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Record Information
Version4.0
Creation Date2013-07-09 16:13:38 UTC
Update Date2017-09-27 08:43:59 UTC
HMDB IDHMDB0061030
Secondary Accession Numbers
  • HMDB61030
Metabolite Identification
Common Nameomega-hydroxyfinasteride
Descriptionomega-hydroxyfinasteride is a metabolite of finasteride. Finasteride (brand names Proscar and Propecia by Merck, among other generic names) is a synthetic 5α-reductase inhibitor, an inhibitor of the enzyme that converts testosterone to dihydrotestosterone (DHT). Finasteride is approved for the treatment of benign prostatic hyperplasia (BPH) and male pattern baldness (MPB). (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC22H34N2O3
Average Molecular Weight374.517
Monoisotopic Molecular Weight374.256942964
IUPAC Name5-hydroxy-N-(2-hydroxypropan-2-yl)-2,15-dimethyl-6-azatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,5-diene-14-carboximidic acid
Traditional Name5-hydroxy-N-(2-hydroxypropan-2-yl)-2,15-dimethyl-6-azatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,5-diene-14-carboximidic acid
CAS Registry NumberNot Available
SMILES
CC(C)(O)N=C(O)C1CCC2C3CCC4N=C(O)C=CC4(C)C3CCC12C
InChI Identifier
InChI=1S/C22H34N2O3/c1-20(2,27)24-19(26)16-7-6-14-13-5-8-17-22(4,12-10-18(25)23-17)15(13)9-11-21(14,16)3/h10,12-17,27H,5-9,11H2,1-4H3,(H,23,25)(H,24,26)
InChI KeyLVMYOUOJYSDZSC-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassAndrostane steroids
Direct ParentAndrogens and derivatives
Alternative Parents
Substituents
  • 20-hydroxysteroid
  • Androgen-skeleton
  • 3-hydroxysteroid
  • Hydroxysteroid
  • 4-azasteroid
  • Azasteroid
  • Cyclic carboximidic acid
  • Alkanolamine
  • Carboximidic acid
  • Carboximidic acid derivative
  • Azacycle
  • Organoheterocyclic compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

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 Solubility0.0037 g/LALOGPS
logP3.6ALOGPS
logP3.56ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)7.32ChemAxon
pKa (Strongest Basic)4.83ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area85.41 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity106.4 m³·mol⁻¹ChemAxon
Polarizability42.6 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-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05r0-0009000000-2497e41f45c3f618818fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gi0-1249000000-11050a89e859716958beView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fkj-8890000000-e52b20bb4e955a6d3fbdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0009000000-8b4b5c41280a08680afeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-5029000000-fa580807caf1113df809View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fr-9031000000-48452bfc8ce3a7f15008View in MoNA
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 IDDBMET00369
      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 ]