4-nitrophenyl (2S)-2-{[(benzyloxy)carbonyl]amino}-3-(1H-indol-3-yl)propanoate

• ChemBase ID: 156203
• Molecular Formular: C25H21N3O6
• Molecular Mass: 459.45074
• Monoisotopic Mass: 459.14303541
• SMILES: c1ccc(cc1)COC(=O)N[C@@H](Cc1c[nH]c2c1cccc2)C(=O)Oc1ccc(cc1)[N+](=O)[O-]
• Canonical SMILES: O=C(N[C@H](C(=O)Oc1ccc(cc1)[N+](=O)[O-])Cc1c[nH]c2c1cccc2)OCc1ccccc1
• InChI: InChI=1S/C25H21N3O6/c29-24(34-20-12-10-19(11-13-20)28(31)32)23(14-18-15-26-22-9-5-4-8-21(18)22)27-25(30)33-16-17-6-2-1-3-7-17/h1-13,15,23,26H,14,16H2,(H,27,30)/t23-/m0/s1
• InChIKey: MGXAOGDOJXOYRA-QHCPKHFHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-nitrophenyl (2S)-2-{[(benzyloxy)carbonyl]amino}-3-(1H-indol-3-yl)propanoate
• IUPAC Traditional name: 4-nitrophenyl (2S)-2-{[(benzyloxy)carbonyl]amino}-3-(1H-indol-3-yl)propanoate
• Synonyms: Z-L-tryptophan 4-nitrophenyl ester; Z-Trp-ONp; Z-L-色氨酸 4-硝基苯酯

Database IDs

• CAS Number: 16624-64-9
• EC Number: 240-674-5
• MDL Number: MFCD00066469
• Beilstein Number: 466195
• PubChem SID: 162250341
• PubChem CID: 12007812

CALCULATED PROPERTIES

• Acid pKa: 12.802726
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 5.0828247
• LogD (pH = 7.4): 5.0828233
• Log P: 5.0828247
• Molar Refractivity: 123.7542 cm^3
• Polarizability: 48.424324 Å^3
• Polar Surface Area: 126.24 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 102-104 °C
• Optical Rotation: [α]20/D -2.1±0.3°, c = 2% in acetone

Safety Information

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

Product Information

• Purity: ≥98.0% (N)
• Grade: purum
• Empirical Formula (Hill Notation): C25H21N3O6