CAS 64-85-7|CAS 55487-63-3|(1S,2R,10S,11S,14S,15S)-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one|δ<sup>4</sup>-Pregnen-21-ol-3,20-dione|11-Deoxycorti...

General Information

Structure

Molecular Formula

C₂₁H₃₀O₃

Molecular Mass

330.4611

Exact Mass

330.21949482

Charge

InChI

InChI=1S/C21H30O3/c1-20-9-7-14(23)11-13(20)3-4-15-16-5-6-18(19(24)12-22)21(16,2)10-8-17(15)20/h11,15-18,22H,3-10,12H2,1-2H3/t15-,16-,17-,18+,20-,21-/m0/s1

InChIKey

ZESRJSPZRDMNHY-YFWFAHHUSA-N

Canonic Smiles

OCC(=O)[C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCC2=CC(=O)CC[C@]12C

Isomeric Smiles

C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@]34C)[C@@H]1CC[C@@H]2C(=O)CO

Calculated Properties

JChem

LogD (pH = 7.4)

3.33

LogD (pH = 5.5)

3.33

Log P

3.33

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

13.86

Polar Surface Area

54.37

Polarizability

38.06

Molar Refractivity

94.41

LOG S

-5.44

Data Source

Names and Identifiers

IUPAC name

(1S,2R,10S,11S,14S,15S)-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one (1S,2R,10S,11S,14S,15S)-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one (1S,3aS,3bS,9aR,9bS,11aS)-1-(2-hydroxyacetyl)-9a,11a-dimethyl-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-one

Synonyms

δ⁴-Pregnen-21-ol-3,20-dione11-DeoxycorticosteroneDEOXYCORTICOSTERONEReichstein's Substance Q21-Hydroxyprogesterone11-DESOXYCORTICOSTERONEDeoxycorticosteroneDesoxycortone4-Pregnen-21-ol-3,20-dioneKendall’s desoxy compound B‘Reichstein Q’DeoxycortoneCortexoneDOC11-Deoxycorticosterone11-Desoxycorticosterone21-Hydroxy-4-pregnene-3,20-dione21-Hydroxyprogesterone11-Dehydroxy-corticosterone11-Deoxy Corticosterone4-Pregnene-21-ol-3,20-dioneNSC 11319DOC-d811-Deoxy Corticosterone-d821-Hydroxypregn-4-ene-3,20-dioneDeoxycortone-d811-Deoxycorticosterone-d8NSC 11319-d811-Desoxycorticosterone-d821-Hydroxy-3,20-dioxopregn-4-ene11-Dehydroxy-corticosterone-d821-Hydroxy-4-pregnane-3,20-dione-d8Cortexone-d8Desoxycorticosterone-d8Desoxycorticosterone21-Hydroxy-3,20-dioxopregn-4-ene-d84-Pregnene-21-ol-3,20-dione-d8Cortexon;CorticormonCorthormonOrmosurrenolDesoxycortone21-Hydroxyprogesterone-d821-Hydroxy-4-pregnane-3,20-dioneOcriten21-Hydroxypregn-4-ene-3,20-dione-d8Desoxycortone-d8DecorteneKendall's desoxy compound B21-Hydroxy-4-pregnene-3,20-dione11-deoxycorticosterone11-Deoxycorticosterone21-hydroxyprogesteroneDesoxycortone4-pregnen-21-ol-3,20-dioneKendall's desoxy compound BdesoxycortoneDeoxycorticosteroneReichstein's substance QCortexoneDOCDESOXYCORTICOSTERONE

IUPAC Traditional name

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

Names and Identifiers

Registration numbers

Properties

Product Information

Download link

≥97% (HPLC)

Obt. by incubation of 9b,10a-pregn-4-ene-3,20-dione with Curvularia spp.

Pharmacology Properties

human ... SERPINA6(866)

Glycogen deposition inhibitor

ACTH secretion inhibitor

Gluconeogenesis promoter

Properties

Related Proteins

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

MP Biomedicals

05203891

MP Biomedicals Rare Chemical collection

02190185

Crystalline

Wikipedia

11-Deoxycorticosterone

Sigma Aldrich

D6875

Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. D6875.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

TRC

D232590

A mineralocorticoid that occurs in adrenal cortex. It acts as a precursor to Aldosterone (A514700).

D232592

Labelled Deoxycorticosterone. A mineralocorticoid that occurs in adrenal cortex. It acts as a precursor to Aldosterone (A514700).

