3-{[(1S)-1-{[(2S)-1-[(2S)-2-{[(1S)-1-[(4-nitrophenyl)carbamoyl]-2-phenylethyl]carbamoyl}pyrrolidin-1-yl]-1-oxopropan-2-yl]carbamoyl}ethyl]carbamoyl}propanoic acid

• ChemBase ID: 106627
• Molecular Formular: C30H36N6O9
• Molecular Mass: 624.64164
• Monoisotopic Mass: 624.25437676
• SMILES: C[C@H](NC(=O)CCC(=O)O)C(=O)N[C@@H](C)C(=O)N1CCC[C@H]1C(=O)N[C@@H](Cc1ccccc1)C(=O)Nc1ccc(cc1)[N+](=O)[O-]
• Canonical SMILES: O=C(N[C@H](C(=O)N[C@H](C(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)Nc1ccc(cc1)[N+](=O)[O-])Cc1ccccc1)C)C)CCC(=O)O
• InChI: InChI=1S/C30H36N6O9/c1-18(31-25(37)14-15-26(38)39)27(40)32-19(2)30(43)35-16-6-9-24(35)29(42)34-23(17-20-7-4-3-5-8-20)28(41)33-21-10-12-22(13-11-21)36(44)45/h3-5,7-8,10-13,18-19,23-24H,6,9,14-17H2,1-2H3,(H,31,37)(H,32,40)(H,33,41)(H,34,42)(H,38,39)/t18-,19-,23-,24-/m0/s1
• InChIKey: LKDMKWNDBAVNQZ-WJNSRDFLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-{[(1S)-1-{[(2S)-1-[(2S)-2-{[(1S)-1-[(4-nitrophenyl)carbamoyl]-2-phenylethyl]carbamoyl}pyrrolidin-1-yl]-1-oxopropan-2-yl]carbamoyl}ethyl]carbamoyl}propanoic acid
• IUPAC Traditional name: 3-{[(1S)-1-{[(2S)-1-[(2S)-2-{[(1S)-1-[(4-nitrophenyl)carbamoyl]-2-phenylethyl]carbamoyl}pyrrolidin-1-yl]-1-oxopropan-2-yl]carbamoyl}ethyl]carbamoyl}propanoic acid
• Synonyms: Suc-Ala-Ala-Pro-Phe-PNA; Suc-AAPF-PNA; Suc-Ala-Ala-Pro-Phe-paranitroanilide; N-Succinyl-Ala-Ala-Pro-Phe-pNA; N-Succinyl-L-alanyl-L-alanyl-L-prolyl-L-phenylalanine 4-nitroanilide; N-Succinyl-Ala-Ala-Pro-Phe p-nitroanilide

Database IDs

• CAS Number: 70967-97-4
• MDL Number: MFCD00077161
• Beilstein Number: 4289896
• PubChem SID: 162089088; 24899742
• PubChem CID: 5496888

CALCULATED PROPERTIES

• Acid pKa: 4.0904903
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -0.6641029
• LogD (pH = 7.4): -2.346195
• Log P: 0.7587191
• Molar Refractivity: 160.6367 cm^3
• Polarizability: 60.94311 Å^3
• Polar Surface Area: 219.83 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMF: soluble25 mg/mL, clear, light yellow

Safety Information

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

Pharmacology Properties

• Gene Information: human ... FKBP10(60681)

Product Information

• Purity: ≥99.0% (HPLC)
• Empirical Formula (Hill Notation): C30H36N6O9

DETAILS

MP Biomedicals - 03PNA085

A colorimetric substrate for Chymotrypsin.

Sigma Aldrich - S7388

Amino Acid Sequence
N-Suc-Ala-Ala-Pro-Phe-pNA
Substrates
Colorimetric substrate for chymotrypsin, human leukocyte cathepsin G, and peptidyl prolyl isomerase.

Sigma Aldrich - 85977

Amino Acid Sequence
N-Suc-Ala-Ala-Pro-Phe-pNA
Other Notes
Sensitive substrate for chymotrypsin1

REFERENCES

• Sawada, H. et al., Experienta, 39:454 (1983)
• Oshima, G. et al., J. Biochem., 94:1615 (1983)
• Powers, J.C. et al., J. Appl. Toxicol., 20:5177 (2000)