl)-L-alanine 2627608 2340731 2408660 1143943 1338007 1092745 L-beta-aspartyl-L-alanine 182416 160397 146609 18612 37007 0 Ala-Asn 53837 52000 79927 61158 30410 18469 α-(2,6-anhydro-3-deoxy-D-arabino-heptulopyranosid)onate 7-phosphate 72501 43488 40051 27296 0 0 N5-acetyl-N5-hydroxy-L-ornithine 51056 54568 26226 34812 16545 0 Sedoheptulose 0 0 0 94337 106162 50321 4-Trimethylammoniobutanoate 40570 33667 19555 131011 129233 112299 L-Carnitine 80368 69523 72860 143032 167295 141539 MOPS 37520780 26811112 2865184 3574365 1875377 2142792 Pyridoxine 253910 332930 188313 244622 221965 679013 Ala-Pro 15266097 13324303 12464423 8734058 9318313 7358775 Proclavaminic acid 530260 511014 478570 486363 316734 281112 Glycyl-leucine 119701 107492 109646 140803 75873 40147 D-Mycinose 52256 14080 13241 12273 14162 0 Gly-Arg 180846 164494 188223 109292 86369 88458 Methacholine 22499 26910 30487 91076 119594 88153 Ne,Ne dimethyllysine 127340 133537 116014 55606 67512 45031 HEPES 339111168 337994528 256050256 194401360 171583376 209955824 Arg-OEt 458911 500518 531536 273063 228986 164605 sn-glycero-3-Phosphocholine 2290775 2055718 1904976 1371043 1378053 1059540 L-Phenylalanine 1504204 1357868 1277441 1175261 731207 742680 L-Tyrosine 910818 921698 640017 965199 512557 368136 4-(L-Alanin-3-yl)-2-hydroxy-cis,cis-muconate 6-semialdehyde 266029 189578 197042 23568 0 0 Temurin 421137 559702 447085 180819 327981 101777 Dihydrobiopterin 5191045 4879914 3903686 2113397 2470684 2317934 Aspartyl-L-proline 13347045 13159322 13061153 5685944 5037432 4317773 (6R)-6-(L-Erythro-1,2-Dihydroxypropyl)-5,6,7,8-tetrahydro-4a-hydroxypterin 881250 826849 729632 348099 350792 300492 Furfural diethyl acetal 90701 180548 153520 218748 168078 195473 Hercynine 18094 20395 18742 85518 81617 100410 Ergothioneine 191380 197594 217167 113663 39780 18869 Asn-Pro 4483382 3651701 3069761 2125675 1743090 1324860 Asp-Gln 146583 137917 121210 78129 24627 71296 gamma-Glutamyl-gamma-aminobutyraldehyde 4051718 3629267 3060083 1784230 1497930 1156132 gamma-Glutamyl-gamma-aminobutyrate 119581 108392 126987 74797 52514 56298 Glu-Thr 5211527 3369688 5121419 843505 717235 456329 Ala-Asn-Gly 210854 219190 132463 296652 85382 51551 9-Oxononanoic acid 0 0 0 79567 0 159422 Azelaic acid 115783 106817 112690 81435 70875 31384 Ala-Ala-Ser 134215 96381 97120 108535 76330 54411 O-Acetylcarnitine 107005 52995 93944 215837 166899 217159 Muramic acid 84484 125695 89158 128390 118057 84930 Ile-Ser 334505 267766 261912 161440 119540 117041 gamma-L-Glutamylputrescine 