(1S,2S,3S,4S,5R,6S,8S,9S,13S,16S,17S)-11-ethyl-3,8-dihydroxy-4,6,16-trimethoxy-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecan-13-yl 2-acetamidobenzoate hydrobromide

• ChemBase ID: 73011
• Molecular Formular: C32H45BrN2O8
• Molecular Mass: 665.6123
• Monoisotopic Mass: 664.23592841
• SMILES: C1C[C@@]2([C@@H]3[C@@]4([C@H]1OC)[C@H]1[C@]5([C@@]([C@@H](C3)C4N(C2)CC)(C[C@@H]([C@H]([C@@H]5OC)C1)OC)O)O)OC(=O)c1c(cccc1)NC(=O)C.Br
• Canonical SMILES: CCN1C[C@@]2(CC[C@@H]([C@]34C1[C@H](C[C@H]23)[C@@]1(O)C[C@@H]([C@H]2C[C@@H]4[C@]1(O)[C@H]2OC)OC)OC)OC(=O)c1ccccc1NC(=O)C.Br
• InChI: InChI=1S/C32H44N2O8.BrH/c1-6-34-16-29(42-28(36)18-9-7-8-10-21(18)33-17(2)35)12-11-25(40-4)31-23(29)14-20(26(31)34)30(37)15-22(39-3)19-13-24(31)32(30,38)27(19)41-5;/h7-10,19-20,22-27,37-38H,6,11-16H2,1-5H3,(H,33,35);1H/t19?,20-,22-,23?,24-,25-,26?,27-,29+,30-,31-,32-;/m0./s1
• InChIKey: CFFYROOPXPKMEQ-NLEWHRNJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,3S,4S,5R,6S,8S,9S,13S,16S,17S)-11-ethyl-3,8-dihydroxy-4,6,16-trimethoxy-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecan-13-yl 2-acetamidobenzoate hydrobromide; (1S,2S,3S,4S,5R,6S,8S,9S,13S,16S,17S)-11-ethyl-3,8-dihydroxy-4,6,16-trimethoxy-11-azahexacyclo[7.7.2.1^2,^5.0^1,^1^0.0^3,^8.0^1^3,^1^7]nonadecan-13-yl 2-acetamidobenzoate hydrobromide
• IUPAC Traditional name: (1S,2S,3S,4S,5R,6S,8S,9S,13S,16S,17S)-11-ethyl-3,8-dihydroxy-4,6,16-trimethoxy-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecan-13-yl 2-acetamidobenzoate hydrobromide; (1S,2S,3S,4S,5R,6S,8S,9S,13S,16S,17S)-11-ethyl-3,8-dihydroxy-4,6,16-trimethoxy-11-azahexacyclo[7.7.2.1^2,^5.0^1,^1^0.0^3,^8.0^1^3,^1^7]nonadecan-13-yl 2-acetamidobenzoate hydrobromide
• Synonyms: Lappaconite Hydrobromide; Allapinine; Lappaconitine hydrobromide

Database IDs

• CAS Number: 97792-45-5
• MDL Number: MFCD00171334
• PubChem SID: 162037931
• PubChem CID: 51346120

CALCULATED PROPERTIES

• Acid pKa: 12.228
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): -1.9101584
• LogD (pH = 7.4): -0.30626667
• Log P: 1.2791553
• Molar Refractivity: 154.0886 cm^3
• Polarizability: 60.684498 Å^3
• Polar Surface Area: 126.79 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: solid

Safety Information

• Storage Condition: -20°C
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 1544
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 28
• Safety Statements: 45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300
• GHS Precautionary statements: P264-P301 + 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 2
• Storage Temperature: 2-8°C

Product Information

• Purity: 96%
• Salt Data: Hydrobromide
• Empirical Formula (Hill Notation): C32H44N2O8 · HBr

DETAILS

Selleck Chemicals - S2387

Research Area: Inflammation
Biological Activity:
Lappaconite Hydrobromide is a kind of alkaloid extracted from Aconitum sinomontanum Nakai and has anti-inflammatory effects. Its absorption percentage in rat stomachs after administration was 9.67%.The absorption percentages at duodenum,jejunum,ileum and colon were 19.61%,11.83%,12.95% and 9.51%, respectively.When the concentration was raised from 10 mg•L-1 to 40 mg•L-1,the uptake of lappaconite hydrobromide was linearly increased,whereas the absorption rate constant kept at the same level.The inhibitors of P-glycoprotein had obvious effects on the absorption in small intestines.Sodium caprate was the best enhancer that did not cause significant changes in the morphology of the intestinal membrane after intestinal administration as compared with other absorption enhancers. [1][2] 

Sigma Aldrich - L8288

Biochem/physiol Actions
Selective blocker of the TTX-sensitive Na+ channels, without influence on the activation threshold of Na+ channels.
Warning
Protect from light.

REFERENCES

• Wang YZ et al. J Tradit Chin Med. 2009 Jun;29(2):141-5.