tert-butyl N-[(2S,3R,5R)-5-benzyl-5-{[(1S)-1-{[(1S)-1-carbamoyl-2-phenylethyl]carbamoyl}-3-methylbutyl]carbamoyl}-3-hydroxy-1-phenylpentan-2-yl]carbamate

• ChemBase ID: 154193
• Molecular Formular: C39H52N4O6
• Molecular Mass: 672.85338
• Monoisotopic Mass: 672.3886854
• SMILES: CC(C)C[C@@H](C(=O)N[C@@H](Cc1ccccc1)C(=O)N)NC(=O)[C@H](Cc1ccccc1)C[C@H]([C@H](Cc1ccccc1)NC(=O)OC(C)(C)C)O
• Canonical SMILES: CC(C[C@@H](C(=O)N[C@H](C(=O)N)Cc1ccccc1)NC(=O)[C@@H](C[C@H]([C@@H](NC(=O)OC(C)(C)C)Cc1ccccc1)O)Cc1ccccc1)C
• InChI: InChI=1S/C39H52N4O6/c1-26(2)21-33(37(47)41-32(35(40)45)24-29-19-13-8-14-20-29)42-36(46)30(22-27-15-9-6-10-16-27)25-34(44)31(23-28-17-11-7-12-18-28)43-38(48)49-39(3,4)5/h6-20,26,30-34,44H,21-25H2,1-5H3,(H2,40,45)(H,41,47)(H,42,46)(H,43,48)/t30-,31+,32+,33+,34-/m1/s1
• InChIKey: MURCDOXDAHPNRQ-ZJKZPDEISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tert-butyl N-[(2S,3R,5R)-5-benzyl-5-{[(1S)-1-{[(1S)-1-carbamoyl-2-phenylethyl]carbamoyl}-3-methylbutyl]carbamoyl}-3-hydroxy-1-phenylpentan-2-yl]carbamate
• IUPAC Traditional name: tert-butyl N-[(2S,3R,5R)-5-benzyl-5-{[(1S)-1-{[(1S)-1-carbamoyl-2-phenylethyl]carbamoyl}-3-methylbutyl]carbamoyl}-3-hydroxy-1-phenylpentan-2-yl]carbamate
• Synonyms: (5S)-(t-Butoxycarbonylamino)-6-phenyl-(4R)hydroxy-(2R)benzylhexanoyl)-L-leu-L-phe-amide; L-685,458

Database IDs

• CAS Number: 292632-98-5
• MDL Number: MFCD03093402
• PubChem SID: 162248332
• PubChem CID: 5479543

CALCULATED PROPERTIES

• Acid pKa: 12.306839
• H Acceptors: 5
• H Donor: 5
• LogD (pH = 5.5): 5.4646764
• LogD (pH = 7.4): 5.464672
• Log P: 5.464677
• Molar Refractivity: 189.3112 cm^3
• Polarizability: 74.33662 Å^3
• Polar Surface Area: 159.85 Å^2
• Rotatable Bonds: 19
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL
• Apperance: white 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

Pharmacology Properties

• Gene Information: human ... APH1A(51107), APH1B(83464), NCSTN(23385), NOTCH1(4851), NOTCH2(4853), NOTCH3(4854), NOTCH4(4855), PSEN1(5663), PSEN2(5664), PSENEN(55851)mouse ... Aph1a(226548), Aph1b(208117), Ncstn(59287), Notch1(18128), Notch2(18129), Notch3(18131), Notch4(18132), Psen1(19164), Psen2(19165), Psenen(66340)rat ... Aph1a(365872), Aph1b(300802), Ncstn(289231), Notch1(25496), Notch2(29492), Notch3(56761), Notch4(406162), Psen1(29192), Psen2(81751), Psenen(292788)

Product Information

• Purity: >96% (HPLC)
• Empirical Formula (Hill Notation): C39H52O6N4

DETAILS

Sigma Aldrich - L1790

Biochem/physiol Actions
L-685,458 is a potent, selective, structurally novel γ-secretase inhibitor; equipotent inhibitor of both Aβ1-42 and Aβ1-40 production.
Legal Information
Manufactured and sold under license from Merck & Co., Inc.