(1S,4R,5S,9S,10S,11R,15R,16R,20R)-5,9,16-trihydroxy-6,18,20-trimethoxy-15-(methoxymethyl)-10,13-dimethyl-13-azahexacyclo[9.7.2.12,5.01,12.03,10.015,19]henicosan-4-yl benzoate

• ChemBase ID: 172791
• Molecular Formular: C34H49NO9
• Molecular Mass: 615.75416
• Monoisotopic Mass: 615.34073215
• SMILES: C12C3[C@H]([C@](C1)(C(CC[C@@H]([C@@]3([C@H]1[C@@H](C3[C@]4([C@@H](CC([C@@]23C1N(C4)C)OC)O)COC)OC)C)O)OC)O)OC(=O)c1ccccc1
• Canonical SMILES: COC[C@@]12CN(C)C3[C@]4(C2[C@@H](OC)[C@@H]3[C@@]2(C3C4C[C@]([C@@H]3OC(=O)c3ccccc3)(O)C(CC[C@@H]2O)OC)C)C(C[C@H]1O)OC
• InChI: InChI=1S/C34H49NO9/c1-31-20(36)12-13-22(41-4)33(39)15-19(24(31)29(33)44-30(38)18-10-8-7-9-11-18)34-23(42-5)14-21(37)32(17-40-3)16-35(2)28(34)25(31)26(43-6)27(32)34/h7-11,19-29,36-37,39H,12-17H2,1-6H3/t19?,20-,21+,22?,23?,24?,25-,26-,27?,28?,29+,31-,32-,33-,34-/m0/s1
• InChIKey: CLNODDZVJJQWNZ-OCQQNLNHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,4R,5S,9S,10S,11R,15R,16R,20R)-5,9,16-trihydroxy-6,18,20-trimethoxy-15-(methoxymethyl)-10,13-dimethyl-13-azahexacyclo[9.7.2.1^2,^5.0^1,^1^2.0^3,^1^0.0^1^5,^1^9]henicosan-4-yl benzoate
• IUPAC Traditional name: (1S,4R,5S,9S,10S,11R,15R,16R,20R)-5,9,16-trihydroxy-6,18,20-trimethoxy-15-(methoxymethyl)-10,13-dimethyl-13-azahexacyclo[9.7.2.1^2,^5.0^1,^1^2.0^3,^1^0.0^1^5,^1^9]henicosan-4-yl benzoate
• Synonyms: (1α,3α,6α,14α,15α,16β)-1,6,16-Trimethoxy-4-(methoxymethyl)-20-methyl-aconitane-3,8,13,14,15-pentol 8-Acetate 14-Benzoate; NSC 77210; Mesaconitine

Database IDs

• CAS Number: 2752-64-9
• PubChem SID: 164228701
• PubChem CID: 71750018

CALCULATED PROPERTIES

• Acid pKa: 12.855675
• H Acceptors: 9
• H Donor: 3
• LogD (pH = 5.5): -3.058912
• LogD (pH = 7.4): -2.0839522
• Log P: 0.39287966
• Molar Refractivity: 160.8212 cm^3
• Polarizability: 64.47613 Å^3
• Polar Surface Area: 127.15 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - M257900

An Aconitine (A189875) analog. Aconitine alkaloid pharmacokinetic analgesic. A highly poisonous, neurotoxic alkaloid.

REFERENCES

• Li, M., et al.: J. Pharm. Biomed. Anal., 53, 1063 (2010)
• Yan, G., et al.: J. Pharm. Biomed. Anal., 53, 421 (2010)