Molecule

FR-900098

AlkaPlorer ID: AK019089

Synonym: None

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

Structure

SMILES: CC(=O)N(O)CCCP(=O)(O)O

InChI: InChI=1S/C5H12NO5P/c1-5(7)6(8)3-2-4-12(9,10)11/h8H,2-4H2,1H3,(H2,9,10,11)

InChIKey: PKMNDDZSIHLLLI-UHFFFAOYSA-N

Reference

Cloning, Expression, and Biochemical Characterization of Streptomyces rubellomurinus Genes Required for Biosynthesis of Antimalarial Compound FR900098

PubChem CID: 162204

CAS: 66508-32-5

LOTUS: LTS0077195

SuperNatural Ⅲ: SN0287855

COCONUT: CNP0255746

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NPAtlas: NPA007537

Source

Species	Genus	Family	Order	Class	Phylum	Kingdom	Domain
Streptomyces rubellomurinus	Streptomyces	Streptomycetaceae	Kitasatosporales	Actinomycetes	Actinomycetota	None	Bacteria

Properties Information

Molecule Weight: 197.127

TPSA？: 98.07

MolLogP？: -0.2080999999999997

Number of H-Donors: 3

Number of H-Acceptors: 3

RingCount: 0

Activities Information

Organism	Target Name	Standard Type	Standard Value	Standard Units	doi
Escherichia coli	Escherichia coli	IZ	32.0	mm	10.1016/j.bmc.2016.11.040
Escherichia coli	Escherichia coli	MIC50	7800.0	nM	10.1021/jm5014264
Escherichia coli	Escherichia coli	MIC50	15600.0	nM	10.1021/jm5014264
Escherichia coli	Escherichia coli	MIC50	62500.0	nM	10.1021/jm5014264
Escherichia coli K-12	1-deoxyxylulose-5-phosphate reductoisomerase	IC50	28.18	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	10.1016/j.ejmech.2020.113055
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	58.0	nM	10.1021/jm051177c
Mycobacterium smegmatis (strain ATCC 700084 / mc(2)155)	1-deoxy-D-xylulose 5-phosphate reductoisomerase	IC50	320.0	nM	10.1016/j.ejmech.2012.02.031
Mycobacterium tuberculosis	1-deoxy-D-xylulose 5-phosphate reductoisomerase	IC50	160.0	nM	10.1016/j.bmcl.2011.07.005
Mycobacterium tuberculosis	1-deoxy-D-xylulose 5-phosphate reductoisomerase	IC50	160.0	nM	10.1016/j.ejmech.2020.113055
Mycobacterium tuberculosis	1-deoxy-D-xylulose 5-phosphate reductoisomerase	IC50	2390.0	nM	10.1016/j.bmcl.2013.11.067
Mycobacterium tuberculosis	1-deoxy-D-xylulose 5-phosphate reductoisomerase	Ki	130.0	nM	10.1021/jm200363d
Mycobacterium tuberculosis	Mycobacterium tuberculosis	IC50	64000.0	nM	10.1021/acsmedchemlett.8b00223
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	nan	None	10.1021/jm100211e
Plasmodium berghei	Plasmodium berghei	Inhibition	93.0	%	10.1021/jm100211e
Plasmodium berghei	Plasmodium berghei	MST	10.8	day	10.1021/jm100211e
Plasmodium falciparum	Plasmodium falciparum	IC50	90.0	nM	10.1021/acs.jmedchem.5b01485
Plasmodium falciparum	Plasmodium falciparum	IC50	160.0	nM	10.1021/jm5019719
Plasmodium falciparum	Plasmodium falciparum	IC50	180.0	nM	10.1016/j.bmcl.2005.12.082
Plasmodium falciparum	Plasmodium falciparum	IC50	240.0	nM	10.1021/jm051177c
Plasmodium falciparum	Plasmodium falciparum	IC50	280.0	nM	10.1021/jm051177c
Plasmodium falciparum	Plasmodium falciparum	IC50	320.0	nM	10.1016/j.bmcl.2005.12.082
Plasmodium falciparum	Plasmodium falciparum	IC50	320.0	nM	10.1021/jm301577q
Plasmodium falciparum	Plasmodium falciparum	IC50	350.0	nM	10.1021/jm5019719
Plasmodium falciparum	Plasmodium falciparum	IC50	420.0	nM	10.1021/jm100211e
Plasmodium falciparum	Plasmodium falciparum	IC50	420.0	nM	10.1021/jm301577q
Plasmodium falciparum	Plasmodium falciparum	IC50	430.0	nM	10.1016/j.bmc.2007.12.001
None	NON-PROTEIN TARGET	Potency	265.9	nM	None
None	No relevant target	pKa	7.35	None	10.1021/jm100211e
None	Unchecked	IC50	4.0	nM	10.1016/j.bmc.2016.11.040
None	Unchecked	IC50	15.0	nM	10.1021/jm5019719
None	Unchecked	IC50	15.11	nM	10.1021/jm301577q
None	Unchecked	IC50	18.0	nM	10.1021/jm4006498
None	Unchecked	IC50	32.0	nM	10.1016/j.bmcl.2007.06.026
None	Unchecked	IC50	51.0	nM	10.1021/jm4006498
None	Unchecked	IC50	62.0	nM	10.1016/j.bmc.2007.12.001
None	Unchecked	IC50	160.0	nM	10.1021/jm2000085
None	Unchecked	Inhibition	73.3	%	10.1016/j.bmc.2016.04.021
None	Unchecked	Ka	1.28	10'7/M	10.1021/ml300071w
None	Unchecked	Ka	1.79	10'6/M	10.1021/ml300071w
None	Unchecked	Ka	7.14	10'6/M	10.1021/ml300071w
None	Unchecked	Ki	11.0	nM	10.1021/ml300071w
None	Unchecked	Ki	19.0	nM	10.1021/jm200363d
None	Unchecked	Ki	19.0	nM	10.1021/ml300071w
None	Unchecked	Ki	19.05	nM	10.1021/jm200363d
None	Unchecked	Ki	48.0	nM	10.1016/j.bmcl.2013.01.097
None	Unchecked	Ki	130.0	nM	10.1021/ml300071w
None	Unchecked	MIC	16.0	ug.mL-1	10.1039/C6MD00365F
None	Unchecked	MIC	1024.0	ug.mL-1	10.1039/C6MD00365F

Metabolism Information

AKRT ID	Reaction	Reaction Link ID
AKRT002287	CC(=O)N(O)CCCP(=O)(O)O>>CC(=O)N(O)C[C@@H](O)CP(=O)(O)O	RXN-15082
AKRT002288	CC(=O)N(O)CCCP(=O)(O)OP(=O)(O)OC[C@H]1O[C@@H](n2ccc(N)nc2=O)[C@H](O)[C@@H]1O>>CC(=O)N(O)CCCP(=O)(O)O	RXN-15081