#METABOLOMICS WORKBENCH ZhanZZ_20231123_204440 DATATRACK_ID:4473 STUDY_ID:ST002989 ANALYSIS_ID:AN004909 PROJECT_ID:PR001861 VERSION 1 CREATED_ON November 29, 2023, 8:47 am #PROJECT PR:PROJECT_TITLE Metabolic profiling of NPM1-deficient reparative BMDMs PR:PROJECT_SUMMARY BMDMs (1×107) were either induced toward the reparative phenotype as described PR:PROJECT_SUMMARY above or left unstimulated. These BMDMs were then used to perform a metabolomics PR:PROJECT_SUMMARY assay at Shanghai Biotree Biotech Co. Ltd. (China). Briefly, for each sample, PR:PROJECT_SUMMARY 500 μl precooled MeOH/H2O (3/1, v/v) was added in. The samples were then PR:PROJECT_SUMMARY vortexed for 30 sec. After precooling in dry ice, the samples were frozen and PR:PROJECT_SUMMARY thawed three times in liquid nitrogen. They were then vortexed for 30 sec and PR:PROJECT_SUMMARY sonicated for 15 min in an ice-water bath. Next, as a subsequent step, the PR:PROJECT_SUMMARY samples were incubated at -40 °C for 1 h and centrifuged at 12000 rpm for 15 PR:PROJECT_SUMMARY min at 4 °C (RCF = 13800 g, R = 8.6 cm). Afterwards, an aliquot of 400 μl of PR:PROJECT_SUMMARY clear supernatant was collected and dried by spinning. As a reconstitution PR:PROJECT_SUMMARY solution, mix 200 ml of ultrapure water with the residue. The reconstituted PR:PROJECT_SUMMARY samples were vortexed before passing through the filter of the centrifuge tube, PR:PROJECT_SUMMARY after which they were transferred to inserts in injection vials for HPLC-MS/MS PR:PROJECT_SUMMARY analysis. The HPIC separation was carried out using an Thermo Scientific Dionex PR:PROJECT_SUMMARY ICS-6000 HPIC System (Thermo Scientific), equipped with Dionex IonPac AS11-HC PR:PROJECT_SUMMARY (2× 250 mm) and AG11-HC (2 mm×50 mm) columns. An AB SCIEX 6500 QTRAP+ triple PR:PROJECT_SUMMARY quadrupole mass spectrometer (AB Sciex), equipped with an electrospray PR:PROJECT_SUMMARY ionization (ESI) interface, in multiple reaction monitoring (MRM) mode, was PR:PROJECT_SUMMARY applied for assay development. AB SCIEX Analyst Work Station Software (1.6.3 AB PR:PROJECT_SUMMARY SCIEX), MultiQuant 3.0.3. software and Chromeleon7 were employed for MRM data PR:PROJECT_SUMMARY acquisition and processing. The finalized dataset, inclusive of compound name, PR:PROJECT_SUMMARY sample name, and concentration, was imported into SIMCA 16.0.2 software PR:PROJECT_SUMMARY (Sartorius Stedim Data Analytics AB, Umea, Sweden) for comprehensive PR:PROJECT_SUMMARY multivariate analysis. The data were subjected to scaling and logarithmic PR:PROJECT_SUMMARY transformation to mitigate the effects of noise and excessive variance of the PR:PROJECT_SUMMARY variables. After that, we utilized the R packages tidyverse, dplyr, magrittr, PR:PROJECT_SUMMARY ggplot2, and ggrepel for data analysis and the construction of a volcano plot. PR:PROJECT_SUMMARY Additionally, the R packages circlize and reshape2 were employed in the creation PR:PROJECT_SUMMARY of a chord diagram. For the generation of a heatmap, we made use of the R PR:PROJECT_SUMMARY package pheatmap. PR:INSTITUTE Renji Hospital, Shanghai Jiao Tong University School of Medicine PR:LAST_NAME Zhan PR:FIRST_NAME Zhenzhen PR:ADDRESS 160 Pujian Road, Shanghai, Shanghai, 200127, China PR:EMAIL zhanzz2022@sjtu.edu.cn