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

• ChemBase ID: 105424
• Molecular Formular: C21H30O3
• Molecular Mass: 330.4611
• Monoisotopic Mass: 330.21949482
• SMILES: C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@]34C)[C@@H]1CC[C@@H]2C(=O)CO
• Canonical SMILES: OCC(=O)[C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCC2=CC(=O)CC[C@]12C
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10S,11S,14S,15S)-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one; (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
• IUPAC Traditional name: 11-deoxycorticosterone; Doc; (1S,2R,10S,11S,14S,15S)-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• Synonyms: ‘Reichstein Q’; 21-Hydroxy-4-pregnene-3,20-dione; 4-Pregnen-21-ol-3,20-dione; Kendall’s desoxy compound B; 21-Hydroxyprogesterone; 11-DESOXYCORTICOSTERONE; 11-Desoxycorticosterone; Deoxycorticosterone; Cortexone; Deoxycortone; Desoxycortone; DOC; 11-Deoxycorticosterone; 11-Deoxycorticosterone; 21-Hydroxyprogesterone; δ^4-Pregnen-21-ol-3,20-dione; Reichstein's Substance Q; DEOXYCORTICOSTERONE; NSC 11319-d8; 4-Pregnene-21-ol-3,20-dione-d8; 11-Deoxy Corticosterone-d8; Desoxycorticosterone; NSC 11319; 4-Pregnene-21-ol-3,20-dione; 11-Deoxy Corticosterone; 21-Hydroxypregn-4-ene-3,20-dione-d8; 11-Deoxycorticosterone-d8; 11-Dehydroxy-corticosterone-d8; 11-Desoxycorticosterone-d8; 21-Hydroxy-3,20-dioxopregn-4-ene-d8; 21-Hydroxy-4-pregnane-3,20-dione-d8; 21-Hydroxyprogesterone-d8; Cortexone-d8; DOC-d8; Deoxycortone-d8; Desoxycorticosterone-d8; Desoxycortone-d8; 21-Hydroxypregn-4-ene-3,20-dione; 11-Dehydroxy-corticosterone; 21-Hydroxy-3,20-dioxopregn-4-ene; 21-Hydroxy-4-pregnane-3,20-dione; Corthormon; Cortexon;Corticormon; Decortene; Kendall's desoxy compound B; Ocriten; Ormosurrenol; Desoxycortone

Database IDs

• CAS Number: 55487-63-3; 64-85-7
• EC Number: 200-596-4
• MDL Number: MFCD00003661
• Beilstein Number: 2062123
• PubChem SID: 162093607; 24894056
• PubChem CID: 6166
• CHEBI ID: 16973
• ATC CODE: H02AA03
• CHEMBL: 1498
• Chemspider ID: 5932
• Unique Ingredient Identifier: 40GP35YQ49
• Wikipedia Title: 11-Deoxycorticosterone

CALCULATED PROPERTIES

• Acid pKa: 13.864724
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 3.3313563
• LogD (pH = 7.4): 3.3313563
• Log P: 3.3313563
• Molar Refractivity: 94.4075 cm^3
• Polarizability: 37.013763 Å^3
• Polar Surface Area: 54.37 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: White Solid; White to Off-White Solid
• Melting Point: 132-134°C; 137-139°C

Safety Information

• Storage Condition: Refrigerator; Room Temperature (15-30°C)
• RTECS: HG0350000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 40-48; R:22
• Safety Statements: 22-24/25; S:36/37/39
• GHS Pictograms: GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H351-H373
• GHS Precautionary statements: P281
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Gene Information: human ... SERPINA6(866)
• Mechanism of Action: ACTH secretion inhibitor; Gluconeogenesis promoter; Glycogen deposition inhibitor

Product Information

• Purity: ≥97% (HPLC)
• Biological Source: Obt. by incubation of 9b,10a-pregn-4-ene-3,20-dione with Curvularia spp.
• Application(s): Mineralocorticoid

DETAILS

MP Biomedicals - 02190185

Crystalline

MP Biomedicals - 05203891

MP Biomedicals Rare Chemical collection

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.

Toronto Research Chemicals - D232590

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

Toronto Research Chemicals - D232592

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

REFERENCES

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