Showing Metabocard for 5alpha-androstane-3alpha,17beta-diol (BASm0002009)
| Common Name | 5alpha-androstane-3alpha,17beta-diol |
|---|---|
| Description | Androstanediol is a metabolite of dihydrotestosterone, itself a metabolite of testosterone. Androstanediol is implicated in the regulation of gonadotropin secretion. As a metabolite of dihydroxytestosterone formed in the peripheral tissues, androstanediol and androstnediol-glucuronide can be used to estimate peripheral androgen activity. Androstanediol is a potential GABA (A) receptor-modulating neurosteroid with anticonvulsant properties and hence could act as a key neuromodulator in the central nervous system. It is considered that androstanediol has hedonic effects; therefore it is anticipated that androgens that are readily metabolized to androstanediol may have higher abuse potential than androgens that are not as easily metabolized to androstanediol. These results add to the growing literature indicating that athletes and non-athletes may be at considerable risk when they abuse androgens. (PMID: 11500254 , 16040068 , 11744084 ). |
| Structure | |
| Molecular Formula | C19H32O2 |
| Average Mass | 292.45620 |
| Monoisotopic Mass | 292.24023 |
| IUPAC Name | (1S,2S,5R,7S,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,14-diol |
| Traditional Name | (1s,2s,5r,7s,10r,11s,15s)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,14-diol |
| CAS Registry Number | 25126-76-5 |
| SMILES | C[C@]12CC[C@@H](O)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O)CC[C@@H]12 |
| InChI Identifier | InChI=1S/C19H32O2/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/h12-17,20-21H,3-11H2,1-2H3/t12-,13+,14-,15-,16-,17?,18-,19-/m0/s1 |
| InChI Key | CBMYJHIOYJEBSB-UNPXRYTGSA-N |
| CHEBI ID | CHEBI:36713 |
| HMDB ID | HMDB0000495 |
| State | Not Available |
| Water Solubility | 1.93e-02 g/l |
| logP | 3.56 |
| logS | -4.18 |
| pKa (Strongest Acidic) | 18.30 |
| pKa (Strongest Basic) | -0.76 |
| Hydrogen Acceptor Count | 2 |
| Hydrogen Donor Count | 2 |
| Polar Surface Area | 40.46 Ų |
| Rotatable Bond Count | 0 |
| Physiological Charge | 0 |
| Formal Charge | 0 |
| Refractivity | 84.63 m³·mol⁻¹ |
| Polarizability | 35.34 |