1-(adamantan-1-ylmethyl)-2-cyano-3-(pyridin-3-ylmethyl)guanidine

ID: ALA4088143

PubChem CID: 137644636

Max Phase: Preclinical

Molecular Formula: C19H25N5

Molecular Weight: 323.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#C/N=C(/NCc1cccnc1)NCC12CC3CC(CC(C3)C1)C2

Standard InChI:  InChI=1S/C19H25N5/c20-13-24-18(22-11-14-2-1-3-21-10-14)23-12-19-7-15-4-16(8-19)6-17(5-15)9-19/h1-3,10,15-17H,4-9,11-12H2,(H2,22,23,24)

Standard InChI Key:  LHCHSXKJJHJESK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
    7.9020   -8.8898    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6186   -8.4727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7414   -4.3338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1402   -4.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5064   -4.2867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7891   -4.7657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1964   -6.0859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5560   -5.5866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7199   -5.5806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5258   -5.1002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1375   -5.5496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9082   -5.5779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6251   -5.9872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7706   -7.2185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3393   -7.2257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3393   -8.0598    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0529   -6.8117    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6254   -6.8122    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4825   -6.7999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1976   -7.2098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9089   -6.7918    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9029   -5.9652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1794   -5.5583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4710   -5.9785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 15 16  2  0
 16  2  1  0
 15 17  1  0
 15 18  1  0
 14 17  1  0
 18 13  1  0
 13 12  1  0
 11 12  1  0
  7 12  1  0
 12  4  1  0
 10 11  1  0
  9 10  1  0
 10  3  1  0
  9  8  1  0
  8  7  1  0
  8  6  1  0
  6  5  1  0
  4  5  1  0
  5  3  1  0
  2  1  3  0
 14 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4088143

   ---

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: 323.44

Molecular Weight (Monoisotopic): 323.2110

AlogP: 2.81

#Rotatable Bonds: 4

Polar Surface Area: 73.10

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.82

CX LogP: 2.46

CX LogD: 2.46

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.51

Np Likeness Score: -1.03

References

1. O'Brien-Brown J, Jackson A, Reekie TA, Barron ML, Werry EL, Schiavini P, McDonnell M, Munoz L, Wilkinson S, Noll B, Wang S, Kassiou M..  (2017)  Discovery and pharmacological evaluation of a novel series of adamantyl cyanoguanidines as P2X7 receptor antagonists.,  130  [PMID:28279849] [10.1016/j.ejmech.2017.02.060]

Source

Source(1):

• Scientific Literature