(2S)-2-[2-(1H-indol-3-yl)acetamido]-3-phenylpropanoic acid

• ChemBase ID: 138743
• Molecular Formular: C19H18N2O3
• Molecular Mass: 322.35782
• Monoisotopic Mass: 322.13174245
• SMILES: c1ccc(cc1)C[C@@H](C(=O)O)NC(=O)Cc1c[nH]c2c1cccc2
• Canonical SMILES: O=C(Cc1c[nH]c2c1cccc2)N[C@H](C(=O)O)Cc1ccccc1
• InChI: InChI=1S/C19H18N2O3/c22-18(11-14-12-20-16-9-5-4-8-15(14)16)21-17(19(23)24)10-13-6-2-1-3-7-13/h1-9,12,17,20H,10-11H2,(H,21,22)(H,23,24)/t17-/m0/s1
• InChIKey: BUGQHORRADGONS-KRWDZBQOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[2-(1H-indol-3-yl)acetamido]-3-phenylpropanoic acid
• IUPAC Traditional name: (2S)-2-[2-(1H-indol-3-yl)acetamido]-3-phenylpropanoic acid
• Synonyms: IAA-L-Phe; N-(3-Indolylacetyl)-L-phenylalanine; (S)-2-(2-(1H-Indol-3-yl)acetaMido)-3-phenylpropanoic acid; N-(3-吲哚乙酰基)-L-苯丙氨酸

Database IDs

• CAS Number: 57105-50-7
• MDL Number: MFCD00075336
• PubChem SID: 162232994; 24861362
• PubChem CID: 644227

CALCULATED PROPERTIES

• Acid pKa: 4.0959682
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 1.4119724
• LogD (pH = 7.4): -0.27190548
• Log P: 2.8295634
• Molar Refractivity: 90.3685 cm^3
• Polarizability: 36.050446 Å^3
• Polar Surface Area: 82.19 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 154-156 °C(lit.)
• Optical Rotation: [α]20/D +36°, c = 3 in ethanol

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: 97%; 99%
• Empirical Formula (Hill Notation): C19H18N2O3