(2S)-3-(1-benzyl-1H-pyrazol-3-yl)-2-{[(benzyloxy)carbonyl]amino}propanoic acid

• ChemBase ID: 155541
• Molecular Formular: C21H21N3O4
• Molecular Mass: 379.40914
• Monoisotopic Mass: 379.15320617
• SMILES: c1ccc(cc1)Cn1ccc(n1)C[C@@H](C(=O)O)NC(=O)OCc1ccccc1
• Canonical SMILES: O=C(N[C@H](C(=O)O)Cc1ccn(n1)Cc1ccccc1)OCc1ccccc1
• InChI: InChI=1S/C21H21N3O4/c25-20(26)19(22-21(27)28-15-17-9-5-2-6-10-17)13-18-11-12-24(23-18)14-16-7-3-1-4-8-16/h1-12,19H,13-15H2,(H,22,27)(H,25,26)/t19-/m0/s1
• InChIKey: DHUVTQUENUPYMW-IBGZPJMESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-3-(1-benzyl-1H-pyrazol-3-yl)-2-{[(benzyloxy)carbonyl]amino}propanoic acid
• IUPAC Traditional name: (2S)-2-{[(benzyloxy)carbonyl]amino}-3-(1-benzylpyrazol-3-yl)propanoic acid
• Synonyms: Nα-Cbz-Nim-benzyl-L-histidine; Nα-Z-N(im)-benzyl-L-histidine; Z-His(Bzl)-OH

Database IDs

• CAS Number: 21929-66-8
• MDL Number: MFCD00037892
• Beilstein Number: 55593
• PubChem SID: 24893199; 162249679
• PubChem CID: 16219190

CALCULATED PROPERTIES

• Acid pKa: 3.5856378
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 1.5055418
• LogD (pH = 7.4): 0.071729876
• Log P: 3.3001845
• Molar Refractivity: 113.7345 cm^3
• Polarizability: 39.712864 Å^3
• Polar Surface Area: 93.45 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥98.0% (TLC)
• Grade: purum
• Empirical Formula (Hill Notation): C21H21N3O4

DETAILS

Sigma Aldrich - C9783

Biochem/physiol Actions
Z-His(Bzl)-OH (Nα-Cbz-Nim-benzyl-L-histidine) is an N-terminal blocked (with CBZ) benzolated (on Imidazole) L-histidine.