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

ID: ALA1203483

PubChem CID: 15729239

Max Phase: Preclinical

Molecular Formula: C20H20ClN5OS

Molecular Weight: 377.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc2[nH]cc(-c3csc(NC(=N)NCc4ccccc4)n3)c2c1.Cl

Standard InChI:  InChI=1S/C20H19N5OS.ClH/c1-26-14-7-8-17-15(9-14)16(11-22-17)18-12-27-20(24-18)25-19(21)23-10-13-5-3-2-4-6-13;/h2-9,11-12,22H,10H2,1H3,(H3,21,23,24,25);1H

Standard InChI Key:  CSFAFOJWBGIBRK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   15.2979    3.0999    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.6251    2.6919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6187    1.4919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028   -1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138   -1.2033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5889    0.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138    1.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1749    2.6315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3751    3.8801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3406    5.0280    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.7308    4.4644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0039    5.2543    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3272    4.5462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3656    3.3468    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6026    5.3373    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9259    4.6293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2012    5.4204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5249    4.7147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7979    5.5080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7474    7.0071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4238    7.7130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1508    6.9196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6243    2.9682    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028    1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 14 26  2  0
 26 11  1  0
 10 27  1  0
 27  7  1  0
 27 28  2  0
 28  4  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: 377.47

Molecular Weight (Monoisotopic): 377.1310

AlogP: 4.44

#Rotatable Bonds: 5

Polar Surface Area: 85.82

Molecular Species: NEUTRAL

HBA: 4

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.91

CX LogP: 4.27

CX LogD: 4.14

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.31

Np Likeness Score: -1.08

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