PR:PHONE 86-21-61569249 #STUDY ST:STUDY_TITLE Targeting NPM1 Epigenetically Promotes Post-infarction Cardiac Repair by ST:STUDY_TITLE Reprogramming Reparative Macrophage Metabolism ST:STUDY_SUMMARY Reparative macrophages play a crucial role in limiting excessive fibrosis and ST:STUDY_SUMMARY promoting cardiac repair after myocardial infarction (MI), highlighting the ST:STUDY_SUMMARY significance of enhancing their reparative phenotype for wound healing. ST:STUDY_SUMMARY Metabolic adaptation orchestrates the phenotypic transition of macrophages; ST:STUDY_SUMMARY however, the precise mechanisms governing metabolic reprogramming of cardiac ST:STUDY_SUMMARY reparative macrophages remain poorly understood. In this study, we investigated ST:STUDY_SUMMARY the role of Nucleophosmin 1 (NPM1) in the metabolic and phenotypic shift of ST:STUDY_SUMMARY cardiac macrophages in the context of MI, and explored the effect of targeting ST:STUDY_SUMMARY NPM1 for ischemic tissue repair. ST:INSTITUTE Renji Hospital, Shanghai Jiao Tong University School of Medicine ST:LAST_NAME Zhan ST:FIRST_NAME Zhenzhen ST:ADDRESS 160 Pujian Road, Shanghai, Shanghai, 200127, China ST:EMAIL zhanzz2022@sjtu.edu.cn ST:PHONE 86-21-61569249 #SUBJECT SU:SUBJECT_TYPE Mammal SU:SUBJECT_SPECIES Mus musculus SU:TAXONOMY_ID 10090 #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 - G1.1 Genotype:Wild-type Treatment=IL-4; RAW_FILE_NAME=G1.1.mzML SUBJECT_SAMPLE_FACTORS - G1.2 Genotype:Wild-type Treatment=IL-4; RAW_FILE_NAME=G1.2.mzML SUBJECT_SAMPLE_FACTORS - G1.3 Genotype:Wild-type Treatment=IL-4; RAW_FILE_NAME=G1.3.mzML SUBJECT_SAMPLE_FACTORS - G1.4 Genotype:Wild-type Treatment=IL-4; RAW_FILE_NAME=G1.4.mzML SUBJECT_SAMPLE_FACTORS - G1.5 Genotype:Wild-type Treatment=IL-4; RAW_FILE_NAME=G1.5.mzML SUBJECT_SAMPLE_FACTORS - G1.6 Genotype:Wild-type Treatment=IL-4; RAW_FILE_NAME=G1.6.mzML SUBJECT_SAMPLE_FACTORS - G1.7 Genotype:Wild-type Treatment=IL-4; RAW_FILE_NAME=G1.7.mzML SUBJECT_SAMPLE_FACTORS - G1.8 Genotype:Wild-type Treatment=IL-4; RAW_FILE_NAME=G1.8.mzML SUBJECT_SAMPLE_FACTORS - G2.1 Genotype:Npm1-knockout Treatment=IL-4; RAW_FILE_NAME=G2.1.mzML SUBJECT_SAMPLE_FACTORS - G2.2 Genotype:Npm1-knockout Treatment=IL-4; RAW_FILE_NAME=G2.2.mzML SUBJECT_SAMPLE_FACTORS - G2.3 Genotype:Npm1-knockout Treatment=IL-4; RAW_FILE_NAME=G2.3.mzML SUBJECT_SAMPLE_FACTORS - G2.4 Genotype:Npm1-knockout Treatment=IL-4; RAW_FILE_NAME=G2.4.mzML SUBJECT_SAMPLE_FACTORS - G2.5 Genotype:Npm1-knockout Treatment=IL-4; RAW_FILE_NAME=G2.5.mzML SUBJECT_SAMPLE_FACTORS - G2.6 Genotype:Npm1-knockout Treatment=IL-4; RAW_FILE_NAME=G2.6.mzML SUBJECT_SAMPLE_FACTORS - G2.7 Genotype:Npm1-knockout Treatment=IL-4; RAW_FILE_NAME=G2.7.mzML SUBJECT_SAMPLE_FACTORS - G2.8 Genotype:Npm1-knockout Treatment=IL-4; RAW_FILE_NAME=G2.8.mzML #COLLECTION CO:COLLECTION_SUMMARY BMDMs (1×10^7) were induced toward the reparative phenotype using recombinant CO:COLLECTION_SUMMARY murine IL-4.BMDMs were counted and washed with PBS. CO:SAMPLE_TYPE Bone marrow #TREATMENT TR:TREATMENT_SUMMARY mouse bone marrow cells were flushed out from mouse femurs using RPMI 1640 and TR:TREATMENT_SUMMARY cultured in a complete RPMI 1640 medium (added with 10% fetal bovine serum and TR:TREATMENT_SUMMARY 1% penicillin/streptomycin) supplemented