(1S,2R,10S,11S,14R,15S)-14-hydroxy-14-[2-hydroxy(2H2)acetyl]-2,15-dimethyl(1,4,4,6,8,8,16,16-2H8)tetracyclo[8.7.0.02,7.011,15]heptadec-6-ene-5,17-dione

• ChemBase ID: 164973
• Molecular Formular: C21H28O5
• Molecular Mass: 360.44402
• Monoisotopic Mass: 360.193674
• SMILES: C1C(=O)C=C2[C@](C1)([C@@H]1[C@@H](CC2)[C@H]2[C@](CC1=O)([C@](CC2)(C(=O)CO)O)C)C
• Canonical SMILES: OCC(=O)[C@@]1(O)CC[C@@H]2[C@]1(C)CC(=O)[C@H]1[C@H]2CCC2=CC(=O)CC[C@]12C
• InChI: InChI=1S/C21H28O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h9,14-15,18,22,26H,3-8,10-11H2,1-2H3/t14-,15-,18?,19-,20-,21-/m0/s1
• InChIKey: MFYSYFVPBJMHGN-VLNSYWPESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10S,11S,14R,15S)-14-hydroxy-14-[2-hydroxy(^2H₂)acetyl]-2,15-dimethyl(1,4,4,6,8,8,16,16-^2H₈)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-ene-5,17-dione
• IUPAC Traditional name: (1S,2R,10S,11S,14R,15S)-14-hydroxy-14-[2-hydroxy(^2H₂)acetyl]-2,15-dimethyl(1,4,4,6,8,8,16,16-^2H₈)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-ene-5,17-dione
• Synonyms: 17,21-Dihydroxy-pregn-4-ene-3,11,20-trione-d8; 17-Hydroxy-11-dehydrocorticosterone-d8; 11-Dehydro-17-hydroxy-corticosterone-d8; Adrenalex-d8; Compound E-d8; Cortisate-d8; Cortivite-d8; Cortogen-d8; Cortone-d8; NSC 9703-d8; Cortisone-d8 (Major)

Database IDs

• PubChem SID: 162259107
• PubChem CID: 71314981

CALCULATED PROPERTIES

• Acid pKa: 12.5762005
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.6606807
• LogD (pH = 7.4): 1.6606778
• Log P: 1.6606807
• Molar Refractivity: 96.4748 cm^3
• Polarizability: 37.741665 Å^3
• Polar Surface Area: 91.67 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Ethanol; Methanol
• Apperance: Off-White Solid
• Melting Point: 211-214°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - C696502

Labelled Cortisone (C696500). Glucocorticoid, anti-inflammatory agent.

REFERENCES

• Honda, A., et al.: J. Biol. Chem., 268, 7759 (1993)
• Narko, K., et al.: J. Clin. Endocrinol. Metab., 86, 1765 (1993)
• Michael, A., et al.: Reproduction, 126, 425 (1993)