N-[(1S,2R)-1-benzyl-3-(cyclopropylamino)-2-hydroxypropyl]-5-[methyl(methylsulfonyl)amino-N'-[(1R)-1-phenylethyl]isophthalamide

ID: ALA221454

Chembl Id: CHEMBL221454

PubChem CID: 44421346

Max Phase: Preclinical

Molecular Formula: C31H38N4O5S

Molecular Weight: 578.74

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H](NC(=O)c1cc(C(=O)N[C@@H](Cc2ccccc2)C(O)CNC2CC2)cc(N(C)S(C)(=O)=O)c1)c1ccccc1

Standard InChI:  InChI=1S/C31H38N4O5S/c1-21(23-12-8-5-9-13-23)33-30(37)24-17-25(19-27(18-24)35(2)41(3,39)40)31(38)34-28(16-22-10-6-4-7-11-22)29(36)20-32-26-14-15-26/h4-13,17-19,21,26,28-29,32,36H,14-16,20H2,1-3H3,(H,33,37)(H,34,38)/t21-,28+,29?/m1/s1

Standard InChI Key:  VPNIQGRFZCTBEZ-YARURSILSA-N

Alternative Forms

1. Parent:

   

   ALA221454

   3-N-[(2S)-4-(cyclopropylamino)-3-hydroxy-1-phenylbutan-2-yl]-5-[methyl(methylsulfonyl)amino]-1-N-[(1R)-1-phenylethyl]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: 578.74

Molecular Weight (Monoisotopic): 578.2563

AlogP: 3.03

#Rotatable Bonds: 13

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: 13.81

CX Basic pKa: 9.42

CX LogP: 2.40

CX LogD: 0.40

Aromatic Rings: 3

Heavy Atoms: 41

QED Weighted: 0.25

Np Likeness Score: -0.57

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]

Source

Source(1):

• Scientific Literature