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Record Information
Version4.0
Creation Date2013-07-09 16:16:14 UTC
Update Date2017-09-27 08:44:00 UTC
HMDB IDHMDB0061065
Secondary Accession Numbers
  • HMDB61065
Metabolite Identification
Common Name1-beta-hydroxymedroxyprogesterone
Description1-beta-hydroxymedroxyprogesterone is a metabolite of medroxyprogesterone. Medroxyprogesterone, also known as 17α-hydroxy-6α-methylprogesterone, and abbreviated as MP, is a steroidal progestin drug which was never marketed for use in humans. An acylated derivative, medroxyprogesterone acetate (MPA), is clinically used as a pharmaceutical medicine. Compared to MPA, MP is over two orders of magnitude less potent as a progestogen. As such, MP itself is not used clinically, though it has seen limited use in veterinary medicine under the trade name Controlestril in France. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC22H32O4
Average Molecular Weight360.4871
Monoisotopic Molecular Weight360.230059512
IUPAC Name(2R,3R,8S,14R,15S)-14-acetyl-3,14-dihydroxy-2,8,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one
Traditional Name(2R,3R,8S,14R,15S)-14-acetyl-3,14-dihydroxy-2,8,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one
CAS Registry NumberNot Available
SMILES
C[C@H]1CC2C3CC[C@](O)(C(C)=O)[C@@]3(C)CCC2[C@@]2(C)[C@H](O)CC(=O)C=C12
InChI Identifier
InChI=1S/C22H32O4/c1-12-9-15-16-6-8-22(26,13(2)23)20(16,3)7-5-17(15)21(4)18(12)10-14(24)11-19(21)25/h10,12,15-17,19,25-26H,5-9,11H2,1-4H3/t12-,15?,16?,17?,19+,20-,21+,22-/m0/s1
InChI KeyKTYQBYVMFWLJBV-FEJNQOGGSA-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
  • 20-oxosteroid
  • 3-oxo-delta-4-steroid
  • 3-oxosteroid
  • 1-hydroxysteroid
  • 17-hydroxysteroid
  • Oxosteroid
  • Hydroxysteroid
  • Delta-4-steroid
  • Cyclohexenone
  • Alpha-hydroxy ketone
  • Tertiary alcohol
  • Cyclic alcohol
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Role

Biological role:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Chemical reaction:

    Biochemical process:

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 Solubility0.026 g/LALOGPS
logP2.93ALOGPS
logP2.61ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)12.69ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity100.02 m³·mol⁻¹ChemAxon
Polarizability40.88 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
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 IDDBMET00410
      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
      METLIN IDNot Available
      PubChem CompoundNot Available
      PDB IDNot Available
      ChEBI 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 ]