(2S)-2-[(2R)-2-amino-3-methylbutanamido]-N-[(1S)-4-carbamimidamido-1-[(4-methoxynaphthalen-2-yl)carbamoyl]butyl]-4-methylpentanamide

• ChemBase ID: 106562
• Molecular Formular: C28H43N7O4
• Molecular Mass: 541.68552
• Monoisotopic Mass: 541.33765289
• SMILES: COc1cc(NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](N)C(C)C)cc2c1cccc2
• Canonical SMILES: COc1cc(NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](C(C)C)N)CC(C)C)CCCNC(=N)N)cc2c1cccc2
• InChI: InChI=1S/C28H43N7O4/c1-16(2)13-22(35-27(38)24(29)17(3)4)26(37)34-21(11-8-12-32-28(30)31)25(36)33-19-14-18-9-6-7-10-20(18)23(15-19)39-5/h6-7,9-10,14-17,21-22,24H,8,11-13,29H2,1-5H3,(H,33,36)(H,34,37)(H,35,38)(H4,30,31,32)/t21-,22-,24+/m0/s1
• InChIKey: LWDYRVMYXLGAEN-WPFOTENUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(2R)-2-amino-3-methylbutanamido]-N-[(1S)-4-carbamimidamido-1-[(4-methoxynaphthalen-2-yl)carbamoyl]butyl]-4-methylpentanamide
• IUPAC Traditional name: (2S)-2-[(2R)-2-amino-3-methylbutanamido]-N-[(1S)-4-carbamimidamido-1-[(4-methoxynaphthalen-2-yl)carbamoyl]butyl]-4-methylpentanamide
• Synonyms: D-Val-Leu-Arg-MNA; D-VLR-MNA; D-Val-Leu-Arg-4-Methoxy-2-Naphthylamine

Database IDs

• PubChem SID: 162105524
• PubChem CID: 21121792

CALCULATED PROPERTIES

• Acid pKa: 12.290851
• H Acceptors: 8
• H Donor: 7
• LogD (pH = 5.5): -3.1140997
• LogD (pH = 7.4): -1.4386598
• Log P: 1.447804
• Molar Refractivity: 162.37779 cm^3
• Polarizability: 59.796146 Å^3
• Polar Surface Area: 184.45 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03MNA066

A fluorogenic/colorimetric substrate for Glandular Kallikrein.

REFERENCES

• Marata, M.A. et al., Can. Res., 48:4158 (1988).
• Shori, D.K. et al., Biochem. Pharmacology, 43(6):1209 (1992).
• Chan, K. et al., Diabetes, 42:113 (1993).