(2S)-1-[(2S)-2-[(2S)-2-{2-[(2S)-5-carbamimidamido-2-acetamidopentanamido]acetamido}-3-phenylpropanamido]-3-phenylpropanoyl]-N-[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]pyrrolidine-2-carboxamide

• ChemBase ID: 106334
• Molecular Formular: C43H48F3N9O8
• Molecular Mass: 875.8919296
• Monoisotopic Mass: 875.3577942
• SMILES: CC(=O)N[C@@H](CCCNC(=N)N)C(=O)NCC(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](Cc1ccccc1)C(=O)N1CCC[C@H]1C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F
• Canonical SMILES: NC(=N)NCCC[C@@H](C(=O)NCC(=O)N[C@H](C(=O)N[C@H](C(=O)N1CCC[C@H]1C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F)Cc1ccccc1)Cc1ccccc1)NC(=O)C
• InChI: InChI=1S/C43H48F3N9O8/c1-25(56)51-31(14-8-18-49-42(47)48)38(59)50-24-36(57)53-32(20-26-10-4-2-5-11-26)39(60)54-33(21-27-12-6-3-7-13-27)41(62)55-19-9-15-34(55)40(61)52-28-16-17-29-30(43(44,45)46)23-37(58)63-35(29)22-28/h2-7,10-13,16-17,22-23,31-34H,8-9,14-15,18-21,24H2,1H3,(H,50,59)(H,51,56)(H,52,61)(H,53,57)(H,54,60)(H4,47,48,49)/t31-,32-,33-,34-/m0/s1
• InChIKey: XQIFOKTYGLREIR-CUPIEXAXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-1-[(2S)-2-[(2S)-2-{2-[(2S)-5-carbamimidamido-2-acetamidopentanamido]acetamido}-3-phenylpropanamido]-3-phenylpropanoyl]-N-[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]pyrrolidine-2-carboxamide
• IUPAC Traditional name: (2S)-1-[(2S)-2-[(2S)-2-{2-[(2S)-5-carbamimidamido-2-acetamidopentanamido]acetamido}-3-phenylpropanamido]-3-phenylpropanoyl]-N-[2-oxo-4-(trifluoromethyl)chromen-7-yl]pyrrolidine-2-carboxamide
• Synonyms: N-Acetyl-Arg-Gly-Phe-Phe-Pro-7-amido-4-trifluoromethylcoumarin; Ac-Arg-Gly-Phe-Phe-Pro-AFC; Ac-RGFFP-AFC; Ac-Arg-Gly-Phe-Phe-Pro-7-Amino-4-trifluoromethylcoumarin

Database IDs

• MDL Number: MFCD03452899
• PubChem SID: 162105952
• PubChem CID: 25108554

CALCULATED PROPERTIES

• Acid pKa: 11.578896
• H Acceptors: 10
• H Donor: 8
• LogD (pH = 5.5): -1.3067843
• LogD (pH = 7.4): -1.3017972
• Log P: 0.5518773
• Molar Refractivity: 233.9721 cm^3
• Polarizability: 84.28881 Å^3
• Polar Surface Area: 254.01 Å^2
• Rotatable Bonds: 19
• Lipinski's Rule of Five: false

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

Pharmacology Properties

• Gene Information: human ... CTSD(1509)mouse ... CTSD(13033)rat ... CTSD(171293)

Product Information

• Purity: ≥95% (HPLC)
• Empirical Formula (Hill Notation): C43H48N9O8F3

DETAILS

MP Biomedicals - 03AFC098

A fluorogenic substrate for Cathepsin D.

Sigma Aldrich - C6983

Amino Acid Sequence
Nac-Arg-Gly-Phe-Phe-Pro-AFC
Application
Fluorogenic cathepsin D substrate.

REFERENCES

• Lojda, Z. et al., Histochem J., 88:505 (1988)
• Nishimura, Y. et al., Biochem. Biophys. Res. Comm., 148:335 (1987).
• Gulmik, S. et al., J. Mol. Bio. 277:265 (1992).