amino(4-(5-(6-(amino(iminio)methyl)-1H-benzo[d]imidazol-2-yl)thiophen-2-yl)phenyl)methaniminium

ID: ALA1232046

Cas Number: 790241-43-9

PubChem CID: 449090

Max Phase: Preclinical

Molecular Formula: C19H16N6S

Molecular Weight: 360.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N=C(N)c1ccc(-c2ccc(-c3nc4ccc(C(=N)N)cc4[nH]3)s2)cc1

Standard InChI:  InChI=1S/C19H16N6S/c20-17(21)11-3-1-10(2-4-11)15-7-8-16(26-15)19-24-13-6-5-12(18(22)23)9-14(13)25-19/h1-9H,(H3,20,21)(H3,22,23)(H,24,25)

Standard InChI Key:  MSQVFIHMHRAMOC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   -1.3230   -0.3126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5384   -0.0577    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0534   -0.7251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5384   -1.3925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3230   -1.1376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7716   -0.7251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2565   -1.3925    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0411   -1.1376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0411   -0.3126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2565   -0.0577    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7556   -1.5501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4701   -1.1376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4701   -0.3126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7556    0.0999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9904    0.1723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7441   -0.1632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4115    0.3217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3253    1.1422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5716    1.4777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9042    0.9928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1845    0.0999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8990   -0.3126    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1845    0.9249    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9927    1.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7464    1.2915    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9065    2.4476    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  5  2  0
  1 15  1  0
  3  2  1  0
  3  4  2  0
  3  6  1  0
  4  5  1  0
  6  7  2  0
  6 10  1  0
  8  7  1  0
  8  9  2  0
 11  8  1  0
  9 10  1  0
 14  9  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 21  1  0
 15 16  1  0
 15 20  2  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 24  1  0
 19 20  1  0
 21 22  1  0
 21 23  2  0
 24 25  2  0
 24 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1232046

   2-(5-{4-[Amino(imino)methyl]phenyl}-2-thienyl)-1H-benzimidazole-6-carboximidamide dihydrochloride

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: 360.45

Molecular Weight (Monoisotopic): 360.1157

AlogP: 3.53

#Rotatable Bonds: 4

Polar Surface Area: 128.42

Molecular Species: BASE

HBA: 4

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.79

CX Basic pKa: 11.62

CX LogP: 1.01

CX LogD: -2.24

Aromatic Rings: 4

Heavy Atoms: 26

QED Weighted: 0.28

Np Likeness Score: -0.70

References

1. Berger ML, Maciejewska D, Vanden Eynde JJ, Mottamal M, Żabiński J, Kaźmierczak P, Rezler M, Jarak I, Piantanida I, Karminski-Zamola G, Mayence A, Rebernik P, Kumar A, Ismail MA, Boykin DW, Huang TL..  (2015)  Pentamidine analogs as inhibitors of [(3)H]MK-801 and [(3)H]ifenprodil binding to rat brain NMDA receptors.,  23  (15): [PMID:26117647] [10.1016/j.bmc.2015.06.012]

2. Depauw S, Lambert M, Jambon S, Paul A, Peixoto P, Nhili R, Marongiu L, Figeac M, Dassi C, Paul-Constant C, Billoré B, Kumar A, Farahat AA, Ismail MA, Mineva E, Sweat DP, Stephens CE, Boykin DW, Wilson WD, David-Cordonnier MH..  (2019)  Heterocyclic Diamidine DNA Ligands as HOXA9 Transcription Factor Inhibitors: Design, Molecular Evaluation, and Cellular Consequences in a HOXA9-Dependant Leukemia Cell Model.,  62  (3.0): [PMID:30645099] [10.1021/acs.jmedchem.8b01448]

3. Ogbonna EN, Paul A, Ross Terrell J, Fang Z, Chen C, Poon GMK, Boykin DW, Wilson WD..  (2022)  Drug design and DNA structural research inspired by the Neidle laboratory: DNA minor groove binding and transcription factor inhibition by thiophene diamidines.,  68  [PMID:35661929] [10.1016/j.bmc.2022.116861]

Source

Source(1):

• Scientific Literature