(1S,2S,7S,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadecane-5,14-dione

• ChemBase ID: 1345
• Molecular Formular: C19H28O2
• Molecular Mass: 288.42442
• Monoisotopic Mass: 288.20893014
• SMILES: O=C1[C@@]2([C@H]([C@H]3[C@@H]([C@@]4([C@@H](CC3)CC(=O)CC4)C)CC2)CC1)C
• Canonical SMILES: O=C1CC[C@]2([C@H](C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CCC2=O)C)C
• InChI: InChI=1S/C19H28O2/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/h12,14-16H,3-11H2,1-2H3/t12-,14-,15-,16-,18-,19-/m0/s1
• InChIKey: RAJWOBJTTGJROA-WZNAKSSCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,7S,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecane-5,14-dione; (1S,2S,7S,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,14-dione
• IUPAC Traditional name: androstanedione
• Synonyms: 5α-Androstane-3,17-dione; 5α-Androsta-3,17-dione; Androstane-3,17-dione; DHA; Dihydroandrostenedione; NSC 60796; NSC 9897; 5α-Androstanedione; (5S,8R,9S,10S,13S,14S)-10,13-dimethyldodecahydro-1H-cyclopenta[a]phenanthrene-3,17(2H,4H)-dione; 5alpha-Androstan-3,17-Dione; Androstanedione

Database IDs

• CAS Number: 846-46-8
• PubChem SID: 160964805; 46508701
• PubChem CID: 222865

CALCULATED PROPERTIES

JChem

• Acid pKa: 19.776207
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 3.9747853
• LogD (pH = 7.4): 3.9747853
• Log P: 3.9747853
• Molar Refractivity: 82.7808 cm^3
• Polarizability: 32.952457 Å^3
• Polar Surface Area: 34.14 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.4
• LOG S: -4.59
• Solubility (Water): 7.39e-03 g/l

DETAILS

DrugBank - DB03620

Drug information: experimental

DrugBank - DB01561

Drug information: illicit; experimental

Toronto Research Chemicals - A637610

5α-Androstanedione is a metabolite of Androstendione (A637550). 5α-Androstanedione is an important intermediate in the conversion of Androstenedione to Androstanolone (A637540).

REFERENCES

• Milewich, L. et al.: J. Steroid CHem., 16, 81 (1982)
• Stanczyk, F.Z. et al.: J. Steroid Biochem. Mol. Biol., 37, 129 (1982)