tert-butyl (2R)-2-[(2S)-2-[2-(3,5-difluorophenyl)acetamido]propanamido]-2-phenylacetate

• ChemBase ID: 154236
• Molecular Formular: C23H26F2N2O4
• Molecular Mass: 432.4603464
• Monoisotopic Mass: 432.18606376
• SMILES: C[C@@H](C(=O)N[C@H](c1ccccc1)C(=O)OC(C)(C)C)NC(=O)Cc1cc(cc(c1)F)F
• Canonical SMILES: O=C(N[C@H](C(=O)N[C@H](c1ccccc1)C(=O)OC(C)(C)C)C)Cc1cc(F)cc(c1)F
• InChI: InChI=1S/C23H26F2N2O4/c1-14(26-19(28)12-15-10-17(24)13-18(25)11-15)21(29)27-20(16-8-6-5-7-9-16)22(30)31-23(2,3)4/h5-11,13-14,20H,12H2,1-4H3,(H,26,28)(H,27,29)/t14-,20+/m0/s1
• InChIKey: DWJXYEABWRJFSP-VBKZILBWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tert-butyl (2R)-2-[(2S)-2-[2-(3,5-difluorophenyl)acetamido]propanamido]-2-phenylacetate
• IUPAC Traditional name: tert-butyl (2R)-2-[(2S)-2-[2-(3,5-difluorophenyl)acetamido]propanamido]-2-phenylacetate
• Synonyms: LY-374973; N-[N-(3,5-Difluorophenacetyl)-L-alanyl]-S-phenylglycine t-butyl ester; DAPT

Database IDs

• CAS Number: 208255-80-5
• MDL Number: MFCD04974585
• PubChem SID: 24893987; 162248375
• PubChem CID: 16219261

CALCULATED PROPERTIES

• Acid pKa: 10.761095
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 3.3908768
• LogD (pH = 7.4): 3.3907113
• Log P: 3.390879
• Molar Refractivity: 110.8319 cm^3
• Polarizability: 42.75823 Å^3
• Polar Surface Area: 84.5 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ~18 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: 2-8°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: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C23H26F2N2O4

DETAILS

Sigma Aldrich - D5942

Frequently Asked Questions
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Biochem/physiol Actions
DAPT is a γ-secretase inhibitor and indirectly an inhibitor of Notch, a γ-secretase substrate. As an inhibitor of γ-secretase, DAPT may be useful in the study of β-amyloid (Aβ) formation. As an inhibitor of Notch, DAPT may advance studies of autoimmune and lymphoproliferative diseases, such as ALPS and lupus erythematosus (SLE). Other γ-secretase substrates include LDL receptor-related protein, E-cadherin and ErbB-4.