1-[(1S,2S,4S,5S,7S,10R,11S,13S,14R,15S)-5-(acetyloxy)-14-hydroxy-2,15-dimethyl-4-(1-methylpiperidin-1-ium-1-yl)tetracyclo[8.7.0.02,7.011,15]heptadecan-13-yl]-1-methylpiperidin-1-ium dibromide

• ChemBase ID: 165350
• Molecular Formular: C33H58Br2N2O3
• Molecular Mass: 690.63322
• Monoisotopic Mass: 688.28141773
• SMILES: [C@H]1([C@H](C[C@H]2[C@](C1)([C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)([C@H]([C@H](C2)[N+]1(CCCCC1)C)O)C)C)OC(=O)C)[N+]1(CCCCC1)C.[Br-].[Br-]
• Canonical SMILES: CC(=O)O[C@H]1C[C@@H]2CC[C@@H]3[C@@H]([C@]2(C[C@@H]1[N+]1(C)CCCCC1)C)CC[C@]1([C@H]3C[C@@H]([C@@H]1O)[N+]1(C)CCCCC1)C.[Br-].[Br-]
• InChI: InChI=1S/C33H58N2O3.2BrH/c1-23(36)38-30-20-24-12-13-25-26(33(24,3)22-29(30)35(5)18-10-7-11-19-35)14-15-32(2)27(25)21-28(31(32)37)34(4)16-8-6-9-17-34;;/h24-31,37H,6-22H2,1-5H3;2*1H/q+2;;/p-2/t24-,25+,26-,27-,28-,29-,30-,31-,32-,33-;;/m0../s1
• InChIKey: SUKULMJPMHYWKC-GMMLHHOXSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(1S,2S,4S,5S,7S,10R,11S,13S,14R,15S)-5-(acetyloxy)-14-hydroxy-2,15-dimethyl-4-(1-methylpiperidin-1-ium-1-yl)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-13-yl]-1-methylpiperidin-1-ium dibromide
• IUPAC Traditional name: 1-[(1S,2S,4S,5S,7S,10R,11S,13S,14R,15S)-5-(acetyloxy)-14-hydroxy-2,15-dimethyl-4-(1-methylpiperidin-1-ium-1-yl)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-13-yl]-1-methylpiperidin-1-ium dibromide
• Synonyms: 1,1'-(3α,17β-Dihydroxy-5α-androstan-2β,16β-ylene)bis[1-methylpiperidinium Dibromide 3-Acetate; 1,1'-[(2β,3α,5α,16β,17β)-3-(Acetyloxy)-17-hydroxyandrostane-2,16-diyl]bis[1-methylpiperidinium]dibromide; Dacuronium Bromide

Database IDs

• CAS Number: 27115-86-2
• PubChem SID: 162259483
• PubChem CID: 14029396

CALCULATED PROPERTIES

• Acid pKa: 12.898565
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -3.7113726
• LogD (pH = 7.4): -3.7113466
• Log P: -3.7113729
• Molar Refractivity: 176.0705 cm^3
• Polarizability: 61.447315 Å^3
• Polar Surface Area: 46.53 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D102700

Dacuronium Bromide is a metabolite of neuromuscular blocking agent Pancuronium (P178500) with much weaker activity.

REFERENCES

• Marshall, I.G. et al.: Br. J. Anaesth., 55, 703 (1983)
• Norman, J. et al.: Br. J. Anaesth., 43, 313 (1983)
• Durant, N.N. et al.: J. Pharm. Pharmacol., 31, 831 (1983)