2-{1-[2-(4-(Cyclopentylethynyl)phenyl)-4-methylthiazol-5-yl]ethylidene}hydrazine-1-carboximidamide

ID: ALA4210054

PubChem CID: 145965449

Max Phase: Preclinical

Molecular Formula: C20H23N5S

Molecular Weight: 365.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C/C(=N\NC(=N)N)c1sc(-c2ccc(C#CC3CCCC3)cc2)nc1C

Standard InChI:  InChI=1S/C20H23N5S/c1-13-18(14(2)24-25-20(21)22)26-19(23-13)17-11-9-16(10-12-17)8-7-15-5-3-4-6-15/h9-12,15H,3-6H2,1-2H3,(H4,21,22,25)/b24-14+

Standard InChI Key:  NVMGKGMNXKYECV-ZVHZXABRSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   27.8326   -3.5040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8315   -4.3276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5436   -4.7407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2533   -4.3272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2505   -3.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5419   -3.0951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9608   -3.0891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7123   -3.4162    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   31.2609   -2.8068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8455   -2.0965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0428   -2.2695    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.0809   -2.8065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4898   -3.5141    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.4893   -2.0945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1791   -1.3445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3111   -3.5138    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.7241   -4.2255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5454   -4.2252    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.3116   -4.9374    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.1193   -4.7398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4114   -5.1476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7002   -5.5615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9540   -5.2300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4040   -5.8382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8179   -6.5494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6210   -6.3781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11  7  2  0
  9 12  1  0
 12 13  2  0
 12 14  1  0
 10 15  1  0
 13 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
  2 20  1  0
 20 21  3  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4210054

   ---

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: 365.51

Molecular Weight (Monoisotopic): 365.1674

AlogP: 3.87

#Rotatable Bonds: 3

Polar Surface Area: 87.15

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.52

CX LogP: 3.90

CX LogD: 3.54

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.33

Np Likeness Score: -1.24

References

1. Elsebaei MM, Mohammad H, Abouf M, Abutaleb NS, Hegazy YA, Ghiaty A, Chen L, Zhang J, Malwal SR, Oldfield E, Seleem MN, Mayhoub AS..  (2018)  Alkynyl-containing phenylthiazoles: Systemically active antibacterial agents effective against methicillin-resistant Staphylococcus aureus (MRSA).,  148  [PMID:29459278] [10.1016/j.ejmech.2018.02.031]

2. Hammad A, Abutaleb NS, Elsebaei MM, Norvil AB, Alswah M, Ali AO, Abdel-Aleem JA, Alattar A, Bayoumi SA, Gowher H, Seleem MN, Mayhoub AS..  (2019)  From Phenylthiazoles to Phenylpyrazoles: Broadening the Antibacterial Spectrum toward Carbapenem-Resistant Bacteria.,  62  (17): [PMID:31369262] [10.1021/acs.jmedchem.9b00720]

Source

Source(1):

• Scientific Literature