(R)-N-(2-(1H-indol-2-yl)ethyl)-2-amino-3-(1H-imidazol-4-yl)propanamide

ID: ALA5070123

PubChem CID: 146440140

Max Phase: Preclinical

Molecular Formula: C16H19N5O

Molecular Weight: 297.36

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  N[C@H](Cc1c[nH]cn1)C(=O)NCCc1cc2ccccc2[nH]1

Standard InChI:  InChI=1S/C16H19N5O/c17-14(8-13-9-18-10-20-13)16(22)19-6-5-12-7-11-3-1-2-4-15(11)21-12/h1-4,7,9-10,14,21H,5-6,8,17H2,(H,18,20)(H,19,22)/t14-/m1/s1

Standard InChI Key:  VQEYOZLBJIZNCZ-CQSZACIVSA-N

Molfile:  

 
     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
    4.0026    0.1274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1776    0.1274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6278   -0.4830    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8773   -0.1488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9632    0.6681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7668    0.8388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1767    1.5481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9985    1.5481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4087    0.8411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1655   -0.5598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4537   -0.1488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2580   -0.5598    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9707   -0.1484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9707    0.6745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6832   -0.5597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3954   -0.1485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1077   -0.5597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8586   -0.2253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4087   -0.8363    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9977   -1.5481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1936   -1.3772    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6832   -1.3822    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  1  0
  3  4  1  0
  5  4  2  0
  5  6  1  0
  6  2  2  0
  6  7  1  0
  8  7  2  0
  9  8  1  0
  1  9  2  0
 10  4  1  0
 11 10  1  0
 12 11  1  0
 13 12  1  0
 13 14  2  0
 15 13  1  0
 15 16  1  0
 16 17  1  0
 18 17  2  0
 19 18  1  0
 20 19  1  0
 21 20  2  0
 21 17  1  0
 15 22  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA5070123

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 297.36

Molecular Weight (Monoisotopic): 297.1590

AlogP: 1.12

#Rotatable Bonds: 6

Polar Surface Area: 99.59

Molecular Species: NEUTRAL

HBA: 3

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.09

CX Basic pKa: 7.84

CX LogP: 0.21

CX LogD: -0.37

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.55

Np Likeness Score: -0.44

References

1.  (2020)  Enhancers of neurolysin activity, 

2. 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(2):

• Scientific Literature
• Patent Bioactivity Data