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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-07-04 18:54:08 UTC
Update Date2019-07-23 07:14:54 UTC
HMDB IDHMDB0060708
Secondary Accession Numbers
  • HMDB60708
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
Data?1563866094
Synonyms
ValueSource
15b-Hydroxycyproterone acetateGenerator
15b-Hydroxycyproterone acetic acidGenerator
15beta-Hydroxycyproterone acetic acidGenerator
15Β-hydroxycyproterone acetateGenerator
15Β-hydroxycyproterone acetic acidGenerator
15 beta-Hydroxycyproterone acetateHMDB
15-OHCPAHMDB
15-Hydroxycyproterone acetateHMDB
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
Description belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassPregnane steroids
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
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity113.36 m³·mol⁻¹ChemAxon
Polarizability45.67 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-1039000000-d7c7f25fd9c59f9e962dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-03kl-4019400000-5123798857097c516297Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0159-0006900000-43df84ad576903ff5437Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0603-0049400000-9423121feac4916fb86bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ec-2095000000-0da727b0a07d93677fb1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-2004900000-dd9bd1f8db1b8e9fd381Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05a9-3009300000-cd9989e4f5cf854b909dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-9027000000-6148c3b024c1123d3af9Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
      Phenol Explorer Compound IDNot Available
      FooDB 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 Compound196706
      PDB IDNot Available
      ChEBI IDNot Available
      Food Biomarker OntologyNot Available
      VMH 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.