Compounds > 3-(n-acetyl-n-hydroxy)aminopropylphosphonic acid
Page last updated: 2024-12-08

3-(n-acetyl-n-hydroxy)aminopropylphosphonic acid

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

3-(N-acetyl-N-hydroxy)aminopropylphosphonic acid: from Streptomyces rubellomurinus sp. nov.; interferes with bacterial cell wall synthesis; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID162204
CHEMBL ID205338
CHEBI ID81398
SCHEMBL ID2741824
MeSH IDM0083072

Synonyms (28)

Synonym
brn 2096083
fr-900098
(3-(acetylhydroxyamino)propyl)phosphonic acid
fr 900098
phosphonic acid, (3-(acetylhydroxyamino)propyl)-
antibiotic fr-900098
{3-[acetyl(hydroxy)amino]propyl}phosphonic acid
66508-32-5
C17942
chebi:81398 ,
CHEMBL205338 ,
ammonium 3-(n-hydroxyacetamido)propylphosphonate
bdbm50181153
3-(n-hydroxyacetamido)propylphosphonic acid
3-[acetyl(hydroxy)amino]propylphosphonic acid
AKOS006277983 ,
F98 ,
3-[ethanoyl(hydroxy)amino]propylphosphonic acid
fr900098
0711y106hv ,
unii-0711y106hv
3-(n-acetyl-n-hydroxy)aminopropylphosphonic acid
NCGC00264108-01
phosphonic acid, p-(3-(acetylhydroxyamino)propyl)-
SCHEMBL2741824
DTXSID50216710
Q27155331
[3-(n-hydroxyacetamido)propyl]phosphonic acid

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" In addition, FR-900098 demonstrated no clastogenic or aneugenic capability or significant adverse effects on blood formation in an in vivo micronucleus test with bone marrow erythrocytes from NMRI mice."( FR-900098, an antimalarial development candidate that inhibits the non-mevalonate isoprenoid biosynthesis pathway, shows no evidence of acute toxicity and genotoxicity.
Fuhst, R; Hintz, M; Jomaa, H; Ortmann, R; Reichenberg, A; Schlitzer, M; Timmesfeld, N; Vilcinskas, A; Wiesner, J; Ziemann, C, 2016)		0.43

Bioavailability

ExcerptReferenceRelevance
" Temporarily masking the polar properties of the phosphonate moiety of the DXR inhibitor FR900098 1 enhanced not only its oral bioavailability but also the intrinsic activity of this series against the parasites."( Double ester prodrugs of FR900098 display enhanced in-vitro antimalarial activity.
Jomaa, H; Ortmann, R; Schlitzer, M; Wiesner, J, 2007)		0.34
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
phosphonoacetic acidA member of the class of phosphonic acids that is phosphonic acid in which the hydrogen attached to the phosphorous is replaced by a carboxymethyl group.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
1-deoxy-D-xylulose 5-phosphate reductoisomeraseMycolicibacterium smegmatis MC2 155IC50 (µMol)0.32000.08000.59751.4800AID653489
1-deoxy-D-xylulose 5-phosphate reductoisomeraseEscherichia coli K-12IC50 (µMol)0.03650.02000.74213.5000AID243156; AID263162; AID263367; AID553590
1-deoxy-D-xylulose 5-phosphate reductoisomeraseMycobacterium tuberculosis H37RvIC50 (µMol)1.27500.08000.41892.3900AID1063497; AID617056
1-deoxy-D-xylulose 5-phosphate reductoisomeraseMycobacterium tuberculosis H37RvKi0.13000.13000.13500.1400AID605762
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (3)

Processvia Protein(s)Taxonomy
isopentenyl diphosphate biosynthetic process, methylerythritol 4-phosphate pathway1-deoxy-D-xylulose 5-phosphate reductoisomeraseEscherichia coli K-12
isoprenoid biosynthetic process1-deoxy-D-xylulose 5-phosphate reductoisomeraseEscherichia coli K-12
isopentenyl diphosphate biosynthetic process, methylerythritol 4-phosphate pathway1-deoxy-D-xylulose 5-phosphate reductoisomeraseEscherichia coli K-12
isopentenyl diphosphate biosynthetic process, methylerythritol 4-phosphate pathway involved in terpenoid biosynthetic process1-deoxy-D-xylulose 5-phosphate reductoisomeraseEscherichia coli K-12
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (6)

Processvia Protein(s)Taxonomy
oxidoreductase activity1-deoxy-D-xylulose 5-phosphate reductoisomeraseEscherichia coli K-12
manganese ion binding1-deoxy-D-xylulose 5-phosphate reductoisomeraseEscherichia coli K-12