33209 41890 43444 70080 38831 22872 beta-Alanyl-L-arginine 75684 101096 100253 153253 91511 79235 Ser-Arg 55072 64350 60084 162239 113212 75656 butyrylcholine 1275763 5876363 670653 24905494 1726284 11868471 N6,N6,N6-Trimethyl-L-lysine 2301156 2401298 2412067 1403240 1356637 1162036 MS_METABOLITE_DATA_END #METABOLITES METABOLITES_START metabolite_name retention time Mass KEGGid Lmid InchiKEY HMDBID 5-Hydroxyconiferaldehyde 4.641705994 194.0579055 C12204 IEHPLRVWOHZKCS-NSCUHMNNSA-N Adenosine 8.538566377 267.0965929 C00212 OIRDTQYFTABQOQ-KQYNXXCUSA-N HMDB00050 Nicotine 4.861783336 162.1156042 C00745 SNICXCGAKADSCV-JTQLQIEISA-N HMDB01934 dAMP 12.38521706 331.0680016 C00360 KHWCHTKSEGGWEX-RRKCRQDMSA-N HMDB00905 AMP 13.519194 347.0628001 C00020 UDMBCSSLTHHNCD-KQYNXXCUSA-N HMDB00045 formycin A 12.98983525 269.1121863 SIVHFRZJFCASNV-JPWDWCJRSA-N dihydrothymidine 15.16393745 244.1058461 FEYHMSUYKIMUAL-UHFFFAOYSA-N GammaGlutamylglutamicacid 17.03280688 276.0960097 C05282 OWQDWQKWSLFFFR-WDSKDSINSA-N HMDB11737 Ala-Gly-Pro 12.65456633 243.1217104 Dethiobiotin 8.649671051 214.1315584 C01909 AUTOLBMXDDTRRT-UHFFFAOYSA-N HMDB03581 9-mercaptodethiobiotin 8.4754089 246.1036276 ZARFDBYKHCOTRH-SFYZADRCSA-N N2-Succinyl-L-arginine 12.83173059 274.1276194 C03296 UMOXFSXIFQOWTD-LURJTMIESA-N Ile-Asn 9.503662618 245.1374474 HZYHBDVRCBDJJV-UHFFFAOYSA-N Lys-Asn 16.22156488 260.1487656 Gly-Gly-Arg 17.30700419 288.1545367 Lys-Thr 15.45527469 247.1531917 Thr-Arg 15.3258051 275.1592348 L-Tryptophan 11.27499482 204.0899306 C00078 QIVBCDIJIAJPQS-VIFPVBQESA-N HMDB00929 Nicotinamide D-ribonucleotide 14.69012893 334.056614 C00455 DAYLJWODMCOQEW-TURQNECASA-N HMDB00229 5'-Methylthioadenosine 6.526277372 297.0894068 C00170 WUUGFSXJNOTRMR-IOSLPCCCSA-N HMDB01173 Heliamine 12.30345401 193.1103778 C09460 CEIXWJHURKEBMQ-UHFFFAOYSA-N Pro-His 12.23017315 252.1220031 L-isoleucyl-L-proline 7.527251987 228.1473804 BBIXOODYWPFNDT-UHFFFAOYSA-N HMDB11174 Lys-Pro 15.22232424 243.1582012 AIXUQKMMBQJZCU-IUCAKERBSA-N Epsilon-(gamma-Glutamyl)-lysine 14.65683958 275.1481036 JPKNLFVGUZRHOB-YUMQZZPRSA-N HMDB03869 Pro-Arg 15.33633898 271.1643969 HMNSRTLZAJHSIK-YUMQZZPRSA-N Glu-Arg 16.57656415 303.1542779 Lys-Val 13.43177985 245.1736012 YQAIUOWPSUOINN-UHFFFAOYSA-N Val-Arg 13.19323367 273.1802566 Thiamin 21.09106288 264.104255 C00378 JZRWCGZRTZMZEH-UHFFFAOYSA-N HMDB00235 Thiamin diphosphate 14.58609627 424.0365922 C00068 AYEKOFBPNLCAJY-UHFFFAOYSA-O HMDB01372 Ala-Asp-Pro 14.92032041 301.1273048 Slaframine 8.959222675 240.1471442 C06185 