ID: ALA1798027

Max Phase: Preclinical

Molecular Formula: C17H23N5S

Molecular Weight: 329.47

Molecule Type: Small molecule

Representations

Canonical SMILES:  CCCCc1ccc(-c2nc(C)c(/C(C)=N/NC(=N)N)s2)cc1

Standard InChI:  InChI=1S/C17H23N5S/c1-4-5-6-13-7-9-14(10-8-13)16-20-11(2)15(23-16)12(3)21-22-17(18)19/h7-10H,4-6H2,1-3H3,(H4,18,19,22)/b21-12+

Standard InChI Key:  KNVYIYGEARCNOK-CIAFOILYSA-N

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

Properties

Molecular Weight: 329.47

Molecular Weight (Monoisotopic): 329.1674

AlogP: 3.67

#Rotatable Bonds: 6

Polar Surface Area: 87.15

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 7.67

CX LogP: 3.61

CX LogD: 3.15

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.43

Np Likeness Score: -1.36

References

1. Mayhoub AS, Khaliq M, Botting C, Li Z, Kuhn RJ, Cushman M..  (2011)  An investigation of phenylthiazole antiflaviviral agents.,  19  (12): [PMID:21612931] [10.1016/j.bmc.2011.04.041]

2. Mohammad H, Mayhoub AS, Ghafoor A, Soofi M, Alajlouni RA, Cushman M, Seleem MN..  (2014)  Discovery and characterization of potent thiazoles versus methicillin- and vancomycin-resistant Staphylococcus aureus.,  57  (4): [PMID:24387054] [10.1021/jm401905m]

3. Seleem MA, Disouky AM, Mohammad H, Abdelghany TM, Mancy AS, Bayoumi SA, Elshafeey A, El-Morsy A, Seleem MN, Mayhoub AS..  (2016)  Second-Generation Phenylthiazole Antibiotics with Enhanced Pharmacokinetic Properties.,  59  (10): [PMID:27187739] [10.1021/acs.jmedchem.6b00233]

4. Yahia E, Mohammad H, Abdelghany TM, Fayed E, Seleem MN, Mayhoub AS..  (2017)  Phenylthiazole antibiotics: A metabolism-guided approach to overcome short duration of action.,  126  [PMID:27918995] [10.1016/j.ejmech.2016.11.042]

5. Mohammad H, Younis W, Chen L, Peters CE, Pogliano J, Pogliano K, Cooper B, Zhang J, Mayhoub A, Oldfield E, Cushman M, Seleem MN..  (2017)  Phenylthiazole Antibacterial Agents Targeting Cell Wall Synthesis Exhibit Potent Activity in Vitro and in Vivo against Vancomycin-Resistant Enterococci.,  60  (6): [PMID:28248504] [10.1021/acs.jmedchem.6b01780]

6. Eid I, Elsebaei MM, Mohammad H, Hagras M, Peters CE, Hegazy YA, Cooper B, Pogliano J, Pogliano K, Abulkhair HS, Seleem MN, Mayhoub AS..  (2017)  Arylthiazole antibiotics targeting intracellular methicillin-resistant Staphylococcus aureus (MRSA) that interfere with bacterial cell wall synthesis.,  139  [PMID:28846967] [10.1016/j.ejmech.2017.08.039]

7. Hagras M, Hegazy YA, Elkabbany AH, Mohammad H, Ghiaty A, Abdelghany TM, Seleem MN, Mayhoub AS..  (2018)  Biphenylthiazole antibiotics with an oxadiazole linker: An approach to improve physicochemical properties and oral bioavailability.,  143  [PMID:29126738] [10.1016/j.ejmech.2017.10.048]

8. Hagras M, Mohammad H, Mandour MS, Hegazy YA, Ghiaty A, Seleem MN, Mayhoub AS..  (2017)  Investigating the Antibacterial Activity of Biphenylthiazoles against Methicillin- and Vancomycin-Resistant Staphylococcus aureus (MRSA and VRSA).,  60  (9): [PMID:28436655] [10.1021/acs.jmedchem.7b00392]

9. Elsebaei MM, Mohammad H, Samir A, Abutaleb NS, Norvil AB, Michie AR, Moustafa MM, Samy H, Gowher H, Seleem MN, Mayhoub AS..  (2019)  Lipophilic efficient phenylthiazoles with potent undecaprenyl pyrophosphatase inhibitory activity.,  175  [PMID:31075608] [10.1016/j.ejmech.2019.04.063]

10. Elsebaei MM, Abutaleb NS, Mahgoub AA, Li D, Hagras M, Mohammad H, Seleem MN, Mayhoub AS..  (2019)  Phenylthiazoles with nitrogenous side chain: An approach to overcome molecular obesity.,  182  [PMID:31446245] [10.1016/j.ejmech.2019.111593]

Source

Source(1):

• Scientific Literature