N-[4-(5-Piperidin-1-ylmethyl-1H-pyrrol-3-yl)-thiazol-2-yl]-guanidine: (maleate)

ID: ALA1744205

PubChem CID: 54583113

Max Phase: Preclinical

Molecular Formula: C18H24N6O4S

Molecular Weight: 304.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N=C(N)Nc1nc(-c2c[nH]c(CN3CCCCC3)c2)cs1.O=C(O)/C=C\C(=O)O

Standard InChI:  InChI=1S/C14H20N6S.C4H4O4/c15-13(16)19-14-18-12(9-21-14)10-6-11(17-7-10)8-20-4-2-1-3-5-20;5-3(6)1-2-4(7)8/h6-7,9,17H,1-5,8H2,(H4,15,16,18,19);1-2H,(H,5,6)(H,7,8)/b;2-1-

Standard InChI Key:  FWKCHAMKLTXDNK-BTJKTKAUSA-N

Molfile:  

     RDKit          2D

 29 30  0  0  0  0  0  0  0  0999 V2000
    5.5459  -22.6661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0217  -21.9952    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4552  -21.7372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7202  -22.6833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8016  -22.2360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0447  -23.3197    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.8946  -22.6833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2637  -21.9034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3692  -20.9115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1203  -20.5789    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6765  -21.1868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8188  -23.0559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9838  -21.7544    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4964  -21.0950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4817  -21.9608    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4817  -23.3885    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6512  -22.5113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8037  -21.6626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2911  -22.3335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1386  -23.1763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9585  -23.0789    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  1  1  0
  7  4  1  0
  8  3  1  0
  9  3  2  0
 10  9  1  0
 11  8  2  0
 12  6  1  0
 13 14  1  0
 14 11  1  0
 15  7  2  0
 16  7  1  0
 17 13  1  0
 18 13  1  0
 19 18  1  0
 20 17  1  0
 21 19  1  0
  5 12  2  0
 10 11  1  0
 21 20  1  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: 304.42

Molecular Weight (Monoisotopic): 304.1470

AlogP: 2.43

#Rotatable Bonds: 4

Polar Surface Area: 93.82

Molecular Species: NEUTRAL

HBA: 4

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.43

CX LogP: 2.12

CX LogD: 0.74

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.52

Np Likeness Score: -1.76

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