(2S)-2-(methylamino)butanedioic acid

• ChemBase ID: 133351
• Molecular Formular: C5H9NO4
• Molecular Mass: 147.12926
• Monoisotopic Mass: 147.05315777
• SMILES: CN[C@@H](CC(=O)O)C(=O)O
• Canonical SMILES: CN[C@H](C(=O)O)CC(=O)O
• InChI: InChI=1S/C5H9NO4/c1-6-3(5(9)10)2-4(7)8/h3,6H,2H2,1H3,(H,7,8)(H,9,10)/t3-/m0/s1
• InChIKey: HOKKHZGPKSLGJE-VKHMYHEASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-(methylamino)butanedioic acid
• IUPAC Traditional name: N-methyl-L-aspartic acid
• Synonyms: (S)-2-(Methylamino)succinic acid; N-Methyl-L-aspartic acid; N-Methyl-L-aspartic acid

Database IDs

• CAS Number: 4226-18-0
• MDL Number: MFCD00069561
• Beilstein Number: 2437887
• PubChem SID: 162227628; 24896836
• PubChem CID: 92982

CALCULATED PROPERTIES

• Acid pKa: 1.4571203
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -3.8783696
• LogD (pH = 7.4): -5.6304536
• Log P: -3.2736425
• Molar Refractivity: 31.3073 cm^3
• Polarizability: 12.69048 Å^3
• Polar Surface Area: 86.63 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Optical Rotation: [α]20/D +16±1°, c = 2% in H2O

Safety Information

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

Pharmacology Properties

• Gene Information: rat ... Gria1(50592), Grik1(29559), Grin2a(24409)

Product Information

• Purity: ≥98.0% (TLC); 97%
• Empirical Formula (Hill Notation): C5H9NO4

DETAILS

Sigma Aldrich - M3387

Other Notes
Inactive isomer of N-methyl-D-aspartic acid (NMDA).

Sigma Aldrich - 65832

Other Notes
Selective N-methylaspartate receptor agonist1,2