4-{2-[(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0?,?.0??,??]heptadec-6-en-14-yl]-2-oxoethoxy}-4-oxobutanoic acid

• ChemBase ID: 109323
• Molecular Formular: C25H34O8
• Molecular Mass: 462.53266
• Monoisotopic Mass: 462.22536805
• SMILES: O=C(O)CCC(=O)OCC(=O)[C@@]1(O)CC[C@H]2[C@H]3[C@H]([C@@H](O)C[C@]12C)[C@@]1(C(=CC(=O)CC1)CC3)C
• Canonical SMILES: OC(=O)CCC(=O)OCC(=O)[C@@]1(O)CC[C@@H]2[C@]1(C)C[C@H](O)[C@H]1[C@H]2CCC2=CC(=O)CC[C@]12C
• InChI: InChI=1S/C25H34O8/c1-23-9-7-15(26)11-14(23)3-4-16-17-8-10-25(32,24(17,2)12-18(27)22(16)23)19(28)13-33-21(31)6-5-20(29)30/h11,16-18,22,27,32H,3-10,12-13H2,1-2H3,(H,29,30)/t16-,17-,18-,22+,23-,24-,25-/m0/s1
• InChIKey: VWQWXZAWFPZJDA-CGVGKPPMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{2-[(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0?,?.0??,??]heptadec-6-en-14-yl]-2-oxoethoxy}-4-oxobutanoic acid; 4-{2-[(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-14-yl]-2-oxoethoxy}-4-oxobutanoic acid
• IUPAC Traditional name: solu-cortef; 4-{2-[(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-14-yl]-2-oxoethoxy}-4-oxobutanoic acid
• Synonyms: 4-{2-[(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-yl]-2-oxoethoxy}-4-oxobutanoic acid; HYDROCORTISONE HEMISUCCINATE; Hydrocortisone hemisuccinate; 11β,17α,21-Trihydroxy-4-pregnene-3,20-dione 21-hemisuccinate; Hydrocortisone 21-hemisuccinate; 氢化可的松 21-半琥珀酸酯; 氢化可的松琥珀酸酯

Database IDs

• CAS Number: 2203-97-6; 83784-20-7
• EC Number: 218-612-3
• MDL Number: MFCD00046256
• PubChem SID: 24895539; 162094771
• PubChem CID: 16623

CALCULATED PROPERTIES

• Acid pKa: 3.6580515
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -0.29817104
• LogD (pH = 7.4): -1.7807376
• Log P: 1.5411546
• Molar Refractivity: 117.4448 cm^3
• Polarizability: 46.39687 Å^3
• Polar Surface Area: 138.2 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Hydrophobicity(logP): 2.002

Safety Information

• RTECS: TU5010147
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Pharmacology Properties

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

Product Information

• Purity: 95%
• Grade: analytical standard, for drug analysis
• Application(s): Antiallergic agent; Antiinflammatory; Immunosuppressive

DETAILS

Sigma Aldrich - H2882

Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. H2882.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

REFERENCES

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