2-hydroxypropane-1,2,3-tricarboxylic acid [(1S,2R,3R,4S,5R,6S,8R,9R,13S,16S,17R,18S)-11-ethyl-8,9-dihydroxy-4,6,16,18-tetramethoxy-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecan-13-yl]methyl 2-[(3S)-3-methyl-2,5-dioxopyrrolidin-1-yl]benzoate

• ChemBase ID: 133111
• Molecular Formular: C43H58N2O17
• Molecular Mass: 874.92382
• Monoisotopic Mass: 874.37354841
• SMILES: CCN1C[C@@]2(CC[C@@H]([C@@]34[C@H]2[C@@H]([C@@](C13)([C@]1(C[C@@H]([C@H]2C[C@@H]4[C@@H]1[C@H]2OC)OC)O)O)OC)OC)COC(=O)c1ccccc1N1C(=O)C[C@@H](C1=O)C.C(C(=O)O)C(CC(=O)O)(C(=O)O)O
• Canonical SMILES: OC(=O)CC(C(=O)O)(CC(=O)O)O.CCN1C[C@@]2(CC[C@@H]([C@]34C1[C@](O)([C@H]([C@@H]23)OC)[C@@]1([C@@H]2[C@H]4C[C@@H]([C@@H]2OC)[C@H](C1)OC)O)OC)COC(=O)c1ccccc1N1C(=O)C[C@@H](C1=O)C
• InChI: InChI=1S/C37H50N2O10.C6H8O7/c1-7-38-17-34(18-49-32(42)20-10-8-9-11-23(20)39-26(40)14-19(2)31(39)41)13-12-25(46-4)36-22-15-21-24(45-3)16-35(43,27(22)28(21)47-5)37(44,33(36)38)30(48-6)29(34)36;7-3(8)1-6(13,5(11)12)2-4(9)10/h8-11,19,21-22,24-25,27-30,33,43-44H,7,12-18H2,1-6H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/t19-,21+,22+,24-,25-,27+,28-,29+,30-,33?,34-,35+,36-,37+;/m0./s1
• InChIKey: INBLZNJHDLEWPS-DDIMIZGISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-hydroxypropane-1,2,3-tricarboxylic acid [(1S,2R,3R,4S,5R,6S,8R,9R,13S,16S,17R,18S)-11-ethyl-8,9-dihydroxy-4,6,16,18-tetramethoxy-11-azahexacyclo[7.7.2.1^2,^5.0^1,^1^0.0^3,^8.0^1^3,^1^7]nonadecan-13-yl]methyl 2-[(3S)-3-methyl-2,5-dioxopyrrolidin-1-yl]benzoate
• IUPAC Traditional name: citro [(1S,2R,3R,4S,5R,6S,8R,9R,13S,16S,17R,18S)-11-ethyl-8,9-dihydroxy-4,6,16,18-tetramethoxy-11-azahexacyclo[7.7.2.1^2,^5.0^1,^1^0.0^3,^8.0^1^3,^1^7]nonadecan-13-yl]methyl 2-[(3S)-3-methyl-2,5-dioxopyrrolidin-1-yl]benzoate
• Synonyms: MLA; [1α,4(S),6β,14α,16β]-20-Ethyl-1,6,14,16-tetramethoxy-4-[[[2-(3-methyl-2,5-dioxo-1-pyrrolidinyl)benzoyl]oxy]methyl]aconitane-7,8-diol citrate salt; Methyllycaconitine citrate salt hydrate

Database IDs

• CAS Number: 21019-30-7(freebase)
• MDL Number: MFCD00153837
• PubChem SID: 162227388; 24896681
• PubChem CID: 16219626

CALCULATED PROPERTIES

• Acid pKa: 12.219123
• H Acceptors: 10
• H Donor: 2
• LogD (pH = 5.5): -2.8995128
• LogD (pH = 7.4): -1.7330413
• Log P: 0.5181931
• Molar Refractivity: 175.6092 cm^3
• Polarizability: 69.96433 Å^3
• Polar Surface Area: 144.3 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble42 mg/mL
• Apperance: white

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥96% (HPLC)
• Biological Source: from Delphinium brownii seeds

DETAILS

Sigma Aldrich - M168

Biochem/physiol Actions
Potent and specific nicotinic receptor antagonist that binds to neuronal α-bungarotoxin sites.