(1R,2S,10S,11S,14R,15S,17S)-1-fluoro-14,17-dihydroxy-14-[2-hydroxy(2H2)acetyl]-2,15-dimethyl(4,4,6-2H3)tetracyclo[8.7.0.02,7.011,15]heptadec-6-en-5-one

• ChemBase ID: 169030
• Molecular Formular: C21H29FO5
• Molecular Mass: 380.4503632
• Monoisotopic Mass: 380.19990225
• SMILES: C1CC(=O)C=C2[C@]1([C@@]1([C@@H](CC2)[C@H]2[C@](C[C@@H]1O)([C@](CC2)(C(=O)CO)O)C)F)C
• Canonical SMILES: OCC(=O)[C@@]1(O)CC[C@@H]2[C@]1(C)C[C@H](O)[C@]1([C@H]2CCC2=CC(=O)CC[C@]12C)F
• InChI: InChI=1S/C21H29FO5/c1-18-7-5-13(24)9-12(18)3-4-15-14-6-8-20(27,17(26)11-23)19(14,2)10-16(25)21(15,18)22/h9,14-16,23,25,27H,3-8,10-11H2,1-2H3/t14-,15-,16-,18-,19-,20-,21-/m0/s1
• InChIKey: AAXVEMMRQDVLJB-BULBTXNYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,10S,11S,14R,15S,17S)-1-fluoro-14,17-dihydroxy-14-[2-hydroxy(^2H₂)acetyl]-2,15-dimethyl(4,4,6-^2H₃)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• IUPAC Traditional name: (1R,2S,10S,11S,14R,15S,17S)-1-fluoro-14,17-dihydroxy-14-[2-hydroxy(^2H₂)acetyl]-2,15-dimethyl(4,4,6-^2H₃)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• Synonyms: (11β)-9-Fluoro-11,17,21-trihydroxypregn-4-ene-3,20-dione-d5; 9α-Fluorohydrocortisone-d5; 9α-Fluoro-17-hydroxycorticosterone-d5; Fluohydrisone-d5; Astonin H-d5; NSC 11318-d5; Fludrocortisone-d5 (Major)

Database IDs

• PubChem SID: 162263162
• PubChem CID: 71316781

CALCULATED PROPERTIES

• Acid pKa: 12.550707
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 1.3187733
• LogD (pH = 7.4): 1.3187703
• Log P: 1.3187734
• Molar Refractivity: 96.928 cm^3
• Polarizability: 38.038094 Å^3
• Polar Surface Area: 94.83 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 238-240°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - F428102

A mineralocorticoid.

REFERENCES

• Florey, K., et al.: Anal. Profiles Drug Subs., 3, 281 (1974)