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.
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes. UK (1994)  |  FDA (1996)
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). 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 ZTI-01 (Fosfomycin for Injection)
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
Search Google for chemical match using the InChIKey YMDXZJFXQJVXBF-STHAYSLISA-N
Search Google for chemicals with the same backbone YMDXZJFXQJVXBF
Search PubMed clinical trials fosfomycin
Search PubMed titles fosfomycin
Search PubMed titles/abstracts fosfomycin
UniChem Compound Search for chemical match using the InChIKey YMDXZJFXQJVXBF-STHAYSLISA-N
UniChem Connectivity Search for chemical match using the InChIKey YMDXZJFXQJVXBF-STHAYSLISA-N