(1S,2R,4R,10R,11S,14R,15S)-4-(acetyloxy)-2,15-dimethyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadec-6-en-14-yl acetate

• ChemBase ID: 171181
• Molecular Formular: C23H32O5
• Molecular Mass: 388.49718
• Monoisotopic Mass: 388.22497412
• SMILES: [C@@H]1(C(=O)C=C2[C@](C1)([C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)([C@@H](CC2)OC(=O)C)C)C)OC(=O)C
• Canonical SMILES: CC(=O)O[C@@H]1C[C@@]2(C)C(=CC1=O)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@H]2OC(=O)C)C
• InChI: InChI=1S/C23H32O5/c1-13(24)27-20-12-23(4)15(11-19(20)26)5-6-16-17-7-8-21(28-14(2)25)22(17,3)10-9-18(16)23/h11,16-18,20-21H,5-10,12H2,1-4H3/t16-,17-,18-,20+,21+,22-,23-/m0/s1
• InChIKey: XEXPFKWHLWMBQT-OLLSANEXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,4R,10R,11S,14R,15S)-4-(acetyloxy)-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-14-yl acetate
• IUPAC Traditional name: (1S,2R,4R,10R,11S,14R,15S)-4-(acetyloxy)-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-14-yl acetate
• Synonyms: 2β,17β-Diacetoxy-4-androsten-3-one; Androst-4-ene-2β,17β-diol-3-one Diacetate; 2β-Hydroxy Testosterone 2,17-Diacetate; (2α,17β)-2,17-Bis(acetyloxy)-androst-4-en-3-one; 2α,17β-Diacetoxyandrost-4-en-3-one; NSC 9787; 2α-Hydroxy Testosterone 2,17-Diacetate

Database IDs

• CAS Number: 21936-08-3; 21936-10-7
• PubChem SID: 164227091
• PubChem CID: 71749292

CALCULATED PROPERTIES

• Acid pKa: 17.45617
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 3.3766081
• LogD (pH = 7.4): 3.3766081
• Log P: 3.3766081
• Molar Refractivity: 104.225 cm^3
• Polarizability: 41.554996 Å^3
• Polar Surface Area: 69.67 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol

DETAILS

Toronto Research Chemicals - H956725

A protected metabolite of Testosterone (T155000) in human.

Toronto Research Chemicals - H956730

A protected metabolite of Testosterone (T155000) in humans and animals.

REFERENCES

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• Reynolds, R., et al.: J. Clin. Endocrinol. Metab., 86, 245 (1997)
• Wolf, C., et al.: Toxicol. Sci. 65, 71 (1997)
• Borlak, J., et al.: Drug Metab. Dispos., 32, 675 (2004)
• Demisch, K. et al.: Eur. J. Biochem., 8, 284 (1969)
• Fernandez, C. et al.: J Chrom. B Biomed. Appl., 677, 363 (1969)
• Capolongo, F. et al.: J. Vet. Pharmacol. Therap., 26, 160 (1969)