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

ID: ALA2448020

PubChem CID: 73357208

Max Phase: Preclinical

Molecular Formula: C21H22Cl3N5S

Molecular Weight: 409.95

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1[nH]c2ccc(Cl)cc2c1-c1nc(NC(=N)NCc2ccccc2)sc1C.Cl.Cl

Standard InChI:  InChI=1S/C21H20ClN5S.2ClH/c1-12-18(16-10-15(22)8-9-17(16)25-12)19-13(2)28-21(26-19)27-20(23)24-11-14-6-4-3-5-7-14;;/h3-10,25H,11H2,1-2H3,(H3,23,24,26,27);2*1H

Standard InChI Key:  CMNQHVLTALKOMD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 31  0  0  0  0  0  0  0  0999 V2000
    7.7946   -2.6786    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.6382    0.6481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9729    0.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7282   -0.2925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1986    0.3900    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3973    1.4225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4528    0.6309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9022   -0.2983    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0742    1.9043    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9901   -0.6769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2158   -0.9464    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.7281    1.4052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0763   -0.2983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9976    0.0114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6518   -1.0153    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5311    1.5601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6633    0.4244    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7950    0.1663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8259   -1.0153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6116    1.6978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0645    0.9464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3398   -0.4532    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.6727   -1.1415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4129   -1.7265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8259   -2.4321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5869   -1.7208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1739   -2.4321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4129   -3.1548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5869   -3.1548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6250   -2.7857    0.0000 Cl  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  2  2  0
  7  2  1  0
  8  4  1  0
  9  6  1  0
 10  3  2  0
 11 10  1  0
 12  7  2  0
 13  8  1  0
 14  7  1  0
 15 13  1  0
 16 12  1  0
 17 13  2  0
 18 14  2  0
 19 15  1  0
 20  6  1  0
 21 18  1  0
 22 18  1  0
 23 10  1  0
 24 19  1  0
 25 24  1  0
 26 24  2  0
 27 26  1  0
 28 25  2  0
 29 27  2  0
  9 12  1  0
 11  4  1  0
 16 21  2  0
 29 28  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: 409.95

Molecular Weight (Monoisotopic): 409.1128

AlogP: 5.70

#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: 5.87

CX LogD: 5.77

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.26

Np Likeness Score: -1.30

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