N-Benzyl-N'-[4-(5-chloro-1H-indol-3-yl)-thiazol-2-yl]-guanidine: hydrochloride

ID: ALA2448017

PubChem CID: 73348089

Max Phase: Preclinical

Molecular Formula: C19H17Cl2N5S

Molecular Weight: 381.89

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cl.N=C(NCc1ccccc1)Nc1nc(-c2c[nH]c3ccc(Cl)cc23)cs1

Standard InChI:  InChI=1S/C19H16ClN5S.ClH/c20-13-6-7-16-14(8-13)15(10-22-16)17-11-26-19(24-17)25-18(21)23-9-12-4-2-1-3-5-12;/h1-8,10-11,22H,9H2,(H3,21,23,24,25);1H

Standard InChI Key:  DKDZUTVICLYNCA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    6.6696   -2.1964    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.6511    0.6491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9848    0.1493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7382   -0.2930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2093    0.3906    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9110   -0.2988    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4668    0.6318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4098    1.4246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0877    1.9071    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0838   -0.2988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2265   -0.9478    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.0020   -0.6779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7425    1.4073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6588   -1.0168    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0125    0.0114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5467    1.5624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6702    0.4250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8110    0.1665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8316   -1.0168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0809    0.9478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3567   -0.4539    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.4180   -1.7291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8316   -2.4357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5908   -1.7233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1772   -2.4357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4180   -3.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5908   -3.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  4  5  2  0
  5  3  1  0
  6  4  1  0
  7  2  1  0
  8  2  2  0
  9  8  1  0
 10  6  1  0
 11 12  1  0
 12  3  2  0
 13  7  2  0
 14 10  1  0
 15  7  1  0
 16 13  1  0
 17 10  2  0
 18 15  2  0
 19 14  1  0
 20 18  1  0
 21 18  1  0
 22 19  1  0
 23 22  1  0
 24 22  2  0
 25 24  1  0
 26 23  2  0
 27 25  2  0
  9 13  1  0
 11  4  1  0
 16 20  2  0
 27 26  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: 381.89

Molecular Weight (Monoisotopic): 381.0815

AlogP: 5.08

#Rotatable Bonds: 4

Polar Surface Area: 76.59

Molecular Species: NEUTRAL

HBA: 3

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 6.85

CX LogP: 5.03

CX LogD: 4.92

Aromatic Rings: 4

Heavy Atoms: 26

QED Weighted: 0.29

Np Likeness Score: -1.35

References

1. LaMattina JL, McCarthy PA, Reiter LA, Holt WF, Yeh LA..  (1990)  Antiulcer agents. 4-substituted 2-guanidinothiazoles: reversible, competitive, and selective inhibitors of gastric H+,K(+)-ATPase.,  33  (2): [PMID:2153817] [10.1021/jm00164a012]

Source

Source(1):

• Scientific Literature