4-((R)-1-Amino-nonyl)-cyclohexanecarboxylic acid pyridin-4-ylamide dihydrochloride

ID: ALA537850

PubChem CID: 45263217

Max Phase: Preclinical

Molecular Formula: C21H37Cl2N3O

Molecular Weight: 345.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCC[C@@H](N)C1CCC(C(=O)Nc2ccncc2)CC1.Cl.Cl

Standard InChI:  InChI=1S/C21H35N3O.2ClH/c1-2-3-4-5-6-7-8-20(22)17-9-11-18(12-10-17)21(25)24-19-13-15-23-16-14-19;;/h13-18,20H,2-12,22H2,1H3,(H,23,24,25);2*1H/t17?,18?,20-;;/m1../s1

Standard InChI Key:  PUTXOPSXBZOGGG-IVWVRKPFSA-N

Molfile:  

     RDKit          2D

 27 26  0  0  0  0  0  0  0  0999 V2000
    8.9915    2.2447    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951   -3.0039    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6375   -0.9049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4915   -5.2571    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8933   -3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5998    1.4987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6380    0.8969    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8934   -5.2570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1925   -3.0070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4915   -3.7571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1924   -6.0070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6028    2.9995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9036    3.7481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5141    9.7479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5111    8.2471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2103    7.4984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9066    5.2489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2073    5.9976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5541   10.3465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4915    2.2447    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  2  4  1  0
  2  5  2  0
  4  8  1  0
  4  9  1  0
  7 10  1  0
  8 10  1  0
  7 11  1  0
  9 11  1  0
  3 12  1  0
  7 13  1  0
 13 14  1  6
 12 15  1  0
 12 16  2  0
  6 17  2  0
 16 17  1  0
  6 18  1  0
 15 18  2  0
 13 19  1  0
 19 20  1  0
 21 22  1  0
 22 23  1  0
 20 24  1  0
 23 25  1  0
 24 25  1  0
 21 26  1  0
M  END

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: 345.53

Molecular Weight (Monoisotopic): 345.2780

AlogP: 4.90

#Rotatable Bonds: 10

Polar Surface Area: 68.01

Molecular Species: BASE

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.44

CX Basic pKa: 10.49

CX LogP: 4.53

CX LogD: 1.77

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.59

Np Likeness Score: -0.74

References

1. Gingras K, Avedissian H, Thouin E, Boulanger V, Essagian C, McKerracher L, Lubell WD..  (2004)  Synthesis and evaluation of 4-(1-aminoalkyl)-N-(4-pyridyl)cyclohexanecarboxamides as Rho kinase inhibitors and neurite outgrowth promoters.,  14  (19): [PMID:15341954] [10.1016/j.bmcl.2004.07.025]

Source

Source(1):

• Scientific Literature