(2S)-2-amino-3-(1H-indol-3-yl)-2-methylpropanoic acid

• ChemBase ID: 174455
• Molecular Formular: C12H14N2O2
• Molecular Mass: 218.25176
• Monoisotopic Mass: 218.1055277
• SMILES: c1ccc2c(c1)[nH]cc2C[C@@](N)(C)C(=O)O
• Canonical SMILES: OC(=O)[C@](Cc1c[nH]c2c1cccc2)(N)C
• InChI: InChI=1S/C12H14N2O2/c1-12(13,11(15)16)6-8-7-14-10-5-3-2-4-9(8)10/h2-5,7,14H,6,13H2,1H3,(H,15,16)/t12-/m0/s1
• InChIKey: ZTTWHZHBPDYSQB-LBPRGKRZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-3-(1H-indol-3-yl)-2-methylpropanoic acid
• IUPAC Traditional name: (2S)-2-amino-3-(1H-indol-3-yl)-2-methylpropanoic acid
• Synonyms: (-)-α-Methyltryptophan; α-Methyl-(S)-tryptophan; L-α-Methyltryptophan; α-Methyl-L-tryptophan

Database IDs

• CAS Number: 16709-25-4
• PubChem SID: 164230365
• PubChem CID: 676155

CALCULATED PROPERTIES

• Acid pKa: 2.5601745
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): -0.65328324
• LogD (pH = 7.4): -0.6552044
• Log P: -0.6530646
• Molar Refractivity: 60.9161 cm^3
• Polarizability: 24.936577 Å^3
• Polar Surface Area: 79.11 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Water
• Apperance: Off-White Solid
• Melting Point: 180-190°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Storage Warning: Moisture Sensitive

DETAILS

Toronto Research Chemicals - M331980

A therapeutic and carrier molecule.

REFERENCES

• Seldon, H., et al.: Brain Res., 249, 211 (1982)
• Leboyer, M., et al.: Biol. Psychiatry, 45, 58 (1982)
• Galuske, R., et al.: Science, 289, 1946 (1982)
• Courchesne, E., et al.: Neurology, 57, 245 (1982)