1-deoxy-D-xylulose-5-phosphate reductoisomerase activity1-deoxy-D-xylulose 5-phosphate reductoisomeraseEscherichia coli K-12
identical protein binding1-deoxy-D-xylulose 5-phosphate reductoisomeraseEscherichia coli K-12
metal ion binding1-deoxy-D-xylulose 5-phosphate reductoisomeraseEscherichia coli K-12
NADPH binding1-deoxy-D-xylulose 5-phosphate reductoisomeraseEscherichia coli K-12
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (1)

Processvia Protein(s)Taxonomy
Dxr protein complex1-deoxy-D-xylulose 5-phosphate reductoisomeraseEscherichia coli K-12
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (55)

Assay IDTitleYearJournalArticle
AID1347083qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: Viability assay - alamar blue signal for LASV Primary Screen2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347086qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lymphocytic Choriomeningitis Arenaviruses (LCMV): LCMV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347082qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: LASV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1197863Antiplasmodial activity against blood stage forms of multidrug-resistant Plasmodium falciparum Dd2 incubated for 3 days by HRP2 detection based ELISA method2015Journal of medicinal chemistry, Feb-26, Volume: 58, Issue:4
Prodrugs of reverse fosmidomycin analogues.
AID673981Inhibition of His6-tagged Plasmodium falciparum DXR expressed in Escherichia coli M15 using DXP as substrate preincubated for 5 mins2012ACS medicinal chemistry letters, Jun-14, Volume: 3, Issue:6
Thermodynamic Investigation of Inhibitor Binding to 1-Deoxy-D-Xylulose-5-Phosphate Reductoisomerase.
AID605762Inhibition of Mycobacterium tuberculosis recombinant DXR expressed in Escherichia coli BL21 (DE3) using DXP as substrate and MgCl2 as cofactor preincubated for 10 mins2011Journal of medicinal chemistry, Jul-14, Volume: 54, Issue:13
Inhibition of 1-deoxy-D-xylulose-5-phosphate reductoisomerase by lipophilic phosphonates: SAR, QSAR, and crystallographic studies.
AID1203544Antibacterial activity against Escherichia coli ATCC 25922 by two-fold broth microdilution method2015Journal of medicinal chemistry, Apr-09, Volume: 58, Issue:7
Synthesis and bioactivity of β-substituted fosmidomycin analogues targeting 1-deoxy-D-xylulose-5-phosphate reductoisomerase.
AID673982Binding affinity to His6-tagged Plasmodium falciparum DXR expressed in Escherichia coli M15 by isothermal titration colorimetric assay in presence of 2 mM NADPH and 150 mM NaCl at 279 K and pH 7.62012ACS medicinal chemistry letters, Jun-14, Volume: 3, Issue:6
Thermodynamic Investigation of Inhibitor Binding to 1-Deoxy-D-Xylulose-5-Phosphate Reductoisomerase.
AID1334839Growth inhibition of Escherichia coli XL1 blue at 2 nmol/disc incubated overnight by paper disc diffusion method2017Bioorganic & medicinal chemistry, 01-15, Volume: 25, Issue:2
Synthesis and biological evaluation of phosphate isosters of fosmidomycin and analogs as inhibitors of Escherichia coli and Mycobacterium smegmatis 1-deoxyxylulose 5-phosphate reductoisomerases.
AID673980Binding affinity to Escherichia coli DXR by isothermal titration colorimetric assay in presence of 2 mM NADPH and 150 mM NaCl at 279 K and pH 7.6 and Mg2+2012ACS medicinal chemistry letters, Jun-14, Volume: 3, Issue:6
Thermodynamic Investigation of Inhibitor Binding to 1-Deoxy-D-Xylulose-5-Phosphate Reductoisomerase.
AID482235Dissociation constant, pKa by NMR titration assay2010Journal of medicinal chemistry, Jul-22, Volume: 53, Issue:14
Synthesis and evaluation of alpha-halogenated analogues of 3-(acetylhydroxyamino)propylphosphonic acid (FR900098) as antimalarials.
AID263162Inhibition of recombinant Escherichia coli DXR2006Journal of medicinal chemistry, Apr-20, Volume: 49, Issue:8
Synthesis and biological evaluation of cyclopropyl analogues of fosmidomycin as potent Plasmodium falciparum growth inhibitors.
