(1S,2S,5R,7R,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-one

• ChemBase ID: 2567
• Molecular Formular: C19H30O2
• Molecular Mass: 290.4403
• Monoisotopic Mass: 290.2245802
• SMILES: C1C[C@@H](O)C[C@H]2CC[C@@H]3[C@@H]([C@@]12C)CC[C@]1([C@H]3CCC1=O)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+/m1/s1
• InChIKey: QGXBDMJGAMFCBF-BNSUEQOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,5R,7R,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-one; (1S,2S,5R,7R,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: α-etiocholanolone
• Synonyms: (3α,5β)-3-Hydroxyandrostan-17-one; 3α-Etiocholanolone; 3α-Hydroxy-5β-androstane-17-one; 5-Isoandrosterone; 5β-Androstan-3α-ol-17-one; 5β-Androstane-3α-ol-17-one; Aetiocholanolone; Etiocholanolone; NSC 50908; α-Etiocholanolone; 5β-Androsterone; Etiocholan-3α-ol-17-one; Etiocholanone solution; ETIOCHOLAN-3α-01-17-ONE; Aetiocholanolone; Etiocholan-3α-ol-17-one; 3α-Hydroxy-5β-androstan-17-one; 5β-Androsterone; Etiocholanone; 本胆烷-3α-醇-17-酮; 苯胆烷醇酮; 还原尿睾酮 溶液; 3α-羟基-5β-雄甾烷-17-酮; 5β-雄酮; 还原尿睾酮; 还原胆烷醇酮

Database IDs

• CAS Number: 53-42-9
• EC Number: 200-835-2
• MDL Number: MFCD00064133
• Beilstein Number: 2217625
• PubChem SID: 160966017; 24894603; 46507911
• PubChem CID: 5880

CALCULATED PROPERTIES

JChem

• Rotatable Bonds: 0
• Lipinski's Rule of Five: true
• 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

ALOGPS 2.1

• Solubility (Water): 6.34e-03 g/l
• Log P: 3.71
• LOG S: -4.66

PROPERTIES

Physical Property

• Flash Point: 2 °C; 35.6 °F

Safety Information

• European Hazard Symbols: Flammable (F); Harmful (Xn)
• German water hazard class: 2; 3
• Risk Statements: 11-20/21/22-36
• Safety Statements: 16-36/37
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H302-H312-H319-H332
• GHS Precautionary statements: P210-P280-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter; Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Drug Control: regulated under CDSA - not available from Sigma-Aldrich Canada
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... SERPINA6(866)rat ... Gabra1(29705), Gabra2(29706), Gabrg2(29709)

Product Information

• Purity: 98%
• Concentration: 100 ng/μL in acetonitrile
• Grade: VETRANAL™, analytical standard
• Empirical Formula (Hill Notation): C19H30O2

DETAILS

MP Biomedicals - 05203853

MP Biomedicals Rare Chemical collection

DrugBank - DB02854

• Drug Groups: experimental
• Description: The 5-beta-reduced isomer of androsterone. Etiocholanolone is a major metabolite of testosterone and androstenedione in many mammalian species including humans. It is excreted in the urine. [PubChem]

Sigma Aldrich - E5126

Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. E5126.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Sigma Aldrich - 32833

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Toronto Research Chemicals - A637630

5β-Androsterone is a metabolite of Testosterone (T155000). β-Androsterone is a stereoisomer of Androsterone (A637535). 5β-Androsterone showed a weak estrogenic action.

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)