(2S,4R)-2-amino-4-methylpentanedioic acid

• ChemBase ID: 3104
• Molecular Formular: C6H11NO4
• Molecular Mass: 161.15584
• Monoisotopic Mass: 161.06880784
• SMILES: C[C@H](C[C@H](N)C(=O)O)C(=O)O
• Canonical SMILES: OC(=O)[C@@H](C[C@@H](C(=O)O)N)C
• InChI: InChI=1S/C6H11NO4/c1-3(5(8)9)2-4(7)6(10)11/h3-4H,2,7H2,1H3,(H,8,9)(H,10,11)/t3-,4+/m1/s1
• InChIKey: KRKRAOXTGDJWNI-DMTCNVIQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4R)-2-amino-4-methylpentanedioic acid
• IUPAC Traditional name: (2S,4R)-2-amino-4-methylpentanedioic acid
• Synonyms: 2s,4r-4-Methylglutamate; SYM-2081; (2S,4R)-4-Methylglutamic acid; (4R)-4-Methyl-L-glutamic Acid; erythro-L-4-Methylglutamic Acid; L-erythro-γ-Methylglutamic Acid; (2S,4R)-4-Methylglutamic Acid

Database IDs

• CAS Number: 31137-74-3
• MDL Number: MFCD00937765
• PubChem SID: 160966548; 46508238; 24895059
• PubChem CID: 46936670; 95883

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.0136228
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -3.8308425
• LogD (pH = 7.4): -5.5816407
• Log P: -2.703642
• Molar Refractivity: 35.8622 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: -1.93
• LOG S: -0.93
• Solubility (Water): 2.29e+01 g/l

PROPERTIES

Physical Property

• Solubility: H2O: >10 mg/mL; Water
• Apperance: White; white solid
• Optical Rotation: [α]23/D +23.2°, c = 0.73 in 6 M HCl(lit.)

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 ... GRIK1(2897), GRIK2(2898), SLC1A1(6505), SLC1A2(6506)rat ... Gria1(50592), Grik1(29559), Grin2a(24409), Slc1a2(29482)

DETAILS

DrugBank - DB03425

Drug information: experimental

Sigma Aldrich - G137

Biochem/physiol Actions
Selective and high affinity kainate receptor antagonist.

Toronto Research Chemicals - M311575

A highly selective and potent agonist for kainate receptors.

REFERENCES

• Jones, K.A., et al.: Neuropharmacology, 36, 853 (1997)
• Shou, L.M., et al.: J. Pharmacol. Exper. Therap., 280, 422 (1997)
• Toms, N.J., et al.: Neuropharmacology, 36, 1483 (1997)
• Ta, L.E., et al.: Brain Res., 858, 106 (1997)