(1S,2R,10S,11S,15S,17S)-17-hydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-6-ene-5,14-dione

• ChemBase ID: 155189
• Molecular Formular: C19H26O3
• Molecular Mass: 302.40794
• Monoisotopic Mass: 302.18819469
• SMILES: C[C@]12CCC(=O)C=C1CC[C@@H]1[C@@H]2[C@H](C[C@]2([C@H]1CCC2=O)C)O
• Canonical SMILES: O=C1CC[C@]2(C(=C1)CC[C@@H]1[C@@H]2[C@@H](O)C[C@]2([C@H]1CCC2=O)C)C
• InChI: InChI=1S/C19H26O3/c1-18-8-7-12(20)9-11(18)3-4-13-14-5-6-16(22)19(14,2)10-15(21)17(13)18/h9,13-15,17,21H,3-8,10H2,1-2H3/t13-,14-,15-,17+,18-,19-/m0/s1
• InChIKey: WSCUHXPGYUMQEX-KCZNZURUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10S,11S,15S,17S)-17-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-ene-5,14-dione
• IUPAC Traditional name: 4-androsten-11β-ol-3,17-dione
• Synonyms: 11β-Hydroxy-4-androstene-3,17-dione; 4-Androsten-11β-ol-3,17-dione

Database IDs

• CAS Number: 382-44-5
• MDL Number: MFCD00051131
• PubChem SID: 162249327; 24890715
• PubChem CID: 94141

CALCULATED PROPERTIES

• Acid pKa: 14.879148
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 2.620186
• LogD (pH = 7.4): 2.620186
• Log P: 2.620186
• Molar Refractivity: 85.2 cm^3
• Polarizability: 33.33251 Å^3
• Polar Surface Area: 54.37 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Drug Control: regulated under CDSA - not available from Sigma-Aldrich Canada

Product Information

• Empirical Formula (Hill Notation): C19H26O3

DETAILS

Sigma Aldrich - A3009

Biochem/physiol Actions
11β-Hydroxy-4-androstene-3,17-dione is a naturally occurring androgen. Plasma levels are very high in 21-hydroxylase deficiency, Cushing’s syndrome, and hyperandrogenism of adrenal origin, and very low in congenital 11-hydroxylase deficiency and adrenal insufficiency.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. A3009.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.