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

ID: ALA5273606

Max Phase: Preclinical

Molecular Formula: C17H18N4O

Molecular Weight: 294.36

Associated Items:

Names and Identifiers

Canonical SMILES:  NC(Cc1c[nH]cn1)C(=O)NCc1cccc2ccccc12

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

Standard InChI Key:  UGYGRDVZHGAERG-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   -0.4337    1.0342    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4337    0.2092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1482   -0.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8628    0.2092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5772   -0.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3600    0.0425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8519   -0.6248    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3813   -1.2784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5772   -1.0283    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1482   -1.0283    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2806   -0.2033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9952    0.2092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7097   -0.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7097   -1.0318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4262   -1.4399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1363   -1.0281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1363   -0.2027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4244    0.2090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4256    1.0290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1384    1.4399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8477    1.0316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8519    0.2096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  8  7  1  0
  9  5  1  0
  9  8  2  0
  3 10  1  0
 11  2  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 18 13  2  0
 17 18  1  0
 18 19  1  0
 20 19  2  0
 21 20  1  0
 22 21  2  0
 17 22  1  0
M  END

Alternative Forms

  1. Parent:

    ALA5273606

    ---

Associated Targets(non-human)

Nln Neurolysin, mitochondrial (179 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Topical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 294.36Molecular Weight (Monoisotopic): 294.1481AlogP: 1.75#Rotatable Bonds: 5
Polar Surface Area: 83.80Molecular Species: NEUTRALHBA: 3HBD: 3
#RO5 Violations: HBA (Lipinski): 5HBD (Lipinski): 4#RO5 Violations (Lipinski):
CX Acidic pKa: 13.08CX Basic pKa: 7.84CX LogP: 1.12CX LogD: 0.54
Aromatic Rings: 3Heavy Atoms: 22QED Weighted: 0.67Np Likeness Score: -0.63

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