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Record Information
Version3.6
Creation Date2013-07-04 18:56:43 UTC
Update Date2016-02-11 08:12:12 UTC
HMDB IDHMDB60745
Secondary Accession NumbersNone
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=1/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-/s2
InChI KeyInChIKey=LOVQKVDREFGPKC-SNUDRIJJNA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as oxosteroids. These are steroid derivatives carrying a C=O group attached to steroid skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassOxosteroids
Direct ParentOxosteroids
Alternative Parents
Substituents
  • 22-oxosteroid
  • 21-oxosteroid
  • Steroid ester
  • 3-alpha-hydroxysteroid
  • 11-hydroxysteroid
  • 11-alpha-hydroxysteroid
  • Oxosteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • Medium-chain keto acid
  • Carbocyclic fatty acid
  • Methyl-branched fatty acid
  • Branched fatty acid
  • Beta-keto acid
  • Fatty acyl
  • Unsaturated fatty acid
  • Keto acid
  • Beta-hydroxy ketone
  • Acetate salt
  • Enone
  • Cyclic alcohol
  • Acryloyl-group
  • Secondary alcohol
  • Ketone
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Membrane (predicted from logP)
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity144.82 m3·mol-1ChemAxon
Polarizability59.27 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
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
NuGOwiki LinkHMDB60745
Metagene LinkHMDB60745
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available