(1S,2S,5R,7S,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadecan-14-one

• ChemBase ID: 125861
• Molecular Formular: C19H30O2
• Molecular Mass: 290.4403
• Monoisotopic Mass: 290.2245802
• SMILES: O=C1[C@]2(CC[C@H]3[C@H]([C@@H]2CC1)CC[C@H]1C[C@H](O)CC[C@]31C)C
• Canonical SMILES: O[C@@H]1CC[C@]2([C@H](C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CCC2=O)C)C
• InChI: InChI=1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-16,20H,3-11H2,1-2H3/t12-,13+,14-,15-,16-,18-,19-/m0/s1
• InChIKey: QGXBDMJGAMFCBF-HLUDHZFRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,5R,7S,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-one
• IUPAC Traditional name: androsterone
• Synonyms: Esterase basic kit; 3α-Hydroxy-5α-androstan-17-one; (3α,5α)-3-Hydroxyandrostan-17-one; 3-Epihydroxyetioallocholan-17-one; 3α-Hydroxy-17-androstanone; 3α-Hydroxyetioallocholan-17-one; 5α-Androsterone; Androkinin; Androtin; Atromide ICI; NSC 9898; U 60366; 5α-Androstan-3α-ol-17-one; Androsterone; Androsterone; 3α-羟基-5α-雄甾烷-17-酮; 雄酮

Database IDs

• CAS Number: 53-41-8
• EC Number: 232-773-7
• MDL Number: MFCD00003618
• Beilstein Number: 2217626
• PubChem SID: 24846609; 24869691; 24853102; 24869692; 162220206
• PubChem CID: 5879
• CHEBI ID: 16032
• CHEMBL: 87285
• Chemspider ID: 5668
• Unique Ingredient Identifier: C24W7J5D5R
• Wikipedia Title: Androsterone

CALCULATED PROPERTIES

• Acid pKa: 18.296396
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.7672846
• LogD (pH = 7.4): 3.7672846
• Log P: 3.7672846
• Molar Refractivity: 83.8089 cm^3
• Polarizability: 33.49998 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethanol; Methanol
• Apperance: White Solid
• Melting Point: 181-184 °C(lit.); 182-184°C
• Optical Rotation: [α]20/D +96±2°, c = 0.7% in ethanol; [α]20/D +96°, c = 0.7 in ethanol

Safety Information

• Storage Condition: Refrigerator
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38-43
• Safety Statements: 26-36/37
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H315-H319-H334-H335
• GHS Precautionary statements: P261-P305 + P351 + P338-P342 + P311
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Drug Control: regulated under CDSA - not available from Sigma-Aldrich Canada
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... SERPINA6(866)rat ... Ar(24208)

Product Information

• Purity: 97%
• Grade: purum; VETRANAL™, analytical standard
• Empirical Formula (Hill Notation): C19H30O2

DETAILS

Sigma Aldrich - 46041

Components
Composition:96667 Esterase from Bacillus subtilis, 10 mg 51963 Esterase from Bacillus subtilis, 10 mg 46051 Esterase from Bacillus stearothermophilus, 10 mg79208 Esterase from Rhizopus oryzae, 100 mg46056 Esterase from Candida lipolytica, 50 mg 46059 Esterase from Mucor miehei, 50 mg 46069 Esterase from horse liver, 50 mg 46071 Esterase from Saccharomyces cerevisiae, 25 mg46058 Esterase from hog liver, 10 mg 75742 Esterase Pseudomonas fluorescens, recombinant from E. coli, 10 mg

Sigma Aldrich - A9755

Biochem/physiol Actions
Anabolic steroid

Sigma Aldrich - 10350

Other Notes
Sales restrictions may apply

Sigma Aldrich - 31579

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 31579.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - A637535

A steroid hormone with weak androgenic activity. It is metabolized from Testosterone (T155000) in the liver and is used in doping analysis to detect testosterone misuse. Controlled Substance.

REFERENCES

• Park, J., et al.: J. Anal. Toxicol., 14, 66 (1990)
• Palonek, E., et al.: J. Steroid Mol. Biol., 55, 121 (1990)
• Aguilera, R., et al.: Clin. Chem. 47, 292 (1990)
• Flenker, U., et al.: Steroids, 73, 408 (1990)