N-(9-Butyl-[1,10]phenanthrolin-2-yl)-benzamide hydrochloride

ID: ALA1202424

PubChem CID: 14896605

Max Phase: Preclinical

Molecular Formula: C23H22ClN3O

Molecular Weight: 355.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCc1ccc2ccc3ccc(NC(=O)c4ccccc4)nc3c2n1.Cl

Standard InChI:  InChI=1S/C23H21N3O.ClH/c1-2-3-9-19-14-12-16-10-11-17-13-15-20(25-22(17)21(16)24-19)26-23(27)18-7-5-4-6-8-18;/h4-8,10-15H,2-3,9H2,1H3,(H,25,26,27);1H

Standard InChI Key:  TXEZURFDBBSCJI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    5.5631    3.6993    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.8908    4.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9291    3.0839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6544    2.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7022    0.7916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4277    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4277   -1.5498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1332   -2.2973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8205   -1.5498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4558   -2.2973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7503   -1.5498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7503    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0631    0.6928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0631    2.1879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7503    2.9537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7385    4.4541    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4333    5.1950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6013    4.5871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4214    6.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8820    7.4382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8909    8.9382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4037    9.6959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7072    8.9535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7160    7.4536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4558    2.1879    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4558    0.6928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8205    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1332    0.6928    0.0000 N   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
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 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
 15 25  1  0
 25 26  2  0
 26 12  1  0
 26 27  1  0
 27  9  1  0
 27 28  2  0
 28  6  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: 355.44

Molecular Weight (Monoisotopic): 355.1685

AlogP: 5.38

#Rotatable Bonds: 5

Polar Surface Area: 54.88

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 4.89

CX LogP: 5.70

CX LogD: 5.69

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.49

Np Likeness Score: -0.84

References

1. de Zwart MA, Bastiaans HM, van der Goot H, Timmerman H..  (1991)  Synthesis and copper-dependent antimycoplasmal activity of amides and amidines derived from 2-amino-1,10-phenanthroline.,  34  (3): [PMID:2002460] [10.1021/jm00107a045]

Source

Source(1):

• Scientific Literature