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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2018-05-20 20:20:33 UTC
HMDB IDHMDB0015570
Secondary Accession Numbers
  • HMDB15570
Metabolite Identification
Common NameFusidic Acid
DescriptionFusidic Acid is only found in individuals that have used or taken this drug. It is an antibiotic isolated from the fermentation broth of Fusidium coccineum. (From Merck Index, 11th ed) It acts by inhibiting translocation during protein synthesis.Fusidic acid works by interfering with bacterial protein synthesis, specifically by preventing the translocation of the elongation factor G (EF-G) from the ribosome. It also can inhibit chloramphenicol acetyltransferase enzymes.
Structure
Thumb
Synonyms
ValueSource
Fucidic acidChEBI
Fucidin acidChEBI
FusidineChEBI
RamycinChEBI
FucidateGenerator
FusidateGenerator
Diethanolamine fusidateHMDB
Fusidate sodiumMeSH
Fusidate, sodiumMeSH
Sodium fusidateMeSH
Acid, fusidicMeSH
FucithalmicMeSH
Fusidate, silverMeSH
Fusidic acid, sodium saltMeSH
Sodium, fusidateMeSH
FusidinMeSH
Silver fusidateMeSH
StanicideMeSH
Chemical FormulaC31H48O6
Average Molecular Weight516.7092
Monoisotopic Molecular Weight516.345089268
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
CAS Registry Number6990-06-3
SMILES
O[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 Identifier
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
InChI KeyIECPWNUMDGFDKC-MZJAQBGESA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as steroid esters. These 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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point192.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0052 g/LNot Available
LogPNot AvailableNot 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 FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zg3-1220920000-4fbe64cafb5b63a36495View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0002-4142039000-719400ebd8739301e695View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-05fr-0002900000-512150f35d55c73b9e09View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-004i-0000900000-eecd35dcbd3fede944c2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0002-0000900000-4a266f99ada066a14539View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000t-0000910000-cd6780540bd1f9be797dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1104900000-c44f17ce63c298e75b23View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ar0-2470900000-d691a48101739910d4c8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01b9-1100940000-fa7d2449ae7aaf8dc6dfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kg9-2402910000-b8101f870ef4c3c8ee94View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a7l-8307900000-a82ef6f5ba610321c69bView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB02703 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB02703 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB02703
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00023903
Chemspider ID2271900
KEGG Compound IDC06694
BioCyc IDCPD0-1606
BiGG IDNot Available
Wikipedia LinkFusidic_acid
METLIN IDNot Available
PubChem Compound3000226
PDB IDFUA
ChEBI ID29013
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  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. [PubMed:16902246 ]
  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. [PubMed:17374880 ]
  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. [PubMed:20044567 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Transporters

General function:
Involved in ATP binding
Specific function:
Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter
Gene Name:
ABCC2
Uniprot ID:
Q92887
Molecular weight:
174205.6
References
  1. Bode KA, Donner MG, Leier I, Keppler D: Inhibition of transport across the hepatocyte canalicular membrane by the antibiotic fusidate. Biochem Pharmacol. 2002 Jul 1;64(1):151-8. [PubMed:12106615 ]
General function:
Involved in ATP binding
Specific function:
Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes
Gene Name:
ABCB11
Uniprot ID:
O95342
Molecular weight:
146405.8
References
  1. Bode KA, Donner MG, Leier I, Keppler D: Inhibition of transport across the hepatocyte canalicular membrane by the antibiotic fusidate. Biochem Pharmacol. 2002 Jul 1;64(1):151-8. [PubMed:12106615 ]