NPASS Natural Product

Natural Product: NPC306022

Natural Product ID:	NPC306022
Common Name:	Fosfomycin
IUPAC Name:	[(2R,3S)-3-methyloxiran-2-yl]phosphonic acid
Synonyms:	Fosfocina; Fosfomycin; Fosfomycin Calcium; Fosfomycin Sodium; Monurol
Molecular Formula:	C3H7O4P
Standard InCHIKey:	YMDXZJFXQJVXBF-STHAYSLISA-N
Standard InCHI:	InChI=1S/C3H7O4P/c1-2-3(7-2)8(4,5)6/h2-3H,1H3,(H2,4,5,6)/t2-,3+/m0/s1
Canonical SMILES:	C[C@@H]1O[C@@H]1P(=O)(O)O
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Reference
NPO22810	Streptomyces	Species	Streptomycetaceae	Bacteria	StreptomeDB*
NPO24176	Streptomyces fradiae	Species	Streptomycetaceae	Bacteria	StreptomeDB*
NPO20916	Streptomyces wedmorensis	Species	Streptomycetaceae	Bacteria	StreptomeDB*
NPO24176.13	Streptomyces fradiae atcc 21096	Subspecies	Streptomycetaceae	Bacteria	StreptomeDB*
NPO19328	Streptomyces syringae	Species	Streptomycetaceae	Bacteria	StreptomeDB*

