2-Guanidino-thiazole-4-carboxylic acid (6-tert-butyl-benzothiazol-2-yl)-amide hydrochloride

ID: ALA538237

PubChem CID: 45264315

Max Phase: Preclinical

Molecular Formula: C16H19ClN6OS2

Molecular Weight: 374.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)c1ccc2nc(NC(=O)c3csc(N=C(N)N)n3)sc2c1.Cl

Standard InChI:  InChI=1S/C16H18N6OS2.ClH/c1-16(2,3)8-4-5-9-11(6-8)25-15(19-9)21-12(23)10-7-24-14(20-10)22-13(17)18;/h4-7H,1-3H3,(H,19,21,23)(H4,17,18,20,22);1H

Standard InChI Key:  OCHBNQXEEOHZLK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
   14.8861    0.9096    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.5889    0.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3215    1.3677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1675    2.5910    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5992    2.1438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138   -1.2033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0872    0.0382    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8031    3.0357    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8208    1.3475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138    1.2033    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6164    0.6439    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.1952    0.1641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1802    2.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028    1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6202    1.4892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2072    2.3788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028   -1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1444    3.1533    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.3171    1.2468    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6291    2.6892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6551    0.8818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6637    2.0816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0
  4  5  2  0
  2  6  2  0
  2  7  1  0
  5  8  1  0
  3  9  1  0
  7  9  1  0
  2 10  1  0
 10 11  1  0
  5 12  1  0
  3 13  2  0
 12 13  1  0
  8 14  2  0
  6 15  1  0
 11 15  1  0
 11 17  2  0
 16 17  1  0
 16 18  1  0
  9 19  2  0
 15 20  2  0
 16 21  2  0
 20 21  1  0
 14 22  1  0
 14 23  1  0
 18 24  1  0
 18 25  1  0
 18 26  1  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: 374.50

Molecular Weight (Monoisotopic): 374.0984

AlogP: 3.21

#Rotatable Bonds: 3

Polar Surface Area: 119.28

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.22

CX Basic pKa: 6.36

CX LogP: 3.77

CX LogD: 3.73

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.48

Np Likeness Score: -2.19

References

1. Schnur RC, Gallaschun RJ, Singleton DH, Grissom M, Sloan DE, Goodwin P, McNiff PA, Fliri AF, Mangano FM, Olson TH..  (1991)  Quantitative structure-activity relationships of antitumor guanidinothiazolecarboxamides with survival enhancement for therapy in the 3LL Lewis lung carcinoma model.,  34  (7): [PMID:2066970] [10.1021/jm00111a009]

Source

Source(1):

• Scientific Literature