(1S,2R,10S,11S,14R,15S)-14-acetyl-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-6-ene-5,17-dione

• ChemBase ID: 165878
• Molecular Formular: C21H28O4
• Molecular Mass: 344.44462
• Monoisotopic Mass: 344.19875938
• SMILES: C1C(=O)C=C2[C@](C1)([C@@H]1[C@@H](CC2)[C@H]2[C@](CC1=O)([C@](CC2)(C(=O)C)O)C)C
• Canonical SMILES: O=C1CC[C@]2(C(=C1)CC[C@@H]1[C@@H]2C(=O)C[C@]2([C@H]1CC[C@]2(O)C(=O)C)C)C
• InChI: InChI=1S/C21H28O4/c1-12(22)21(25)9-7-16-15-5-4-13-10-14(23)6-8-19(13,2)18(15)17(24)11-20(16,21)3/h10,15-16,18,25H,4-9,11H2,1-3H3/t15-,16-,18+,19-,20-,21-/m0/s1
• InChIKey: PUKLDDOGISCFCP-JSQCKWNTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10S,11S,14R,15S)-14-acetyl-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-ene-5,17-dione
• IUPAC Traditional name: 21-deoxycortisone
• Synonyms: 17-Hydroxypregn-4-ene-3,11,20-trione; 17α-Hydroxy-11-oxoprogesterone; 17α-Hydroxypregn-4-ene-3,11,20-trione; 21-Desoxycortisone; 4-Pregnene-17α-ol-3,11,20-trione; 6-Pregn-4-en-17α-ol-3,11,20-trione; NSC 38722; 21-Deoxy Cortisone

Database IDs

• CAS Number: 1882-82-2
• PubChem SID: 162260011
• PubChem CID: 102178

CALCULATED PROPERTIES

• Acid pKa: 12.6837845
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 2.4779286
• LogD (pH = 7.4): 2.4779265
• Log P: 2.4779286
• Molar Refractivity: 94.7726 cm^3
• Polarizability: 37.098347 Å^3
• Polar Surface Area: 71.44 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D232610

A Cortisone derivative, a glucocorticoid.

REFERENCES

• Mickelson, K., et al.: Biochemistry, 20, 6211 (1981)
• Westphal, U., et al.: J. Steroid Biochem., 19, 1 (1981)