3-{[(1S)-1-{[(1S)-1-{[(1S)-1-[(4-nitrophenyl)carbamoyl]ethyl]carbamoyl}ethyl]carbamoyl}ethyl]carbamoyl}propanoic acid

• ChemBase ID: 133735
• Molecular Formular: C19H25N5O8
• Molecular Mass: 451.4305
• Monoisotopic Mass: 451.17031279
• SMILES: C[C@@H](C(=O)N[C@@H](C)C(=O)N[C@@H](C)C(=O)Nc1ccc(cc1)[N+](=O)[O-])NC(=O)CCC(=O)O
• Canonical SMILES: O=C(N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)Nc1ccc(cc1)[N+](=O)[O-])C)C)C)CCC(=O)O
• InChI: InChI=1S/C19H25N5O8/c1-10(20-15(25)8-9-16(26)27)17(28)21-11(2)18(29)22-12(3)19(30)23-13-4-6-14(7-5-13)24(31)32/h4-7,10-12H,8-9H2,1-3H3,(H,20,25)(H,21,28)(H,22,29)(H,23,30)(H,26,27)/t10-,11-,12-/m0/s1
• InChIKey: GVUGADOWXGKRAE-SRVKXCTJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-{[(1S)-1-{[(1S)-1-{[(1S)-1-[(4-nitrophenyl)carbamoyl]ethyl]carbamoyl}ethyl]carbamoyl}ethyl]carbamoyl}propanoic acid
• IUPAC Traditional name: 3-{[(1S)-1-{[(1S)-1-{[(1S)-1-[(4-nitrophenyl)carbamoyl]ethyl]carbamoyl}ethyl]carbamoyl}ethyl]carbamoyl}propanoic acid
• Synonyms: N-Succinyl-L-alanyl-L-alanyl-L-alanine 4-nitroanilide; N-Succinyl-tri-L-alanine 4-nitroanilide; N-Succinyl-Ala-Ala-Ala-p-nitroanilide

Database IDs

• CAS Number: 52299-14-6
• EC Number: 257-823-5
• MDL Number: MFCD00036774
• Beilstein Number: 2928351
• PubChem SID: 162228012; 24899617
• PubChem CID: 5484223

CALCULATED PROPERTIES

• Acid pKa: 4.0904903
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -2.056576
• LogD (pH = 7.4): -3.738673
• Log P: -0.6337539
• Molar Refractivity: 111.0312 cm^3
• Polarizability: 41.759556 Å^3
• Polar Surface Area: 199.52 Å^2
• Rotatable Bonds: 11
• 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: 2-8°C

Product Information

• Purity: ≥99.0% (enzymatic)
• Empirical Formula (Hill Notation): C19H25N5O8

DETAILS

Sigma Aldrich - S4760

Substrates
Elastase substrate.

Sigma Aldrich - 85975

Other Notes
Chromogenic substrate for the assay of pancreatic elastase1,2