(2S)-5-carbamimidamido-N-(4-methyl-2-oxo-2H-chromen-7-yl)-2-[(2S)-3-phenyl-2-[(2R)-pyrrolidin-2-ylformamido]propanamido]pentanamide

• ChemBase ID: 106414
• Molecular Formular: C30H37N7O5
• Molecular Mass: 575.65868
• Monoisotopic Mass: 575.28561732
• SMILES: Cc1cc(=O)oc2c1ccc(NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@@H]1NCCC1)c2
• Canonical SMILES: NC(=N)NCCC[C@@H](C(=O)Nc1ccc2c(c1)oc(=O)cc2C)NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H]1CCCN1
• InChI: InChI=1S/C30H37N7O5/c1-18-15-26(38)42-25-17-20(11-12-21(18)25)35-28(40)23(10-6-14-34-30(31)32)36-29(41)24(16-19-7-3-2-4-8-19)37-27(39)22-9-5-13-33-22/h2-4,7-8,11-12,15,17,22-24,33H,5-6,9-10,13-14,16H2,1H3,(H,35,40)(H,36,41)(H,37,39)(H4,31,32,34)/t22-,23+,24+/m1/s1
• InChIKey: LATXIQYQVGEJJC-SGNDLWITSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-5-carbamimidamido-N-(4-methyl-2-oxo-2H-chromen-7-yl)-2-[(2S)-3-phenyl-2-[(2R)-pyrrolidin-2-ylformamido]propanamido]pentanamide
• IUPAC Traditional name: (2S)-5-carbamimidamido-N-(4-methyl-2-oxochromen-7-yl)-2-[(2S)-3-phenyl-2-[(2R)-pyrrolidin-2-ylformamido]propanamido]pentanamide
• Synonyms: D-Pro-Phe-Arg-AMC; D-PFR-AMC; D-Pro-Phe-Arg-7-Amino-4-Methylcoumarin

Database IDs

• PubChem SID: 162105444
• PubChem CID: 25108604

CALCULATED PROPERTIES

• Acid pKa: 12.107031
• H Acceptors: 8
• H Donor: 7
• LogD (pH = 5.5): -4.468716
• LogD (pH = 7.4): -3.3693357
• Log P: 0.6557583
• Molar Refractivity: 168.7538 cm^3
• Polarizability: 60.359215 Å^3
• Polar Surface Area: 187.53 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03AMC059

HYGROSCOPIC. A fluorogenic substrate for Thrombin.

REFERENCES

• McRae, B. J. et al., Biochem., 20:7196 (1981).
• Kato, H. et al., Throm. Res., 56:77 (1988).