UQNSGOYQGBXKSN-MCIGGMRASA-N His-Leu 7.775955474 268.1534534 C05010 MMFKFJORZBJVNF-UHFFFAOYSA-N Thr-Ala-Pro 15.20713846 287.1483362 psicoselysine 21.00533624 308.1581515 BFSYFTQDGRDJNV-ONJAQYSBSA-O Ile-Arg 11.90249382 287.195789 Darlingine 13.28605929 241.1077084 C10857 WBTZDCUVPGAROE-UHFFFAOYSA-N 6,7-Dimethyl-8-(1-D-ribityl)lumazine 13.1205604 326.1223806 C04332 SXDXRJZUAJBNFL-XKSSXDPKSA-N HMDB03826 Glu-Ala-Pro 14.6843584 315.1428779 Glu-Ala-Val 10.9282767 317.1585173 Succinyladenosine 14.66651796 383.1076928 VKGZCEJTCKHMRL-VWJPMABRSA-N HMDB00912 Hypaphorine 8.234585773 246.136697 C09213 AOHCBEAZXHZMOR-ZDUSSCGKSA-N Pro-Tyr 10.03718838 278.1264692 OIDKVWTWGDWMHY-NWDGAFQWSA-N S-Inosyl-L-homocysteine 14.79917417 385.1055851 C03431 VNPWVMVYUSNFAW-WFMPWKQPSA-N S-Adenosyl-L-homocysteine 12.95454748 384.1213515 C00021 ZJUKTBDSGOFHSH-WFMPWKQPSA-N HMDB00939 Ala-Asp-Gly-Pro 15.69631849 358.1488864 Ala-Ala-Ala-Pro 9.89810779 328.1742255 N-Acetyllactosamine 13.23065025 383.1427199 C00611 KFEUJDWYNGMDBV-LODBTCKLSA-N HMDB01542 CDP-choline 15.00540685 488.1078119 C00307 RZZPDXZPRHQOCG-OJAKKHQRSA-N HMDB01413 Trp-Asn 9.808274527 318.1323472 S-Adenosyl-L-methionine 16.20315442 398.1370119 C00019 MEFKEPWMEQBLKI-AIRLBKTGSA-N HMDB01185 Glu-Glu-Pro 17.19005342 373.1482578 L-Tyrosyl-L-arginine 13.68732831 337.1750676 C02993 JXNRXNCCROJZFB-RYUDHWBXSA-N HMDB05768 Ala-Val-Gly-Pro 9.34907489 342.189953 Ala-Thr-Ala-Gln 15.50160814 389.1907333 Ala-Asp-Gly-Arg 15.24474527 417.1973929 Ala-Lys-Ala-Ala 13.55210992 359.2163727 Febrifugine 8.587228605 301.1424774 C10677 FWVHWDSCPKXMDB-LSDHHAIUSA-N Glu-Glu-His 13.23793237 413.1547793 dTDP-3-amino-2,3,6-trideoxy-D-threo-hexopyranos-4-ulose 14.6609712 529.0868375 C12318 IVWGOICUSBJICO-OJEZURLMSA-N Ala-Leu-Asn-Ser 14.40172297 403.2063114 Ala-Asp-Ser-Arg 11.9407558 447.2084194 Lys-Trp 8.656779766 349.210892 DZHDVYLBNKMLMB-ZFWWWQNUSA-N Asp-Val-Pro-Ser 9.694867346 416.1905063 Asn-Lys-Gly-Pro 15.06014436 414.2224648 Ile-Lys-Pro 20.7152799 356.2420358 14-Methyl-8Z-hexadecen-1-ol 7.605810388 271.2875502 LMFA05000203 QRFJDYPDABYWFH-ALCCZGGFSA-N Prekinamycin 16.04870759 318.0646903 C12393 ZVCNREZZUJIBAG-UHFFFAOYSA-N Ala-Leu-Asn-Pro 9.002378855 413.2271336 Ala-Lys-Asp-Pro 14.60924437 214.6111131 [SP amino(18:0/2:0)] 2S-aminooctadecane-1,3R-diol 7.56011621 301.298135 LMSP01080055 OTKJDMGTUTTYMP-ROUUACIJSA-N Ala-Phe-Thr-Ser 8.541216625 424.1947445 Ala-Glu-Glu-His 15.80661763 484.1921658 Glu-Glu-Pro-Thr 16.21261592 474.1958379 Ala-Leu-Met-Val 8.319188848 432.2407796 Ala-Lys-Lys-Asp 13.53465522 