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name Structure Reference Source Properties Activities Metabolism

Antibiotic FR 31564

AlkaPlorer ID: AK016157

Synonym: 'Fosmidomycin', 'FR 31564', 'Antibiotic FR 31564'

IUPAC Name: 3-[formyl(hydroxy)amino]propylphosphonic acid

Structure

SMILES: O=CN(O)CCCP(=O)(O)O

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InChI: InChI=1S/C4H10NO5P/c6-4-5(7)2-1-3-11(8,9)10/h4,7H,1-3H2,(H2,8,9,10)

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InChIKey: GJXWDTUCERCKIX-UHFFFAOYSA-N

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Properties Information

Molecule Weight: 183.1

TPSA？: 98.07

MolLogP？: -0.5982000000000002

Number of H-Donors: 3

Number of H-Acceptors: 3

RingCount: 0

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Acinetobacter Acinetobacter MIC 100.0 ug.mL-1 10.1016/j.bmcl.2011.09.123
Arabidopsis thaliana 1-deoxy-D-xylulose 5-phosphate reductoisomerase, chloroplastic IC50 100.0 nM 10.1002/ps.3479
Bacillus anthracis Bacillus anthracis MIC 0.78 ug.mL-1 10.1016/j.bmcl.2011.09.123
Bacillus anthracis Bacillus anthracis MIC 100000.0 nM 10.1021/jm9012592
Enterococcus faecalis Enterococcus faecalis MIC 200.0 ug.mL-1 10.1016/j.bmcl.2011.09.123
Escherichia coli 1-deoxy-D-xylulose 5-phosphate reductoisomerase IC50 438.0 nM 10.1021/jm5014264
Escherichia coli Escherichia coli GI nan None 10.1016/j.bmc.2016.11.040
Escherichia coli Escherichia coli IC50 220.0 nM 10.1021/jm060492b
Escherichia coli Escherichia coli IZ 0.0 mm 10.1021/jm060492b
Escherichia coli Escherichia coli IZ 19.0 mm 10.1021/jm060492b
Escherichia coli Escherichia coli IZ 20.0 mm 10.1021/jm060492b
Escherichia coli Escherichia coli IZ 34.0 mm 10.1016/j.bmc.2016.11.040
Escherichia coli Escherichia coli MBC 2500.0 uM 10.1021/jm060492b
Escherichia coli Escherichia coli MIC 6.25 ug.mL-1 10.1016/j.bmcl.2011.09.123
Escherichia coli Escherichia coli MIC 12.5 ug.mL-1 10.1016/j.bmcl.2011.09.123
Escherichia coli Escherichia coli MIC 10000.0 nM 10.1021/jm9012592
Escherichia coli Escherichia coli MIC 312000.0 nM 10.1021/jm060492b
Escherichia coli Escherichia coli MIC50 980.0 nM 10.1021/jm5014264
Escherichia coli Escherichia coli MIC50 7800.0 nM 10.1021/jm5014264
Escherichia coli Escherichia coli MIC50 250000.0 nM 10.1021/jm5014264
Escherichia coli Escherichia coli Ratio 0.13 None 10.1021/jm060492b
Escherichia coli K-12 1-deoxyxylulose-5-phosphate reductoisomerase IC50 19.95 nM 10.1021/jm0491501
Escherichia coli K-12 1-deoxyxylulose-5-phosphate reductoisomerase IC50 30.0 nM 10.1016/j.bmcl.2005.12.082
Escherichia coli K-12 1-deoxyxylulose-5-phosphate reductoisomerase IC50 30.0 nM 10.1021/ml100243r
Escherichia coli K-12 1-deoxyxylulose-5-phosphate reductoisomerase IC50 32.0 nM 10.1016/j.bmc.2014.05.004
Escherichia coli K-12 1-deoxyxylulose-5-phosphate reductoisomerase IC50 32.0 nM 10.1021/jm5010978
Escherichia coli K-12 1-deoxyxylulose-5-phosphate reductoisomerase IC50 48.0 nM 10.1021/jm051177c
Escherichia coli K-12 1-deoxyxylulose-5-phosphate reductoisomerase IC50 1853000.0 nM 10.1021/jm060492b
Escherichia coli K-12 1-deoxyxylulose-5-phosphate reductoisomerase Inhibition nan % 10.1038/nchembio.221
Escherichia coli K-12 D-alanylalanine synthetase Inhibition nan % 10.1038/nchembio.221