with 20 ng/ml M-CSF for 7 days to TR:TREATMENT_SUMMARY generate mature BMDMs. BMDMs were stimulated with 20 ng/ml IL-4 for 12 h to TR:TREATMENT_SUMMARY induce a reparative phenotype. #SAMPLEPREP SP:SAMPLEPREP_SUMMARY For each sample, 500 μl precooled MeOH/H2O (3/1, v/v) was added in. The samples SP:SAMPLEPREP_SUMMARY were then vortexed for 30 sec. After precooling in dry ice, the samples were SP:SAMPLEPREP_SUMMARY frozen and thawed three times in liquid nitrogen. They were then vortexed for 30 SP:SAMPLEPREP_SUMMARY sec and sonicated for 15 min in an ice-water bath. Next, as a subsequent step, SP:SAMPLEPREP_SUMMARY the samples were incubated at -40 °C for 1 h and centrifuged at 12000 rpm for SP:SAMPLEPREP_SUMMARY 15 min at 4 °C (RCF = 13800 g, R = 8.6 cm). Afterwards, an aliquot of 400 μl SP:SAMPLEPREP_SUMMARY of clear supernatant was collected and dried by spinning. As a reconstitution SP:SAMPLEPREP_SUMMARY solution, mix 200 ml of ultrapure water with the residue. The reconstituted SP:SAMPLEPREP_SUMMARY samples were vortexed before passing through the filter of the centrifuge tube, SP:SAMPLEPREP_SUMMARY after which they were transferred to inserts in injection vials for HPLC-MS/MS SP:SAMPLEPREP_SUMMARY analysis. #CHROMATOGRAPHY CH:CHROMATOGRAPHY_TYPE Ion exchange CH:INSTRUMENT_NAME Thermo Scientific Dionex ICS-6000 HPIC CH:COLUMN_NAME Dionex IonPac AS11-HC (250 × 2mm, 9um, 2000Ã) and AG11-HC (50 × 2 mm, CH:COLUMN_NAME 13um) CH:SOLVENT_A 100 mM NaOH/water; water CH:SOLVENT_B water CH:SOLVENT_C 2 mM acetic acid in methanol CH:FLOW_GRADIENT 0.15 mL/min: 0min:20%/80%, 3.01min:20%/80%,12min:50%/50%, 21min:100%/100%, CH:FLOW_GRADIENT 26min:100%/100%, 26.1min:20%/80%,0min:80%/20%, 30min:80%/20% CH:FLOW_RATE 0.15 mL/min CH:COLUMN_TEMPERATURE 30 ℃ #ANALYSIS AN:ANALYSIS_TYPE MS #MS MS:INSTRUMENT_NAME ABI Sciex 6500+ MS:INSTRUMENT_TYPE QTRAP MS:MS_TYPE ESI MS:ION_MODE UNSPECIFIED MS:MS_COMMENTS AB SCIEX Analyst Work Station Software (1.6.3 AB SCIEX), MultiQuant MS:MS_COMMENTS 3.0.3.software and Chromeleon7 were employed for MRM data acquisition and MS:MS_COMMENTS processing. #MS_METABOLITE_DATA MS_METABOLITE_DATA:UNITS pmol MS_METABOLITE_DATA_START Samples G1.1 G1.2 G1.3 G1.4 G1.5 G1.6 G1.7 G1.8 G2.1 G2.2 G2.3 G2.4 G2.5 G2.6 G2.7 G2.8 Factors Genotype:Wild-type Genotype:Wild-type Genotype:Wild-type Genotype:Wild-type Genotype:Wild-type Genotype:Wild-type Genotype:Wild-type Genotype:Wild-type Genotype:Npm1-knockout Genotype:Npm1-knockout Genotype:Npm1-knockout Genotype:Npm1-knockout Genotype:Npm1-knockout Genotype:Npm1-knockout Genotype:Npm1-knockout Genotype:Npm1-knockout 2-Hydroxyglutaric acid 353.56935 286.052825 272.18305 282.9775 239.459175 231.02065 424.797925 340.7256 228.3125088 221.9584252 236.7526931 288.9175097 299.9956142 249.488631 283.1123649 319.2852282 2-Isopropylmalic acid 0.9983 2.22485 1.34145 2.02645 1.675625 1.95355 2.642275 1.66305 2.508801918 2.447072767 2.43124356 2.641776648 2.583294632 2.535454724 1.931518668 2.819041185 3-Phosphoglyceric acid 662.716875 602.808875 572.15265 524.734 463.308625 635.65915 676.59855 506.1987 1371.690532 1240.373248 1363.876254 964.2621714 675.422913 714.2932569 982.1174217 891.5440832 4-Hydroxyphenylpyruvic acid 81.3248 96.284175 93.56405 84.309575 99.989375 