fosfomycin   Click here for help

GtoPdb Ligand ID: 10813

Synonyms: Monurol® | phosphomycin | phosphonomycin | Veramina®
Approved drug PDB Ligand
fosfomycin is an approved drug (UK (1994), FDA (1996))
Compound class: Synthetic organic
Comment: Fosfomycin is a phosphonic acid antibacterial, with broad antibacterial activity against Gram +ve and Gram -ve pathogens [1]. It was originally isolated from certain types of Streptomyces, but it is now made synthetically.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 1
Topological polar surface area 79.87
Molecular weight 138.01
XLogP -1.58
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES C[C@@H]1O[C@@H]1P(=O)(O)O
Isomeric SMILES C[C@@H]1O[C@@H]1P(=O)(O)O
InChI InChI=1S/C3H7O4P/c1-2-3(7-2)8(4,5)6/h2-3H,1H3,(H2,4,5,6)/t2-,3+/m0/s1
InChI Key YMDXZJFXQJVXBF-STHAYSLISA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (UK (1994), FDA (1996))
WHO Essential Medicine WHO Essential Medicines List (EML) (22nd List, 2021). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
[(2R,3S)-3-methyloxiran-2-yl]phosphonic acid
International Nonproprietary Names Click here for help
INN number INN
3014 fosfomycin
Synonyms Click here for help
Monurol® | phosphomycin | phosphonomycin | Veramina®
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo 1249
Other databases
CAS Registry No. 23155-02-4 (source: WHO INN record)
ChEMBL Ligand CHEMBL1757
DrugCentral Ligand 1243
GtoPdb PubChem SID 405560254
PubChem CID 446987
RCSB PDB Ligand FCN
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UniChem Compound Search for chemical match using the InChIKey YMDXZJFXQJVXBF-STHAYSLISA-N
UniChem Connectivity Search for chemical match using the InChIKey YMDXZJFXQJVXBF-STHAYSLISA-N