(4S)-4-{[(tert-butoxy)carbonyl]amino}-5-(4-nitrophenoxy)-5-oxopentanoic acid

• ChemBase ID: 155955
• Molecular Formular: C16H20N2O8
• Molecular Mass: 368.3386
• Monoisotopic Mass: 368.12196561
• SMILES: CC(C)(C)OC(=O)N[C@@H](CCC(=O)O)C(=O)Oc1ccc(cc1)[N+](=O)[O-]
• Canonical SMILES: O=C([C@@H](NC(=O)OC(C)(C)C)CCC(=O)O)Oc1ccc(cc1)[N+](=O)[O-]
• InChI: InChI=1S/C16H20N2O8/c1-16(2,3)26-15(22)17-12(8-9-13(19)20)14(21)25-11-6-4-10(5-7-11)18(23)24/h4-7,12H,8-9H2,1-3H3,(H,17,22)(H,19,20)/t12-/m0/s1
• InChIKey: TXKOUVRCDMSOJZ-LBPRGKRZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-{[(tert-butoxy)carbonyl]amino}-5-(4-nitrophenoxy)-5-oxopentanoic acid
• IUPAC Traditional name: (4S)-4-[(tert-butoxycarbonyl)amino]-5-(4-nitrophenoxy)-5-oxopentanoic acid
• Synonyms: L-Glutamic acid 1-(4-nitroanilide)

Database IDs

• CAS Number: 24032-35-7
• EC Number: 245-994-9
• MDL Number: MFCD00038111
• Beilstein Number: 3036815
• PubChem SID: 24873020; 162250093
• PubChem CID: 16213661

CALCULATED PROPERTIES

• Acid pKa: 3.7465358
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 0.550227
• LogD (pH = 7.4): -0.9820527
• Log P: 2.3040721
• Molar Refractivity: 88.0321 cm^3
• Polarizability: 34.00253 Å^3
• Polar Surface Area: 147.75 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 184-186 °C
• Optical Rotation: [α]20/D +80±2°, c = 1% in 5 M HCl

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: ≥98.0% (T)
• Empirical Formula (Hill Notation): C11H13N3O5

DETAILS

Sigma Aldrich - 49622

Other Notes
Chromogenic substrate for the assay (determination of liberated 4-nitroaniline at 410 nm) of aminopeptidase A (EC 3.4.11.7)1