(1S,2R,3R,4R,5R,6R,7S,8S,9R,10R,13S,16S,17R,18R)-8-(acetyloxy)-5,7-dihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-methyl-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecan-4-yl benzoate

• ChemBase ID: 171476
• Molecular Formular: C33H45NO10
• Molecular Mass: 615.7111
• Monoisotopic Mass: 615.30434665
• SMILES: C1C[C@@]2([C@@H]3[C@@]4([C@H]1OC)[C@H]1[C@H]5[C@]([C@@H]([C@@H]3OC)[C@H]4N(C2)C)([C@H]([C@H]([C@]([C@@H]5OC(=O)c2ccccc2)(C1)O)OC)O)OC(=O)C)COC
• Canonical SMILES: COC[C@]12CC[C@@H]([C@@]34[C@@H]2[C@@H](OC)[C@@H]([C@H]3N(C1)C)[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
• InChI: InChI=1S/C33H45NO10/c1-17(35)44-33-21-19(14-31(38,28(42-6)26(33)36)27(21)43-29(37)18-10-8-7-9-11-18)32-20(40-4)12-13-30(16-39-3)15-34(2)25(32)22(33)23(41-5)24(30)32/h7-11,19-28,36,38H,12-16H2,1-6H3/t19-,20+,21?,22?,23+,24?,25-,26+,27-,28-,30+,31-,32+,33+/m1/s1
• InChIKey: FIDOCHXHMJHKRW-RMZOHWMFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,3R,4R,5R,6R,7S,8S,9R,10R,13S,16S,17R,18R)-8-(acetyloxy)-5,7-dihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-methyl-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: (1S,2R,3R,4R,5R,6R,7S,8S,9R,10R,13S,16S,17R,18R)-8-(acetyloxy)-5,7-dihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-methyl-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,6α,14α,15α,16β)1,6,16-Trimethoxy-4-(methoxymethyl)-20-methylaconitane-8,13,14,15-tetrol 8-Acetate 14-Benzoate; Hypaconitine

Database IDs

• CAS Number: 6900-87-4
• PubChem SID: 164227386
• PubChem CID: 71749430

CALCULATED PROPERTIES

• Acid pKa: 12.539222
• H Acceptors: 9
• H Donor: 2
• LogD (pH = 5.5): -3.0442588
• LogD (pH = 7.4): -2.0412328
• Log P: 0.40357673
• Molar Refractivity: 155.5842 cm^3
• Polarizability: 62.82602 Å^3
• Polar Surface Area: 133.22 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - H998150

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)