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

• ChemBase ID: 106319
• Molecular Formular: C27H38F3N7O5
• Molecular Mass: 597.6297296
• Monoisotopic Mass: 597.28865201
• 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(F)(F)F
• Canonical SMILES: CC(C[C@@H](C(=O)N[C@H](C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F)CCCNC(=N)N)NC(=O)[C@@H](C(C)C)N)C
• InChI: InChI=1S/C27H38F3N7O5/c1-13(2)10-19(37-25(41)22(31)14(3)4)24(40)36-18(6-5-9-34-26(32)33)23(39)35-15-7-8-16-17(27(28,29)30)12-21(38)42-20(16)11-15/h7-8,11-14,18-19,22H,5-6,9-10,31H2,1-4H3,(H,35,39)(H,36,40)(H,37,41)(H4,32,33,34)/t18-,19-,22+/m0/s1
• InChIKey: TZVXRHVBYKVNOR-CNNODRBYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(2R)-2-amino-3-methylbutanamido]-N-[(1S)-4-carbamimidamido-1-{[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]carbamoyl}butyl]-4-methylpentanamide
• IUPAC Traditional name: (2S)-2-[(2R)-2-amino-3-methylbutanamido]-N-[(1S)-4-carbamimidamido-1-{[2-oxo-4-(trifluoromethyl)chromen-7-yl]carbamoyl}butyl]-4-methylpentanamide
• Synonyms: D-Val-Leu-Arg-AFC; D-VLR-AFC; D-Val-Leu-Arg-7-Amino-4-trifluoromethylcoumarin; D-Val-Leu-Arg 7-amido-4-trifluoromethylcoumarin

Database IDs

• MDL Number: MFCD02094148
• PubChem SID: 162105946
• PubChem CID: 25108539

CALCULATED PROPERTIES

• Acid pKa: 12.055635
• H Acceptors: 8
• H Donor: 7
• LogD (pH = 5.5): -3.471941
• LogD (pH = 7.4): -1.7946361
• Log P: 1.01098
• Molar Refractivity: 160.1695 cm^3
• Polarizability: 56.366512 Å^3
• Polar Surface Area: 201.52 Å^2
• Rotatable Bonds: 14
• 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

Product Information

• Purity: ≥90% (HPLC)

DETAILS

MP Biomedicals - 03AFC066

HYGROSCOPIC. A fluorogenic substrate for Glandular Kallikrein.

Sigma Aldrich - V2888

Biochem/physiol Actions
Glandular tissue kallikrein substrate

REFERENCES

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