5-(2-Guanidino-thiazol-4-yl)-2-methyl-1H-pyrrole-3-carboxylic acid dimethylamide: (maleate)

ID: ALA1744204

PubChem CID: 54587000

Max Phase: Preclinical

Molecular Formula: C16H20N6O5S

Molecular Weight: 292.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1[nH]c(-c2csc(N=C(N)N)n2)cc1C(=O)N(C)C.O=C(O)/C=C\C(=O)O

Standard InChI:  InChI=1S/C12H16N6OS.C4H4O4/c1-6-7(10(19)18(2)3)4-8(15-6)9-5-20-12(16-9)17-11(13)14;5-3(6)1-2-4(7)8/h4-5,15H,1-3H3,(H4,13,14,16,17);1-2H,(H,5,6)(H,7,8)/b;2-1-

Standard InChI Key:  LWAOPCYYVMCALL-BTJKTKAUSA-N

Molfile:  

     RDKit          2D

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    8.9419  -21.9737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6031  -21.9450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2582  -22.4449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6897  -22.8758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9423  -22.4449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1552  -22.2036    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7234  -22.2380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7006  -21.1865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8732  -21.1693    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8623  -22.8931    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1724  -23.5309    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.0349  -22.8931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9595  -23.2665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8785  -23.0482    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3440  -21.7037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6154  -23.5998    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6212  -22.1691    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2005  -20.5257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6657  -23.3240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2580  -23.5998    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  3  2  0
  3  1  1  0
  4  6  2  0
  5  2  1  0
  6  5  1  0
  7  1  1  0
  8  1  2  0
  9  8  1  0
 10  4  1  0
 11 13  1  0
 12 10  2  3
 13  5  2  0
 14  7  1  0
 15  7  2  0
 16 12  1  0
 17 12  1  0
 18  8  1  0
 19 14  1  0
 20 14  1  0
  2  9  1  0
 11  4  1  0
 21 22  2  0
 21 23  1  0
 22 24  1  0
 24 25  2  0
 24 26  1  0
 23 27  1  0
 23 28  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: 292.37

Molecular Weight (Monoisotopic): 292.1106

AlogP: 1.05

#Rotatable Bonds: 3

Polar Surface Area: 113.39

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.04

CX Basic pKa: 7.31

CX LogP: 0.45

CX LogD: 0.20

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.58

Np Likeness Score: -1.56

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