(1S,2R,10S,11S,14R,15S,17S)-14-acetyl-14,17-dihydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-6-en-5-one

• ChemBase ID: 133612
• Molecular Formular: C21H30O4
• Molecular Mass: 346.4605
• Monoisotopic Mass: 346.21440944
• SMILES: CC(=O)[C@]1(CC[C@@H]2[C@@]1(C[C@@H]([C@H]1[C@H]2CCC2=CC(=O)CC[C@]12C)O)C)O
• Canonical SMILES: O=C1CC[C@]2(C(=C1)CC[C@@H]1[C@@H]2[C@@H](O)C[C@]2([C@H]1CC[C@]2(O)C(=O)C)C)C
• InChI: InChI=1S/C21H30O4/c1-12(22)21(25)9-7-16-15-5-4-13-10-14(23)6-8-19(13,2)18(15)17(24)11-20(16,21)3/h10,15-18,24-25H,4-9,11H2,1-3H3/t15-,16-,17-,18+,19-,20-,21-/m0/s1
• InChIKey: LCZBQMKVFQNSJR-UJPCIWJBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10S,11S,14R,15S,17S)-14-acetyl-14,17-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• IUPAC Traditional name: 21-deoxyhydrocortisone
• Synonyms: 11β,17α-Dihydroxy-4-pregnene-3,20-dione; 11β,17α-Dihydroxyprogesterone; 21-Desoxycortisol; 4-Pregnene-11β,17α-diol-3,20-dione; 21-Deoxycortisol; (11β)-11,17-Dihydroxypregn-4-ene-3,20-dione; 11β,17-Dihydroxypogesterone; 11β,17α-Dihydroxypregn-4-ene-3,20-dione; 21-Dehydrohydrocortisone; 21-Deoxyhydrocortisone; Pregn-4-ene-11β,17α-diol-3,20-dione; 21-Deoxy Cortisol

Database IDs

• CAS Number: 641-77-0
• EC Number: 211-375-7
• MDL Number: MFCD00056476
• PubChem SID: 162227889; 24899039
• PubChem CID: 92827

CALCULATED PROPERTIES

• Acid pKa: 12.692432
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 2.0924144
• LogD (pH = 7.4): 2.0924122
• Log P: 2.0924144
• Molar Refractivity: 95.6978 cm^3
• Polarizability: 37.642807 Å^3
• Polar Surface Area: 74.6 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

DETAILS

Sigma Aldrich - P9521

Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. P9521.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - D232605

A metabolite of Fluticasone propionate (F599500).

REFERENCES

• Li, S., et al.: Science, 303, 540 (2004)
• Fliri, A., et al.: J. Med. Chem., 48, 6918 (2004)
• Ekins, S., et al.: J. Pharmacol. Toxicol. Methods, 53, 38 (2004)