(2S)-2-[(2R)-2-amino-3-methylbutanamido]-N-[(1S)-4-carbamimidamido-1-[(4-methyl-2-oxo-2H-chromen-7-yl)carbamoyl]butyl]-4-methylpentanamide

• ChemBase ID: 106420
• Molecular Formular: C27H41N7O5
• Molecular Mass: 543.65834
• Monoisotopic Mass: 543.31691745
• SMILES: CC(C)C[C@H](NC(=O)[C@H](N)C(C)C)C(=O)N[C@@H](CCCNC(=N)N)C(=O)Nc1ccc2c(c1)oc(=O)cc2C
• Canonical SMILES: CC(C[C@@H](C(=O)N[C@H](C(=O)Nc1ccc2c(c1)oc(=O)cc2C)CCCNC(=N)N)NC(=O)[C@@H](C(C)C)N)C
• InChI: InChI=1S/C27H41N7O5/c1-14(2)11-20(34-26(38)23(28)15(3)4)25(37)33-19(7-6-10-31-27(29)30)24(36)32-17-8-9-18-16(5)12-22(35)39-21(18)13-17/h8-9,12-15,19-20,23H,6-7,10-11,28H2,1-5H3,(H,32,36)(H,33,37)(H,34,38)(H4,29,30,31)/t19-,20-,23+/m0/s1
• InChIKey: XGIJXFDFJRZNBB-SXWKCWPCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(2R)-2-amino-3-methylbutanamido]-N-[(1S)-4-carbamimidamido-1-[(4-methyl-2-oxo-2H-chromen-7-yl)carbamoyl]butyl]-4-methylpentanamide
• IUPAC Traditional name: (2S)-2-[(2R)-2-amino-3-methylbutanamido]-N-[(1S)-4-carbamimidamido-1-[(4-methyl-2-oxochromen-7-yl)carbamoyl]butyl]-4-methylpentanamide
• Synonyms: D-Val-Leu-Arg-AMC; D-VLR-AMC; D-Val-Leu-Arg-7-Amino-4-Methylcoumarin; D-Val-Leu-Arg 7-amido-4-methylcoumarin

Database IDs

• MDL Number: MFCD03453032
• PubChem SID: 162105448
• PubChem CID: 25108609

CALCULATED PROPERTIES

• Acid pKa: 12.185391
• H Acceptors: 8
• H Donor: 7
• LogD (pH = 5.5): -3.8363886
• LogD (pH = 7.4): -2.1604948
• Log P: 0.6970636
• Molar Refractivity: 159.237 cm^3
• Polarizability: 57.031635 Å^3
• Polar Surface Area: 201.52 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: solid

Safety Information

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

DETAILS

MP Biomedicals - 03AMC066

HYGROSCOPIC. A fluorogenic substrate for Glandular Kallikrein.

Sigma Aldrich - V2763

Biochem/physiol Actions
Glandular tissue kallikrein substrate

REFERENCES

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