Biological Activity

Activity Type	# Activity
IC50	20
MIC	93
Others	72

Activity Type	# Activity
Cell Line	6
Individual Protein	7
Organism	156
Others	16

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	16	ug/ml	3086556
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	32	ug/ml	3086556
NPT2716	Individual Protein	UDP-N-acetylglucosamine 1-carboxyvinyltransferase	Escherichia coli K-12	IC50	=	118	nM	16945528
NPT2717	Individual Protein	UDP-N-acetylglucosamine 1-carboxyvinyltransferase	Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG12228)	IC50	=	10500	nM	16945528
NPT2	Others	Unspecified		IC50	=	460	nM	18261901
NPT2	Others	Unspecified		IC50	=	1370	nM	18261901
NPT2	Others	Unspecified		MIC	=	8	ug/ml	18261901
NPT2	Others	Unspecified		MIC	=	16	ug/ml	18261901
NPT2	Others	Unspecified		IC50	=	1360	nM	18261901
NPT2	Others	Unspecified		IC50	=	15000	nM	17988876
NPT1122	Organism	Haemophilus influenzae	Haemophilus influenzae	MIC	=	0.12	ug/ml	17325223
NPT1122	Organism	Haemophilus influenzae	Haemophilus influenzae	MIC	=	256	ug/ml	17325223
NPT1122	Organism	Haemophilus influenzae	Haemophilus influenzae	MIC	=	0.06	ug/ml	17325223
NPT1122	Organism	Haemophilus influenzae	Haemophilus influenzae	MIC	=	2	ug/ml	17325223
NPT1122	Organism	Haemophilus influenzae	Haemophilus influenzae	MIC	=	1	ug/ml	17325223
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	1024	ug/ml	17502406
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	25	ug/ml	18056270
NPT605	Organism	Homo sapiens	Homo sapiens	Activity	=	0.31	%	20022146
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	512	ug/ml	19841148
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	Activity	=	61.8	%	19901089
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	Activity	=	63.2	%	19901089
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	Activity	=	14.7	%	19901089
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	Activity	=	2.9	%	19901089
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC50	=	16	ug/ml	19901089
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC50	=	64	ug/ml	19901089
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC90	=	32	ug/ml	19901089
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC90	=	128	ug/ml	19901089
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	=	32	ug/ml	19901089
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	=	256	ug/ml	19901089
NPT1863	Organism	Staphylococcus saprophyticus	Staphylococcus saprophyticus	MIC50	=	128	ug/ml	18362191
NPT1863	Organism	Staphylococcus saprophyticus	Staphylococcus saprophyticus	MIC90	>=	512	ug/ml	18362191
NPT1863	Organism	Staphylococcus saprophyticus	Staphylococcus saprophyticus	MIC	=	64	ug/ml	18362191
NPT1863	Organism	Staphylococcus saprophyticus	Staphylococcus saprophyticus	MIC	>=	512	ug/ml	18362191
NPT1863	Organism	Staphylococcus saprophyticus	Staphylococcus saprophyticus	MIC	=	128	ug/ml	18362191
NPT1863	Organism	Staphylococcus saprophyticus	Staphylococcus saprophyticus	MIC	=	256	ug/ml	18362191
NPT2	Others	Unspecified		MIC	=	50000	nM	20729083
NPT2	Others	Unspecified		Inhibition	=	96	%	20729083
NPT2	Others	Unspecified		Inhibition	=	100	%	20729083
NPT2	Others	Unspecified		IC50	=	100	nM	20729083
NPT2	Others	Unspecified		Inhibition	=	99	%	20729083
NPT2	Others	Unspecified		MBC	=	0.2	nM	20729083
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	12	ug/ml	18824611
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	0.5	ug/ml	18824611
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	2	ug/ml	18824611
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	0.5	ug/ml	20404116
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	1	ug/ml	20404116
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	64	ug/ml	20404116
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	128	ug/ml	20404116
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	256	ug/ml	20404116
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	256	ug/ml	20404116
NPT1550	Organism	Bacillus anthracis	Bacillus anthracis	IC50	=	126	ug/ml	18378720
NPT1550	Organism	Bacillus anthracis	Bacillus anthracis	MIC	>	2048	ug/ml	18378720
NPT1550	Organism	Bacillus anthracis	Bacillus anthracis	IC50	=	18	ug/ml	18378720
NPT2642	Organism	Bacillus pumilus	Bacillus pumilus	MIC	>	512	ug/ml	19075069
NPT5739	Organism	Enterobacteriaceae	Enterobacteriaceae	MIC50	=	0.5	ug/ml	19124661
NPT5739	Organism	Enterobacteriaceae	Enterobacteriaceae	MIC90	=	64	ug/ml	19124661
NPT5739	Organism	Enterobacteriaceae	Enterobacteriaceae	Activity	=	91.3	%	19124661
NPT5739	Organism	Enterobacteriaceae	Enterobacteriaceae	MIC50	=	4	ug/ml	19124661
NPT5739	Organism	Enterobacteriaceae	Enterobacteriaceae	MIC90	=	8	ug/ml	19124661
NPT5739	Organism	Enterobacteriaceae	Enterobacteriaceae	Activity	=	100	%	19124661
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	1	ug/ml	19451283
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	96	ug/ml	19451283
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	0.38	ug/ml	19451283
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	1.5	ug/ml	19451283
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	1024	ug/ml	19451283
NPT19	Organism	Escherichia coli	Escherichia coli	Activity	=	100	%	19687248
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	Activity	=	88.8	%	19687248
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	Activity	=	60	%	19687248
NPT2710	Organism	Streptococcus agalactiae	Streptococcus agalactiae	Activity	=	50	%	19687248
NPT1863	Organism	Staphylococcus saprophyticus	Staphylococcus saprophyticus	Activity	=	100	%	19687248
NPT2939	Organism	Salmonella sp.	Salmonella sp.	Activity	=	66.6	%	19687248
NPT5738	Organism	Enterobacter sp.	Enterobacter sp.	Activity	=	75	%	19687248
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	Activity	=	58.3	%	19687248
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	Activity	=	0	%	19687248
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	Activity	=	85	%	19687248
NPT1521	Organism	Stenotrophomonas maltophilia	Stenotrophomonas maltophilia	Activity	=	66.6	%	19687248
NPT172	Organism	Proteus mirabilis	Proteus mirabilis	Activity	=	96.7	%	19687248
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	Activity	=	100	%	19687248
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	Activity	=	91.8	%	19687248
NPT747	Organism	Acinetobacter baumannii	Acinetobacter baumannii	Activity	=	9	%	19687248
NPT1248	Organism	Serratia marcescens	Serratia marcescens	Activity	=	66.6	%	19687248
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	Activity	=	82.3	%	19687248
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	Activity	=	75	%	19687248
NPT5738	Organism	Enterobacter sp.	Enterobacter sp.	Activity	=	100	%	19687248
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	Activity	=	17	%	19687248
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	Activity	=	100	%	19687248
NPT4997	Organism	Klebsiella oxytoca	Klebsiella oxytoca	Activity	=	0	%	19687248
NPT19	Organism	Escherichia coli	Escherichia coli	Activity	=	97	%	20585127
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	1.38	ug/ml	20585127
NPT1238	Organism	Staphylococcus	Staphylococcus	Ratio	=	1.01		20679509
NPT1238	Organism	Staphylococcus	Staphylococcus	Ratio	=	0.78		20679509
NPT1238	Organism	Staphylococcus	Staphylococcus	Ratio	=	0.75		20679509
NPT1238	Organism	Staphylococcus	Staphylococcus	Ratio	=	0.65		20679509
NPT1238	Organism	Staphylococcus	Staphylococcus	Ratio	=	0.69		20679509
NPT1238	Organism	Staphylococcus	Staphylococcus	Ratio	=	0.63		20679509
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	0.004	ug/ml	20679509
NPT1238	Organism	Staphylococcus	Staphylococcus	MIC	=	0.016	ug/ml	20679509
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	0.064	ug/ml	20679509
NPT1238	Organism	Staphylococcus	Staphylococcus	MIC	=	0.032	ug/ml	20679509
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	0.016	ug/ml	20679509
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	0.001	ug/ml	20679509
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	0.001	ug/ml	20679509
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	0.032	ug/ml	20679509
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	2	ug/ml	20585113
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	0.5	ug/ml	20585113
NPT563	Organism	Escherichia coli O157:H7	Escherichia coli O157:H7	MIC	=	16	ug/ml	20585113
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	8	ug/ml	20713658
NPT2760	Organism	Streptomyces scabiei	Streptomyces scabiei	IZ	=	16	mm	10.1584/jpestics.28.183
NPT2760	Organism	Streptomyces scabiei	Streptomyces scabiei	IZ	=	17	mm	10.1584/jpestics.28.183
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	1	ug/ml	23266177
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	2	ug/ml	23266177
NPT2	Others	Unspecified		IC50	>=	100000	nM	23266177
NPT2309	Cell Line	CAPAN-1	Homo sapiens	IC50	>=	100000	nM	23266177
NPT2306	Cell Line	Ca-Ski	Homo sapiens	IC50	>=	100000	nM	23266177
NPT1938	Cell Line	Calu-6	Homo sapiens	IC50	>=	100000	nM	23266177
NPT2489	Cell Line	MeWo	Homo sapiens	IC50	>=	100000	nM	23266177
NPT762	Cell Line	A-431	Homo sapiens	IC50	>=	100000	nM	23266177
NPT941	Cell Line	HaCaT	Homo sapiens	IC50	>=	100000	nM	23266177
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	4	ug/ml	23266177
NPT2	Others	Unspecified		IC50	=	1100	nM	23266177
NPT2	Others	Unspecified		IC50	=	10500	nM	23266177
NPT2716	Individual Protein	UDP-N-acetylglucosamine 1-carboxyvinyltransferase	Escherichia coli K-12	IC50	=	100	nM	23266177
NPT19	Organism	Escherichia coli	Escherichia coli	Ratio	=	16		23473681
NPT243	Individual Protein	Dopamine D2 receptor	Homo sapiens	Inhibition	=	29	%	24088053
NPT243	Individual Protein	Dopamine D2 receptor	Homo sapiens	Activity	=	0.09	%	24088053
NPT242	Individual Protein	Dopamine D1 receptor	Homo sapiens	Inhibition	=	-1.3	%	24088053
NPT242	Individual Protein	Dopamine D1 receptor	Homo sapiens	Activity	=	-1.2	%	24088053
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MBC	=	32	ug/ml	24360606
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MBC	=	64	ug/ml	24360606
NPT314	Organism	Bacillus cereus	Bacillus cereus	MBC	=	32	ug/ml	24360606
NPT1548	Organism	Pseudomonas aeruginosa PAO1	Pseudomonas aeruginosa PAO1	MBC	=	64	ug/ml	24360606
NPT1521	Organism	Stenotrophomonas maltophilia	Stenotrophomonas maltophilia	MBC	=	256	ug/ml	24360606
NPT4842	Organism	Acinetobacter haemolyticus	Acinetobacter haemolyticus	MBC	=	128	ug/ml	24360606
NPT19	Organism	Escherichia coli	Escherichia coli	MBC	=	128	ug/ml	24360606
NPT19	Organism	Escherichia coli	Escherichia coli	MBC	=	32	ug/ml	24360606
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	64	ug/ml	24360606
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	8	ug/ml	24360606
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	32	ug/ml	24360606
NPT1548	Organism	Pseudomonas aeruginosa PAO1	Pseudomonas aeruginosa PAO1	MIC	=	64	ug/ml	24360606
NPT1521	Organism	Stenotrophomonas maltophilia	Stenotrophomonas maltophilia	MIC	=	256	ug/ml	24360606
NPT4842	Organism	Acinetobacter haemolyticus	Acinetobacter haemolyticus	MIC	=	128	ug/ml	24360606
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	32	ug/ml	24360606
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	8	ug/ml	25050164

