N-Benzyl-N'-[4-(5-methyl-1H-pyrrol-3-yl)-thiazol-2-yl]-guanidine: (maleate)

ID: ALA1744197

PubChem CID: 54583069

Max Phase: Preclinical

Molecular Formula: C20H21N5O4S

Molecular Weight: 311.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(-c2csc(NC(=N)NCc3ccccc3)n2)c[nH]1.O=C(O)/C=C\C(=O)O

Standard InChI:  InChI=1S/C16H17N5S.C4H4O4/c1-11-7-13(9-18-11)14-10-22-16(20-14)21-15(17)19-8-12-5-3-2-4-6-12;5-3(6)1-2-4(7)8/h2-7,9-10,18H,8H2,1H3,(H3,17,19,20,21);1-2H,(H,5,6)(H,7,8)/b;2-1-

Standard InChI Key:  UFZNNFOQPHHFFN-BTJKTKAUSA-N

Molfile:  

     RDKit          2D

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    7.8065  -21.3436    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2431  -21.0860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5130  -22.0304    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5792  -21.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6888  -22.0304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8237  -22.6771    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.0501  -21.2577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1458  -20.2732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5964  -22.4082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9013  -19.9356    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4508  -20.5366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2653  -22.7458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2767  -21.3092    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4411  -22.7344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0290  -23.4555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2749  -20.4507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2048  -23.4498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4411  -24.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0290  -24.8749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7927  -24.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1990  -24.8749    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  5  1  0
  4  1  1  0
  5  2  1  0
  6  4  1  0
  7  1  1  0
  8  3  1  0
  9  3  2  0
 10  7  1  0
 11  9  1  0
 12  8  2  0
 13  6  1  0
 14  6  2  0
 15 13  1  0
 16 15  1  0
 17 12  1  0
 18 16  2  0
 19 16  1  0
 20 19  2  0
 21 18  1  0
 22 20  1  0
  5 10  2  0
 11 12  1  0
 22 21  2  0
 23 24  2  0
 23 25  1  0
 24 26  1  0
 26 27  2  0
 26 28  1  0
 25 29  1  0
 25 30  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: 311.41

Molecular Weight (Monoisotopic): 311.1205

AlogP: 3.58

#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: 7.66

CX LogP: 3.60

CX LogD: 3.16

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.44

Np Likeness Score: -1.46

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