94.12045 87.942 91.0897 122.1228408 98.08766312 61.52194483 41.64580102 34.27246617 49.44260163 69.91575844 76.30630261 6-Phosphogluconic acid 240.5202 118.50755 94.94755 96.25725 208.67475 299.734575 61.190625 29.993825 2089.805422 1126.168022 2045.773817 1550.940041 1189.820744 618.0879713 698.801929 654.9214016 Adenosine diphosphate 2114.284425 36.3303 22.5604 1305.470875 1001.837425 27.086525 2846.81925 768.754775 246.5635409 150.6115049 158.577258 210.3189543 230.9646058 154.7419443 208.1178201 176.8085079 Adenosine triphosphate 1151.344325 451.242 306.68855 32.6418 955.101 383.8435 29.38434418 16.81402494 18.35588701 29.57093422 52.61077333 11.55427639 19.51661074 13.16886605 alpha-Ketoglutaric acid 46.966425 42.69085 28.317425 22.268875 30.4687 17.7156 24.656575 54.2128 104.7069477 227.8293493 324.8937877 427.5779611 161.9903358 226.5613289 310.6725448 105.3285927 alpha-Ketoisovaleric acid 25.363475 22.25485 16.678125 17.108875 18.335575 15.863825 16.758275 18.602575 56.8180971 67.32409939 153.3764063 115.7874865 73.55982223 86.6117799 69.80701848 56.48264555 cis-Aconitic acid 142.72585 78.073575 59.35565 61.885475 60.217275 73.642875 54.870625 67.2949 44.1868953 47.08093876 42.9280689 48.77017857 63.2198374 41.3403344 47.48063324 62.95108537 Citric acid 10861.06818 6320.028325 5254.9558 5318.3068 5790.589625 5948.684775 4920.32775 5889.8297 1470.137788 1822.039889 1617.594548 1797.215163 2019.103682 1612.570293 2045.675616 2598.775782 Cyclic 3',5'-AMP 2.4274 2.700175 1.7547 2.82715 2.063525 1.476475 3.1914 2.3114 1.127090398 0.559968002 0.588582005 0.872871475 0.918696002 0.773300193 0.775131339 0.825607328 Cysteic acid 23.6559 34.77775 24.7695 19.988625 38.222225 36.519525 27.833225 22.15095 22.4449095 29.59169437 26.2065915 19.62099371 20.02688361 17.44688431 22.95097957 21.12511369 Dihydroxyacetone phosphate 108.8036 5.231825 1.517725 8.479625 44.45085 52.816875 3.947717022 2.130330769 1.720359284 3.016108964 2.877974999 2.121851729 1.211040243 2.45501641 Erythrose 4-phosphate 164.9558617 90.29594313 82.66809379 77.01068887 152.3298416 203.9690535 2188.542304 1250.506069 2124.983126 1591.68055 1220.954712 736.7872766 803.2816613 775.5216648 Flavin mononucleotide 204.208275 104.122475 141.716 141.9549 63.9606 118.497375 75.5057 76.8903 11.59709649 20.51669325 27.35110786 26.99196743 11.00362564 28.48225136 24.82489916 23.28291556 Flavine-adenine dinucleotide 21.019175 75.79235 36.160925 43.942825 68.763325 29.230475 67.936625 61.2197 53.81868162 42.27086514 41.62153622 47.54833205 50.839745 28.55180846 38.99803906 33.06660901 Fructose 1,6-bisphosphate 611.176075 36.5929 14.30885 49.965075 12.2116 251.541975 304.56045 94.06668043 87.10310608 83.70723932 96.03520149 94.61920482 83.93948939 67.56516889 100.1152065 Fructose 6-phosphate 155.41775 141.25605 105.980425 77.46165 120.2498 113.6612 61.217525 48.223225 654.2762055 548.4679478 609.4765139 370.863175 304.065568 571.3848644 408.0286632 674.0641751 Fumaric acid 960.33405 795.787775 746.7286 768.102225 682.651825 692.1097 633.1991 647.9366 1101.39748 957.8690712 919.5849389 951.0395128 886.1094843 1190.989904 912.0767175 1083.759618 Glucaric acid 16.189625 19.0524 14.237975 14.0773 15.18215 14.886475 12.81655 12.56145 14.8300905 16.56604766 17.7126193 