460.2640805 FA methyl(18:0) 5.525449994 315.313496 LMFA01020015 BEOUGZFCUMNGOU-UHFFFAOYSA-N HMDB04085 Thr-Trp-Pro 8.26452369 402.1896621 Asn-Leu-Pro-Pro 10.25012201 439.2430298 NAD+ 13.62606163 331.5543906 C00003 BAWFJGJZGIEFAR-NNYOXOHSSA-O HMDB00902 Glu-Ile-Gln-Lys 11.59774766 516.2906083 Arg-Leu-Lys-Asp 11.36036205 530.3177619 3Z,6Z,9Z,12Z,15Z-Tricosapentaene 7.571835089 331.3234693 LMFA11000180 WZOLXZVFYDHGLR-CUUFJFTBSA-N LysoPE(18:1) 4.436861517 465.3220168 LMGP02060004 CDONWGCJDDHTLP-DJYGDJEFSA-N Bis(2-ethylhexyl)phthalate 3.84100287 390.2768323 C03690 BJQHLKABXJIVAM-UHFFFAOYSA-N LysoPC(O-16:1) 4.370690087 479.337607 LMGP01060029 PLQWZMJRHVARFU-NFPSEPLVSA-N LysoPC(16:0) 4.409481401 495.3328021 C04230 LMGP01050018 ASWBNKHCZGQVJV-HSZRJFAPSA-N HMDB10382 Pro-Thr-Trp-Pro 7.449984317 499.2424288 Gln-Thr-Trp-Pro 8.124563953 530.2486245 Erythrophleguine 4.012213249 449.277889 C08682 DFDLSTQZQLKKOB-KQYSUTHUSA-N 3-oxohexacosanoic acid 7.535328984 427.4023599 LMFA01060181 PJQXMTFEXFYZCU-UHFFFAOYSA-N LysoPC(18:1) 4.347540704 521.3482988 LMGP01050106 HEEMBWYZIJABCR-ZXAYODBVSA-N LysoPC(18:0) 4.324089769 523.364058 C04230 LMGP01050026 IHNKQIMGVNPMTC-RUZDIDTESA-N HMDB10384 [ST (3:0)] cholest-5Z,7Z,24-trien-3beta-ol 4.72728236 382.3228577 C05107 LMST01010121 RUSSPKPUXDSHNC-DDPQNLDTSA-N HMDB03896 [ST] (5Z,7E)-9,10-seco-5,7,10(19)-cholestatriene 5.217339824 368.3441806 LMST03020618 FXKMDILIEQILCA-VDVRBEGSSA-N 5beta-cholestan-3alpha,4alpha,11beta,12beta,21-pentol-3,21-disulphate 3.709130361 612.2636822 LMST01010329 KLTBPPZMCKDFRK-KZIJYIICSA-N PD 123177 7.444916678 497.2438496 C15552 KLVDUSUYBDMJKR-UHFFFAOYSA-N (24R,24'R)-Fucosterol epoxide 3.770307855 428.3654087 C03910 LMST01040151 XUBCLKHKJZCPFZ-UMKPQZCOSA-N Phosphonoacetaldehyde 14.40390623 123.9923176 C03167 YEMKIGUKNDOZEG-UHFFFAOYSA-N DG(32:0) 3.703869181 585.532978 PE(32:0) 3.735248743 691.514599 SM(d32:1) 4.166576409 674.5348039 LMSP03010035 RPTUKVYGSPDHGQ-PSALXKTOSA-N PC(30:0) 3.959066043 705.5297884 LMGP01010702 RFVFQQWKPSOBED-PSXMRANNSA-N SM(d33:1) 4.143490395 688.5510369 LMSP03010037 CGMZWBZSOINWHL-YPDYIYJKSA-N DG(36:2) 3.71350149 637.563827 C00165 LMGL02010049 AFSHUZFNMVJNKX-LLWMBOQKSA-N HMDB07218 SM(d34:2) 4.132071379 700.5505809 LMSP03010040 QQFVICUNTBNUKN-QQRIYSRRSA-N SM(d34:1) 4.126631438 702.5667045 LMSP03010042 OQCPQFVKIYWGRP-GWQJGLRPSA-N L-Alanine 14.53932497 89.04768781 C00041 QNAYBMKLOCPYGJ-REOHCLBHSA-N HMDB00161 PS(34:1) 3.613212254 761.5190126 QRWCPZZFGKGUHF-FQGNUJBYSA-N PS(34:0) 3.583463839 763.5345318 WZFUPCSEUKNOBF-AARKOHAPSA-N