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 NPC306022 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	5810
0.1-0.2	21424
0.2-0.3	3196
0.3-0.4	371
0.4-0.5	75
0.5-0.6	8
0.6-0.7	5
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.6897	Remote Similarity	NPC314978
0.6774	Remote Similarity	NPC68114
0.6	Remote Similarity	NPC266566
0.6	Remote Similarity	NPC31433
0.6	Remote Similarity	NPC321170
0.5758	Remote Similarity	NPC120097
0.5625	Remote Similarity	NPC317545

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC306022 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	5266
0.1-0.2	3203
0.2-0.3	484
0.3-0.4	145
0.4-0.5	46
0.5-0.6	6
0.6-0.7	8
0.7-0.8	2
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	NPD8218	Approved
0.7	Intermediate Similarity	NPD8220	Approved
0.7	Intermediate Similarity	NPD8219	Approved
0.6333	Remote Similarity	NPD8559	Clinical (unspecified phase)
0.625	Remote Similarity	NPD9038	Approved
0.6207	Remote Similarity	NPD7384	Approved
0.6176	Remote Similarity	NPD8236	Phase 1
0.6176	Remote Similarity	NPD8235	Approved
0.6176	Remote Similarity	NPD8234	Approved
0.6	Remote Similarity	NPD8237	Approved
0.6	Remote Similarity	NPD7385	Approved

Structure

External Identifiers

PubChem CID	446987
ChEMBL	CHEMBL1757
ZINC

Physicochemical Properties

Molecular Weight:	138.01
ALogP:	-0.6449
MLogP:	1.24
XLogP:	-1.578
# Rotatable Bonds:	4
Polar Surface Area:	79.87
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	8

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