(2R,3R,4R,5R,6R,7S,8S,9R,10R,13R,14R,16S,17S,18R)-8-(acetyloxy)-11-ethyl-5,7,14-trihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecan-4-yl benzoate

• ChemBase ID: 159519
• Molecular Formular: C34H47NO11
• Molecular Mass: 645.73708
• Monoisotopic Mass: 645.31491133
• SMILES: C1[C@H]([C@@]2([C@@H]3C4([C@H]1OC)[C@H]1[C@H]5[C@]([C@@H]([C@@H]3OC)[C@@H]4N(C2)CC)([C@H]([C@H]([C@]([C@@H]5OC(=O)c2ccccc2)(C1)O)OC)O)OC(=O)C)COC)O
• Canonical SMILES: COC[C@@]12CN(CC)[C@@H]3C4([C@@H]2[C@@H](OC)[C@@H]3[C@]2([C@@H]3[C@H]4C[C@@]([C@@H]3OC(=O)c3ccccc3)([C@@H]([C@@H]2O)OC)O)OC(=O)C)[C@H](C[C@H]1O)OC
• InChI: InChI=1S/C34H47NO11/c1-7-35-15-31(16-41-3)20(37)13-21(42-4)33-19-14-32(40)28(45-30(39)18-11-9-8-10-12-18)22(19)34(46-17(2)36,27(38)29(32)44-6)23(26(33)35)24(43-5)25(31)33/h8-12,19-29,37-38,40H,7,13-16H2,1-6H3/t19-,20-,21+,22?,23?,24+,25?,26?,27+,28-,29-,31+,32-,33?,34+/m1/s1
• InChIKey: XFSBVAOIAHNAPC-ZUWWRREYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R,5R,6R,7S,8S,9R,10R,13R,14R,16S,17S,18R)-8-(acetyloxy)-11-ethyl-5,7,14-trihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1^2,^5.0^1,^1^0.0^3,^8.0^1^3,^1^7]nonadecan-4-yl benzoate
• IUPAC Traditional name: (2R,3R,4R,5R,6R,7S,8S,9R,10R,13R,14R,16S,17S,18R)-8-(acetyloxy)-11-ethyl-5,7,14-trihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1^2,^5.0^1,^1^0.0^3,^8.0^1^3,^1^7]nonadecan-4-yl benzoate
• Synonyms: (1α,3α,6α,14α,15α,16β)-20-Ethyl-1,6,16-trimethoxy-4-(methoxymethyl)aconitane-3,8,13,14,15-pentol 8-Acetate 14-Benzoate; Aconitine

Database IDs

• CAS Number: 302-27-2
• PubChem SID: 162253654
• PubChem CID: 71313016

CALCULATED PROPERTIES

• Acid pKa: 12.5342245
• H Acceptors: 10
• H Donor: 3
• LogD (pH = 5.5): -3.971408
• LogD (pH = 7.4): -2.853777
• Log P: -0.5432204
• Molar Refractivity: 161.8047 cm^3
• Polarizability: 65.31721 Å^3
• Polar Surface Area: 153.45 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethy Acetate
• Apperance: Off-White Solid
• Melting Point: 196-198°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - A189875

Neurotoxin. Activates tetrodotoxin-sensitive Na+ channels, inducing presynaptic depolarization, thus blocking the nerve action potential which, in turn, blocks the release of neurotransmitters and decreases the end plate potential at the neuromuscular jun

REFERENCES

• Derbre, S., et al.: Anal. Bioanal. Chem., 398, 1747 (2010)
• Li, M., et al.: J. Pharm. Biomed. Anal., 53, 1063 (2010)