ID: ALA457526

Max Phase: Preclinical

Molecular Formula: C23H19FN2O7S

Molecular Weight: 486.48

Molecule Type: Small molecule

Representations

Canonical SMILES:  N#Cc1ccc(COc2ccc3cc(S(=O)(=O)N[C@H](CCC(=O)O)C(=O)O)ccc3c2)c(F)c1

Standard InChI:  InChI=1S/C23H19FN2O7S/c24-20-9-14(12-25)1-2-17(20)13-33-18-5-3-16-11-19(6-4-15(16)10-18)34(31,32)26-21(23(29)30)7-8-22(27)28/h1-6,9-11,21,26H,7-8,13H2,(H,27,28)(H,29,30)/t21-/m1/s1

Standard InChI Key:  IRJUSGUHNFMVCK-OAQYLSRUSA-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: 486.48

Molecular Weight (Monoisotopic): 486.0897

AlogP: 3.03

#Rotatable Bonds: 10

Polar Surface Area: 153.79

Molecular Species: ACID

HBA: 6

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 2.97

CX Basic pKa:

CX LogP: 3.05

CX LogD: -3.74

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.40

Np Likeness Score: -1.19

References

1. Humljan J, Kotnik M, Contreras-Martel C, Blanot D, Urleb U, Dessen A, Solmajer T, Gobec S..  (2008)  Novel naphthalene-N-sulfonyl-D-glutamic acid derivatives as inhibitors of MurD, a key peptidoglycan biosynthesis enzyme.,  51  (23): [PMID:19007109] [10.1021/jm800762u]

2. Sosič I, Barreteau H, Simčič M, Sink R, Cesar J, Zega A, Grdadolnik SG, Contreras-Martel C, Dessen A, Amoroso A, Joris B, Blanot D, Gobec S..  (2011)  Second-generation sulfonamide inhibitors of D-glutamic acid-adding enzyme: activity optimisation with conformationally rigid analogues of D-glutamic acid.,  46  (7): [PMID:21524830] [10.1016/j.ejmech.2011.04.011]

3. Simčič M, Pureber K, Kristan K, Urleb U, Kocjan D, Grdadolnik SG..  (2014)  A novel 2-oxoindolinylidene inhibitor of bacterial MurD ligase: Enzyme kinetics, protein-inhibitor binding by NMR and a molecular dynamics study.,  83  [PMID:24952377] [10.1016/j.ejmech.2014.06.021]

Source

Source(1):

• Scientific Literature