(2S)-2-{[(2S)-1-[(2R)-2-amino-3-phenylpropanoyl]pyrrolidin-2-yl]formamido}-5-carbamimidamido-N-(4-methyl-2-oxo-2H-chromen-7-yl)pentanamide

• ChemBase ID: 106419
• 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]1CCCN1C(=O)[C@H](N)Cc1ccccc1)c2
• Canonical SMILES: NC(=N)NCCC[C@@H](C(=O)Nc1ccc2c(c1)oc(=O)cc2C)NC(=O)[C@@H]1CCCN1C(=O)[C@@H](Cc1ccccc1)N
• InChI: InChI=1S/C30H37N7O5/c1-18-15-26(38)42-25-17-20(11-12-21(18)25)35-27(39)23(9-5-13-34-30(32)33)36-28(40)24-10-6-14-37(24)29(41)22(31)16-19-7-3-2-4-8-19/h2-4,7-8,11-12,15,17,22-24H,5-6,9-10,13-14,16,31H2,1H3,(H,35,39)(H,36,40)(H4,32,33,34)/t22-,23+,24+/m1/s1
• InChIKey: WVKWAAVROMOBBL-SGNDLWITSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{[(2S)-1-[(2R)-2-amino-3-phenylpropanoyl]pyrrolidin-2-yl]formamido}-5-carbamimidamido-N-(4-methyl-2-oxo-2H-chromen-7-yl)pentanamide
• IUPAC Traditional name: (2S)-2-{[(2S)-1-[(2R)-2-amino-3-phenylpropanoyl]pyrrolidin-2-yl]formamido}-5-carbamimidamido-N-(4-methyl-2-oxochromen-7-yl)pentanamide
• Synonyms: D-Phe-Pro-Arg-AMC; D-FPR-AMC; D-Phe-Pro-Arg-7-Amino-4-Methylcoumarin

Database IDs

• PubChem SID: 162105575
• PubChem CID: 15021810

CALCULATED PROPERTIES

• Acid pKa: 12.361071
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): -3.6491516
• LogD (pH = 7.4): -1.9770759
• Log P: 0.55520755
• Molar Refractivity: 168.8759 cm^3
• Polarizability: 60.359215 Å^3
• Polar Surface Area: 192.73 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03AMC064

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).