(1S,2R,10R,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-6-en-5-one

• ChemBase ID: 102717
• Molecular Formular: C21H30O4
• Molecular Mass: 346.4605
• Monoisotopic Mass: 346.21440944
• SMILES: O=C1C=C2[C@]([C@H]3CC[C@@]4([C@@](O)(C(=O)CO)CC[C@H]4[C@@H]3CC2)C)(C)CC1
• Canonical SMILES: OCC(=O)[C@@]1(O)CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCC2=CC(=O)CC[C@]12C
• InChI: InChI=1S/C21H30O4/c1-19-8-5-14(23)11-13(19)3-4-15-16(19)6-9-20(2)17(15)7-10-21(20,25)18(24)12-22/h11,15-17,22,25H,3-10,12H2,1-2H3/t15-,16+,17+,19+,20+,21+/m1/s1
• InChIKey: WHBHBVVOGNECLV-OBQKJFGGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10R,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one; (1S,2R,10R,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
• IUPAC Traditional name: 11-deoxycortisol; (1S,2R,10R,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• Synonyms: 17,21-Dihydroxypregn-4-en-3,20-dione; Cortifen; NSC 18317; Reichstein S; Reichstein's Compound S; SKF 3050; 11-Deoxy Cortisol; (8R,9S,10R,13S,14S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one; Cortoxelone; 17,21-Dihydroxypregn-4-ene-3,20-dione; 11-Desoxycortisol; 11-Deoxyhydrocortisone; 11-Desoxyhydrocortisone; Reichstein's Substance S; Compound S; Cortodoxone; 11-Deoxy-17-hydroxycorticosterone; Cortexolone; 11-Deoxycortisol; 17α,21-Dihydroxy-4-pregnene-3,20-dione; 17α-Hydroxycortexone; 17,21-Dihydroxy-4-pregnene-3,20-dione; 17,21-Dihydroxyprogesterone; 4-Pregnene-17α,21-diol-3,20-dione; REICHSTEIN'S SUBSTANCE S; 17α,21-Dihydroxy-4-pregnene-3,20-dione; 17α-Hydroxycortexone; 4-Pregnene-17α,21-diol-3,20-dione; Reichstein’s Compound S; Reichstein’s substance S; Cortodoxone cortifen

Database IDs

• CAS Number: 152-58-9
• EC Number: 205-805-2
• MDL Number: MFCD00003662
• PubChem SID: 162090247; 24278671
• PubChem CID: 440707
• CHEBI ID: 28324
• CHEMBL: 253144
• Chemspider ID: 389582
• KEGG ID: D03595
• Unique Ingredient Identifier: WDT5SLP0HQ
• Wikipedia Title: Cortodoxone

CALCULATED PROPERTIES

• Acid pKa: 12.591038
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 2.5839312
• LogD (pH = 7.4): 2.5839283
• Log P: 2.5839312
• Molar Refractivity: 95.8075 cm^3
• Polarizability: 37.642807 Å^3
• Polar Surface Area: 74.6 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dioxane; DMSO
• Apperance: White to Off-White Solid
• Melting Point: 192-202°C; 208 °C (dec.)(lit.); 208°C; 215 °C

Safety Information

• Storage Condition: -20°C Freezer; Room Temperature (15-30°C)
• RTECS: TU5011500
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

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

Product Information

• Purity: ≥98%
• Biological Source: Found in the blood and urine of humans and other mammals
• Application(s): Antiinflammatory drug; Immunosuppressive

DETAILS

MP Biomedicals - 02102804

Crystalline

Sigma Aldrich - R0500

Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. R0500.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - D232600

Glucocorticoid receptor binding.

REFERENCES

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• Aldrich Library of 13C and 1H FT NMR Spectra , 1992, 3 , 584B, (nmr)
• Aldrich Library of FT-IR Spectra, 1st edn. , 1985, 2 , 1054C, (ir)
• Reichstein, T. et al. , Helv. Chim. Acta , 1938, 21 , 1197, (isol, synth)
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