Escherichia coli K-12 UDP-N-acetylglucosamine 1-carboxyvinyltransferase Inhibition nan % 10.1038/nchembio.221
Escherichia coli K-12 UDP-N-acetylmuramoylalanine--D-glutamate ligase Inhibition nan % 10.1038/nchembio.221
Escherichia coli (strain K12) 4-hydroxy-tetrahydrodipicolinate reductase Inhibition nan % 10.1038/nchembio.221
Escherichia coli (strain K12) 50S ribosomal protein L2 Inhibition nan % 10.1038/nchembio.221
Escherichia coli (strain K12) 50S ribosomal protein L28 Inhibition nan % 10.1038/nchembio.221
Escherichia coli (strain K12) Antitoxin YefM Inhibition nan % 10.1038/nchembio.221
Escherichia coli (strain K12) Cell division protein FtsX Inhibition nan % 10.1038/nchembio.221
Escherichia coli (strain K12) Cell shape-determining protein MreC Inhibition nan % 10.1038/nchembio.221
Escherichia coli (strain K12) Glutamyl-tRNA reductase Inhibition nan % 10.1038/nchembio.221
Escherichia coli (strain K12) Glycerate kinase Inhibition nan % 10.1038/nchembio.221
Escherichia coli (strain K12) Multifunctional CCA protein Inhibition nan % 10.1038/nchembio.221
Escherichia coli (strain K12) Outer membrane FadL protein Inhibition nan % 10.1038/nchembio.221
Escherichia coli (strain K12) Outer membrane protein TolC Inhibition nan % 10.1038/nchembio.221
Escherichia coli (strain K12) Probable phospholipid ABC transporter-binding protein MlaB Inhibition nan % 10.1038/nchembio.221
Escherichia coli (strain K12) Prolipoprotein diacylglyceryl transferase Inhibition nan % 10.1038/nchembio.221
Escherichia coli (strain K12) Thymidylate kinase Inhibition nan % 10.1038/nchembio.221
Escherichia coli (strain K12) Transcriptional regulatory protein BaeR Inhibition nan % 10.1038/nchembio.221
Escherichia coli (strain K12) tRNA(Ile)-lysidine synthase Inhibition nan % 10.1038/nchembio.221
Escherichia coli (strain K12) tRNA threonylcarbamoyladenosine biosynthesis protein TsaE Inhibition nan % 10.1038/nchembio.221
Escherichia coli (strain K12) Uncharacterized protein ydfW in Qin prophage region Inhibition nan % 10.1038/nchembio.221
Escherichia coli (strain K12) Uncharacterized protein YdiL Inhibition nan % 10.1038/nchembio.221
Homo sapiens Homo sapiens Activity 0.3 % 10.1016/j.ejmech.2009.11.034
Homo sapiens MRC5 IC50 62000.0 nM 10.1021/jm200694q
Micrococcus luteus Micrococcus luteus MIC 1000000.0 nM 10.1021/jm9012592
Mycobacterium smegmatis (strain ATCC 700084 / mc(2)155) 1-deoxy-D-xylulose 5-phosphate reductoisomerase IC50 80.0 nM 10.1016/j.ejmech.2012.02.031
Mycobacterium smegmatis (strain ATCC 700084 / mc(2)155) 1-deoxy-D-xylulose 5-phosphate reductoisomerase IC50 510.0 nM 10.1016/j.ejmech.2012.02.031
Mycobacterium tuberculosis 1-deoxy-D-xylulose 5-phosphate reductoisomerase IC50 80.0 nM 10.1016/j.bmcl.2011.07.005
Mycobacterium tuberculosis 1-deoxy-D-xylulose 5-phosphate reductoisomerase IC50 80.0 nM 10.1021/jm200363d
Mycobacterium tuberculosis 1-deoxy-D-xylulose 5-phosphate reductoisomerase IC50 80.0 nM 10.1021/jm4006498
Mycobacterium tuberculosis 1-deoxy-D-xylulose 5-phosphate reductoisomerase IC50 80.0 nM 10.1074/jbc.m701935200
Mycobacterium tuberculosis 1-deoxy-D-xylulose 5-phosphate reductoisomerase IC50 230.0 nM 10.1021/jm4012559
Mycobacterium tuberculosis 1-deoxy-D-xylulose 5-phosphate reductoisomerase IC50 440.0 nM 10.1016/j.bmcl.2013.11.067
