(1S,2S,10S,11S,14R,15S,17S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyl-18-oxapentacyclo[8.8.0.01,17.02,7.011,15]octadec-6-en-5-one

• ChemBase ID: 170042
• Molecular Formular: C21H28O5
• Molecular Mass: 360.44402
• Monoisotopic Mass: 360.193674
• SMILES: C1CC(=O)C=C2[C@]1([C@@]13[C@@H](CC2)[C@H]2[C@](C[C@@H]1O3)([C@](CC2)(C(=O)CO)O)C)C
• Canonical SMILES: OCC(=O)[C@@]1(O)CC[C@@H]2[C@]1(C)C[C@@H]1O[C@@]31[C@H]2CCC1=CC(=O)CC[C@]31C
• InChI: InChI=1S/C21H28O5/c1-18-7-5-13(23)9-12(18)3-4-15-14-6-8-20(25,16(24)11-22)19(14,2)10-17-21(15,18)26-17/h9,14-15,17,22,25H,3-8,10-11H2,1-2H3/t14-,15-,17-,18-,19-,20-,21+/m0/s1
• InChIKey: FJCQSIDXADHVFH-FEUSSREZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,10S,11S,14R,15S,17S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyl-18-oxapentacyclo[8.8.0.0^1,^1^7.0^2,^7.0^1^1,^1^5]octadec-6-en-5-one
• IUPAC Traditional name: (1S,2S,10S,11S,14R,15S,17S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyl-18-oxapentacyclo[8.8.0.0^1,^1^7.0^2,^7.0^1^1,^1^5]octadec-6-en-5-one
• Synonyms: (9β,11β)-9,11-Epoxy-17,21-dihydroxypregn-4-ene-3,20-dione; 9β,11β-Epoxy-17,21-dihydroxypregn-4-ene-3,20-dione; Hydrocortisone (9β,11β)-Epoxide

Database IDs

• CAS Number: 10072-97-6
• PubChem SID: 164225952
• PubChem CID: 112075

CALCULATED PROPERTIES

• Acid pKa: 12.586617
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.5893852
• LogD (pH = 7.4): 1.5893823
• Log P: 1.5893852
• Molar Refractivity: 95.11 cm^3
• Polarizability: 37.63588 Å^3
• Polar Surface Area: 87.13 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off-White Solid
• Melting Point: 185-188°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - H714590

A Hydrocortisone derivative formed by microbiological epoxidation of Hydrocortisone (H714615).

REFERENCES

• Kurosawa, Y., et al.: Agric. Biol. Chem., 25 838 (1961)