AID1334846Growth inhibition of Mycobacterium smegmatis incubated overnight by paper disc diffusion method2017Bioorganic & medicinal chemistry, 01-15, Volume: 25, Issue:2
Synthesis and biological evaluation of phosphate isosters of fosmidomycin and analogs as inhibitors of Escherichia coli and Mycobacterium smegmatis 1-deoxyxylulose 5-phosphate reductoisomerases.
AID605760Inhibition of Escherichia coli recombinant DXR using DXP as substrate and MgCl2 as cofactor preincubated for 10 mins2011Journal of medicinal chemistry, Jul-14, Volume: 54, Issue:13
Inhibition of 1-deoxy-D-xylulose-5-phosphate reductoisomerase by lipophilic phosphonates: SAR, QSAR, and crystallographic studies.
AID1334837Inhibition of Escherichia coli His6-tagged DXR preincubated for 2 mins in presence of NADPH followed by DXP substrate addition2017Bioorganic & medicinal chemistry, 01-15, Volume: 25, Issue:2
Synthesis and biological evaluation of phosphate isosters of fosmidomycin and analogs as inhibitors of Escherichia coli and Mycobacterium smegmatis 1-deoxyxylulose 5-phosphate reductoisomerases.
AID322182Antimalarial activity against Plasmodium falciparum 3D7 in infected human erythrocytes after 48 hrs2008Bioorganic & medicinal chemistry, Mar-15, Volume: 16, Issue:6
Synthesis of beta- and gamma-oxa isosteres of fosmidomycin and FR900098 as antimalarial candidates.
AID322181Inhibition of Escherichia coli DXR2008Bioorganic & medicinal chemistry, Mar-15, Volume: 16, Issue:6
Synthesis of beta- and gamma-oxa isosteres of fosmidomycin and FR900098 as antimalarial candidates.
AID263164Inhibition of Plasmodium falciparum 3D72006Journal of medicinal chemistry, Apr-20, Volume: 49, Issue:8
Synthesis and biological evaluation of cyclopropyl analogues of fosmidomycin as potent Plasmodium falciparum growth inhibitors.
AID482246Antiplasmodial activity against Plasmodium berghei ANKA infected in mice (Mus musculus) assessed as mice (Mus musculus) survival at 50 mg/kg, intraperitoneal for 5 consecutive days measured on day 7 post parasitic infection2010Journal of medicinal chemistry, Jul-22, Volume: 53, Issue:14
Synthesis and evaluation of alpha-halogenated analogues of 3-(acetylhydroxyamino)propylphosphonic acid (FR900098) as antimalarials.
AID263367Inhibition of recombinant Escherichia coli DXR2006Bioorganic & medicinal chemistry letters, Apr-01, Volume: 16, Issue:7
Synthesis of alpha-substituted fosmidomycin analogues as highly potent Plasmodium falciparum growth inhibitors.
AID1197864Antiplasmodial activity against blood stage forms of chloroquine-sensitive Plasmodium falciparum 3D7 incubated for 3 days by HRP2 detection based ELISA method2015Journal of medicinal chemistry, Feb-26, Volume: 58, Issue:4
Prodrugs of reverse fosmidomycin analogues.
AID1197862Inhibition of recombinant Plasmodium falciparum IspC using [3,4,5-13C3]1-Deoxy-D-xylulose 5-phosphate substrate by photometric assay2015Journal of medicinal chemistry, Feb-26, Volume: 58, Issue:4
Prodrugs of reverse fosmidomycin analogues.
AID1203543Antibacterial activity against Escherichia coli ATCC 8739 by two-fold broth microdilution method2015Journal of medicinal chemistry, Apr-09, Volume: 58, Issue:7
Synthesis and bioactivity of β-substituted fosmidomycin analogues targeting 1-deoxy-D-xylulose-5-phosphate reductoisomerase.
AID738622Inhibition of recombinant Toxoplasma gondii DXR catalytic domain (68 to 513) expressed in Escherichia coli BL21 using DXP as substrate after 10 mins by Uv-spectrophotometric analysis2013Bioorganic & medicinal chemistry letters, Apr-01, Volume: 23, Issue:7
Expression, characterization and inhibition of Toxoplasma gondii 1-deoxy-D-xylulose-5-phosphate reductoisomerase.
AID673979Inhibition of Escherichia coli DXR using DXP as substrate preincubated for 5 mins2012ACS medicinal chemistry letters, Jun-14, Volume: 3, Issue:6
Thermodynamic Investigation of Inhibitor Binding to 1-Deoxy-D-Xylulose-5-Phosphate Reductoisomerase.