PE(35:1) 4.539295556 731.5454832 LMGP02010509 JKNRVUASURIXEH-YWTUKGCKSA-N PC(32:0) 3.918642138 733.5609866 NRPOMZRRLOEOKX-KXQOOQHDSA-N PS(36:5) 3.654520124 781.4879265 BUZGPRVYXXZJOM-LCWFRSHRSA-N PS(36:4) 3.631784293 783.5034415 ZTNFQEXYTMNFHG-SOFXVBFTSA-N PS(36:3) 3.61160975 785.5194368 MWONMGIZXLAUBR-KSXMTAOISA-M PC(34:2) 3.890183335 757.5607464 LMGP01020033 PXPSGTINXJQLBR-VQJSHJPSSA-N [SP (24:0)] N-(15Z-tetracosenoyl)-sphing-4-enine 3.706098959 647.6211026 C00195 LMSP02010009 VJSBNBBOSZJDKB-KPEYJIHVSA-N HMDB04953 PS(36:0) 3.574923581 791.565528 TZCPCKNHXULUIY-RGULYWFUSA-N PC(34:1) 3.893671072 759.576196 PE(38:1) 3.867279483 773.5926925 VDNXNFMAFDYQSI-JHWHEROUSA-N PC(36:4) 4.204135209 781.5598157 LMGP01040051 HVVJCLFLKMGEIY-SJARJILFSA-N PE(39:2) 4.310111966 785.5917525 LMGP02010813 SEHASXPRKLRHPR-VZDDXLEPSA-N [PI(36:0) 3.62775673 879.5818983 LMGP06010002 BNQXGMKDXNGGJW-ORROODQUSA-N SM(d40:2) 4.093200635 784.6454269 LMSP03010071 FOULCGVQZYQEQM-DNXGLLHMSA-N PC(38:6) 3.830071081 805.5605928 PC(38:5) 3.830632062 807.5763839 PC(38:2) 3.804719174 835.6059248 SM(d42:3) 4.01855482 810.6616726 LMSP03010080 TXFLWJQVQCDUDZ-BRUGZULGSA-N SM(d18:1/24:1(15Z)) 4.021738468 812.6760397 C00550 LMSP03010007 WKZHECFHXLTOLJ-QYKFWSDSSA-O HMDB12107 PC(40:7) 3.825963204 831.5755358 ZEAKXAXFIRHBSN-WDYLLCCDSA-N PC(40:6) 3.798634919 833.5917737 FAUYAENFVCNTAL-PFFNLMTBSA-N Diethanolamine 19.92169246 105.0790118 C06772 ZBCBWPMODOFKDW-UHFFFAOYSA-N HMDB04437 Phosphodimethylethanolamine 13.54938777 169.0503178 C13482 BLHVJAAEHMLMOI-UHFFFAOYSA-N Creatine 14.23474742 131.0694355 C00300 CVSVTCORWBXHQV-UHFFFAOYSA-N HMDB00064 4-Aminobutanal 10.46945832 87.06837776 C00555 DZQLQEYLEYWJIB-UHFFFAOYSA-N HMDB01080 4-Aminobutanoate 15.02598768 103.0633498 C00334 LMFA01100039 BTCSSZJGUNDROE-UHFFFAOYSA-N HMDB00112 PS(52:0) 3.568215985 1027.77972 LMGP03010041 DMBATYOPPCIICJ-YWPJBLNKSA-N L-Glutamine 14.84924401 146.0691309 C00064 ZDXPYRJPNDTMRX-VKHMYHEASA-N HMDB00641 D-Ribose 11.62709961 172.0348299 C00121 HMFHBZSHGGEWLO-SOOFDHNKSA-N HMDB00283 Piperidine 10.45104184 85.08909812 C01746 NQRYJNQNLNOLGT-UHFFFAOYSA-N L-Valine 11.77571836 117.0789823 C00183 KZSNJWFQEVHDMF-BYPYZUCNSA-N HMDB00883 L-Methionine 11.17294239 149.0510463 C00073 FFEARJCKVFRZRR-BYPYZUCNSA-N HMDB00696 L-Ornithine 22.08594816 132.0899048 C00077 AHLPHDHHMVZTML-BYPYZUCNSA-N HMDB00214 Choline 20.71987347 103.0997208 C00114 OEYIOHPDSNJKLS-UHFFFAOYSA-N HMDB00097 Choline phosphate 14.455695 183.0660648 C00588 YHHSONZFOIEMCP-UHFFFAOYSA-O HMDB01565 Hypoxanthine 