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

ID: ALA1202267

PubChem CID: 44367655

Max Phase: Preclinical

Molecular Formula: C19H17BrClN5S

Molecular Weight: 381.89

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Br.N=C(NCc1ccccc1)Nc1nc(-c2cc3cc(Cl)ccc3[nH]2)cs1

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

Standard InChI Key:  SGQXCGCHTKCADP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   14.2759   -3.8379    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -3.3560    1.3452    0.0000 Cl  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
    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
    4.0896    0.0290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0305    1.1747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4203    0.6103    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.3129   -0.8859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4569   -1.8534    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1915   -3.3306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0624   -3.7370    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3375   -4.2997    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0721   -5.7769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2180   -6.7461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9549   -8.2228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1022   -9.1891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5127   -8.6787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7759   -7.2020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6286   -6.2357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8568   -1.2462    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10  6  1  0
 10 11  2  0
 11  3  1  0
  8 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 15 27  2  0
 27 12  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: 13.63

CX Basic pKa: 6.80

CX LogP: 4.95

CX LogD: 4.85

Aromatic Rings: 4

Heavy Atoms: 26

QED Weighted: 0.29

Np Likeness Score: -1.57

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