14.93140445 14.23653405 13.88423373 16.03674149 18.67948891 Gluconic acid 329.673025 275.73665 276.759625 287.322675 184.49395 186.7567 329.347775 348.3432 163.0151055 190.3151584 175.7770048 204.2375119 210.7861738 145.1066916 173.1577766 175.5066298 Glucose 6-phosphate 638.693875 283.901 276.5219 255.635025 187.336025 282.099575 217.861225 117.332275 3261.805574 2202.462296 2668.56532 1544.435977 1369.535684 2613.516311 1519.9425 2947.531881 Glucuronic acid 34.534125 36.766075 30.176075 26.037375 29.171675 31.14115 29.993675 30.099925 14.3474459 19.69507163 18.65107681 18.24964337 22.38355634 18.73940312 20.33668719 24.50621448 Glyceric acid 67.969925 52.161725 59.43455 49.92865 41.689075 46.06175 49.9907 50.25775 318.3611303 276.2499055 299.8091892 369.4888966 488.0762279 312.6117377 178.3615004 372.39925 Glycerol 3-phosphate 658.4046 705.461825 699.258325 623.0087 672.65575 749.49825 364.101425 332.71955 756.5621292 600.4178923 549.0117924 450.4658677 432.8545014 346.0969149 565.6869013 395.9758102 Glycolic acid 59.32735 48.404275 44.45485 33.05985 38.328725 42.4541 49.348775 57.621375 207.0821493 176.7924961 173.3681844 225.9544584 233.6445147 187.0015716 142.6359213 232.1491296 Glyoxylic acid 49.66495 91.303625 70.2327 62.345575 67.101225 60.5451 61.49945 74.292825 17.04075284 21.79654614 13.21698472 16.74906442 17.87327617 14.94416849 13.03106174 23.65371715 Guanosine diphosphate 800.49475 221.124175 378.470325 664.5608 454.166875 161.91735 659.957775 710.10885 135.840589 62.30172478 101.9952335 91.8183564 64.90023695 69.85004813 110.2555808 66.67535604 Guanosine triphosphate 507.530375 41.1526 55.256975 241.940175 147.3307 53.1318 326.832575 430.661575 17.05777751 8.404034986 11.49729539 19.30266828 16.9905775 8.145539998 9.588230157 8.954586742 Hippuric acid 84.891125 94.045825 92.576925 87.391925 93.73615 91.98465 79.02665 91.05205 115.6508565 94.4445708 56.74161605 37.14462858 32.3259329 46.39041421 62.45705733 72.58557897 Homogentisic acid 52.152675 54.955825 52.250025 49.65575 55.129275 55.50655 56.384375 57.94735 30.50616027 34.44649776 27.77981318 20.06063751 16.89871028 23.21529573 26.12690709 29.1119375 Indoleacetic acid 142.39365 79.432525 61.2998 63.41835 60.503775 73.27235 54.649925 67.5647 44.75567062 48.59103904 43.46979046 50.52439511 63.26921334 40.4689789 46.7224165 65.13213063 L-Lactic acid 25065.27828 24975.23693 23473.99115 22571.72168 20923.24483 20671.19365 17124.54673 19895.49365 17102.27453 14433.65165 15865.38718 13853.33711 13542.35555 16384.47102 12177.25791 17099.54674 Maleic acid 6.396475 6.00105 5.386175 5.81885 3.972775 5.784375 4.8998 4.280025 6.64044072 6.352010205 6.937068082 6.328437127 6.099886196 4.969111641 4.19636373 7.479738307 Malic acid 3704.620975 2850.2124 2190.42265 2360.80625 2299.418425 2281.157425 3131.52355 2502.99705 4024.259647 3586.658291 3568.899033 4202.086225 4091.850765 4594.223061 3198.257948 4494.183008 Mannose 6-phosphate 126.0992 101.2012 87.337 87.544325 83.9294 104.46065 66.09015 56.46215 436.3181666 372.05325 458.7579581 143.7807584 86.45796831 335.3812148 261.3273107 376.2001876 Methylmalonic acid 16.52332045 20.99338638 16.95372154 16.26431332 18.06796292 19.4371785 112.447279 67.80503481 12.14972528 21.7805212 25.04508238 16.83265503 15.468153 