CHEBI:28915 - fosfomycin

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ChEBI Name fosfomycin
ChEBI ID CHEBI:28915
Definition A phosphonic acid having an (R,S)-1,2-epoxypropyl group attached to phosphorus.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:42503, CHEBI:8159, CHEBI:24100
Supplier Information
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Formula C3H7O4P
Net Charge 0
Average Mass 138.05900
Monoisotopic Mass 138.008
InChI InChI=1S/C3H7O4P/c1-2-3(7-2)8(4,5)6/h2-3H,1H3,(H2,4,5,6)/t2-,3+/m0/s1
InChIKey YMDXZJFXQJVXBF-STHAYSLISA-N
SMILES C[C@@H]1O[C@@H]1P(O)(O)=O
Roles Classification
Biological Role(s): EC 2.5.1.7 (UDP-N-acetylglucosamine 1-carboxyvinyltransferase) inhibitor
An EC 2.5.1.* (non-methyl-alkyl or aryl transferase) inhibitor that interferes with the action of UDP-N-acetylglucosamine 1-carboxyvinyltransferase (EC 2.5.1.7).
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
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ChEBI Ontology
Outgoing fosfomycin (CHEBI:28915) has functional parent phosphonic acid (CHEBI:44976)
fosfomycin (CHEBI:28915) has role antimicrobial agent (CHEBI:33281)
fosfomycin (CHEBI:28915) has role EC 2.5.1.7 (UDP-N-acetylglucosamine 1-carboxyvinyltransferase) inhibitor (CHEBI:78379)
fosfomycin (CHEBI:28915) is a epoxide (CHEBI:32955)
fosfomycin (CHEBI:28915) is a phosphonic acids (CHEBI:26069)
fosfomycin (CHEBI:28915) is conjugate acid of (1R,2S)-epoxypropylphosphonate(1−) (CHEBI:62247)
Incoming (1R,2S)-epoxypropylphosphonate(1−) (CHEBI:62247) is conjugate base of fosfomycin (CHEBI:28915)
IUPAC Name
[(2R,3S)-3-methyloxiran-2-yl]phosphonic acid
INNs Sources
fosfomicina ChemIDplus
fosfomycin KEGG DRUG
fosfomycine ChemIDplus
fosfomycinum ChemIDplus
Synonyms Sources
(-)-(1R,2S)-(1,2-Epoxypropyl)phosphonic acid ChemIDplus
(1R,2S)-epoxypropylphosphonic acid MetaCyc
(2R-cis)-(3-Methyloxiranyl)phosphonic acid ChemIDplus
1R-cis-(1,2-epoxypropyl)phosphonic acid ChEBI
cis-(1R,2S)-epoxypropylphosphonic acid MetaCyc
FCM KEGG DRUG
FOSFOMYCIN PDBeChem
L-cis-1,2-epoxypropylphosphonic acid MetaCyc
Phosphomycin ChemIDplus
phosphonemycin MetaCyc
Phosphonomycin KEGG COMPOUND
Phosphonomycin KEGG COMPOUND
Manual Xrefs Databases
1243 DrugCentral
C00000789 KNApSAcK
C06454 KEGG COMPOUND
CPD0-1113 MetaCyc
D04253 KEGG DRUG
DB00828 DrugBank
FCN PDBeChem
View more database links
Registry Numbers Types Sources
1680831 Reaxys Registry Number Reaxys
23155-02-4 CAS Registry Number KEGG COMPOUND
23155-02-4 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
105327 PubMed citation Europe PMC
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7030849 PubMed citation Europe PMC
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Last Modified
22 February 2017