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2203-97-6 molecular structure
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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 and InChIs

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

Cite this record

CBID:109323 http://www.chembase.cn/molecule-109323.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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[8.7.0.02,7.011,15]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[8.7.0.02,7.011,15]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
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

CALCULATED PROPERTIES

JChem
Acid pKa 3.6580515  H Acceptors
H Donor LogD (pH = 5.5) -0.29817104 
LogD (pH = 7.4) -1.7807376  Log P 1.5411546 
Molar Refractivity 117.4448 cm3 Polarizability 46.39687 Å3
Polar Surface Area 138.2 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Hydrophobicity(logP)
2.002 expand Show data source
RTECS
TU5010147 expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
3 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
-20°C expand Show data source
Mechanism of Action
ACTH antagonist expand Show data source
ACTH secretion inhibitor expand Show data source
Calcium mobilizer expand Show data source
Glucocorticoid expand Show data source
Gluconeogenesis promoter expand Show data source
Glycogen deposition inhibitor expand Show data source
Immunosuppressive expand Show data source
Phosphorus-mobilizer expand Show data source
Purity
95% expand Show data source
Grade
analytical standard, for drug analysis expand Show data source
Certificate of Analysis
Download expand Show data source
Application(s)
Antiallergic agent expand Show data source
Antiinflammatory expand Show data source
Immunosuppressive expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - H2882 external link
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

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
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  • • Reichstein, T., Helv. Chim. Acta, 1937, 20, 953, (isol)
  • • v. Euw, J. et al., Helv. Chim. Acta, 1942, 25, 988, (struct)
  • • Zaffaroni, A. et al., J.A.C.S., 1951, 73, 1390, (biosynth)
  • • Wendler, N.L. et al., J.A.C.S., 1951, 73, 3818, (synth)
  • • Heller, E., Z. Naturforsch., B, 1959, 14, 298, (ir)
  • • U.S. Pat., 1960, 2 936 313; CA, 54, 19783, (phosphate)
  • • Shirasaka, M., Chem. Pharm. Bull., 1961, 9, 152, (synth)
  • • Saucy, G. et al., Helv. Chim. Acta, 1966, 49, 1529; 1967, 50, 1394, (synth, ir, uv, pmr)
  • • van der Sijde, D. et al., Rec. Trav. Chim. (J. R. Neth. Chem. Soc.), 1966, 85, 721, (synth)
  • • Smit, A. et al., Rec. Trav. Chim. (J. R. Neth. Chem. Soc.), 1966, 85, 731, (synth, struct, pmr)
  • • Bhacca, N.S. et al., J.A.C.S., 1973, 95, 8421, (cmr)
  • • Haskins, N.J. et al., Biomed. Mass Spectrom., 1974, 1, 423, (ms)
  • • Fiegel, G., Arzneim.-Forsch., 1975, 25, 560, (use)
  • • Ger. Pat., 1979, 2 826 257; CA, 93, 26657, (butyrate, propionate)
  • • Genard, P., Org. Mass Spectrom., 1979, 12, 396, (pmr)
  • • Castellano, E.E. et al., Acta Cryst. B, 1980, 36, 3063, (cryst. struct)
  • • Florey, K., Anal. Profiles Drug Subst., 1983, 12, 277, (rev, synth, pharmacol, anal)
  • • Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 6346; 6986; 7335
  • • Minagawa, K. et al., J.C.S. Perkin 1, 1988, 587, (synth)
  • • Kirk, D.N. et al., J.C.S. Perkin 2, 1990, 1567, (pmr)
  • • Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 734
  • • Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, BAV275; HHR000; CNS750; HHQ800; HHQ825; HHQ850; HHQ875
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PATENTS

PATENTS

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INTERNET

INTERNET

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