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Record Information
Version3.6
Creation Date2013-07-09 16:17:46 UTC
Update Date2017-08-15 23:27:35 UTC
HMDB IDHMDB0061092
Secondary Accession Numbers
  • HMDB61092
Metabolite Identification
Common Namefluticasone 17beta-carboxylic acid
Descriptionfluticasone 17beta-carboxylic acid is a metabolite of fluticasone propionate. Fluticasone propionate is a corticosteroid derived from fluticasone used to treat asthma and allergic rhinitis (hay fever). It is also used to treat eosinophilic esophagitis. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC21H26F2O5
Average Molecular Weight396.4249
Monoisotopic Molecular Weight396.174830352
IUPAC Name(1R,2S,8S,13R,14R,15S,17S)-1,8-difluoro-14,17-dihydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-diene-14-carboxylic acid
Traditional Name(1R,2S,8S,13R,14R,15S,17S)-1,8-difluoro-14,17-dihydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-diene-14-carboxylic acid
CAS Registry NumberNot Available
SMILES
C[C@@H]1CC2C3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]2(C)[C@@]1(O)C(O)=O
InChI Identifier
InChI=1S/C21H26F2O5/c1-10-6-12-13-8-15(22)14-7-11(24)4-5-18(14,2)20(13,23)16(25)9-19(12,3)21(10,28)17(26)27/h4-5,7,10,12-13,15-16,25,28H,6,8-9H2,1-3H3,(H,26,27)/t10-,12?,13?,15+,16+,18+,19+,20+,21+/m1/s1
InChI KeyQSVBUQTYFQFEHC-FULJYSEXSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassSteroids and steroid derivatives
Direct ParentAndrogens and derivatives
Alternative Parents
Substituents
  • 20-hydroxysteroid
  • Androgen-skeleton
  • 3-oxo-delta-1,4-steroid
  • Hydroxysteroid
  • Halo-steroid
  • 6-halo-steroid
  • 9-halo-steroid
  • 3-oxosteroid
  • 17-hydroxysteroid
  • 11-hydroxysteroid
  • 11-beta-hydroxysteroid
  • Oxosteroid
  • Delta-1,4-steroid
  • Hydroxy acid
  • Alpha-hydroxy acid
  • Cyclic alcohol
  • Tertiary alcohol
  • Cyclic ketone
  • Secondary alcohol
  • Fluorohydrin
  • Halohydrin
  • Ketone
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Organooxygen compound
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Alkyl halide
  • Organofluoride
  • Organohalogen compound
  • Alkyl fluoride
  • 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
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 Solubility0.075 mg/mLALOGPS
logP1.94ALOGPS
logP1.83ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)4.36ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity97.06 m3·mol-1ChemAxon
Polarizability39.03 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
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 IDDBMET00450
      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 LinkHMDB0061092
      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