Mycobacterium tuberculosis 1-deoxy-D-xylulose 5-phosphate reductoisomerase Kd 40.0 nM 10.1021/jm4006498
Mycobacterium tuberculosis 1-deoxy-D-xylulose 5-phosphate reductoisomerase Ki 140.0 nM 10.1021/jm200363d
Mycobacterium tuberculosis Mycobacterium tuberculosis MIC 500.0 ug.mL-1 10.1016/j.bmcl.2011.09.123
Mycobacterium tuberculosis Mycobacterium tuberculosis MIC99 500.0 ug ml-1 10.1039/c3md00085k
Mycolicibacterium smegmatis Mycolicibacterium smegmatis GI nan None 10.1016/j.bmc.2016.11.040
Mycolicibacterium smegmatis Mycolicibacterium smegmatis GI nan None 10.1016/j.ejmech.2012.02.031
Mycolicibacterium smegmatis Mycolicibacterium smegmatis MIC50 250000.0 nM 10.1021/jm5014264
Plasmodium berghei Plasmodium berghei Activity 92.0 % 10.1021/jm200694q
Plasmodium berghei Plasmodium berghei Activity nan None 10.1021/jm100211e
Plasmodium berghei Plasmodium berghei Inhibition 82.0 % 10.1021/jm100211e
Plasmodium berghei Plasmodium berghei MST 11.5 day 10.1021/jm100211e
Plasmodium berghei Plasmodium berghei Survival nan None 10.1021/jm200694q
Plasmodium falciparum Plasmodium falciparum Activity 100.0 % 10.1016/j.bmcl.2015.02.020
Plasmodium falciparum Plasmodium falciparum EC50 440.0 nM 10.1021/ml300419r
Plasmodium falciparum Plasmodium falciparum EC50 1100.0 nM 10.1021/ml100243r
Plasmodium falciparum Plasmodium falciparum EC50 1170.0 nM 10.1021/ml300419r
Plasmodium falciparum Plasmodium falciparum IC50 290.0 nM 10.1021/acs.jmedchem.5b01485
Plasmodium falciparum Plasmodium falciparum IC50 360.0 nM 10.1016/j.bmcl.2005.12.082
Plasmodium falciparum Plasmodium falciparum IC50 400.0 nM 10.1021/jm051177c
Plasmodium falciparum Plasmodium falciparum IC50 480.0 nM 10.1021/jm051177c
Plasmodium falciparum Plasmodium falciparum IC50 810.0 nM 10.1016/j.bmcl.2015.03.077
Plasmodium falciparum Plasmodium falciparum IC50 810.0 nM 10.1021/jm5019719
Plasmodium falciparum Plasmodium falciparum IC50 880.0 nM 10.1016/j.bmcl.2015.02.020
Plasmodium falciparum Plasmodium falciparum IC50 880.0 nM 10.1021/jm5019719
Plasmodium falciparum Plasmodium falciparum IC50 1000.0 nM 10.1021/jm301577q
Plasmodium falciparum Plasmodium falciparum IC50 1100.0 nM 10.1016/j.bmcl.2005.12.082
Plasmodium falciparum Plasmodium falciparum IC50 1200.0 nM 10.1016/j.bmc.2007.12.001
Plasmodium falciparum Plasmodium falciparum IC50 1300.0 nM 10.1021/jm5019719
Plasmodium falciparum Plasmodium falciparum IC50 1730.0 nM 10.1021/jm100211e
Plasmodium falciparum Plasmodium falciparum IC50 3700.0 nM 10.1021/jm200694q
Plasmodium vinckei Plasmodium vinckei ED90 5.0 mg kg-1 10.1021/acs.jmedchem.5b01485
Plasmodium vinckei Plasmodium vinckei ED90 20.0 mg kg-1 10.1021/acs.jmedchem.5b01485
Pseudomonas aeruginosa Pseudomonas aeruginosa MIC 20000.0 nM 10.1021/jm9012592
Staphylococcus aureus Staphylococcus aureus MIC 200.0 ug.mL-1 10.1016/j.bmcl.2011.09.123
Synechocystis sp. (strain PCC 6803 / Kazusa) 1-deoxyxylulose-5-phosphate reductoisomerase Ki 21.0 nM 10.1016/j.bmcl.2004.08.023
None ADMET CL 3.0 uL.min-1.(10^6cells)-1 10.6019/CHEMBL3301361
None ADMET CL 3.02 mL.min-1.g-1 10.6019/CHEMBL3301361
None ADMET F 30.0 % 10.1021/acs.jmedchem.5b01485
None ADMET log10(%HIA +10) 1.602 None 10.1016/j.ejmech.2010.11.005
None ADMET T1/2 1.0 hr 10.1021/jm200363d
None ADMET T1/2 1.0 hr 10.1021/ml100243r