AID1197865Antiplasmodial activity against blood stage forms of chloroquine-sensitive Plasmodium falciparum D10 incubated for 3 days by HRP2 detection based ELISA method2015Journal of medicinal chemistry, Feb-26, Volume: 58, Issue:4
Prodrugs of reverse fosmidomycin analogues.
AID617056Inhibition of Mycobacterium tuberculosis DXR assessed as reduction of 1-deoxy-D-xylulose 5-phosphate into 2-C-methyl-D-erythritol-4-phosphate measured for every 5 secs upto 500 secs by spectrophotometry analysis2011Bioorganic & medicinal chemistry letters, Sep-15, Volume: 21, Issue:18
Substitution of the phosphonic acid and hydroxamic acid functionalities of the DXR inhibitor FR900098: an attempt to improve the activity against Mycobacterium tuberculosis.
AID243156Inhibitory concentration against DOXP reductoisomerase2005Journal of medicinal chemistry, May-19, Volume: 48, Issue:10
AFMoC enhances predictivity of 3D QSAR: a case study with DOXP-reductoisomerase.
AID1324381Inhibition of Plasmodium falciparum DXR at 20 uM using DOXP as substrate preincubated for 5 mins followed by substrate addition measured for 10 mins in presence of NADPH by spectrophotometric analysis2016Bioorganic & medicinal chemistry, 12-01, Volume: 24, Issue:23
Synthesis and antimalarial activity of N-benzylated (N-arylcarbamoyl)alkylphosphonic acid derivatives.
AID762072Inhibition of Escherichia coli DXR using DXP as substrate measured every 5 secs for 250 secs in presence of NADPH2013Journal of medicinal chemistry, Aug-08, Volume: 56, Issue:15
DXR inhibition by potent mono- and disubstituted fosmidomycin analogues.
AID722449Inhibition of Escherichia coli DXR assessed as reduction of NADPH in NADP+ by spectrophotometric analysis2013Journal of medicinal chemistry, Jan-10, Volume: 56, Issue:1
Alpha-heteroatom derivatized analogues of 3-(acetylhydroxyamino)propyl phosphonic acid (FR900098) as antimalarials.
AID762070Inhibition of Plasmodium falciparum DXR using DXP as substrate measured every 5 secs for 250 secs in presence of NADPH2013Journal of medicinal chemistry, Aug-08, Volume: 56, Issue:15
DXR inhibition by potent mono- and disubstituted fosmidomycin analogues.
AID722448Antimalarial activity against Plasmodium falciparum 3D7 assessed as parasite growth inhibition2013Journal of medicinal chemistry, Jan-10, Volume: 56, Issue:1
Alpha-heteroatom derivatized analogues of 3-(acetylhydroxyamino)propyl phosphonic acid (FR900098) as antimalarials.
AID722446Antimalarial activity against Plasmodium falciparum K1 infected in human erythrocytes assessed as parasite growth inhibition2013Journal of medicinal chemistry, Jan-10, Volume: 56, Issue:1
Alpha-heteroatom derivatized analogues of 3-(acetylhydroxyamino)propyl phosphonic acid (FR900098) as antimalarials.
AID673984Binding affinity to Mycobacterium tuberculosis DXR by isothermal titration colorimetric assay in presence of 2 mM NADPH and 150 mM NaCl at 279 K and pH 7.62012ACS medicinal chemistry letters, Jun-14, Volume: 3, Issue:6
Thermodynamic Investigation of Inhibitor Binding to 1-Deoxy-D-Xylulose-5-Phosphate Reductoisomerase.
AID1425917Antibacterial activity against Francisella novicida U112 after 48 hrs2016MedChemComm, , Volume: 7, Issue:10
Potentiation of the Fosmidomycin analogue FR 900098 with substituted 2-oxazolines against
AID263369Antimalarial activity against Plasmodium falciparum 3D72006Bioorganic & medicinal chemistry letters, Apr-01, Volume: 16, Issue:7
Synthesis of alpha-substituted fosmidomycin analogues as highly potent Plasmodium falciparum growth inhibitors.
AID1625278Antimalarial activity against Plasmodium falciparum Dd2 assessed as reduction in parasite viability by [3H]-hypoxanthine incorporation assay2016Journal of medicinal chemistry, 06-23, Volume: 59, Issue:12
Antimalarial Chemotherapy: Natural Product Inspired Development of Preclinical and Clinical Candidates with Diverse Mechanisms of Action.
