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

• ChemBase ID: 166123
• Molecular Formular: C32H55BrN2O3
• Molecular Mass: 595.6947
• Monoisotopic Mass: 594.33960563
• SMILES: [Br-].[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)OC(=O)C)C)C)O)N1CCCCC1
• Canonical SMILES: CC(=O)O[C@@H]1[C@H](C[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CC[C@@H]2[C@]1(C)C[C@H](N1CCCCC1)[C@H](C2)O)[N+]1(C)CCCCC1.[Br-]
• InChI: InChI=1S/C32H55N2O3.BrH/c1-22(35)37-30-28(34(4)17-9-6-10-18-34)20-26-24-12-11-23-19-29(36)27(33-15-7-5-8-16-33)21-32(23,3)25(24)13-14-31(26,30)2;/h23-30,36H,5-21H2,1-4H3;1H/q+1;/p-1/t23-,24+,25-,26-,27-,28-,29-,30+,31-,32-;/m0./s1
• InChIKey: UPUCOGXSWOPTGS-BBQNUDADSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(1S,2S,4S,5S,7S,10R,11S,13S,14S,15S)-14-(acetyloxy)-5-hydroxy-2,15-dimethyl-4-(piperidin-1-yl)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-13-yl]-1-methylpiperidin-1-ium bromide
• IUPAC Traditional name: 1-[(1S,2S,4S,5S,7S,10R,11S,13S,14S,15S)-14-(acetyloxy)-5-hydroxy-2,15-dimethyl-4-(piperidin-1-yl)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-13-yl]-1-methylpiperidin-1-ium bromide
• Synonyms: 1-[(2β,3α,5α,16β,17β)-17-(Αcetyloxy)-3-hydroxy-2-(1-piperidinyl)androstan-16-yl]-1-methylpiperidinium Bromide; 3-Hydroxyvecuronium Bromide; Org 7268; 3-Desacetyl Vecuronium Bromide

Database IDs

• CAS Number: 73319-13-8
• PubChem SID: 162260256
• PubChem CID: 70423045

CALCULATED PROPERTIES

• Acid pKa: 14.585938
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -3.019329
• LogD (pH = 7.4): -2.2124531
• Log P: 0.45096374
• Molar Refractivity: 160.1569 cm^3
• Polarizability: 59.66921 Å^3
• Polar Surface Area: 49.77 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D288715

A metabolite of Vecuronium (V102500), in human plasma.

REFERENCES

• Wang, S., et al.: Clin. Pharmacol. Ther., 53, 410 (1993)
• Bertilsson, L., et al.: Clin. Pharmacokinet., 29, 192 (1993)
• Aklillu, E., et al.: J. Pharmacol. Exp. Ther., 278, 441 (1993)