1-((8-(4-tert-butylphenyl)-1,5-naphthyridin-4-yl)methyl)guanidine

ID: ALA2413358

PubChem CID: 71817835

Max Phase: Preclinical

Molecular Formula: C20H23N5

Molecular Weight: 333.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)c1ccc(-c2ccnc3c(CNC(=N)N)ccnc23)cc1

Standard InChI:  InChI=1S/C20H23N5/c1-20(2,3)15-6-4-13(5-7-15)16-9-11-23-17-14(12-25-19(21)22)8-10-24-18(16)17/h4-11H,12H2,1-3H3,(H4,21,22,25)

Standard InChI Key:  BQAPBOBYFZVYEJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   26.4895  -14.5454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4884  -15.3728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2032  -15.7856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2014  -14.1327    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.9167  -14.5418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9175  -15.3686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6328  -15.7796    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.3478  -15.3648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3431  -14.5348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6271  -14.1277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6223  -13.3078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3361  -12.8921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3321  -12.0679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6149  -11.6583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9004  -12.0791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9079  -12.9019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2051  -16.6106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4916  -17.0247    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.6095  -10.8335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3212  -10.4162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8923  -10.4257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6034  -10.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4935  -17.8497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7801  -18.2639    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.2089  -18.2606    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
 10 11  1  0
  3 17  1  0
 17 18  1  0
 14 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
 18 23  1  0
 23 24  2  0
 23 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2413358

   2-[[8-(4-Tert-butylphenyl)-1,5-naphthyridin-4-yl]methyl]guanidine

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: 333.44

Molecular Weight (Monoisotopic): 333.1953

AlogP: 3.58

#Rotatable Bonds: 3

Polar Surface Area: 87.68

Molecular Species: BASE

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 11.96

CX LogP: 3.28

CX LogD: 0.87

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.50

Np Likeness Score: -0.57

References

1. Parhi AK, Zhang Y, Saionz KW, Pradhan P, Kaul M, Trivedi K, Pilch DS, LaVoie EJ..  (2013)  Antibacterial activity of quinoxalines, quinazolines, and 1,5-naphthyridines.,  23  (17): [PMID:23891185] [10.1016/j.bmcl.2013.06.048]

Source

Source(1):

• Scientific Literature