AID607182Inhibition of Mycobacterium tuberculosis DXR-catalyzed NADPH-dependent rearrangement and reduction of DXP to form MEP measured every 5 secs for 500 secs by spectrophotometric analysis2011Journal of medicinal chemistry, Jul-28, Volume: 54, Issue:14
Design, synthesis, and X-ray crystallographic studies of α-aryl substituted fosmidomycin analogues as inhibitors of Mycobacterium tuberculosis 1-deoxy-D-xylulose 5-phosphate reductoisomerase.
AID1203545Antibacterial activity against Escherichia coli K-12 by two-fold broth microdilution method2015Journal of medicinal chemistry, Apr-09, Volume: 58, Issue:7
Synthesis and bioactivity of β-substituted fosmidomycin analogues targeting 1-deoxy-D-xylulose-5-phosphate reductoisomerase.
AID673983Inhibition of Mycobacterium tuberculosis DXR using DXP as substrate preincubated for 5 mins2012ACS medicinal chemistry letters, Jun-14, Volume: 3, Issue:6
Thermodynamic Investigation of Inhibitor Binding to 1-Deoxy-D-Xylulose-5-Phosphate Reductoisomerase.
AID263368Antimalarial activity against Plasmodium falciparum Dd22006Bioorganic & medicinal chemistry letters, Apr-01, Volume: 16, Issue:7
Synthesis of alpha-substituted fosmidomycin analogues as highly potent Plasmodium falciparum growth inhibitors.
AID653492Antimycobacterial activity against Mycobacterium smegmatis at 400 nmol/disc after 24 hrs by paper disc diffusion method2012European journal of medicinal chemistry, May, Volume: 51Growth inhibition of Mycobacterium smegmatis by prodrugs of deoxyxylulose phosphate reducto-isomerase inhibitors, promising anti-mycobacterial agents.
AID1063497Inhibition of Mycobacterium tuberculosis Dxr2014Bioorganic & medicinal chemistry letters, Jan-15, Volume: 24, Issue:2
The effect of chain length and unsaturation on Mtb Dxr inhibition and antitubercular killing activity of FR900098 analogs.
AID553590Inhibition of Escherichia coli DXR2011ACS medicinal chemistry letters, Feb-10, Volume: 2, Issue:2
Structures of 1-Deoxy-D-Xylulose-5-Phosphate Reductoisomerase/Lipophilic Phosphonate Complexes.
AID482242Antiplasmodial activity against Plasmodium berghei ANKA infected in mice (Mus musculus) assessed as suppression of parasitaemia at 50 mg/kg, intraperitoneal for 5 consecutive days measured on day 4 post parasitic infection2010Journal of medicinal chemistry, Jul-22, Volume: 53, Issue:14
Synthesis and evaluation of alpha-halogenated analogues of 3-(acetylhydroxyamino)propylphosphonic acid (FR900098) as antimalarials.
AID1203547Antibacterial activity against Mycobacterium smegmatis ATCC 700084 after 24 to 48 hrs by two-fold broth microdilution method2015Journal of medicinal chemistry, Apr-09, Volume: 58, Issue:7
Synthesis and bioactivity of β-substituted fosmidomycin analogues targeting 1-deoxy-D-xylulose-5-phosphate reductoisomerase.
AID1203546Antibacterial activity against Mycobacterium smegmatis ATCC 607 after 24 to 48 hrs by two-fold broth microdilution method2015Journal of medicinal chemistry, Apr-09, Volume: 58, Issue:7
Synthesis and bioactivity of β-substituted fosmidomycin analogues targeting 1-deoxy-D-xylulose-5-phosphate reductoisomerase.
AID1425919Antibacterial activity against Francisella philomiragia ATCC 25015 after 48 hrs2016MedChemComm, , Volume: 7, Issue:10
Potentiation of the Fosmidomycin analogue FR 900098 with substituted 2-oxazolines against
AID308577Inhibition of Escherichia coli DXR2007Bioorganic & medicinal chemistry letters, Sep-01, Volume: 17, Issue:17
Synthesis and evaluation of alpha,beta-unsaturated alpha-aryl-substituted fosmidomycin analogues as DXR inhibitors.
AID482251Antiplasmodial activity against Plasmodium berghei ANKA infected in mice (Mus musculus) assessed as mean survival time at 50 mg/kg, intraperitoneal for 5 consecutive days2010Journal of medicinal chemistry, Jul-22, Volume: 53, Issue:14
Synthesis and evaluation of alpha-halogenated analogues of 3-(acetylhydroxyamino)propylphosphonic acid (FR900098) as antimalarials.
