2-[(1S,2R,10S,11S,14R,15S)-14-hydroxy-2,15-dimethyl-5,17-dioxotetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-14-yl]-2-oxoethyl acetate

• ChemBase ID: 119291
• Molecular Formular: C23H28O6
• Molecular Mass: 400.46482
• Monoisotopic Mass: 400.18858862
• SMILES: [C@]12([C@@](C(=O)COC(=O)C)(CC[C@H]1[C@H]1[C@@H]([C@@]3(C(=CC(=O)C=C3)CC1)C)C(=O)C2)O)C
• Canonical SMILES: CC(=O)OCC(=O)[C@@]1(O)CC[C@@H]2[C@]1(C)CC(=O)[C@H]1[C@H]2CCC2=CC(=O)C=C[C@]12C
• InChI: InChI=1S/C23H28O6/c1-13(24)29-12-19(27)23(28)9-7-17-16-5-4-14-10-15(25)6-8-21(14,2)20(16)18(26)11-22(17,23)3/h6,8,10,16-17,20,28H,4-5,7,9,11-12H2,1-3H3/t16-,17-,20+,21-,22-,23-/m0/s1
• InChIKey: MOVRKLZUVNCBIP-RFZYENFJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1S,2R,10S,11S,14R,15S)-14-hydroxy-2,15-dimethyl-5,17-dioxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-14-yl]-2-oxoethyl acetate
• IUPAC Traditional name: cortancyl; 2-[(1S,2R,10S,11S,14R,15S)-14-hydroxy-2,15-dimethyl-5,17-dioxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-14-yl]-2-oxoethyl acetate
• Synonyms: 2-((8S,9S,10R,13S,14S,17R)-17-hydroxy-10,13-dimethyl-3,11-dioxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate; Delta-Corlin; Prednisone acetate; 21-(Acetyloxy)-17-hydroxy-pregna-1,4-diene-3,11,20-trione; 21-Acetoxy-17α-hydroxypregna-1,4-diene-3,11,20-trione; Prednisone Acetate; 1-Cortisone 21-Acetate; 1-Dehydrocortisone Acetate; Cortancyl; Delcortin; Δ-Corlin; Deltalone; Ferrosan; Nisone; NSC 10965; Prednisone 21-Acetate

Database IDs

• CAS Number: 125-10-0
• PubChem SID: 162107478
• PubChem CID: 91438

CALCULATED PROPERTIES

• Acid pKa: 12.601158
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 2.0996296
• LogD (pH = 7.4): 2.0996268
• Log P: 2.0996296
• Molar Refractivity: 106.7196 cm^3
• Polarizability: 41.342445 Å^3
• Polar Surface Area: 97.74 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dioxane; DMSO; Methanol
• Apperance: White Solid
• Melting Point: 240-242°C (dec.)

Safety Information

• Storage Condition: Refrigerator

Pharmacology Properties

• Mechanism of Action: ACTH antagonist; ACTH secretion inhibitor; Calcium mobilizer; Corticosteroid; Gluconeogenesis promoter; Glycogen deposition inhibitor; Phosphorus mobilizer

Product Information

• Biological Source: Obt. from pregn-4-ene-3,11,20-trione by incubation with Corynebacterium simplex
• Application(s): Antiinflammatory; Immunosuppressive

DETAILS

Toronto Research Chemicals - P703825

Adrenocortical steroid antiinflammatory.

REFERENCES

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