2-({5-[(Z)-amino(imino)methyl]-1H-benzimidazol-2-yl}methyl)-1H-benzimidazole-5-carboximidamide hydrochloride

ID: ALA542712

PubChem CID: 45261811

Max Phase: Preclinical

Molecular Formula: C17H17ClN8

Molecular Weight: 332.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cl.N=C(N)c1ccc2[nH]c(Cc3nc4cc(C(=N)N)ccc4[nH]3)nc2c1

Standard InChI:  InChI=1S/C17H16N8.ClH/c18-16(19)8-1-3-10-12(5-8)24-14(22-10)7-15-23-11-4-2-9(17(20)21)6-13(11)25-15;/h1-6H,7H2,(H3,18,19)(H3,20,21)(H,22,24)(H,23,25);1H

Standard InChI Key:  DAYQQTRNIVUDTR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    0.5542   -5.3917    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.4917   -1.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2542   -0.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7667   -1.0875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1250   -1.8667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3125   -1.2542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7667    0.2500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9875   -0.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7042   -2.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0792   -0.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9875   -0.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4417   -2.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1583   -1.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3167   -4.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4458   -0.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3542   -3.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2667   -1.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6667   -3.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1583   -2.0750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5875   -4.9292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1375   -2.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2667    0.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4458   -0.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0917   -3.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0125   -4.9917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8708   -0.8375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  3 10  1  0
  4  3  2  0
  5  2  2  0
  6  2  1  0
  7  3  1  0
  8  4  1  0
  9  5  1  0
 10  2  1  0
 11  7  1  0
 12  6  1  0
 13 15  1  0
 14 16  1  0
 15 17  1  0
 16 18  1  0
 17  8  2  0
 18  9  2  0
 19 13  2  0
 20 14  2  0
 21 12  2  0
 22 11  2  0
 23 22  1  0
 24 21  1  0
 25 14  1  0
 26 13  1  0
 12  9  1  0
 11  8  1  0
 24 16  2  0
 23 15  2  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: 332.37

Molecular Weight (Monoisotopic): 332.1498

AlogP: 1.60

#Rotatable Bonds: 4

Polar Surface Area: 157.10

Molecular Species: BASE

HBA: 4

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.94

CX Basic pKa: 11.30

CX LogP: -0.22

CX LogD: -4.06

Aromatic Rings: 4

Heavy Atoms: 25

QED Weighted: 0.25

Np Likeness Score: -0.63

References

1. Costanzo MJ, Yabut SC, Almond HR, Andrade-Gordon P, Corcoran TW, De Garavilla L, Kauffman JA, Abraham WM, Recacha R, Chattopadhyay D, Maryanoff BE..  (2003)  Potent, small-molecule inhibitors of human mast cell tryptase. Antiasthmatic action of a dipeptide-based transition-state analogue containing a benzothiazole ketone.,  46  (18): [PMID:12930148] [10.1021/jm030050p]

Source

Source(1):

• Scientific Literature