AID1422836Antimicrobial activity against Mycobacterium tuberculosis H37Ra ATCC 25177 after 7 days by luminometric method2018ACS medicinal chemistry letters, Oct-11, Volume: 9, Issue:10
Acyloxybenzyl and Alkoxyalkyl Prodrugs of a Fosmidomycin Surrogate as Antimalarial and Antitubercular Agents.
AID482237Antiplasmodial activity against Plasmodium falciparum K1 by micro dilution assay2010Journal of medicinal chemistry, Jul-22, Volume: 53, Issue:14
Synthesis and evaluation of alpha-halogenated analogues of 3-(acetylhydroxyamino)propylphosphonic acid (FR900098) as antimalarials.
AID263163Inhibition of Plasmodium falciparum Dd22006Journal of medicinal chemistry, Apr-20, Volume: 49, Issue:8
Synthesis and biological evaluation of cyclopropyl analogues of fosmidomycin as potent Plasmodium falciparum growth inhibitors.
AID653489Inhibition of Mycobacterium smegmatis DSM 43756 ATCC 19420 N-terminal his-tagged DXR expressed in XL1-blue Escherichia coli using NADPH and DXP as substrate preincubated for 2 mins with substrate before compound addition2012European journal of medicinal chemistry, May, Volume: 51Growth inhibition of Mycobacterium smegmatis by prodrugs of deoxyxylulose phosphate reducto-isomerase inhibitors, promising anti-mycobacterial agents.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (50)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (2.00)18.7374
1990's2 (4.00)18.2507
2000's17 (34.00)29.6817
2010's28 (56.00)24.3611
2020's2 (4.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.42

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index11.42 (24.57)
Research Supply Index3.93 (2.92)
Research Growth Index5.35 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.42)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (4.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other48 (96.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
2-(3-pyridine)acetic acid
3-pyridylacetic acid : A monocarboxylic acid that is acetic acid substituted by a (pyridin-3-yl) group. It is a metabolite of nicotine and other tobacco alkaloids.		2.0610monocarboxylic acid;
pyridines		human xenobiotic metabolite
fosmidomycin
fosmidomycin: from Streptomyces lavendulae; RN given refers to parent cpd; structure in second source. fosmidomycin : Propylphosphonic acid in which one of the hydrogens at position 3 is substituted by a formyl(hydroxy)amino group. An antibiotic obtained from Streptomyces lavendulae, it specifically inhibits DXP reductoisomerase (EC 1.1.1.267), a key enzyme in the non-mevalonate pathway of isoprenoid biosynthesis.		7.9340hydroxamic acid;
phosphonic acids		antimicrobial agent;
bacterial metabolite;
EC 1.1.1.267 (1-deoxy-D-xylulose-5-phosphate reductoisomerase) inhibitor
picolinic acid
picolinic acid: iron-chelating agent that inhibits DNA synthesis; may interfere with iron-dependent production of stable free organic radical which is essential for ribonucleotide reductase formation of deoxyribonucleotides; RN given refers to parent cpd; structure in Merck Index, 9th ed, #7206. picolinic acid : A pyridinemonocarboxylic acid in which the carboxy group is located at position 2. It is an intermediate in the metabolism of tryptophan.		2.0610pyridinemonocarboxylic acidhuman metabolite;
MALDI matrix material
isopentenyl pyrophosphate
isopentenyl pyrophosphate: substrate for isopentenyl pyrophosphate isomerase; RN given refers to unlabeled cpd; a nonpeptide mycobacterial antigen that stimulates gamma delta T cells. isopentenyl diphosphate : A prenol phosphate comprising 3-methylbut-3-en-1-ol having an O-diphosphate substituent.		4.0830prenol phosphateantigen;
antioxidant;
epitope;
Escherichia coli metabolite;
mouse metabolite;
phosphoantigen
chloroquine
Chloroquine: The prototypical antimalarial agent with a mechanism that is not well understood. It has also been used to treat rheumatoid arthritis, systemic lupus erythematosus, and in the systemic therapy of amebic liver abscesses.. chloroquine : An aminoquinoline that is quinoline which is substituted at position 4 by a [5-(diethylamino)pentan-2-yl]amino group at at position 7 by chlorine. It is used for the treatment of malaria, hepatic amoebiasis, lupus erythematosus, light-sensitive skin eruptions, and rheumatoid arthritis.		2.7830aminoquinoline;