ChEBI

CHEBI:16973

A mineralocorticoid that is progesterone substituted at position 21 by a hydroxy group.

Molecule Details

References

PubChem Literature

From Data Sources

• Bohl, C., et al.: J. Med.Chem., 47, 3765 (2004)

• Smith, J., et al.: Steroids, 73, 1160 (2004)

• Bohl, C., et al.: J. Med.Chem., 47, 3765 (2004)

• Smith, J., et al.: Steroids, 73, 1160 (2004)

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 6984, (synonyms)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, DAQ600; DAQ800

• Schambelan, M. et al., J. Clin. Endocrinol. Metab., 1972, 34, 695, (metab)

• Zaffaroni, A. et al., Experientia, 1955, 11, 219, (synth)

• Numazawa, M. et al., J.O.C., 1985, 50, 81, (synth)

• Schindler, W. et al., Helv. Chim. Acta, 1941, 24, 371, (synth)

• U.S. Pat., 1966, 3 254 098; CA, 65, 8999, (synth)

• Gonzalez, M.D. et al., Org. Magn. Reson., 1984, 22, 586, (cmr)

• Reichstein, T. et al., Helv. Chim. Acta, 1937, 20, 1164; 1938, 21, 1197, (isol)

• Grostic, M.F. et al., J.O.C., 1968, 33, 1740, (ms)

• van der Sijde, D. et al., Rec. Trav. Chim. (J. R. Neth. Chem. Soc.), 1969, 88, 1437, (synth)

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 583C; 602C, (nmr)

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 1054B, (ir)

• Dideberg, O. et al., Acta Cryst. B, 1973, 29, 103, (cryst struct)

• Kirk, D.N. et al., J.C.S. Perkin 2, 1990, 1567, (pmr)

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 727

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

IUPAC name

Synonyms

IUPAC Traditional name

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

Molecule Details

MP Biomedicals

05203891

MP Biomedicals Rare Chemical collection

02190185

Crystalline

Wikipedia

11-Deoxycorticosterone

Sigma Aldrich

D6875

TRC

D232590

A mineralocorticoid that occurs in adrenal cortex. It acts as a precursor to Aldosterone (A514700).

D232592

Labelled Deoxycorticosterone. A mineralocorticoid that occurs in adrenal cortex. It acts as a precursor to Aldosterone (A514700).

ChEBI

CHEBI:16973

A mineralocorticoid that is progesterone substituted at position 21 by a hydroxy group.

References

PubChem Literature

From Data Sources

• Bohl, C., et al.: J. Med.Chem., 47, 3765 (2004)

• Smith, J., et al.: Steroids, 73, 1160 (2004)

• Bohl, C., et al.: J. Med.Chem., 47, 3765 (2004)

• Smith, J., et al.: Steroids, 73, 1160 (2004)

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 6984, (synonyms)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, DAQ600; DAQ800

• Schambelan, M. et al., J. Clin. Endocrinol. Metab., 1972, 34, 695, (metab)

• Zaffaroni, A. et al., Experientia, 1955, 11, 219, (synth)

• Numazawa, M. et al., J.O.C., 1985, 50, 81, (synth)

• Schindler, W. et al., Helv. Chim. Acta, 1941, 24, 371, (synth)

• U.S. Pat., 1966, 3 254 098; CA, 65, 8999, (synth)

• Gonzalez, M.D. et al., Org. Magn. Reson., 1984, 22, 586, (cmr)

• Reichstein, T. et al., Helv. Chim. Acta, 1937, 20, 1164; 1938, 21, 1197, (isol)

• Grostic, M.F. et al., J.O.C., 1968, 33, 1740, (ms)

• van der Sijde, D. et al., Rec. Trav. Chim. (J. R. Neth. Chem. Soc.), 1969, 88, 1437, (synth)

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 583C; 602C, (nmr)

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 1054B, (ir)

• Dideberg, O. et al., Acta Cryst. B, 1973, 29, 103, (cryst struct)

• Kirk, D.N. et al., J.C.S. Perkin 2, 1990, 1567, (pmr)

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 727

Bioactivity

PubChem BioAssay

Properties

Product Information

Download link

≥97% (HPLC)

Obt. by incubation of 9b,10a-pregn-4-ene-3,20-dione with Curvularia spp.

Pharmacology Properties

human ... SERPINA6(866)

Glycogen deposition inhibitor

ACTH secretion inhibitor

Gluconeogenesis promoter

Molecule

ID:105424