CAS 152-58-9|11-deoxycortisol|11-Deoxy-17-hydroxycorticosterone|17,21-Dihydroxyprogesterone|17,21-Dihydroxy-4-pregnene-3,20-dione|(1S,2R,10R,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethy...

General Information

Structure

Molecular Formula

C₂₁H₃₀O₄

Molecular Mass

346.4605

Exact Mass

346.21440944

Charge

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

Canonic 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

Isomeric 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

Calculated Properties

JChem

LogD (pH = 7.4)

2.58

LogD (pH = 5.5)

2.58

Log P

2.58

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

12.59

Polar Surface Area

74.60

Polarizability

38.80

Molar Refractivity

95.81

LOG S

-4.48

Data Source

Names and Identifiers

IUPAC Traditional name

11-deoxycortisol (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

Synonyms

11-Deoxy-17-hydroxycorticosterone17,21-Dihydroxyprogesterone17,21-Dihydroxy-4-pregnene-3,20-dione11-Deoxycortisol17α,21-Dihydroxy-4-pregnene-3,20-dione4-Pregnene-17α,21-diol-3,20-dione17α-HydroxycortexoneREICHSTEIN'S SUBSTANCE SCortexolone(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)-one11-DesoxyhydrocortisoneCortodoxoneReichstein's Substance SCompound S11-DeoxyhydrocortisoneCortoxelone17,21-Dihydroxypregn-4-ene-3,20-dione11-Desoxycortisol4-Pregnene-17α,21-diol-3,20-dione17α-HydroxycortexoneReichstein’s substance S17α,21-Dihydroxy-4-pregnene-3,20-dioneReichstein’s Compound S11-Deoxy CortisolCortifenNSC 18317Reichstein's Compound S17,21-Dihydroxypregn-4-en-3,20-dioneReichstein SCortodoxone cortifenSKF 305011-deoxycortisol11-Deoxycortisol11-deoxycortisolCortodoxone11-desoxy-17-hydroxycorticosteronecortodoxone

IUPAC name

(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 (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 (1R,3aS,3bR,9aR,9bS,11aS)-1-hydroxy-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

Names and Identifiers

Registration numbers

Properties

Product Information

Certificate of Analysis

Download link

Purity

≥98%

Application(s)

Antiinflammatory drug

Immunosuppressive

Biological Source

Found in the blood and urine of humans and other mammals

Safety Information

Storage Condition

Room Temperature (15-30°C)

-20°C Freezer

MSDS Link

Download link

RTECS

TU5011500

Personal Protective Equipment

Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

Crystalline

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.

TRC

D232600

Glucocorticoid receptor binding.

ChEBI

CHEBI:28324

A deoxycortisol that is cortisol in which the hydroxy group at position 11 has been replaced by a hydrogen.

Molecule Details

References

PubChem Literature

From Data Sources

• Dardis, A., et al.: J. Endocrinol., 179, 131 (1990)

• Bird, I., et al.: Endocrinology, 134, 2468 (1990)

• Auchus, R., et al.: J. Biol. Chem., 273, 3158 (1990)

• Gazdar, A., et al.: Cancer Res., 50, 5488, (1990)

• Julian, P.L. et al. , J.A.C.S. , 1950, 72 , 5145, (synth)

• Dupont, L. et al. , Acta Cryst. , 1973, 29 , 205, (cryst struct)

• Gallagher, T.F. et al. , J.A.C.S. , 1949, 71 , 3262, (synth)

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

• Reichstein, T. et al. , Helv. Chim. Acta , 1938, 21 , 1197, (isol, synth)

• Tseikinskii, V.M. et al. , Bioorg. Khim. , 1979, 5 , 1537, (cryst struct)

• Aldrich Library of 13C and 1H FT NMR Spectra , 1992, 3 , 584B, (nmr)

• Smit, A. et al. , Rec. Trav. Chim. (J. R. Neth. Chem. Soc.) , 1966, 85, 731, (synth)

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

• Boar, R.B. , J.C.S. Perkin 1 , 1975, 1275, (pmr)

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

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

IUPAC Traditional name

11-deoxycortisol (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

Synonyms

IUPAC name

Molecule Details

Crystalline

R0500

D232600

Glucocorticoid receptor binding.

ChEBI

CHEBI:28324

A deoxycortisol that is cortisol in which the hydroxy group at position 11 has been replaced by a hydrogen.

References

PubChem Literature

From Data Sources

• Dardis, A., et al.: J. Endocrinol., 179, 131 (1990)

• Bird, I., et al.: Endocrinology, 134, 2468 (1990)

• Auchus, R., et al.: J. Biol. Chem., 273, 3158 (1990)

• Gazdar, A., et al.: Cancer Res., 50, 5488, (1990)

• Julian, P.L. et al. , J.A.C.S. , 1950, 72 , 5145, (synth)

• Dupont, L. et al. , Acta Cryst. , 1973, 29 , 205, (cryst struct)

• Gallagher, T.F. et al. , J.A.C.S. , 1949, 71 , 3262, (synth)

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

• Reichstein, T. et al. , Helv. Chim. Acta , 1938, 21 , 1197, (isol, synth)

• Tseikinskii, V.M. et al. , Bioorg. Khim. , 1979, 5 , 1537, (cryst struct)

• Aldrich Library of 13C and 1H FT NMR Spectra , 1992, 3 , 584B, (nmr)

• Smit, A. et al. , Rec. Trav. Chim. (J. R. Neth. Chem. Soc.) , 1966, 85, 731, (synth)

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

• Boar, R.B. , J.C.S. Perkin 1 , 1975, 1275, (pmr)

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

Bioactivity

PubChem BioAssay

Properties

Product Information

Certificate of Analysis

Download link

Purity

≥98%

Application(s)

Antiinflammatory drug

Immunosuppressive

Biological Source

Found in the blood and urine of humans and other mammals

Safety Information

Storage Condition

Room Temperature (15-30°C)

-20°C Freezer

MSDS Link

Download link

RTECS

TU5011500

Personal Protective Equipment

Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

Molecule

ID:102717