benzyl (2S)-2-amino-3-(1H-indol-3-yl)propanoate

• ChemBase ID: 149495
• Molecular Formular: C18H18N2O2
• Molecular Mass: 294.34772
• Monoisotopic Mass: 294.13682783
• SMILES: c1ccc(cc1)COC(=O)[C@H](Cc1c[nH]c2c1cccc2)N
• Canonical SMILES: N[C@H](C(=O)OCc1ccccc1)Cc1c[nH]c2c1cccc2
• InChI: InChI=1S/C18H18N2O2/c19-16(18(21)22-12-13-6-2-1-3-7-13)10-14-11-20-17-9-5-4-8-15(14)17/h1-9,11,16,20H,10,12,19H2/t16-/m0/s1
• InChIKey: TYQYRKDGHAPZRF-INIZCTEOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl (2S)-2-amino-3-(1H-indol-3-yl)propanoate
• IUPAC Traditional name: benzyl (2S)-2-amino-3-(1H-indol-3-yl)propanoate
• Synonyms: L-Tryptophan benzyl ester; L-色氨酸苯甲酯

Database IDs

• CAS Number: 4299-69-8
• MDL Number: MFCD02683457
• PubChem SID: 24877855; 162243660
• PubChem CID: 7016092

CALCULATED PROPERTIES

• Acid pKa: 16.14567
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 1.6240561
• LogD (pH = 7.4): 2.9234633
• Log P: 3.046744
• Molar Refractivity: 85.5845 cm^3
• Polarizability: 34.82217 Å^3
• Polar Surface Area: 68.11 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 77-80 °C(lit.)
• Optical Rotation: [α]20/D +9.9°, c = 1 in ethanol

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 ... TACR1(6869)

Product Information

• Purity: 98%
• Empirical Formula (Hill Notation): C18H18N2O2

DETAILS

Sigma Aldrich - 532029

Packaging
1, 5 g in glass bottle