(2R,3R)-2,3-dihydroxybutanedioic acid (3R)-3-[(prop-2-yn-1-yl)amino]-2,3-dihydro-1H-inden-5-yl N-ethyl-N-methylcarbamate

• ChemBase ID: 172171
• Molecular Formular: C20H26N2O8
• Molecular Mass: 422.42904
• Monoisotopic Mass: 422.1689158
• SMILES: [C@H]([C@@H](O)C(=O)O)(O)C(=O)O.c1(ccc2c(c1)[C@@H](CC2)NCC#C)OC(=O)N(C)CC
• Canonical SMILES: OC(=O)[C@@H]([C@H](C(=O)O)O)O.C#CCN[C@@H]1CCc2c1cc(cc2)OC(=O)N(CC)C
• InChI: InChI=1S/C16H20N2O2.C4H6O6/c1-4-10-17-15-9-7-12-6-8-13(11-14(12)15)20-16(19)18(3)5-2;5-1(3(7)8)2(6)4(9)10/h1,6,8,11,15,17H,5,7,9-10H2,2-3H3;1-2,5-6H,(H,7,8)(H,9,10)/t15-;1-,2-/m11/s1
• InChIKey: DZMNQRCPJKPTNC-KBYGAXRISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R)-2,3-dihydroxybutanedioic acid (3R)-3-[(prop-2-yn-1-yl)amino]-2,3-dihydro-1H-inden-5-yl N-ethyl-N-methylcarbamate
• IUPAC Traditional name: L(+)-tartaric acid; ladostigil
• Synonyms: N-Ethyl-N-methylcarbamic Acid (3R)-2,3-Dihydro-3-(2-propyn-1-ylamino)-1H-inden-5-yl Ester (2R,3R)-2,3-Dihydroxybutanedioate; TV 3326; Ladostigil Tartrate

Database IDs

• CAS Number: 209394-46-7
• PubChem SID: 164228081
• PubChem CID: 6918440

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -0.38675445
• LogD (pH = 7.4): 1.3013921
• Log P: 2.3817775
• Molar Refractivity: 78.8181 cm^3
• Polarizability: 30.237608 Å^3
• Polar Surface Area: 41.57 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - L168700

A novel brain-selective MAO inhibitor, Ladostigil can selectively reverse the behavioral and neurochemical effects induced by prenatal stress without affecting the behavior of controls. Antidepressant.

REFERENCES

• Masubuchi, Y., et al.: J. Pharm. Pharmacol., 48, 925 (1996)
• Weinstock, M., et al.: Brain Res., 595, 195 (1996)
• Kitada, Y., et al.: Eur. J. Pharmacol., 72, 145 (1996)