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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-07-04 18:56:43 UTC
Update Date2017-10-23 19:15:47 UTC
HMDB IDHMDB0060745
Secondary Accession Numbers
  • HMDB60745
Metabolite Identification
Common Name3-keto Fusidic acid
Description3-keto Fusidic acid is a metabolite of fusidic acid. Fusidic acid is a bacteriostatic antibiotic that is often used topically in creams and eyedrops, but may also be given systemically as tablets or injections. The global problem of advancing antimicrobial resistance has led to a renewed interest in its use recently. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC31H46O7
Average Molecular Weight530.6927
Monoisotopic Molecular Weight530.324353826
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-methyl-3-oxohept-5-enoic acid
Traditional 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-methyl-3-oxohept-5-enoic acid
CAS Registry NumberNot Available
SMILES
C[C@@H]1[C@H](O)CC[C@@]2(C)[C@H]1CC[C@@]1(C)[C@H]2[C@H](O)C[C@H]2\C([C@H](C[C@]12C)OC(C)=O)=C(\C(O)=O)C(=O)CC=C(C)C
InChI Identifier
InChI=1S/C31H46O7/c1-16(2)8-9-22(34)26(28(36)37)25-20-14-23(35)27-29(5)12-11-21(33)17(3)19(29)10-13-30(27,6)31(20,7)15-24(25)38-18(4)32/h8,17,19-21,23-24,27,33,35H,9-15H2,1-7H3,(H,36,37)/b26-25-/t17-,19-,20-,21+,23+,24-,27-,29-,30-,31-/m0/s1
InChI KeyLOVQKVDREFGPKC-COCAZOITSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as oxosteroids. These are steroid derivatives carrying a C=O group attached to steroid skeleton.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassSteroids and steroid derivatives
Direct ParentOxosteroids
Alternative Parents
Substituents
  • 22-oxosteroid
  • 21-oxosteroid
  • Steroid ester
  • 3-hydroxysteroid
  • Hydroxysteroid
  • 3-alpha-hydroxysteroid
  • 11-hydroxysteroid
  • 11-alpha-hydroxysteroid
  • Oxosteroid
  • Medium-chain keto acid
  • Hydroxy fatty acid
  • Beta-keto acid
  • Methyl-branched fatty acid
  • Branched fatty acid
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Keto acid
  • Beta-hydroxy ketone
  • Unsaturated fatty acid
  • Cyclic alcohol
  • Enone
  • Acryloyl-group
  • Secondary alcohol
  • Carboxylic acid ester
  • Ketone
  • Carboxylic acid derivative
  • Carboxylic acid
  • Carbonyl group
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

  Tissue and substructures:

  Cell and elements:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Role

Biological role:

  Molecular messenger:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Chemical reaction:

    Biochemical process:

    Cellular process:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0044 g/LALOGPS
logP3.99ALOGPS
logP3.75ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)4.29ChemAxon
pKa (Strongest Basic)-0.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area121.13 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity144.82 m³·mol⁻¹ChemAxon
Polarizability59.27 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, Positivesplash10-01bc-2240960000-62979044ae559eda57f2View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0cdi-3010139000-26ea010b4f7e8b1a5036View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dj-0000950000-90460657538d5e831d09View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0c01-1102910000-abd89a0cf42e90d52324View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0670-3031900000-510a4b168f98745407c0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-02vr-1000960000-4251dc2f0aa878c206ceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pvi-2900710000-376b6408d842395ada4cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-6004900000-e543cdbb854469e0f18cView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      DrugBank Metabolite IDDBMET00715
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDNot Available
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem CompoundNot Available
      PDB IDNot Available
      ChEBI IDNot Available
      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.