benzyl 2-[(1-{[(hydroxycarbamoyl)methyl]carbamoyl}-3-methylbutyl)carbamoyl]pyrrolidine-1-carboxylate

• ChemBase ID: 155526
• Molecular Formular: C21H30N4O6
• Molecular Mass: 434.4861
• Monoisotopic Mass: 434.2165347
• SMILES: CC(C)CC(C(=O)NCC(=O)NO)NC(=O)C1CCCN1C(=O)OCc1ccccc1
• Canonical SMILES: ONC(=O)CNC(=O)C(NC(=O)C1CCCN1C(=O)OCc1ccccc1)CC(C)C
• InChI: InChI=1S/C21H30N4O6/c1-14(2)11-16(19(27)22-12-18(26)24-30)23-20(28)17-9-6-10-25(17)21(29)31-13-15-7-4-3-5-8-15/h3-5,7-8,14,16-17,30H,6,9-13H2,1-2H3,(H,22,27)(H,23,28)(H,24,26)
• InChIKey: VVGFLHRPYCTXGJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl 2-[(1-{[(hydroxycarbamoyl)methyl]carbamoyl}-3-methylbutyl)carbamoyl]pyrrolidine-1-carboxylate
• IUPAC Traditional name: benzyl 2-({1-[(hydroxycarbamoyl)methylcarbamoyl]-3-methylbutyl}carbamoyl)pyrrolidine-1-carboxylate
• Synonyms: Z-Pro-Leu-Gly hydroxamate

Database IDs

• CAS Number: 103145-74-0
• MDL Number: MFCD00083286
• PubChem SID: 162249664; 24893070
• PubChem CID: 561533

CALCULATED PROPERTIES

• Acid pKa: 8.753895
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): 0.6585079
• LogD (pH = 7.4): 0.64002776
• Log P: 0.6587487
• Molar Refractivity: 111.2277 cm^3
• Polarizability: 43.47366 Å^3
• Polar Surface Area: 137.07 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: acetic acid: water (1:1): soluble50 mg/mL; methanol: soluble50 mg/mL

Safety Information

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

Pharmacology Properties

• Gene Information: human ... MMP1 (includes EG:4312)(4312)mouse ... MMP1 (includes EG:4312)(83995)rat ... MMP1 (includes EG:4312)(300339)

Product Information

• Purity: ≥97% (TLC)
• Empirical Formula (Hill Notation): C21H30N4O6

DETAILS

Sigma Aldrich - C8537

Amino Acid Sequence
Z-Pro-Leu-Gly
Biochem/physiol Actions
A hydroxamate inhibitor of human collagenases (MMP-1; matrix metalloproteinase 1). It is a substrate analog that interacts with the zinc moiety of MMP-1.