Fusidic Acid (CHEM022335)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:28:39 UTC
Update Date2026-04-13 21:53:17 UTC
Accession NumberCHEM022335
Identification
Common NameFusidic Acid
ClassSmall Molecule
DescriptionAn antibiotic isolated from the fermentation broth of Fusidium coccineum. (From Merck Index, 11th ed) It acts by inhibiting translocation during protein synthesis. It is often used topically in creams and eyedrops but is available in systemic formulations including tablets and injections.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Fucidic acidChEBI
Fucidin acidChEBI
FusidineChEBI
RamycinChEBI
FAKegg
FucidateGenerator
FusidateGenerator
Diethanolamine fusidateHMDB
Fusidate sodiumHMDB
Fusidate, sodiumHMDB
Sodium fusidateHMDB
Acid, fusidicHMDB
FucithalmicHMDB
Fusidate, silverHMDB
Fusidic acid, sodium saltHMDB
Sodium, fusidateHMDB
FusidinHMDB
Silver fusidateHMDB
StanicideHMDB
(-)-FusidateHMDB
Fusidic acidMeSH
Chemical FormulaC31H48O6
Average Molecular Mass516.709 g/mol
Monoisotopic Mass516.345 g/mol
CAS Registry Number6990-06-3
IUPAC Name2-[(1S,2S,5R,6S,7S,10S,11S,13S,14Z,15R,17R)-13-(acetyloxy)-5,17-dihydroxy-2,6,10,11-tetramethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-ylidene]-6-methylhept-5-enoic acid
Traditional Namediscoid
SMILESO[C@@H]1CC[C@@]2(C)[C@@]([H])(CC[C@@]3(C)[C@@]2([H])[C@H](O)C[C@@]2([H])\C([C@@H](OC(=O)C)C[C@]32C)=C(/CCC=C(C)C)C(O)=O)[C@@H]1C
InChI IdentifierInChI=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
InChI KeyIECPWNUMDGFDKC-MZJAQBGESA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as steroid esters. Steroid esters are compounds containing a steroid moiety which bears a carboxylic acid ester group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroid esters
Direct ParentSteroid esters
Alternative Parents
Substituents
  • Steroid ester
  • 3-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • 11-hydroxysteroid
  • 11-alpha-hydroxysteroid
  • Hydroxysteroid
  • Medium-chain fatty acid
  • Branched fatty acid
  • Methyl-branched fatty acid
  • Hydroxy fatty acid
  • Fatty acyl
  • Fatty acid
  • Unsaturated fatty acid
  • Dicarboxylic acid or derivatives
  • Cyclic alcohol
  • Carboxylic acid ester
  • Secondary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Alcohol
  • Organooxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0052 g/LALOGPS
logP4.97ALOGPS
logP4.42ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)4.66ChemAxon
pKa (Strongest Basic)-0.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area104.06 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity144.12 m³·mol⁻¹ChemAxon
Polarizability59.77 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zg3-1220920000-4fbe64cafb5b63a36495Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0002-4142039000-719400ebd8739301e695Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-05fr-0002900000-512150f35d55c73b9e09Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-004i-0000900000-eecd35dcbd3fede944c2Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0002-0000900000-4a266f99ada066a14539Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000t-0000910000-cd6780540bd1f9be797dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1104900000-c44f17ce63c298e75b23Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ar0-2470900000-d691a48101739910d4c8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01b9-1100940000-fa7d2449ae7aaf8dc6dfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kg9-2402910000-b8101f870ef4c3c8ee94Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a7l-8307900000-a82ef6f5ba610321c69bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0670-0000930000-bc2ecd6f1f350fb06fb0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-1101900000-79e36a28e5dcfe7776aeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0adj-5904000000-0902e38713a6d36001ffSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0uxr-0000930000-1aa8d1754461a685d391Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000610000-1e0c6ee7aa2357107f9fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9103640000-a5d17cb68c815198cd76Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB02703
HMDB IDHMDB0015570
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00023903
BiGG IDNot Available
BioCyc IDCPD0-1606
METLIN IDNot Available
PDB IDFUA
Wikipedia LinkFusidic_acid
Chemspider ID2271900
ChEBI ID29013
PubChem Compound ID3000226
Kegg Compound IDC06694
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
5. The lipid handbook with CD-ROM
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=11412963
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=12937375
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=13899435
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=13996455
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=15843024
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=17082187
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=20797618
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=22066960
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=22100514
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=22197537
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=22290345
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=22308410
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=22354299
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=22612900
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=22645663
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=22888356
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=23102978
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=23114758
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=23147726
25. https://www.ncbi.nlm.nih.gov/pubmed/?term=8624493