(2R,3R,4R,5R,6S,7S,8R,9R,10S,13R,14R,16R,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: 138938
• Molecular Formular: C34H47NO11
• Molecular Mass: 645.73708
• Monoisotopic Mass: 645.31491133
• SMILES: CCN1C[C@@]2([C@@H](C[C@H](C34[C@@H]1[C@@H]([C@@H](C23)OC)[C@@]1([C@@H]2[C@H]4C[C@@]([C@@H]2OC(=O)c2ccccc2)([C@H]([C@@H]1O)OC)O)OC(=O)C)OC)O)COC
• Canonical SMILES: COC[C@@]12CN(CC)[C@@H]3C4(C2[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-WSORPINJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R,5R,6S,7S,8R,9R,10S,13R,14R,16R,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,6S,7S,8R,9R,10S,13R,14R,16R,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: Acetylbenzoylaconine; Aconitine; 乙酰苯甲酰阿康碱; 乌头碱

Database IDs

• CAS Number: 302-27-2
• EC Number: 206-121-7
• MDL Number: MFCD00082375
• Beilstein Number: 74608
• PubChem SID: 162233189; 24844894; 24891304
• PubChem CID: 6419868

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: ethanol: soluble35 mg/mL; H2O: soluble0.3 mg/mL
• Apperance: white crystalline
• Melting Point: 200-205 °C (dec.)
• Optical Rotation: [α]20/D +20±4°, c = 1% in chloroform

Safety Information

• RTECS: AR5960000
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 1544
• German water hazard class: 2
• Hazard Class: 6.1
• Packing Group: 1
• Risk Statements: 26/28
• Safety Statements: 24-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H330
• GHS Precautionary statements: P260-P264-P284-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 1544 6.1/PG 1

Product Information

• Purity: ≥95% (HPLC); ≥95.0% (HPLC); 95%
• Grade: purum
• Quality: crystallized
• Empirical Formula (Hill Notation): C34H47NO11

DETAILS

Sigma Aldrich - A8001

Application
Aconitine is a neurotoxin which activates tetrodotoxin-sensitive Na+ channels, inducing presynaptic depolarization and blocking the release of neurotransmitters. Aconitine also blocks norepinephrine reuptake. In the heart, aconitine induces ventricular tachycardia after intracoronary injection.
Biochem/physiol Actions
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 junction. Aconitine also blocks norepinephrine reuptake. In the heart, aconitine induces ventricular tachycardia after intracoronary injection. In cultured ventricular myocytes, aconitine increases the duration of the action potential and induces the appearance of early after depolarization.