NPASS Natural Product

Natural Product: NPC314838

Natural Product ID:	NPC314838
Common Name:	Fosmidomycin
IUPAC Name:	3-[formyl(hydroxy)amino]propylphosphonic acid
Synonyms:	Fosmidomycin
Molecular Formula:	C4H10NO5P
Standard InCHIKey:	GJXWDTUCERCKIX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C4H10NO5P/c6-4-5(7)2-1-3-11(8,9)10/h4,7H,1-3H2,(H2,8,9,10)
Canonical SMILES:	O=CN(CCCP(=O)(O)O)O
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO13952	Streptomyces lavendulae	Species	Streptomycetaceae	Bacteria				StreptomeDB*

Biological Activity

Activity Type	# Activity
EC50	3
IC50	50
Kd	1
Ki	10
MIC	13
Others	18
Potency	2

Activity Type	# Activity
Cell Line	1
Individual Protein	20
Organism	42
Others	34

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT5917	Individual Protein	1-deoxyxylulose-5-phosphate reductoisomerase	Synechocystis sp. (strain PCC 6803 / Kazusa)	Ki	=	21	nM	15454217
NPT3945	Individual Protein	1-deoxyxylulose-5-phosphate reductoisomerase	Escherichia coli K-12	IC50	=	19.95	nM	15887963
NPT3945	Individual Protein	1-deoxyxylulose-5-phosphate reductoisomerase	Escherichia coli K-12	IC50	=	48	nM	16610809
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	480	nM	16610809
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	400	nM	16610809
NPT3945	Individual Protein	1-deoxyxylulose-5-phosphate reductoisomerase	Escherichia coli K-12	IC50	=	30	nM	16439126
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	360	nM	16439126
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	1100	nM	16439126
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	312000	nM	17149863
NPT19	Organism	Escherichia coli	Escherichia coli	MBC	=	2.5	nM	17149863
NPT19	Organism	Escherichia coli	Escherichia coli	Ratio	=	0.13		17149863
NPT3945	Individual Protein	1-deoxyxylulose-5-phosphate reductoisomerase	Escherichia coli K-12	IC50	=	1853000	nM	17149863
NPT2	Others	Unspecified		IC50	=	200	nM	17149863
NPT19	Organism	Escherichia coli	Escherichia coli	IC50	=	220	nM	17149863
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	20	mm	17149863
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	19	mm	17149863
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	0	mm	17149863
NPT2	Others	Unspecified		IC50	=	34	nM	17583502
NPT2	Others	Unspecified		IC50	=	54	nM	18158249
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	1200	nM	18158249
NPT3946	Individual Protein	1-deoxy-D-xylulose 5-phosphate reductoisomerase	Mycobacterium tuberculosis	IC50	=	80	nM	17491006
NPT2	Others	Unspecified		IC50	=	30	nM	17491006
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	10000	nM	19888756
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	20000	nM	19888756
NPT1550	Organism	Bacillus anthracis	Bacillus anthracis	MIC	=	100000	nM	19888756
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	>	1000000	nM	19888756
NPT2	Others	Unspecified		IC50	=	80	nM	19888756
NPT605	Organism	Homo sapiens	Homo sapiens	Activity	=	0.3	%	20022146
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	1730	nM	20568776
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	Inhibition	=	82	%	20568776
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	EC50	=	1100	nM	21379374
NPT3945	Individual Protein	1-deoxyxylulose-5-phosphate reductoisomerase	Escherichia coli K-12	IC50	=	30	nM	21379374
NPT2	Others	Unspecified		Inhibition	=	99.3	%	21216609
NPT2	Others	Unspecified		Ki	=	26.92	nM	21561155
NPT2	Others	Unspecified		Ki	=	27	nM	21561155
NPT3946	Individual Protein	1-deoxy-D-xylulose 5-phosphate reductoisomerase	Mycobacterium tuberculosis	Ki	=	140	nM	21561155
NPT3946	Individual Protein	1-deoxy-D-xylulose 5-phosphate reductoisomerase	Mycobacterium tuberculosis	IC50	=	80	nM	21561155
NPT2	Others	Unspecified		IC50	=	80	nM	21678907
NPT3946	Individual Protein	1-deoxy-D-xylulose 5-phosphate reductoisomerase	Mycobacterium tuberculosis	IC50	=	80	nM	21824775
NPT2	Others	Unspecified		IC50	=	140	nM	21866890
NPT2	Others	Unspecified		IC50	=	220	nM	21866890
NPT2	Others	Unspecified		Ratio	=	1		21866890
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	3700	nM	21866890
NPT171	Cell Line	MRC5	Homo sapiens	IC50	>	62000	nM	21866890
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	Activity	=	92	%	21866890
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	6.25	ug/ml	22024034
NPT1466	Organism	Escherichia coli K12	Escherichia coli K-12	MIC	=	12.5	ug/ml	22024034
NPT1207	Organism	Acinetobacter	Acinetobacter	MIC	=	100	ug/ml	22024034
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC	>	500	ug/ml	22024034
