(2R,3S)-2-amino-3-methylpentanedioic acid

• ChemBase ID: 1666
• Molecular Formular: C6H11NO4
• Molecular Mass: 161.15584
• Monoisotopic Mass: 161.06880784
• SMILES: C[C@@H](CC(=O)O)[C@@H](N)C(=O)O
• Canonical SMILES: OC(=O)C[C@@H]([C@H](C(=O)O)N)C
• InChI: InChI=1S/C6H11NO4/c1-3(2-4(8)9)5(7)6(10)11/h3,5H,2,7H2,1H3,(H,8,9)(H,10,11)/t3-,5+/m0/s1
• InChIKey: FHJNAFIJPFGZRI-WVZVXSGGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S)-2-amino-3-methylpentanedioic acid
• IUPAC Traditional name: (3r)-3-methyl-L-glutamic acid; @(3r)-3-methyl-L-glutamic acid
• Synonyms: (3r)-3-Methyl-L-Glutamic Acid; (±)-threo-3-Methylglutamic acid; 3MG; threo-3-Methylglutamate; T3MG; 2s,3r-2-Amino-3-Methylpentanedioic Acid

Database IDs

• CAS Number: 63088-04-0
• MDL Number: MFCD09836097
• PubChem SID: 160965123; 46506110; 46508849
• PubChem CID: 6604760

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.0174649
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -3.970985
• LogD (pH = 7.4): -5.728246
• Log P: -2.880448
• Molar Refractivity: 35.7593 cm^3
• Polarizability: 14.494345 Å^3
• Polar Surface Area: 100.62 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -3.3
• LOG S: -0.63
• Solubility (Water): 3.81e+01 g/l

PROPERTIES

Physical Property

• Solubility: H2O: >1.5 mg/dL
• Apperance: white to off-white powder

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Storage Temperature: room temp

Product Information

• Purity: (single spot, TLC)
• Empirical Formula (Hill Notation): C6H11NO4

DETAILS

DrugBank - DB03810

Drug information: experimental

DrugBank - DB01898

Drug information: experimental

Sigma Aldrich - T2455

Biochem/physiol Actions
T3MG is a selective inhibitor of excitatory amino acid transporters GLT-1, EAAT2, and EAAT4. T3MG has long been utilized as a gold standard in the study of general EAAT function. It has more recently been shown to be selective for EAAT2 and EAAT4 as compared to EAAT1 and EAAT3 in electrophysiology and glutamate/aspartate uptake assays. Although there are other EAAT2-selective compounds, this is the first tool with selectivity for EAAT4. T3MG is not a substrate for the transporters themselves, nor does it have activity at glutamate ion channels.