methyl (2S)-2-[(2S)-2-({benzyl[(2R,3S)-3-{[(tert-butoxy)carbonyl]amino}-2-hydroxy-4-phenylbutyl]carbamoyl}amino)-4-methylpentanamido]-3-methylbutanoate

• ChemBase ID: 154039
• Molecular Formular: C35H52N4O7
• Molecular Mass: 640.80998
• Monoisotopic Mass: 640.38360002
• SMILES: CC(C)C[C@@H](C(=O)N[C@@H](C(C)C)C(=O)OC)NC(=O)N(Cc1ccccc1)C[C@H]([C@H](Cc1ccccc1)NC(=O)OC(C)(C)C)O
• Canonical SMILES: COC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)N(Cc1ccccc1)C[C@H]([C@H](Cc1ccccc1)NC(=O)OC(C)(C)C)O)CC(C)C
• InChI: InChI=1S/C35H52N4O7/c1-23(2)19-28(31(41)38-30(24(3)4)32(42)45-8)36-33(43)39(21-26-17-13-10-14-18-26)22-29(40)27(20-25-15-11-9-12-16-25)37-34(44)46-35(5,6)7/h9-18,23-24,27-30,40H,19-22H2,1-8H3,(H,36,43)(H,37,44)(H,38,41)/t27-,28-,29+,30-/m0/s1
• InChIKey: DINAVFJXFRFCRE-ZXYZSCNASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S)-2-[(2S)-2-({benzyl[(2R,3S)-3-{[(tert-butoxy)carbonyl]amino}-2-hydroxy-4-phenylbutyl]carbamoyl}amino)-4-methylpentanamido]-3-methylbutanoate
• IUPAC Traditional name: methyl (2S)-2-[(2S)-2-({benzyl[(2R,3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-4-phenylbutyl]carbamoyl}amino)-4-methylpentanamido]-3-methylbutanoate
• Synonyms: N-[[[(2R,3S)-3-[[(1,1-dimethylethoxy)carbonyl]amino]-2-hydroxy-4-phenylbutyl](phenylmethyl)amino]carbonyl]-L-leucyl-L-valine methyl ester; WPE-III-31-C; III-31-C

Database IDs

• CAS Number: 398515-96-3
• PubChem SID: 162248178
• PubChem CID: 9874174

CALCULATED PROPERTIES

• Acid pKa: 12.35573
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): 4.9670753
• LogD (pH = 7.4): 4.967071
• Log P: 4.9670753
• Molar Refractivity: 175.5826 cm^3
• Polarizability: 69.135 Å^3
• Polar Surface Area: 146.3 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: ≥9 mg/mL
• Apperance: solid

Safety Information

• Storage Condition: desiccated
• 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: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C35H52N4O7

DETAILS

Sigma Aldrich - C0619

Biochem/physiol Actions
III-31-C is a (hydroxyethyl)urea γ-secretase inhibitor that binds to γ-secretase at the substrate docking site. DAPT, also a γ-secretase inhibitor binds to the substrate docking site as well. III-31-C is useful for the affinity isolation and characterization of the protease complex and for testing other ihhibitors that affect the γ-secretase active site. The γ-secretase complex is composed of presenilin as a catalytic component and three integral membrane proteins, nicastrin, Aph-1 and Pen-2.