(2R)-N-[(1S)-2,2-dimethyl-1-{[(1R)-1-phenylethyl]carbamoyl}propyl]-N'-hydroxy-2-[3-(3-methyl-4-phenylphenyl)propyl]butanediamide

• ChemBase ID: 154905
• Molecular Formular: C34H43N3O4
• Molecular Mass: 557.72292
• Monoisotopic Mass: 557.32535687
• SMILES: Cc1cc(ccc1c1ccccc1)CCC[C@H](CC(=O)NO)C(=O)N[C@H](C(=O)N[C@H](C)c1ccccc1)C(C)(C)C
• Canonical SMILES: ONC(=O)C[C@H](C(=O)N[C@@H](C(C)(C)C)C(=O)N[C@@H](c1ccccc1)C)CCCc1ccc(c(c1)C)c1ccccc1
• InChI: InChI=1S/C34H43N3O4/c1-23-21-25(19-20-29(23)27-16-10-7-11-17-27)13-12-18-28(22-30(38)37-41)32(39)36-31(34(3,4)5)33(40)35-24(2)26-14-8-6-9-15-26/h6-11,14-17,19-21,24,28,31,41H,12-13,18,22H2,1-5H3,(H,35,40)(H,36,39)(H,37,38)/t24-,28-,31-/m1/s1
• InChIKey: JJHRUUKMPWUYIB-HVOSOHGQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-N-[(1S)-2,2-dimethyl-1-{[(1R)-1-phenylethyl]carbamoyl}propyl]-N'-hydroxy-2-[3-(3-methyl-4-phenylphenyl)propyl]butanediamide
• IUPAC Traditional name: (2R)-N-[(1S)-2,2-dimethyl-1-{[(1R)-1-phenylethyl]carbamoyl}propyl]-N'-hydroxy-2-[3-(3-methyl-4-phenylphenyl)propyl]butanediamide
• Synonyms: (2R)-N1-[(1S)-2,2-Dimethyl-1-({[(1R)-1-phenylethyl]amino}carbonyl)propyl]-2-{3-[(3-methyl-4-phenyl)-phenyl]propyl}-(N4-hydroxy)butanediamide; UK-356,618; UK-356618; (2R)-N1-[(1S)-2,2-Dimethyl-1-[[[(1R)-1-phenylethyl]amino]carbonyl]propyl]-N4-hydroxy-2-[3-(2-methyl[1,1'-biphenyl]-4-yl)propyl]butanediamide; UK 356618; PF-03890101; UK-356618

Database IDs

• CAS Number: 230961-08-7
• MDL Number: MFCD19443865
• PubChem SID: 162249043
• PubChem CID: 10370504

CALCULATED PROPERTIES

• Acid pKa: 8.899392
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): 6.249121
• LogD (pH = 7.4): 6.2358193
• Log P: 6.2492943
• Molar Refractivity: 162.2151 cm^3
• Polarizability: 64.43837 Å^3
• Polar Surface Area: 107.53 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: ≥25 mg/mL; Methanol
• Apperance: Beige Solid; white to tan powder
• Melting Point: 95-105°C
• Optical Rotation: [α]/D >+25.0°, c = 0.5 in methanol

Safety Information

• Storage Condition: -20°C Freezer
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C34H43N3O4

DETAILS

Sigma Aldrich - PZ0152

Legal Information
Sold for research purposes under agreement from Pfizer Inc.
Biochem/physiol Actions
UK-356,618 is a potent, selective inhibitor of Matrix metalloproteinase MMP3 (stromelysin-1). MMP-3 IC50 = 5.9 nM, selectivity is 140-fold vs MMP-1, -2, -9, and -14.

Toronto Research Chemicals - U700585

Potent and selective inhibitor of matrix metalloprotease-3 (MMP-3) (IC50 = 5.9 nM). Displays selectivity over a range of MMPs (IC50 values are 73, 840, 1790, 1900 and 51000 for MMP-13, MMP-9, MMP-2, MMP-14 and MMP-1 respectively).

REFERENCES

• Fray, M.J. et al.: Bioorg. Med. Chem. Lett., 11, 571 (2001)
• Fray, M.J. et al.: J. Med. Chem., 46, 3514 (2001)