Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-04 18:54:08 UTC
Update Date2021-09-14 15:46:01 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

Biological location

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0042 g/LALOGPS
logP10(3.02) g/LALOGPS
logP10(2.26) g/LChemAxon
logS10(-5) g/LALOGPS
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
Predicted Spectral Properties

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
15beta-hydroxycyproterone acetate,1TMS,#1CC(=O)O[C@]1(C(C)=O)CC(O[Si](C)(C)C)[C@H]2[C@@H]3C=C(Cl)C4=CC(=O)C5CC5[C@]4(C)[C@H]3CC[C@@]21C3306.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
15beta-hydroxycyproterone acetate,1TMS,#2CC(=O)O[C@]1(C(C)=O)CC(O)[C@H]2[C@@H]3C=C(Cl)C4=CC(O[Si](C)(C)C)=C5CC5[C@]4(C)[C@H]3CC[C@@]21C3300.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
15beta-hydroxycyproterone acetate,1TMS,#3C=C(O[Si](C)(C)C)[C@@]1(OC(C)=O)CC(O)[C@H]2[C@@H]3C=C(Cl)C4=CC(=O)C5CC5[C@]4(C)[C@H]3CC[C@@]21C3265.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
15beta-hydroxycyproterone acetate,1TBDMS,#1CC(=O)O[C@]1(C(C)=O)CC(O[Si](C)(C)C(C)(C)C)[C@H]2[C@@H]3C=C(Cl)C4=CC(=O)C5CC5[C@]4(C)[C@H]3CC[C@@]21C3563.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
15beta-hydroxycyproterone acetate,1TBDMS,#2CC(=O)O[C@]1(C(C)=O)CC(O)[C@H]2[C@@H]3C=C(Cl)C4=CC(O[Si](C)(C)C(C)(C)C)=C5CC5[C@]4(C)[C@H]3CC[C@@]21C3543.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
15beta-hydroxycyproterone acetate,1TBDMS,#3C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(OC(C)=O)CC(O)[C@H]2[C@@H]3C=C(Cl)C4=CC(=O)C5CC5[C@]4(C)[C@H]3CC[C@@]21C3514.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 15beta-hydroxycyproterone acetate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-1039000000-d7c7f25fd9c59f9e962d2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 15beta-hydroxycyproterone acetate GC-MS (1 TMS) - 70eV, Positivesplash10-03kl-4019400000-5123798857097c5162972017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 15beta-hydroxycyproterone acetate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15beta-hydroxycyproterone acetate 10V, Positive-QTOFsplash10-0159-0006900000-43df84ad576903ff54372017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15beta-hydroxycyproterone acetate 20V, Positive-QTOFsplash10-0603-0049400000-9423121feac4916fb86b2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15beta-hydroxycyproterone acetate 40V, Positive-QTOFsplash10-00ec-2095000000-0da727b0a07d93677fb12017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15beta-hydroxycyproterone acetate 10V, Negative-QTOFsplash10-001i-2004900000-dd9bd1f8db1b8e9fd3812017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15beta-hydroxycyproterone acetate 20V, Negative-QTOFsplash10-05a9-3009300000-cd9989e4f5cf854b909d2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15beta-hydroxycyproterone acetate 40V, Negative-QTOFsplash10-0ab9-9027000000-6148c3b024c1123d3af92017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15beta-hydroxycyproterone acetate 10V, Positive-QTOFsplash10-001i-0004900000-c2f97d6ed26b4951f64a2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15beta-hydroxycyproterone acetate 20V, Positive-QTOFsplash10-05yl-0039200000-0f873989d1098e665ba82021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15beta-hydroxycyproterone acetate 40V, Positive-QTOFsplash10-003r-2492300000-f46dd4b1e9fce154110c2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15beta-hydroxycyproterone acetate 10V, Negative-QTOFsplash10-0089-1009800000-92c12d4eebdc327777392021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15beta-hydroxycyproterone acetate 20V, Negative-QTOFsplash10-05fr-5009000000-29bfdb843483318f15792021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15beta-hydroxycyproterone acetate 40V, Negative-QTOFsplash10-052f-9000000000-8d78c4eda9cf80c8b5392021-10-12Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
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
MarkerDB IDNot Available
Good Scents 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.