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

ID: ALA536267

Max Phase: Preclinical

Molecular Formula: C14H23Cl2N3O

Molecular Weight: 247.34

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Y-27632

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

Standard InChI:  InChI=1S/C14H21N3O.2ClH/c1-10(15)11-2-4-12(5-3-11)14(18)17-13-6-8-16-9-7-13;;/h6-12H,2-5,15H2,1H3,(H,16,17,18);2*1H/t10-,11?,12?;;/m1../s1

Standard InChI Key:  IDDDVXIUIXWAGJ-DDSAHXNVSA-N

Molfile:  

     RDKit          2D

 20 19  0  0  0  0  0  0  0  0999 V2000
    8.9915   -1.5038    0.0000 Cl  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
   -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
    2.5973   -1.5031    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
    2.5951   -3.0039    0.0000 N   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
    3.8934   -5.2570    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
    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
    6.4915   -5.2571    0.0000 N   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 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6022    2.6987    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4915   -1.5038    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  2  7  1  0
  6  7  1  0
  2  8  1  0
  8  9  2  0
  8 10  1  0
 11 12  2  0
 10 13  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 11 16  1  0
 15 16  2  0
  5 17  1  0
 17 18  1  0
 17 19  1  1
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: 247.34

Molecular Weight (Monoisotopic): 247.1685

AlogP: 2.17

#Rotatable Bonds: 3

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: 10.45

CX LogP: 1.34

CX LogD: -1.41

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.86

Np Likeness Score: -1.25

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]

2. 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]

3. Fedorov O, Marsden B, Pogacic V, Rellos P, Müller S, Bullock AN, Schwaller J, Sundström M, Knapp S..  (2007)  A systematic interaction map of validated kinase inhibitors with Ser/Thr kinases.,  104  (51): [PMID:18077363] [10.1073/pnas.0708800104]

Source

Source(1):

• Scientific Literature