2-amino-3-(5-methyl-1H-indol-3-yl)propanoic acid

• ChemBase ID: 105952
• Molecular Formular: C12H14N2O2
• Molecular Mass: 218.25176
• Monoisotopic Mass: 218.1055277
• SMILES: Cc1cc2c([nH]cc2CC(N)C(=O)O)cc1
• Canonical SMILES: Cc1cc2c(CC(C(=O)O)N)c[nH]c2cc1
• InChI: InChI=1S/C12H14N2O2/c1-7-2-3-11-9(4-7)8(6-14-11)5-10(13)12(15)16/h2-4,6,10,14H,5,13H2,1H3,(H,15,16)
• InChIKey: HUNCSWANZMJLPM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-3-(5-methyl-1H-indol-3-yl)propanoic acid
• IUPAC Traditional name: 5-methyltryptophan
• Synonyms: 5-Methyl-DL-tryptophan; 5-METHYL-DL-TRYPTOPHAN

Database IDs

• CAS Number: 951-55-3
• EC Number: 213-453-6
• MDL Number: MFCD00005652
• Beilstein Number: 20225
• PubChem SID: 24896560; 24885947; 162092639
• PubChem CID: 92852

CALCULATED PROPERTIES

• Acid pKa: 2.6138084
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): -0.57212096
• LogD (pH = 7.4): -0.5755945
• Log P: -0.57190967
• Molar Refractivity: 61.244 cm^3
• Polarizability: 24.856588 Å^3
• Polar Surface Area: 79.11 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: ~275 °C (dec.)

Safety Information

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

Product Information

• Purity: ≥99.0% (NT)
• Grade: puriss.
• Empirical Formula (Hill Notation): C12H14N2O2

DETAILS

MP Biomedicals - 02195320

Crystalline

Sigma Aldrich - M0534

Biochem/physiol Actions
5-Methyl-DL-tryptophan inhibits the synthesis of anthranilate compounds that are the first steps in the biosynthesis of tryptophan in Neurospora crassa.1 5-Methyl-DL-tryptophan is a corepressor of the E. coli trp repressor.2,3
5-Methyl-DL-tryptophan may be used to select genetic mutants of PS strain of Methanococcus voltae (archaebacteria). 5-Methyl-tryptophan is a repressor trp operon expression. 5-Methyl-tryptophan is a substrate for tryptophanase. 5-Methyl-tryptophan inhibits the induction of anthranilate synthase activity by elicitors in oats.