N-Benzyl-N'-[4-(1H-pyrrol-2-yl)-thiazol-2-yl]-guanidine: (0.5 maleate)

ID: ALA1744210

PubChem CID: 15729216

Max Phase: Preclinical

Molecular Formula: C19H19N5O4S

Molecular Weight: 297.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N=C(NCc1ccccc1)Nc1nc(-c2ccc[nH]2)cs1.O=C(O)/C=C\C(=O)O

Standard InChI:  InChI=1S/C15H15N5S.C4H4O4/c16-14(18-9-11-5-2-1-3-6-11)20-15-19-13(10-21-15)12-7-4-8-17-12;5-3(6)1-2-4(7)8/h1-8,10,17H,9H2,(H3,16,18,19,20);1-2H,(H,5,6)(H,7,8)/b;2-1-

Standard InChI Key:  UKPDFPRCQQQMRB-BTJKTKAUSA-N

Molfile:  

     RDKit          2D

 29 30  0  0  0  0  0  0  0  0999 V2000
    7.1620  -21.8079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6318  -21.1376    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4052  -21.3783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3370  -21.8251    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5120  -21.8251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6490  -22.4611    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.0698  -20.8798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4224  -22.1975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3334  -20.1064    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0881  -22.5298    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7287  -21.3783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1584  -20.1236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3990  -20.9084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0995  -21.1033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2631  -22.5298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8506  -23.2345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0256  -23.2345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2631  -23.9564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8506  -24.6725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6131  -23.9564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0256  -24.6725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8045  -18.0543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6295  -18.0543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3920  -18.7687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0420  -18.7687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8670  -18.7687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6295  -19.4832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5670  -18.7687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8045  -19.4832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  1  1  0
  5  4  1  0
  6  1  1  0
  7  3  1  0
  8  6  1  0
  9  7  1  0
 10  5  1  0
 11  7  2  0
 12  9  1  0
 13 11  1  0
 14  5  2  0
 15 10  1  0
 16 15  1  0
 17 16  2  0
 18 16  1  0
 19 18  2  0
 20 17  1  0
 21 19  1  0
  3  8  2  0
 12 13  2  0
 21 20  2  0
 22 23  2  0
 22 24  1  0
 23 25  1  0
 25 26  2  0
 25 27  1  0
 24 28  1  0
 24 29  2  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: 297.39

Molecular Weight (Monoisotopic): 297.1048

AlogP: 3.27

#Rotatable Bonds: 4

Polar Surface Area: 76.59

Molecular Species: NEUTRAL

HBA: 3

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.83

CX LogP: 3.33

CX LogD: 2.76

Aromatic Rings: 3

Heavy Atoms: 21

QED Weighted: 0.44

Np Likeness Score: -1.39

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