CHEBI:29013 - fusidic acid

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name fusidic acid
ChEBI ID CHEBI:29013
Definition A steroid antibiotic that is isolated from the fermentation broth of Fusidium coccineum.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:42742, CHEBI:5201, CHEBI:24133
Supplier Information ChemicalBook:CB8431174, eMolecules:17497561, ZINC000008143796
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Fusidic acid, sold under the brand name Fucidin among others, is a steroid antibiotic that is often used topically in creams or ointments and eyedrops but may also be given systemically as tablets or injections. As of October 2008, the global problem of advancing antimicrobial resistance has led to a renewed interest in its use.
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Formula C31H48O6
Net Charge 0
Average Mass 516.70920
Monoisotopic Mass 516.34509
InChI InChI=1S/C31H48O6/c1-17(2)9-8-10-20(28(35)36)26-22-15-24(34)27-29(5)13-12-23(33)18(3)21(29)11-14-30(27,6)31(22,7)16-25(26)37-19(4)32/h9,18,21-25,27,33-34H,8,10-16H2,1-7H3,(H,35,36)/b26-20-/t18-,21-,22-,23+,24+,25-,27-,29-,30-,31-/m0/s1
InChIKey IECPWNUMDGFDKC-MZJAQBGESA-N
SMILES [H][C@@]12CC[C@@]3(C)[C@@]([H])([C@H](O)C[C@@]4([H])\C([C@H](C[C@]34C)OC(C)=O)=C(/CCC=C(C)C)C(O)=O)[C@@]1(C)CC[C@@H](O)[C@H]2C
Metabolite of Species Details
Escherichia coli (NCBI:txid562) See: PubMed
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
EC 2.7.1.33 (pantothenate kinase) inhibitor
An EC 2.7.1.* (phosphotransferases with an alcohol group as acceptor) inhibitor that interferes with the action of pantothenate kinase (EC 2.7.1.33).
protein synthesis inhibitor
A compound, usually an anti-bacterial agent or a toxin, which inhibits the synthesis of a protein.
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
(via carbocyclic antibiotic )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing fusidic acid (CHEBI:29013) has parent hydride 5α-cholestane (CHEBI:35515)
fusidic acid (CHEBI:29013) has role Escherichia coli metabolite (CHEBI:76971)
fusidic acid (CHEBI:29013) has role EC 2.7.1.33 (pantothenate kinase) inhibitor (CHEBI:77194)
fusidic acid (CHEBI:29013) has role protein synthesis inhibitor (CHEBI:48001)
fusidic acid (CHEBI:29013) is a α,β-unsaturated monocarboxylic acid (CHEBI:79020)
fusidic acid (CHEBI:29013) is a 11α-hydroxy steroid (CHEBI:19129)
fusidic acid (CHEBI:29013) is a 3α-hydroxy steroid (CHEBI:36835)
fusidic acid (CHEBI:29013) is a steroid acid (CHEBI:47891)
fusidic acid (CHEBI:29013) is a steroid antibiotic (CHEBI:26761)
fusidic acid (CHEBI:29013) is a sterol ester (CHEBI:35915)
fusidic acid (CHEBI:29013) is conjugate acid of fusidate (CHEBI:71321)
Incoming fusidate (CHEBI:71321) is conjugate base of fusidic acid (CHEBI:29013)
IUPAC Name
(2Z)-2-[(17Z)-16β-acetoxy-3α,11α-dihydroxy-4α,8α,10,14β-tetramethyl-5α,9β,13α-gonan-17-ylidene]-6-methylhept-5-enoic acid
Synonyms Sources
fucidic acid ChEBI
Fucidin acid ChemIDplus
Fusidic acid KEGG COMPOUND
Fusidine ChemIDplus
Ramycin ChemIDplus
Manual Xrefs Databases
1261 DrugCentral
1776 VSDB
C00023903 KNApSAcK
C06694 KEGG COMPOUND
CPD0-1606 MetaCyc
D04281 KEGG DRUG
DB02703 DrugBank
FUA PDBeChem
Fusidic_acid Wikipedia
HMDB0015570 HMDB
LMPR0106040001 LIPID MAPS
View more database links
Registry Numbers Types Sources
2197692 Reaxys Registry Number Reaxys
5672885 Beilstein Registry Number Beilstein
6990-06-3 CAS Registry Number ChemIDplus
Citations Waiting for Citations
Last Modified
22 February 2017