(2S,10S,11S,13S,14R,15S)-14-hydroxy-14-[2-hydroxy(2H2)acetyl]-2,13,15-trimethyl(6,8,8-2H3)-18-oxapentacyclo[8.8.0.01,17.02,7.011,15]octadeca-3,6-dien-5-one

• ChemBase ID: 162007
• Molecular Formular: C22H28O5
• Molecular Mass: 372.45472
• Monoisotopic Mass: 372.193674
• SMILES: C1=C[C@]2(C(=CC1=O)CC[C@@H]1C32C(C[C@]2([C@H]1C[C@@H]([C@@]2(C(=O)CO)O)C)C)O3)C
• Canonical SMILES: OCC(=O)[C@@]1(O)[C@@H](C)C[C@@H]2[C@]1(C)CC1OC31[C@H]2CCC1=CC(=O)C=C[C@]31C
• InChI: InChI=1S/C22H28O5/c1-12-8-16-15-5-4-13-9-14(24)6-7-19(13,2)22(15)18(27-22)10-20(16,3)21(12,26)17(25)11-23/h6-7,9,12,15-16,18,23,26H,4-5,8,10-11H2,1-3H3/t12-,15-,16-,18?,19-,20-,21-,22?/m0/s1
• InChIKey: GBDXNHBVYAMODG-ARBQUQLTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,10S,11S,13S,14R,15S)-14-hydroxy-14-[2-hydroxy(^2H₂)acetyl]-2,13,15-trimethyl(6,8,8-^2H₃)-18-oxapentacyclo[8.8.0.0^1,^1^7.0^2,^7.0^1^1,^1^5]octadeca-3,6-dien-5-one
• IUPAC Traditional name: (2S,10S,11S,13S,14R,15S)-14-hydroxy-14-[2-hydroxy(^2H₂)acetyl]-2,13,15-trimethyl(6,8,8-^2H₃)-18-oxapentacyclo[8.8.0.0^1,^1^7.0^2,^7.0^1^1,^1^5]octadeca-3,6-dien-5-one
• Synonyms: (9β,11β,16β)-9,11-Epoxy-17,21-dihydroxy-16-methylpregna-1,4-diene-3,20-dione-d5; 9β,11β-Epoxy-17,21-dihydroxy-16β-methylpregna-1,4-diene-3,20-dione-d5; Betamethasone-d5 9,11-Epoxide

Database IDs

• PubChem SID: 162256142
• PubChem CID: 71313953

CALCULATED PROPERTIES

• Acid pKa: 12.450934
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.9521815
• LogD (pH = 7.4): 1.9521776
• Log P: 1.9521815
• Molar Refractivity: 100.6749 cm^3
• Polarizability: 39.224995 Å^3
• Polar Surface Area: 87.13 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - B327037

Labelled metabolite of Beclometasone (B131000)

REFERENCES

• Foe, K., et al.: Drug Metab. Disposition, 26, 132 (1998)
• Xiong, Y., et al.: J. Pharm. Biomed. Anal., 49, 646 (1998)