2-Guanidino-thiazole-4-carboxylic acid (5-nitro-benzothiazol-2-yl)-amide hydrochloride

ID: ALA538002

PubChem CID: 45264487

Max Phase: Preclinical

Molecular Formula: C12H10ClN7O3S2

Molecular Weight: 363.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cl.N=C(N)Nc1nc(C(=O)Nc2nc3cc([N+](=O)[O-])ccc3s2)cs1

Standard InChI:  InChI=1S/C12H9N7O3S2.ClH/c13-10(14)18-11-16-7(4-23-11)9(20)17-12-15-6-3-5(19(21)22)1-2-8(6)24-12;/h1-4H,(H,15,17,20)(H4,13,14,16,18);1H

Standard InChI Key:  TTXPQDGQHBUMAG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
   14.9590   -0.0425    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
    6.3513   -1.2462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2249   -2.4499    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6461   -1.9702    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    0.0320    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6217    1.4865    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8699   -2.8344    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8506   -1.2602    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
    8.6290   -0.4703    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.1973   -0.0230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2331   -2.2065    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
    0.2917   -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
   -3.6319    2.6865    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6560    0.8780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2606   -2.3052    0.0000 O   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
   12.2133   -2.8987    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.3428   -1.0115    0.0000 N   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  9  1  0
  3 10  1  0
  7 10  1  0
  2 11  1  0
  6 12  1  0
  5 13  1  0
  3 14  2  0
 13 14  1  0
  9 15  1  0
  8 16  1  0
 11 17  1  0
 12 17  1  0
 12 18  2  0
 16 18  1  0
  8 19  1  0
  8 20  2  0
 10 21  2  0
 16 22  2  0
 17 23  2  0
 22 23  1  0
 15 24  2  0
 15 25  1  0
M  CHG  2   8   1  19  -1
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: 363.38

Molecular Weight (Monoisotopic): 363.0208

AlogP: 2.22

#Rotatable Bonds: 4

Polar Surface Area: 159.92

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.74

CX Basic pKa: 5.59

CX LogP: 2.53

CX LogD: 2.52

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.24

Np Likeness Score: -2.52

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