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

ID: ALA1744201

PubChem CID: 15729222

Max Phase: Preclinical

Molecular Formula: C16H22N6O4S

Molecular Weight: 278.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1[nH]c(-c2csc(N=C(N)N)n2)cc1CN(C)C.O=C(O)/C=C\C(=O)O

Standard InChI:  InChI=1S/C12H18N6S.C4H4O4/c1-7-8(5-18(2)3)4-9(15-7)10-6-19-12(16-10)17-11(13)14;5-3(6)1-2-4(7)8/h4,6,15H,5H2,1-3H3,(H4,13,14,16,17);1-2H,(H,5,6)(H,7,8)/b;2-1-

Standard InChI Key:  SENWZCWJYVKOQJ-BTJKTKAUSA-N

Molfile:  

     RDKit          2D

 27 27  0  0  0  0  0  0  0  0999 V2000
    5.9318  -23.0722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8452  -22.1413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1843  -22.6412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3972  -22.3999    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1839  -22.1700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1152  -21.3656    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1043  -23.0894    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5002  -22.6412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9426  -21.3829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4144  -23.7272    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.2769  -23.0894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2016  -23.4629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9654  -22.4344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8574  -23.7962    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8632  -22.3654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1206  -23.2446    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4425  -20.7220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9077  -23.5204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5000  -23.7962    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  1  0
  3  4  1  0
  4  1  2  0
  5  8  1  0
  6  2  1  0
  7  1  1  0
  8  2  2  0
  9  6  1  0
 10  1  1  0
 11  7  2  3
 12 10  1  0
 13  5  1  0
 14 11  1  0
 15 11  1  0
 16 13  1  0
 17  9  1  0
 18 16  1  0
 19 16  1  0
  3 12  2  0
  9  5  2  0
 20 21  2  0
 20 22  1  0
 21 23  1  0
 23 24  2  0
 23 25  1  0
 22 26  1  0
 22 27  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: 278.38

Molecular Weight (Monoisotopic): 278.1314

AlogP: 1.41

#Rotatable Bonds: 4

Polar Surface Area: 96.32

Molecular Species: BASE

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.65

CX LogP: 1.10

CX LogD: -0.61

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.58

Np Likeness Score: -1.40

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