18.79340476 28.3054678 35.44349891 Mevalonic acid 0.486925 0.389125 0.5372 0.324675 0.458075 0.3971 0.2896 0.413325 0.27900286 0.347683143 0.344735062 0.209994081 0.191168826 0.405349386 0.416508146 0.387094582 Orotic acid 27.109175 17.52755 9.56325 10.0463 15.0174 13.544375 7.8337 10.629225 7.131975184 6.43913042 6.597807868 7.857658349 8.864492369 8.021338855 4.762920753 8.268447574 Phosphoenolpyruvic acid 91.91465 122.944675 200.33355 142.79705 43.9814 153.5757 263.77065 121.0941 809.0013843 710.342385 900.9907031 384.5843352 161.3744071 244.4300173 549.8648826 329.6930166 Picolinic acid 47.17525 52.596475 49.8011 46.6176 54.910025 56.706625 53.210975 52.843925 28.24978753 30.727252 25.71476053 17.8783955 17.16871072 20.16074293 23.06379307 26.62568835 Pyruvic acid 429.733975 886.8944 427.414175 176.1382 206.118575 256.092925 168.96895 133.7453 950.3275155 2303.647996 2346.925922 2474.728783 975.2839205 1699.815637 1674.117414 2720.321101 Quinolinic acid 49.595025 53.80185 50.375375 49.308875 55.205275 55.973475 54.340425 55.984475 29.84466832 33.87101401 26.99624083 20.42697036 18.39348717 20.30238776 26.2447505 28.58744371 Ribose 5-phosphate 159.814975 574.424875 500.873075 282.7686 188.70095 194.9397 400.7963 281.464025 559.0288284 560.8129937 431.5946565 828.0001311 356.9019853 684.2615519 421.3239898 660.3010248 Sedoheptulose 7-phosphate 101.8683858 523.388219 242.4551751 216.5095357 160.0632227 98.99311641 304.5773304 309.152449 480.4240364 405.3777143 458.8148311 435.391628 345.3297148 457.6057562 655.420462 459.7637579 Succinic acid 3674.601525 4433.571175 4374.13825 4265.9666 3583.39515 3650.1083 7553.247325 5872.130825 692.4150083 1256.898368 1443.501451 1302.665122 1328.17583 1400.07539 1883.699744 1798.962832 Ureidopropionic acid 2.04695 2.381475 2.717725 2.670425 1.524375 1.2909 2.1819 1.71345 7.958298665 5.426703967 6.571685678 6.989716131 10.90366591 5.732122368 2.882234797 5.2282722 MS_METABOLITE_DATA_END #METABOLITES METABOLITES_START metabolite_name KEGG ID 2-Hydroxyglutaric acid C03196 2-Isopropylmalic acid C02504 3-Phosphoglyceric acid C00197 4-Hydroxyphenylpyruvic acid C01179 6-Phosphogluconic acid C00345 Adenosine diphosphate C00008 Adenosine triphosphate C00002 alpha-Ketoglutaric acid C00026 alpha-Ketoisovaleric acid C00141 cis-Aconitic acid C00417 Citric acid C00158 Cyclic 3',5'-AMP C00575 Cysteic acid C00506 Dihydroxyacetone phosphate C00111 Erythrose 4-phosphate C00279 Flavin mononucleotide C00061 Flavine-adenine dinucleotide C00016 Fructose 1,6-bisphosphate C05378 Fructose 6-phosphate C00085 Fumaric acid C00122 Glucaric acid C00818 Gluconic acid C00257 Glucose 6-phosphate C00668 Glucuronic acid C00191 Glyceric acid C00258 Glycerol 3-phosphate C00093 Glycolic acid C00160 Glyoxylic acid C00048 Guanosine diphosphate C00035 Guanosine triphosphate C00044 Hippuric acid C01586 Homogentisic acid C00544 Indoleacetic acid C00954 L-Lactic acid C00186 Maleic acid C01384 Malic acid C00149 Mannose 6-phosphate C00275 Methylmalonic acid C02170 Mevalonic acid C00418 Orotic acid C00295 Phosphoenolpyruvic acid C00074 Picolinic acid C10164 Pyruvic acid C00022 Quinolinic acid C03722 Ribose 5-phosphate C00117 Sedoheptulose 7-phosphate C05382 Succinic acid C00042 Ureidopropionic acid C02642 METABOLITES_END #END