3-(2-carboxy-2-phenyleth-1-en-1-yl)-4,6-dichloro-1H-indole-2-carboxylic acid

• ChemBase ID: 155388
• Molecular Formular: C18H11Cl2NO4
• Molecular Mass: 376.19024
• Monoisotopic Mass: 375.0065132
• SMILES: c1ccc(cc1)/C(=C/c1c2c(cc(cc2Cl)Cl)[nH]c1C(=O)O)/C(=O)O
• Canonical SMILES: Clc1cc(Cl)c2c(c1)[nH]c(c2/C=C(/c1ccccc1)\C(=O)O)C(=O)O
• InChI: InChI=1S/C18H11Cl2NO4/c19-10-6-13(20)15-12(16(18(24)25)21-14(15)7-10)8-11(17(22)23)9-4-2-1-3-5-9/h1-8,21H,(H,22,23)(H,24,25)
• InChIKey: LPWVUDLZUVBQGP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(2-carboxy-2-phenyleth-1-en-1-yl)-4,6-dichloro-1H-indole-2-carboxylic acid
• IUPAC Traditional name: 3-(2-carboxy-2-phenyleth-1-en-1-yl)-4,6-dichloro-1H-indole-2-carboxylic acid
• Synonyms: MDL 105,519; (E)-4,6-Dichloro-3-(2-phenyl-2-carboxyethenyl)indole-2-carboxylic acid

Database IDs

• CAS Number: 161230-88-2
• MDL Number: MFCD00935267
• PubChem SID: 162249526; 24277992
• PubChem CID: 5353745

CALCULATED PROPERTIES

• Acid pKa: 3.4296546
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 1.2325034
• LogD (pH = 7.4): -1.8386326
• Log P: 4.6886096
• Molar Refractivity: 95.3418 cm^3
• Polarizability: 37.177406 Å^3
• Polar Surface Area: 90.39 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >20 mg/mL
• Apperance: white to off-white solid

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Gene Information: human ... GRIN1(2902)rat ... Grin1(24408)

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C18H11Cl2NO4

DETAILS

Sigma Aldrich - M216

Biochem/physiol Actions
MDL 105,519 is a high affinity NMDA glutamate receptor antagonist at the glycine site.
Legal Information
Sold under exclusive license from Hoechst Marion Roussel, Inc.