(2R)-N-hydroxy-3-methyl-2-[N-(propan-2-yloxy)4-phenylbenzenesulfonamido]butanamide

• ChemBase ID: 154015
• Molecular Formular: C20H26N2O5S
• Molecular Mass: 406.49584
• Monoisotopic Mass: 406.15624294
• SMILES: CC(C)[C@H](C(=O)NO)N(OC(C)C)S(=O)(=O)c1ccc(cc1)c1ccccc1
• Canonical SMILES: ONC(=O)[C@H](N(S(=O)(=O)c1ccc(cc1)c1ccccc1)OC(C)C)C(C)C
• InChI: InChI=1S/C20H26N2O5S/c1-14(2)19(20(23)21-24)22(27-15(3)4)28(25,26)18-12-10-17(11-13-18)16-8-6-5-7-9-16/h5-15,19,24H,1-4H3,(H,21,23)/t19-/m1/s1
• InChIKey: DGZZVIWCMGVHGV-LJQANCHMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-N-hydroxy-3-methyl-2-[N-(propan-2-yloxy)4-phenylbenzenesulfonamido]butanamide
• IUPAC Traditional name: (2R)-N-hydroxy-2-(N-isopropoxy4-phenylbenzenesulfonamido)-3-methylbutanamide
• Synonyms: (2R)-2-[([1,1′-Biphenyl]-4-ylsulfonyl)(1-methylethoxy)amino]-N-hydroxy-3-methyl-butanamide; (R)-N-Hydroxy-2-(N-isopropoxybiphenyl-4-ylsulfonamido)-3-methylbutanamide; ARP 101; APR 101

Database IDs

• CAS Number: 849773-64-4
• MDL Number: MFCD09753277
• PubChem SID: 162248154
• PubChem CID: 11292680

CALCULATED PROPERTIES

• Acid pKa: 8.687089
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 3.7221775
• LogD (pH = 7.4): 3.700702
• Log P: 3.7224584
• Molar Refractivity: 106.824 cm^3
• Polarizability: 43.79638 Å^3
• Polar Surface Area: 95.94 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >20 mg/mL; H2O: insoluble
• Apperance: solid

Safety Information

• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 25
• Safety Statements: 45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301
• GHS Precautionary statements: P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C20H26N2O5S

DETAILS

Sigma Aldrich - A8356

Application
ARP 101 is a MMP-2 selective inhibitor. ARP 101 has diverse physiological roles including wound healing, cancer metastasis, angiogenesis, tissue remodeling in development, and embryogenesis.
Biochem/physiol Actions
ARP 101 is a MMP-2 selective inhibitor (Gelatinase A, EC 3.4.24.24; TBE-1; LG4A; MONA; Type IV Collagenase). ARP 101 has diverse physiological roles including wound healing, cancer metastasis, angiogenesis, tissue remodeling in development and embryogenesis. IC50 = 0.81 nM on MMP-2.