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

• ChemBase ID: 104358
• Molecular Formular: C12H14N2O2
• Molecular Mass: 218.25176
• Monoisotopic Mass: 218.1055277
• SMILES: CC(N)(Cc1c[nH]c2c1cccc2)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)
• InChIKey: ZTTWHZHBPDYSQB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-3-(1H-indol-3-yl)-2-methylpropanoic acid
• IUPAC Traditional name: 2-amino-3-(1H-indol-3-yl)-2-methylpropanoic acid
• Synonyms: α-METHYL-DL-TRYPTOPHAN; α-Methyl-DL-tryptophan

Database IDs

• CAS Number: 153-91-3
• MDL Number: MFCD00038416
• PubChem SID: 162091878; 24897245
• PubChem CID: 95438

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

• Apperance: light yellow crystalline

Safety Information

• Storage Condition: 0°C
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

DETAILS

MP Biomedicals - 02155679

Light yellow crystals.

Sigma Aldrich - M8377

Biochem/physiol Actions
α-methyl-DL-tryptophan is a blocker of ATBo, an amino acid transporter whose expression is upregulated in cancer.