9.85511452 136.0385125 C00262 FDGQSTZJBFJUBT-UHFFFAOYSA-N HMDB00157 Adenine 9.063204992 135.0544621 C00147 GFFGJBXGBJISGV-UHFFFAOYSA-N HMDB00034 Guanine 12.05524339 151.049387 C00242 UYTPUPDQBNUYGX-UHFFFAOYSA-N HMDB00132 5,6-Dihydrothymine 14.35124014 128.0585191 C00906 NBAKTGXDIBVZOO-UHFFFAOYSA-N HMDB00079 L-Proline 12.34728618 115.063347 C00148 ONIBWKKTOPOVIA-BYPYZUCNSA-N HMDB00162 5-Aminolevulinate 14.12141722 131.0582903 C00430 LMFA01100055 ZGXJTSGNIOSYLO-UHFFFAOYSA-N HMDB01149 D-Glucono-1,5-lactone 14.20418868 178.047982 C00198 PHOQVHQSTUBQQK-SQOUGZDYSA-N HMDB00150 L-Pipecolate 11.84579824 129.0789744 C00408 HXEACLLIILLPRG-YFKPBYRVSA-N HMDB00716 O-Acetyl-L-homoserine 10.65701518 161.0687987 C01077 FCXZBWSIAGGPCB-YFKPBYRVSA-N FA hydroxy(6:0) 9.293936455 149.1052371 LMFA01050011 NYHNVHGFPZAZGA-UHFFFAOYSA-N HMDB01624 L-Citrulline 15.65706059 175.0956693 C00327 RHGKLRLOHDJJDR-BYPYZUCNSA-N HMDB00904 L-Ieucine 10.31770521 131.0946474 C00123 ROHFNLRQFUQHCH-YFKPBYRVSA-N HMDB00687 N-hydroxyisoleucine 7.530928932 147.0894441 YEGAKLYOVHUQIJ-UHFFFAOYSA-M L-Lysine 22.71763797 146.1055462 C00047 KDXKERNSBIXSRK-YFKPBYRVSA-N HMDB00182 L-Arginine 24.16766964 174.1116821 C00062 ODKSFYDXXFIFQN-BYPYZUCNSA-N HMDB00517 3-deoxy-D-galactose 9.760436697 188.0660085 RUIACMUVCHMOMF-HSUXUTPPSA-N Mannitol 13.6827009 204.0610254 C00392 FBPFZTCFMRRESA-UHFFFAOYSA-N HMDB00765 Nicotinate 7.688354252 123.0320251 C00253 PVNIIMVLHYAWGP-UHFFFAOYSA-N HMDB01488 Nicotinamide 6.538797962 122.048019 C00153 DFPAKSUCGFBDDF-UHFFFAOYSA-N HMDB01406 2,3-Dimethylmaleate 14.312006 144.0422363 C00922 CGBYBGVMDAPUIH-ARJAWSKDSA-N 3-(Pyrazol-1-yl)-L-alanine 15.37892007 155.0695247 C01162 PIGOPELHGLPKLL-YFKPBYRVSA-N L-beta-aspartyl-L-alanine 14.81313451 204.0749147 ARSVRKCVNFIICJ-UHFFFAOYSA-N HMDB11162 Ala-Asn 12.94743853 203.0906024 α-(2,6-anhydro-3-deoxy-D-arabino-heptulopyranosid)onate 7-phosphate 16.3781175 272.0298961 N5-acetyl-N5-hydroxy-L-ornithine 11.1557753 190.0953085 Sedoheptulose 14.37020037 232.0557803 C02076 HAIWUXASLYEWLM-QTSLKERKSA-N HMDB03219 4-Trimethylammoniobutanoate 12.71464264 145.1102196 C01181 JHPNVNIEXXLNTR-UHFFFAOYSA-O HMDB01161 L-Carnitine 12.68039282 161.1050979 C00487 PHIQHXFUZVPYII-UHFFFAOYSA-O HMDB00062 MOPS 6.856913801 209.072179 DVLFYONBTKHTER-UHFFFAOYSA-N Pyridoxine 7.816578674 169.0738784 C00314 LXNHXLLTXMVWPM-UHFFFAOYSA-N HMDB00239 Ala-Pro 11.37787707 186.1004529 WPWUFUBLGADILS-WDSKDSINSA-N Proclavaminic acid 12.99205127 202.0952811 C06658 NMCINKPVAOXDJH-VDTYLAMSSA-N Glycyl-leucine 12.3560902 188.1159814 