(R)-2-amino-3-(1H-imidazol-4-yl)-N-(naphthalen-2-ylmethyl)propanamide

ID: ALA5280409

Max Phase: Preclinical

Molecular Formula: C17H18N4O

Molecular Weight: 294.36

Names and Identifiers

Canonical SMILES:  N[C@H](Cc1c[nH]cn1)C(=O)NCc1ccc2ccccc2c1

Standard InChI:  InChI=1S/C17H18N4O/c18-16(8-15-10-19-11-21-15)17(22)20-9-12-5-6-13-3-1-2-4-14(13)7-12/h1-7,10-11,16H,8-9,18H2,(H,19,21)(H,20,22)/t16-/m1/s1

Standard InChI Key:  PLHYVMRZZZJNDB-MRXNPFEDSA-N

Molfile:  

 
     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   -3.6628   -1.0526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8751   -0.8076    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8751    0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1749    0.4049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4749    0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4749   -0.8076    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7748    0.4049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0746    0.0007    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6254    0.4049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3254    0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7748    1.2133    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6420    0.2416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1241   -0.4123    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0257    0.4047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7234    0.0011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7234   -0.8075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0275   -1.2110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3254   -0.8110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4218    0.4038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1223   -0.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1241   -0.8048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4267   -1.2133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  2  3  1  0
  4  3  1  0
  5  4  1  0
  5  6  1  6
  7  5  1  0
  8  7  1  0
  8  9  1  0
  9 10  1  0
  7 11  2  0
  3 12  2  0
  1 13  1  0
 12 13  1  0
 14 10  2  0
 15 14  1  0
 16 15  2  0
 17 16  1  0
 18 17  2  0
 10 18  1  0
 15 19  1  0
 20 19  2  0
 21 20  1  0
 22 21  2  0
 16 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5280409

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 294.36

Molecular Weight (Monoisotopic): 294.1481

AlogP: 1.75

#Rotatable Bonds: 5

Polar Surface Area: 83.80

Molecular Species: NEUTRAL

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.09

CX Basic pKa: 7.84

CX LogP: 1.12

CX LogD: 0.54

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.67

Np Likeness Score: -0.51

References

1. Rahman MS, Kumari S, Esfahani SH, Nozohouri S, Jayaraman S, Kinarivala N, Kocot J, Baez A, Farris D, Abbruscato TJ, Karamyan VT, Trippier PC..  (2021)  Discovery of First-in-Class Peptidomimetic Neurolysin Activators Possessing Enhanced Brain Penetration and Stability.,  64  (17.0): [PMID:34436882] [10.1021/acs.jmedchem.1c00759]

Source

Source(1):

• Scientific Literature