organochlorine compound;
secondary amino compound;
tertiary amino compound		anticoronaviral agent;
antimalarial;
antirheumatic drug;
autophagy inhibitor;
dermatologic drug
isoniazid
Hydra: A genus of freshwater polyps in the family Hydridae, order Hydroida, class HYDROZOA. They are of special interest because of their complex organization and because their adult organization corresponds roughly to the gastrula of higher animals.. hydrazide : Compounds derived from oxoacids RkE(=O)l(OH)m (l =/= 0) by replacing -OH by -NRNR2 (R groups are commonly H). (IUPAC).		2.0710carbohydrazideantitubercular agent;
drug allergen
xanthenes
Xanthenes: Compounds with three aromatic rings in linear arrangement with an OXYGEN in the center ring.		2.0710xanthene
resazurin
resazurin: used as indicator in detection of hyposulfite (sulfoxylate); in food research (reductase test); structure		2.0710phenoxazine
erythromycin
Erythromycin: A bacteriostatic antibiotic macrolide produced by Streptomyces erythreus. Erythromycin A is considered its major active component. In sensitive organisms, it inhibits protein synthesis by binding to 50S ribosomal subunits. This binding process inhibits peptidyl transferase activity and interferes with translocation of amino acids during translation and assembly of proteins.. erythromycin : Any of several wide-spectrum macrolide antibiotics obtained from actinomycete Saccharopolyspora erythraea (formerly known as Streptomyces erythraeus).. erythromycin A : An erythromycin that consists of erythronolide A having 2,6-dideoxy-3-C-methyl-3-O-methyl-alpha-L-ribo-hexopyranosyl and 3,4,6-trideoxy-3-(dimethylamino)-beta-D-xylo-hexopyranosyl residues attahced at positions 4 and 6 respectively.		3.2310cyclic ketone;
erythromycin
phenylphosphonic acid
phenylphosphonic acid: RN given refers to parent cpd; NM same as N1		2.0610benzenes
manganese
Manganese: A trace element with atomic symbol Mn, atomic number 25, and atomic weight 54.94. It is concentrated in cell mitochondria, mostly in the pituitary gland, liver, pancreas, kidney, and bone, influences the synthesis of mucopolysaccharides, stimulates hepatic synthesis of cholesterol and fatty acids, and is a cofactor in many enzymes, including arginase and alkaline phosphatase in the liver. (From AMA Drug Evaluations Annual 1992, p2035). manganese(4+) : A manganese cation that is monoatomic and has a formal charge of +4.		2.0710elemental manganese;
manganese group element atom		Escherichia coli metabolite;
micronutrient
mefloquine
(-)-(11S,2'R)-erythro-mefloquine : An optically active form of [2,8-bis(trifluoromethyl)quinolin-4-yl]-(2-piperidyl)methanol having (-)-(11S,2'R)-erythro-configuration. An antimalarial agent, used in racemic form, which acts as a blood schizonticide; its mechanism of action is unknown.		2.1110[2,8-bis(trifluoromethyl)quinolin-4-yl]-(2-piperidyl)methanolantimalarial
atovaquone
Atovaquone: A hydroxynaphthoquinone that has antimicrobial activity and is being used in antimalarial protocols.. atovaquone : A naphthoquinone compound having a 4-(4-chlorophenyl)cyclohexyl group at the 2-position and a hydroxy substituent at the 3-position.		3.2310hydroxy-1,2-naphthoquinone
benzylphosphonic acid
[no description available]		2.0610benzenes
2-pyridylacetic acid
2-pyridylacetic acid: a betahistine metabolite; structure in first source		2.0610pyridines
n-hydroxy-4-phosphonobutanamide
N-hydroxy-4-phosphonobutanamide: structure given in first source		2.7630
organophosphonates
hydrogenphosphite : A divalent inorganic anion resulting from the removal of a proton from two of the hydroxy groups of phosphorous acid.		3.1550divalent inorganic anion;
phosphite ion
erythritol
[no description available]		2.4920butane-1,2,3,4-tetrolantioxidant;
human metabolite;
plant metabolite
2-phenyl-2-oxazoline
2-phenyl-2-oxazoline: structure in first source		2.1310
mevalonic acid
Mevalonic Acid: A dihydroxy monocarboxylic acid and precursor in the biosynthetic pathway known as the mevalonate pathway, which produces terpenes and steroids that are vital for diverse cellular functions.. mevalonic acid : A racemate composed of equimolar amounts of (R)- and (S)-mevalonic acid.. (R)-mevalonic acid : The (R)-enantiomer of mevalonic acid.		4.08303,5-dihydroxy-3-methylpentanoic acid
