4-((S)-1-Amino-butyl)-cyclohexanecarboxylic acid pyridin-4-ylamide dihydrochloride

ID: ALA556558

PubChem CID: 45263186

Max Phase: Preclinical

Molecular Formula: C16H27Cl2N3O

Molecular Weight: 275.40

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C16H25N3O.2ClH/c1-2-3-15(17)12-4-6-13(7-5-12)16(20)19-14-8-10-18-11-9-14;;/h8-13,15H,2-7,17H2,1H3,(H,18,19,20);2*1H/t12?,13?,15-;;/m0../s1

Standard InChI Key:  ZVNDRDPVMVXNGZ-BTAMWQLWSA-N

Molfile:  

     RDKit          2D

 22 21  0  0  0  0  0  0  0  0999 V2000
    8.9915   -0.3791    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
   -3.9060    4.9481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4915   -0.3791    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  1
 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
 20 21  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: 275.40

Molecular Weight (Monoisotopic): 275.1998

AlogP: 2.95

#Rotatable Bonds: 5

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: 2.31

CX LogD: -0.46

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.87

Np Likeness Score: -1.10

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