N-[(1S,2R)-1-benzyl-3-(ter-butylamino)-3-hydroxypropyl]-N'-[(1R)-1-(4-fluorophenyl)ethyl]-5-[methyl(methylsulfonyl)amino]isophthalamide

ID: ALA266891

Chembl Id: CHEMBL266891

PubChem CID: 11342515

Max Phase: Preclinical

Molecular Formula: C32H41FN4O5S

Molecular Weight: 612.77

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H](NC(=O)c1cc(C(=O)N[C@@H](Cc2ccccc2)[C@H](O)CNC(C)(C)C)cc(N(C)S(C)(=O)=O)c1)c1ccc(F)cc1

Standard InChI:  InChI=1S/C32H41FN4O5S/c1-21(23-12-14-26(33)15-13-23)35-30(39)24-17-25(19-27(18-24)37(5)43(6,41)42)31(40)36-28(16-22-10-8-7-9-11-22)29(38)20-34-32(2,3)4/h7-15,17-19,21,28-29,34,38H,16,20H2,1-6H3,(H,35,39)(H,36,40)/t21-,28+,29-/m1/s1

Standard InChI Key:  BILACAQKFWZXQE-SPTGULJVSA-N

Alternative Forms

1. Parent:

   

   ALA266891

   1-N-[(2S,3R)-4-(tert-butylamino)-3-hydroxy-1-phenylbutan-2-yl]-3-N-[(1R)-1-(4-fluorophenyl)ethyl]-5-(N-methylmethanesulfonamido)benzene-1,3-dicarboxamide

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 612.77

Molecular Weight (Monoisotopic): 612.2782

AlogP: 3.80

#Rotatable Bonds: 12

Polar Surface Area: 127.84

Molecular Species: BASE

HBA: 6

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.87

CX Basic pKa: 9.92

CX LogP: 3.13

CX LogD: 0.69

Aromatic Rings: 3

Heavy Atoms: 43

QED Weighted: 0.25

Np Likeness Score: -0.80

References

1. Stachel SJ, Coburn CA, Steele TG, Jones KG, Loutzenhiser EF, Gregro AR, Rajapakse HA, Lai MT, Crouthamel MC, Xu M, Tugusheva K, Lineberger JE, Pietrak BL, Espeseth AS, Shi XP, Chen-Dodson E, Holloway MK, Munshi S, Simon AJ, Kuo L, Vacca JP..  (2004)  Structure-based design of potent and selective cell-permeable inhibitors of human beta-secretase (BACE-1).,  47  (26): [PMID:15588077] [10.1021/jm049379g]

2. Al-Nadaf A, Abu Sheikha G, Taha MO..  (2010)  Elaborate ligand-based pharmacophore exploration and QSAR analysis guide the synthesis of novel pyridinium-based potent beta-secretase inhibitory leads.,  18  (9): [PMID:20378363] [10.1016/j.bmc.2010.03.043]

Source

Source(1):

• Scientific Literature