2-(3-(5-carbamimidoylpyridin-2-yl)phenyl)-1H-benzo[d]imidazole-6-carboximidamide

ID: ALA1650570

PubChem CID: 11221987

Max Phase: Preclinical

Molecular Formula: C20H17N7

Molecular Weight: 355.41

Molecule Type: Small molecule

Names and Identifiers

Synonyms: DB853 | SCHEMBL5395887|CHEMBL1650570|DB853

Canonical SMILES:  N=C(N)c1ccc(-c2cccc(-c3nc4ccc(C(=N)N)cc4[nH]3)c2)nc1

Standard InChI:  InChI=1S/C20H17N7/c21-18(22)12-4-7-16-17(9-12)27-20(26-16)13-3-1-2-11(8-13)15-6-5-14(10-25-15)19(23)24/h1-10H,(H3,21,22)(H3,23,24)(H,26,27)

Standard InChI Key:  AIBDUBLHZYMOJS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   -3.7770   -9.2844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7782  -10.1147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0630  -10.5290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3412  -10.1143    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3444   -9.2804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0649   -8.8702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4957  -10.5276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2120  -10.1127    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4969  -11.3553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7172   -8.8696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0023   -9.2838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2884   -8.8676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2918   -8.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0149   -7.6296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7259   -8.0481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4230   -9.2798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5123  -10.0973    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1792   -8.9461    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7286   -9.5579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3146  -10.2654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7201  -10.9756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5396  -10.9795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9518  -10.2674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5438   -9.5600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9514  -11.6976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5353  -12.4132    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7791  -11.7000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
 13 14  1  0
  2  7  1  0
 14 15  2  0
 15 10  1  0
  3  4  2  0
 12 16  1  0
 16 17  1  0
  7  8  2  0
 17 20  1  0
 19 18  1  0
 18 16  2  0
  7  9  1  0
  4  5  1  0
 19 20  2  0
  5 10  1  0
 20 21  1  0
  2  3  1  0
 21 22  2  0
 10 11  2  0
 22 23  1  0
  5  6  2  0
 23 24  2  0
 24 19  1  0
 11 12  1  0
 22 25  1  0
  6  1  1  0
 25 26  1  0
 12 13  2  0
 25 27  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1650570

   2-[3-(5-carbamimidoylpyridin-2-yl)phenyl]-3H-benzimidazole-5-carboximidamide

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: 355.41

Molecular Weight (Monoisotopic): 355.1545

AlogP: 2.86

#Rotatable Bonds: 4

Polar Surface Area: 141.31

Molecular Species: BASE

HBA: 4

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.65

CX Basic pKa: 11.53

CX LogP: 1.15

CX LogD: -2.74

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.28

Np Likeness Score: -1.00

References

1. Gillingwater K, Kumar A, Anbazhagan M, Boykin DW, Tidwell RR, Brun R..  (2009)  In vivo investigations of selected diamidine compounds against Trypanosoma evansi using a mouse model.,  53  (12): [PMID:19786604] [10.1128/aac.00422-09]

Source

Source(1):

• Scientific Literature