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Record Information
Version3.6
Creation Date2013-07-04 18:54:08 UTC
Update Date2017-03-02 22:05:20 UTC
HMDB IDHMDB60708
Secondary Accession NumbersNone
Metabolite Identification
Common Name15beta-hydroxycyproterone acetate
Description15beta-hydroxycyproterone acetate is a metabolite of cyproterone. Cyproterone is a steroidal antiandrogen which was never marketed. An acylated derivative, cyproterone acetate, is widely used clinically used as an antiandrogen and progestin. While cyproterone is sometimes used as a synonym for cyproterone acetate, what is almost always being referred to is actually cyproterone acetate and not cyproterone. (Wikipedia)
Structure
Thumb
Synonyms
ValueSource
15 beta-Hydroxycyproterone acetateMeSH
15-OHCPAMeSH
15-Hydroxycyproterone acetateMeSH
Chemical FormulaC24H29ClO5
Average Molecular Weight432.937
Monoisotopic Molecular Weight432.170351745
IUPAC Name(1S,2S,11R,12S,15R,16S)-15-acetyl-9-chloro-13-hydroxy-2,16-dimethyl-6-oxopentacyclo[9.7.0.0²,⁸.0³,⁵.0¹²,¹⁶]octadeca-7,9-dien-15-yl acetate
Traditional Name(1S,2S,11R,12S,15R,16S)-15-acetyl-9-chloro-13-hydroxy-2,16-dimethyl-6-oxopentacyclo[9.7.0.0²,⁸.0³,⁵.0¹²,¹⁶]octadeca-7,9-dien-15-yl acetate
CAS Registry NumberNot Available
SMILES
CC(=O)O[C@@]1(CC(O)[C@H]2[C@@H]3C=C(Cl)C4=CC(=O)C5CC5[C@]4(C)[C@H]3CC[C@]12C)C(C)=O
InChI Identifier
InChI=1S/C24H29ClO5/c1-11(26)24(30-12(2)27)10-20(29)21-14-8-18(25)17-9-19(28)13-7-16(13)23(17,4)15(14)5-6-22(21,24)3/h8-9,13-16,20-21,29H,5-7,10H2,1-4H3/t13?,14-,15+,16?,20?,21-,22+,23+,24+/m1/s1
InChI KeyHRANPRDGABOKNQ-RXHWKJIASA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassSteroids and steroid derivatives
Direct ParentGluco/mineralocorticoids, progestogins and derivatives
Alternative Parents
Substituents
  • Progestogin-skeleton
  • Steroid ester
  • 20-oxosteroid
  • 3-oxosteroid
  • 6-halo-steroid
  • Halo-steroid
  • 15-hydroxysteroid
  • Oxosteroid
  • Hydroxysteroid
  • Cyclohexenone
  • Alpha-acyloxy ketone
  • Cyclic alcohol
  • Carboxylic acid ester
  • Secondary alcohol
  • Ketone
  • Carboxylic acid derivative
  • Chloroalkene
  • Haloalkene
  • Vinyl halide
  • Vinyl chloride
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxygen compound
  • Organooxygen compound
  • Organochloride
  • Organic oxide
  • Organohalogen compound
  • 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 Solubility0.0042 mg/mLALOGPS
logP3.02ALOGPS
logP2.26ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)14.79ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area80.67 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity113.36 m3·mol-1ChemAxon
Polarizability45.67 Å3ChemAxon
Number of Rings5ChemAxon
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 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 IDDBMET00672
      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 LinkHMDB60708
      Metagene LinkHMDB60708
      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