(1S,2R,5R,10R,11S,15S)-2,15-dimethyl-14-oxotetracyclo[8.7.0.02,7.011,15]heptadec-7-en-5-yl acetate

• ChemBase ID: 165378
• Molecular Formular: C21H30O3
• Molecular Mass: 330.4611
• Monoisotopic Mass: 330.21949482
• SMILES: C1[C@H](CC2=CC[C@@H]3[C@@H]([C@]2(C1)C)CC[C@]1([C@H]3CCC1=O)C)OC(=O)C
• Canonical SMILES: CC(=O)O[C@@H]1CC[C@]2(C(=CC[C@@H]3[C@@H]2CC[C@]2([C@H]3CCC2=O)C)C1)C
• InChI: InChI=1S/C21H30O3/c1-13(22)24-15-8-10-20(2)14(12-15)4-5-16-17-6-7-19(23)21(17,3)11-9-18(16)20/h4,15-18H,5-12H2,1-3H3/t15-,16+,17+,18+,20+,21+/m1/s1
• InChIKey: NCMZQTLCXHGLOK-KPKYYQPRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,5R,10R,11S,15S)-2,15-dimethyl-14-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-5-yl acetate
• IUPAC Traditional name: (1S,2R,5R,10R,11S,15S)-2,15-dimethyl-14-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-5-yl acetate
• Synonyms: (3β)-3-(Acetyloxy)androst-5-en-17-one; 17-Oxoandrost-5-en-3β-yl Acetate; 3β-Acetoxy-5-androstene-17-one; 3β-Hydroxy-5-androstene-17-one Acetate; Dehydroisoandrosterone Acetate; Prasterone Acetate; SKF 2847; Dehydro Epiandrosterone 3-Acetate

Database IDs

• CAS Number: 853-23-6
• PubChem SID: 162259511
• PubChem CID: 11121082

CALCULATED PROPERTIES

• Acid pKa: 19.957706
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 3.8028305
• LogD (pH = 7.4): 3.8028305
• Log P: 3.8028305
• Molar Refractivity: 93.8104 cm^3
• Polarizability: 37.086353 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 169-171°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - D229590

A metabolite of Dehydroepiandrosterone. This mammalian pro-hormone promotes brain and immune function.

REFERENCES

• Waxman, D., et al.: Methods Enzymol, 206, 462 (1991)
• Moebius, F., et al.: Biochemistry, 35, 16871 (1991)
• Jost, B., et al.: Biochem. J., 327, 95 (1991)
• Lacour, T., et al.: J. Biol. Chem., 273, 23984 (1991)
• Shi, J., et al.: Steroids, 65, 124 (1991)