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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2020-02-26 21:40:18 UTC
HMDB IDHMDB0014759
Secondary Accession Numbers
  • HMDB14759
Metabolite Identification
Common NameOxandrolone
DescriptionOxandrolone, also known as oxandrin or anavar, belongs to the class of organic compounds known as steroid lactones. These are sterol lipids containing a lactone moiety linked to the steroid skeleton. Oxandrolone is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1582753218
Synonyms
ValueSource
OxandrolonaChEBI
OxandrolonumChEBI
OxandrinKegg
OssandroloneHMDB
AnavarHMDB
Chemical FormulaC19H30O3
Average Molecular Weight306.4397
Monoisotopic Molecular Weight306.219494826
IUPAC Name(1S,2S,7S,10R,11S,14S,15S)-14-hydroxy-2,14,15-trimethyl-4-oxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-one
Traditional Nameoxandrolone
CAS Registry Number53-39-4
SMILES
[H][C@@]12CC[C@](C)(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])CC(=O)OC[C@]12C
InChI Identifier
InChI=1S/C19H30O3/c1-17-11-22-16(20)10-12(17)4-5-13-14(17)6-8-18(2)15(13)7-9-19(18,3)21/h12-15,21H,4-11H2,1-3H3/t12-,13+,14-,15-,17-,18-,19-/m0/s1
InChI KeyQSLJIVKCVHQPLV-PEMPUTJUSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as steroid lactones. These are sterol lipids containing a lactone moiety linked to the steroid skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroid lactones
Direct ParentSteroid lactones
Alternative Parents
Substituents
  • Steroid lactone
  • 3-oxosteroid
  • Hydroxysteroid
  • 3-oxo-5-alpha-steroid
  • 17-hydroxysteroid
  • Oxosteroid
  • 2-oxasteroid
  • Naphthopyran
  • Naphthalene
  • Delta valerolactone
  • Delta_valerolactone
  • Oxane
  • Pyran
  • Tertiary alcohol
  • Cyclic alcohol
  • Lactone
  • Carboxylic acid ester
  • Organoheterocyclic compound
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Organic oxide
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point236.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.014 g/LNot Available
LogP4.2Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.014 g/LALOGPS
logP3.36ALOGPS
logP2.95ChemAxon
logS-4.3ALOGPS
pKa (Strongest Basic)-0.53ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity84.75 m³·mol⁻¹ChemAxon
Polarizability35.29 ųChemAxon
Number of Rings4ChemAxon
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, Positivesplash10-002f-0390000000-881235f7ef2bc770fa8bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0jbl-2159000000-7b4f8fa117bf83f48aa4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0093000000-ff28afe3ea6df5ec0584Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-054t-0291000000-adf27119d3b4725b18e1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ukd-6970000000-1edee804a2bf0d5c829dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0049000000-7f9b88506345bf035691Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-0096000000-dad47b16a1db69463c49Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-3090000000-503154ac4d18300bfe1eSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00621 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00621 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00621
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5667
KEGG Compound IDC07346
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkOxandrolone
METLIN IDNot Available
PubChem Compound5878
PDB IDNot Available
ChEBI ID7820
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Demling RH, DeSanti L: Oxandrolone induced lean mass gain during recovery from severe burns is maintained after discontinuation of the anabolic steroid. Burns. 2003 Dec;29(8):793-7. [PubMed:14636753 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

General function:
Involved in DNA binding
Specific function:
Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3
Gene Name:
AR
Uniprot ID:
P10275
Molecular weight:
98987.9
References
  1. Juul A: The effects of oestrogens on linear bone growth. Hum Reprod Update. 2001 May-Jun;7(3):303-13. [PubMed:11392377 ]
  2. Zhao J, Bauman WA, Huang R, Caplan AJ, Cardozo C: Oxandrolone blocks glucocorticoid signaling in an androgen receptor-dependent manner. Steroids. 2004 May;69(5):357-66. [PubMed:15219414 ]
  3. Bi LX, Wiren KM, Zhang XW, Oliveira GV, Klein GL, Mainous EG, Herndon DN: The effect of oxandrolone treatment on human osteoblastic cells. J Burns Wounds. 2007 Mar 7;6:e4. [PubMed:17364004 ]
  4. Cadwallader AB, Rollins DE, Lim CS: Effect of anabolic-androgenic steroids and glucocorticoids on the kinetics of hAR and hGR nucleocytoplasmic translocation. Mol Pharm. 2010 Jun 7;7(3):689-98. doi: 10.1021/mp900259w. [PubMed:20230007 ]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]