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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:13:38 UTC
Update Date2021-09-14 15:47:57 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
Data?1563866137
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
Description 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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+185.32931661259
DarkChem[M-H]-179.10731661259
DeepCCS[M-2H]-219.23630932474
DeepCCS[M+Na]+194.46330932474
AllCCS[M+H]+194.632859911
AllCCS[M+H-H2O]+192.132859911
AllCCS[M+NH4]+196.832859911
AllCCS[M+Na]+197.432859911
AllCCS[M-H]-194.532859911
AllCCS[M+Na-2H]-195.332859911
AllCCS[M+HCOO]-196.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
omega-hydroxyfinasterideCC(C)(O)N=C(O)C1CCC2C3CCC4N=C(O)C=CC4(C)C3CCC12C3601.1Standard polar33892256
omega-hydroxyfinasterideCC(C)(O)N=C(O)C1CCC2C3CCC4N=C(O)C=CC4(C)C3CCC12C2582.5Standard non polar33892256
omega-hydroxyfinasterideCC(C)(O)N=C(O)C1CCC2C3CCC4N=C(O)C=CC4(C)C3CCC12C2990.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
omega-hydroxyfinasteride,1TMS,isomer #1CC(C)(N=C(O)C1CCC2C3CCC4N=C(O)C=CC4(C)C3CCC12C)O[Si](C)(C)C3106.6Semi standard non polar33892256
omega-hydroxyfinasteride,1TMS,isomer #2CC(C)(O)N=C(O[Si](C)(C)C)C1CCC2C3CCC4N=C(O)C=CC4(C)C3CCC12C2980.7Semi standard non polar33892256
omega-hydroxyfinasteride,1TMS,isomer #3CC(C)(O)N=C(O)C1CCC2C3CCC4N=C(O[Si](C)(C)C)C=CC4(C)C3CCC12C3022.8Semi standard non polar33892256
omega-hydroxyfinasteride,2TMS,isomer #1CC(C)(N=C(O[Si](C)(C)C)C1CCC2C3CCC4N=C(O)C=CC4(C)C3CCC12C)O[Si](C)(C)C3051.1Semi standard non polar33892256
omega-hydroxyfinasteride,2TMS,isomer #2CC(C)(N=C(O)C1CCC2C3CCC4N=C(O[Si](C)(C)C)C=CC4(C)C3CCC12C)O[Si](C)(C)C3084.7Semi standard non polar33892256
omega-hydroxyfinasteride,2TMS,isomer #3CC(C)(O)N=C(O[Si](C)(C)C)C1CCC2C3CCC4N=C(O[Si](C)(C)C)C=CC4(C)C3CCC12C3005.7Semi standard non polar33892256
omega-hydroxyfinasteride,3TMS,isomer #1CC(C)(N=C(O[Si](C)(C)C)C1CCC2C3CCC4N=C(O[Si](C)(C)C)C=CC4(C)C3CCC12C)O[Si](C)(C)C3091.9Semi standard non polar33892256
omega-hydroxyfinasteride,1TBDMS,isomer #1CC(C)(N=C(O)C1CCC2C3CCC4N=C(O)C=CC4(C)C3CCC12C)O[Si](C)(C)C(C)(C)C3321.4Semi standard non polar33892256
omega-hydroxyfinasteride,1TBDMS,isomer #2CC(C)(O)N=C(O[Si](C)(C)C(C)(C)C)C1CCC2C3CCC4N=C(O)C=CC4(C)C3CCC12C3196.5Semi standard non polar33892256
omega-hydroxyfinasteride,1TBDMS,isomer #3CC(C)(O)N=C(O)C1CCC2C3CCC4N=C(O[Si](C)(C)C(C)(C)C)C=CC4(C)C3CCC12C3236.1Semi standard non polar33892256
omega-hydroxyfinasteride,2TBDMS,isomer #1CC(C)(N=C(O[Si](C)(C)C(C)(C)C)C1CCC2C3CCC4N=C(O)C=CC4(C)C3CCC12C)O[Si](C)(C)C(C)(C)C3479.5Semi standard non polar33892256
omega-hydroxyfinasteride,2TBDMS,isomer #2CC(C)(N=C(O)C1CCC2C3CCC4N=C(O[Si](C)(C)C(C)(C)C)C=CC4(C)C3CCC12C)O[Si](C)(C)C(C)(C)C3506.9Semi standard non polar33892256
omega-hydroxyfinasteride,2TBDMS,isomer #3CC(C)(O)N=C(O[Si](C)(C)C(C)(C)C)C1CCC2C3CCC4N=C(O[Si](C)(C)C(C)(C)C)C=CC4(C)C3CCC12C3400.5Semi standard non polar33892256
omega-hydroxyfinasteride,3TBDMS,isomer #1CC(C)(N=C(O[Si](C)(C)C(C)(C)C)C1CCC2C3CCC4N=C(O[Si](C)(C)C(C)(C)C)C=CC4(C)C3CCC12C)O[Si](C)(C)C(C)(C)C3662.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - omega-hydroxyfinasteride GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-3498000000-6dfd2a1a08a27d6352e92017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - omega-hydroxyfinasteride GC-MS (3 TMS) - 70eV, Positivesplash10-004i-2013090000-d0b455cd2b26e2d081e32017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - omega-hydroxyfinasteride 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 - omega-hydroxyfinasteride 10V, Positive-QTOFsplash10-05r0-0009000000-2497e41f45c3f618818f2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - omega-hydroxyfinasteride 20V, Positive-QTOFsplash10-0gi0-1249000000-11050a89e859716958be2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - omega-hydroxyfinasteride 40V, Positive-QTOFsplash10-0fkj-8890000000-e52b20bb4e955a6d3fbd2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - omega-hydroxyfinasteride 10V, Negative-QTOFsplash10-00di-0009000000-8b4b5c41280a08680afe2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - omega-hydroxyfinasteride 20V, Negative-QTOFsplash10-00di-5029000000-fa580807caf1113df8092017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - omega-hydroxyfinasteride 40V, Negative-QTOFsplash10-05fr-9031000000-48452bfc8ce3a7f150082017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - omega-hydroxyfinasteride 10V, Positive-QTOFsplash10-004i-0019000000-7f4c1c5413047e2b81702021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - omega-hydroxyfinasteride 20V, Positive-QTOFsplash10-0ab9-3479000000-74525f85786d801d135a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - omega-hydroxyfinasteride 40V, Positive-QTOFsplash10-05fr-0960000000-e68d68c93bdc5737e6362021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - omega-hydroxyfinasteride 10V, Negative-QTOFsplash10-0a4i-0009000000-6e9e7dd12a581f32cd2c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - omega-hydroxyfinasteride 20V, Negative-QTOFsplash10-00di-0069000000-336d44558bd7299858292021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - omega-hydroxyfinasteride 40V, Negative-QTOFsplash10-0ab9-4093000000-a856b8d2227ec93ccccf2021-09-25Wishart 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 Compound131770009
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.