None ADMET T1/2 1.0 hr 10.1021/ml300419r
None NON-PROTEIN TARGET Hepatotoxicity (acute) 0.0 % 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (animal toxicity known) nan None 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (benign tumour) 0.0 None 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (granulomatous hepatitis) 0.0 None 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (mechanism) nan None 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (moderate) 1.0 None 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (moderate) 7.7 % 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (time to onset) nan None 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Potency 472.8 nM None
None NON-PROTEIN TARGET Potency 530.5 nM None
None Unchecked Hepatotoxicity (acute) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (association with vascular disease) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (choleostasis) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (chronic liver disease) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (cirrhosis) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (comment) nan None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (cytolytic) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (malignant tumour) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (severe hepatitis) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (steatosis) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (successful reintroduction) nan None 10.1016/s0399-8320(04)95062-2
None Unchecked IC50 30.0 nM 10.1074/jbc.m701935200
None Unchecked IC50 32.0 nM 10.1016/j.bmcl.2012.09.021
None Unchecked IC50 32.0 nM 10.1016/j.bmcl.2013.01.080
None Unchecked IC50 32.0 nM 10.1021/jm4006498
None Unchecked IC50 34.0 nM 10.1016/j.bmcl.2007.06.026
None Unchecked IC50 35.0 nM 10.1039/C2MD00298A
None Unchecked IC50 36.0 nM 10.1021/jm5014264
None Unchecked IC50 42.0 nM 10.1016/j.bmc.2016.11.040
None Unchecked IC50 50.0 nM 10.1021/jm4006498
None Unchecked IC50 54.0 nM 10.1016/j.bmc.2007.12.001
None Unchecked IC50 80.0 nM 10.1021/jm2000085
None Unchecked IC50 80.0 nM 10.1021/jm9012592
None Unchecked IC50 140.0 nM 10.1021/jm200694q
None Unchecked IC50 160.0 nM 10.1021/jm5019719
None Unchecked IC50 200.0 nM 10.1021/jm060492b
None Unchecked IC50 220.0 nM 10.1021/jm200694q
None Unchecked IC50 221.0 nM 10.1021/jm4012559
None Unchecked IC50 250.0 nM 10.1016/j.bmcl.2012.09.021
None Unchecked IC50 310.0 nM 10.1039/c3md00085k
None Unchecked Inhibition 99.3 % 10.1016/j.bmc.2010.11.062
None Unchecked Ka 1.28 10'7/M 10.1021/ml300071w
None Unchecked Ka 3.45 10'6/M 10.1021/ml300071w
None Unchecked Ka 5.6 10'6/M 10.1021/ml300071w
None Unchecked Ka 6.67 10'6/M 10.1021/ml300071w
None Unchecked Ka 7.35 10'6/M 10.1021/ml300071w
None Unchecked Ki 21.0 nM 10.1021/ml300071w
None Unchecked Ki 21.0 nM 10.1021/ml300419r
None Unchecked Ki 26.92 nM 10.1021/jm200363d
None Unchecked Ki 27.0 nM 10.1021/jm200363d
None Unchecked Ki 27.0 nM 10.1021/ml300071w
None Unchecked Ki 34.0 nM 10.1021/ml300419r
None Unchecked Ki 90.0 nM 10.1016/j.bmcl.2013.01.097
None Unchecked Ki 140.0 nM 10.1021/ml300071w
None Unchecked Ratio 1.0 None 10.1021/jm200694q
None Unchecked Ratio IC50 8.0 None 10.1016/j.bmcl.2012.09.021

Metabolism Information