2-c-methylerythritol 4-phosphate
2-C-methylerythritol 4-phosphate: structure in first source		2.0710tetritol phosphateEscherichia coli metabolite
1-deoxy-d-xylulose 5-phosphate
deoxyxylulose phosphate: structure in first source. 1-deoxy-D-xylulose 5-phosphate : The 5-phospho derivative of 1-deoxy-D-xylulose.		2.1510xylulose phosphateEscherichia coli metabolite
clindamycin
Clindamycin: An antibacterial agent that is a semisynthetic analog of LINCOMYCIN.. clindamycin : A carbohydrate-containing antibiotic that is the semisynthetic derivative of lincomycin, a natural antibiotic.		3.2310
fosfomycin
Fosfomycin: An antibiotic produced by Streptomyces fradiae.. fosfomycin : A phosphonic acid having an (R,S)-1,2-epoxypropyl group attached to phosphorus.		7.42350epoxide;
phosphonic acids		antimicrobial agent;
EC 2.5.1.7 (UDP-N-acetylglucosamine 1-carboxyvinyltransferase) inhibitor
zithromax
Azithromycin: A semi-synthetic macrolide antibiotic structurally related to ERYTHROMYCIN. It has been used in the treatment of Mycobacterium avium intracellulare infections, toxoplasmosis, and cryptosporidiosis.. azithromycin : A macrolide antibiotic useful for the treatment of bacterial infections.		3.2310macrolide antibioticantibacterial drug;
environmental contaminant;
xenobiotic
flavin-adenine dinucleotide
Flavin-Adenine Dinucleotide: A condensation product of riboflavin and adenosine diphosphate. The coenzyme of various aerobic dehydrogenases, e.g., D-amino acid oxidase and L-amino acid oxidase. (Lehninger, Principles of Biochemistry, 1982, p972)		2.2110flavin adenine dinucleotide;
vitamin B2		cofactor;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
prosthetic group
nadp
[no description available]		2.7930
fosmidomycin monosodium salt
[no description available]		2.1710
artesunate
artesunic acid: RN given for (3R-(3alpha,5abeta,6beta,8abeta,9alpha,10alpha,12beta,(2aR*))-isomer; succinic ester of artemether		2.1110artemisinin derivative;
cyclic acetal;
dicarboxylic acid monoester;
hemisuccinate;
semisynthetic derivative;
sesquiterpenoid		antimalarial;
antineoplastic agent;
ferroptosis inducer
arterolane
arterolane: a trioxolane with antimalarial activity; structure in first source. arterolane : An oxaspiro compound that is dispiro[cyclohexane-1,3'-[1,2,4]trioxolane-5',2''-tricyclo[3.3.1.1(3,7)]decane] substituted by a 2-[(2-amino-2-methylpropyl)amino]-2-oxoethyl group at position 4s. Its maleic acid salt is used as an antimalarial drug in combination with piperaquine.		3.2310
oz 439
artefenomel: an antimalarial ozonide; structure in first source		3.2310
6-chloro-7-methoxy-2-methyl-3-(4-(4-(trifluoromethoxy)phenoxy)phenyl)quinolin-4(1h)-one
6-Chloro-7-methoxy-2-methyl-3-(4-(4-(trifluoromethoxy)phenoxy)phenyl)quinolin-4(1H)-one: structure in first source		3.2310
ConditionIndicatedRelationship StrengthStudiesTrials
Infections, Plasmodium
[description not available]		06.83130
Malaria
A protozoan disease caused in humans by four species of the PLASMODIUM genus: PLASMODIUM FALCIPARUM; PLASMODIUM VIVAX; PLASMODIUM OVALE; and PLASMODIUM MALARIAE; and transmitted by the bite of an infected female mosquito of the genus ANOPHELES. Malaria is endemic in parts of Asia, Africa, Central and South America, Oceania, and certain Caribbean islands. It is characterized by extreme exhaustion associated with paroxysms of high FEVER; SWEATING; shaking CHILLS; and ANEMIA. Malaria in ANIMALS is caused by other species of plasmodia.		06.83130
Acute Disease
Disease having a short and relatively severe course.		02.0510
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		02.4420
Plasmodium falciparum Malaria
[description not available]		05.260
Malaria, Falciparum
Malaria caused by PLASMODIUM FALCIPARUM. This is the severest form of malaria and is associated with the highest levels of parasites in the blood. This disease is characterized by irregularly recurring febrile paroxysms that in extreme cases occur with acute cerebral, renal, or gastrointestinal manifestations.		05.260