(2S)-3-methyl-2-(methylamino)butanoic acid

• ChemBase ID: 154615
• Molecular Formular: C6H13NO2
• Molecular Mass: 131.17292
• Monoisotopic Mass: 131.09462866
• SMILES: CC(C)[C@@H](C(=O)O)NC
• Canonical SMILES: CN[C@H](C(=O)O)C(C)C
• InChI: InChI=1S/C6H13NO2/c1-4(2)5(7-3)6(8)9/h4-5,7H,1-3H3,(H,8,9)/t5-/m0/s1
• InChIKey: AKCRVYNORCOYQT-YFKPBYRVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-3-methyl-2-(methylamino)butanoic acid
• IUPAC Traditional name: (2S)-3-methyl-2-(methylamino)butanoic acid
• Synonyms: (S)-3-Methyl-2-(methylamino)butyric acid; N-Me-Val-OH; N-Methyl-L-valine

Database IDs

• CAS Number: 2480-23-1
• MDL Number: MFCD00037754
• Beilstein Number: 1721712
• PubChem SID: 162248753
• PubChem CID: 444080

CALCULATED PROPERTIES

• Acid pKa: 2.3466575
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -1.730237
• LogD (pH = 7.4): -1.7301812
• Log P: -1.7300676
• Molar Refractivity: 34.2675 cm^3
• Polarizability: 13.835553 Å^3
• Polar Surface Area: 49.33 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Optical Rotation: [α]/D +25.0±1.0°, c = 1 in 1 M HCl

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2
• Risk Statements: 36
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H319
• GHS Precautionary statements: P305 + P351 + P338

Product Information

• Purity: ≥98% (TLC)
• Compostion: carbon, 54.1-55.7%; nitrogen, 10.4-11.0%
• Empirical Formula (Hill Notation): C6H13NO2

DETAILS

Sigma Aldrich - 90119

Biochem/physiol Actions
N-Methyl amino acids play an important role in investigations on prevention or therapy of Alzheimer′s disease1, neurofibrillary tangles or amyloid plaque are physiological characteristics of this disease and ?-amyloid(40) fibrillogenesis and disassembly of ?-amyloid(40) fibrils is inhibited by short ?-amyloid congeners containing N-methyl amino acids at alternate residue.