(1S,2R,10R,11S,14S,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadeca-6,8-dien-5-one

• ChemBase ID: 178182
• Molecular Formular: C19H26O2
• Molecular Mass: 286.40854
• Monoisotopic Mass: 286.19328007
• SMILES: C1C(=O)C=C2[C@](C1)([C@@H]1[C@@H](C=C2)[C@H]2[C@](CC1)([C@H](CC2)O)C)C
• Canonical SMILES: O=C1CC[C@]2(C(=C1)C=C[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2O)C)C
• InChI: InChI=1S/C19H26O2/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/h3-4,11,14-17,21H,5-10H2,1-2H3/t14-,15-,16-,17-,18-,19-/m0/s1
• InChIKey: UMDCOKNNLDEKJB-DYKIIFRCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10R,11S,14S,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-6,8-dien-5-one
• IUPAC Traditional name: 6-dehydrotestosterone
• Synonyms: (17β)-17-Hydroxyandrosta-4,6-dien-3-one; 17β-Hydroxy-Δ4,6-androstadien-3-one; 4,6-Androstadiene-17β-ol-3-one; 6,7-Dehydrotestosterone; 6-Dehydrotestosterone; Androst-4,6-dien-17β-ol-3-one; Androsta-4,6-dien-17β-ol-3-one; NSC 75560; Δ4,6-Androstadien-3-one-17β-ol; Δ6-Testosterone

Database IDs

• CAS Number: 2484-30-2
• PubChem SID: 164234092
• PubChem CID: 17209

CALCULATED PROPERTIES

• Acid pKa: 19.444408
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.0035017
• LogD (pH = 7.4): 3.0035017
• Log P: 3.0035017
• Molar Refractivity: 85.5464 cm^3
• Polarizability: 33.02064 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - T155030

A metabolite of Testosterone (T155000). Controlled substance.

REFERENCES

• Peng, S., et al.: Steroids, 67, 39 (2002)
• Pozo, O., et al.: Drug Metab. Dispos., 37, 2153 (2002)