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	200	ug/ml	22024034
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	200	ug/ml	22024034
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	>	200	ug/ml	22024034
NPT1550	Organism	Bacillus anthracis	Bacillus anthracis	MIC	=	0.78	ug/ml	22024034
NPT3947	Individual Protein	1-deoxy-D-xylulose 5-phosphate reductoisomerase	Mycobacterium smegmatis (strain ATCC 700084 / mc(2)155)	IC50	=	80	nM	22405649
NPT3947	Individual Protein	1-deoxy-D-xylulose 5-phosphate reductoisomerase	Mycobacterium smegmatis (strain ATCC 700084 / mc(2)155)	IC50	=	510	nM	22405649
NPT2	Others	Unspecified		Ki	=	27	nM	23050057
NPT2	Others	Unspecified		Ki	=	21	nM	23050057
NPT2	Others	Unspecified		Ki	=	140	nM	23050057
NPT2	Others	Unspecified		Ratio IC50	=	8		23025997
NPT2	Others	Unspecified		IC50	=	32	nM	23025997
NPT2	Others	Unspecified		IC50	=	250	nM	23025997
NPT5918	Individual Protein	1-deoxy-D-xylulose 5-phosphate reductoisomerase, chloroplastic	Arabidopsis thaliana	IC50	=	100	nM	23471898
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	1000	nM	23215035
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	EC50	=	1170	nM	23795240
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	EC50	=	440	nM	23795240
NPT2	Others	Unspecified		Ki	=	34	nM	23795240
NPT2	Others	Unspecified		Ki	=	21	nM	23795240
NPT2	Others	Unspecified		IC50	=	32	nM	23414808
NPT2	Others	Unspecified		Ki	=	90	nM	23428849
NPT3946	Individual Protein	1-deoxy-D-xylulose 5-phosphate reductoisomerase	Mycobacterium tuberculosis	IC50	=	80	nM	23819803
NPT3946	Individual Protein	1-deoxy-D-xylulose 5-phosphate reductoisomerase	Mycobacterium tuberculosis	Kd	=	40	nM	23819803
NPT2	Others	Unspecified		IC50	=	32	nM	23819803
NPT2	Others	Unspecified		IC50	=	50	nM	23819803
NPT3946	Individual Protein	1-deoxy-D-xylulose 5-phosphate reductoisomerase	Mycobacterium tuberculosis	IC50	=	230	nM	24032981
NPT2	Others	Unspecified		IC50	=	221	nM	24032981
NPT3946	Individual Protein	1-deoxy-D-xylulose 5-phosphate reductoisomerase	Mycobacterium tuberculosis	IC50	=	440	nM	24360562
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC99	>	500	ug/ml	23914289
NPT2	Others	Unspecified		IC50	=	310	nM	23914289
NPT2	Others	Unspecified		Potency		472.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		530.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		IC50	=	35	nM	10.1039/C2MD00298A
NPT3945	Individual Protein	1-deoxyxylulose-5-phosphate reductoisomerase	Escherichia coli K-12	IC50	=	32	nM	24890653
NPT3945	Individual Protein	1-deoxyxylulose-5-phosphate reductoisomerase	Escherichia coli K-12	IC50	=	32	nM	25210872
NPT2	Others	Unspecified		IC50	=	810	nM	25881827
NPT2	Others	Unspecified		IC50	=	880	nM	25754494
NPT2	Others	Unspecified		Activity	=	100	%	25754494
NPT2	Others	Unspecified		IC50	=	160	nM	25633870
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	810	nM	25633870
NPT757	Organism	Plasmodium falciparum 3D7	Plasmodium falciparum 3D7	IC50	=	880	nM	25633870
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	1300	nM	25633870
NPT5919	Individual Protein	1-deoxy-D-xylulose 5-phosphate reductoisomerase	Escherichia coli	IC50	=	438	nM	25781377
NPT2	Others	Unspecified		IC50	=	36	nM	25781377
NPT1140	Organism	Escherichia coli ATCC 8739	Escherichia coli ATCC 8739	MIC50	=	980	nM	25781377
NPT19	Organism	Escherichia coli	Escherichia coli	MIC50	=	250000	nM	25781377
NPT1466	Organism	Escherichia coli K12	Escherichia coli K-12	MIC50	=	7800	nM	25781377
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	MIC50	>	250000	nM	25781377

Similar Natural Products in NPASS

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC314838 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	10506
0.1-0.2	18422
0.2-0.3	1633
0.3-0.4	294
0.4-0.5	28
0.5-0.6	4
0.6-0.7	0
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8333	Intermediate Similarity	NPC314567
0.8333	Intermediate Similarity	NPC79954

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC314838 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	1299
0.1-0.2	6700
0.2-0.3	860
0.3-0.4	242
0.4-0.5	46
0.5-0.6	13
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD8546	Phase 3
0.5625	Remote Similarity	NPD9242	Discontinued

Structure

External Identifiers

PubChem CID	572
ChEMBL	CHEMBL203125
ZINC

Physicochemical Properties

Molecular Weight:	183.03
ALogP:	-2.701
MLogP:	1.13
XLogP:	-2.239
# Rotatable Bonds:	8
Polar Surface Area:	107.88
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	0
# Heavy Atoms:	11

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