C02155 DKEXFJVMVGETOO-LURJTMIESA-N HMDB00759 D-Mycinose 9.457121946 209.126215 C11913 SXWBIRCAXZNEGK-RTRLPJTCSA-N Gly-Arg 17.03122946 231.1330138 Methacholine 12.64798305 159.1258305 C07471 NZWOPGCLSHLLPA-UHFFFAOYSA-N Ne,Ne dimethyllysine 21.18721394 174.1368788 C05545 HMDB13287 HEPES 10.47839518 238.0981398 JKMHFZQWWAIEOD-UHFFFAOYSA-N Arg-OEt 21.32880495 202.143022 C01404 AKGWUHIOEVNNPC-LURJTMIESA-N sn-glycero-3-Phosphocholine 13.83882522 257.1025815 C00670 SUHOQUVVVLNYQR-MRVPVSSYSA-O HMDB00086 L-Phenylalanine 9.712372278 165.0790371 C00079 COLNVLDHVKWLRT-QMMMGPOBSA-N HMDB00159 L-Tyrosine 12.7796904 181.0739427 C00082 OUYCCCASQSFEME-QMMMGPOBSA-N HMDB00158 4-(L-Alanin-3-yl)-2-hydroxy-cis,cis-muconate 6-semialdehyde 14.50328947 229.058739 C04796 FNEGJFDTWWXQES-QTWONPPNSA-N Temurin 9.451314831 224.0909345 QGDOQULISIQFHQ-UHFFFAOYSA-N HMDB04328 Dihydrobiopterin 10.05805288 239.1022917 C00268 ZHQJVZLJDXWFFX-RPDRRWSUSA-N HMDB02215 Aspartyl-L-proline 15.52770558 230.0901544 UKGGPJNBONZZCM-WDSKDSINSA-N HMDB02335 (6R)-6-(L-Erythro-1,2-Dihydroxypropyl)-5,6,7,8-tetrahydro-4a-hydroxypterin 11.9166591 226.1065675 C06486 HMDB12482 Furfural diethyl acetal 4.659711865 170.0941914 C14280 SEILDMUKBMYIEZ-UHFFFAOYSA-N Hercynine 11.62189297 197.1165046 C05575 GPPYTCRVKHULJH-QMMMGPOBSA-O Ergothioneine 14.6066811 229.0881905 C05570 SSISHJJTAXXQAX-ZETCQYMHSA-O HMDB03045 Asn-Pro 13.37873199 229.1061558 Asp-Gln 15.85902646 261.0961876 gamma-Glutamyl-gamma-aminobutyraldehyde 11.48874071 216.1108763 C15700 JZNLEPLZUABCSQ-ZETCQYMHSA-N gamma-Glutamyl-gamma-aminobutyrate 14.20236411 232.1057788 C15767 MKYPKZSGLSOGLL-LURJTMIESA-N HMDB12161 Glu-Thr 14.58643839 248.1007337 Ala-Asn-Gly 13.58673665 260.1120855 9-Oxononanoic acid 4.58999526 172.1098618 C16322 LMFA01060160 WLGDDELKYAWBBL-UHFFFAOYSA-N Azelaic acid 11.34874212 188.1052781 C08261 LMFA01170054 BDJRBEYXGGNYIS-UHFFFAOYSA-N HMDB00784 Ala-Ala-Ser 12.0753807 247.1166056 O-Acetylcarnitine 10.24917499 203.1155053 C02571 RDHQFKQIGNGIED-MRVPVSSYSA-O HMDB00201 Muramic acid 14.38303693 251.1004931 C06470 MSFSPUZXLOGKHJ-PGYHGBPZSA-N HMDB03254 Ile-Ser 8.116677663 218.1264912 gamma-L-Glutamylputrescine 16.34714628 217.1425971 C15699 WKGTVHGVLRCTCF-ZETCQYMHSA-N HMDB12230 beta-Alanyl-L-arginine 16.36262073 245.1488339 C05340 DLRGFJGVZXSSTP-LURJTMIESA-N Ser-Arg 16.31306818 261.144123 butyrylcholine 7.528900919 173.1415814 YRIBGSCJIMXMPJ-UHFFFAOYSA-N HMDB13223 N6,N6,N6-Trimethyl-L-lysine 21.39064769 188.1525455 C03793 MXNRLFUSFKVQSK-QMMMGPOBSA-N HMDB01325 METABOLITES_END #END