| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
ID: ALA528988
Max Phase: Preclinical
Molecular Formula: C19H23NO7S
Molecular Weight: 409.46
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: CCCCOc1ccc2cc(S(=O)(=O)N[C@H](CCC(=O)O)C(=O)O)ccc2c1
Standard InChI: InChI=1S/C19H23NO7S/c1-2-3-10-27-15-6-4-14-12-16(7-5-13(14)11-15)28(25,26)20-17(19(23)24)8-9-18(21)22/h4-7,11-12,17,20H,2-3,8-10H2,1H3,(H,21,22)(H,23,24)/t17-/m1/s1
Standard InChI Key: UAGYXJBYAFGRFR-QGZVFWFLSA-N
Associated Targets(non-human)
UDP-N-acetylmuramoylalanine--D-glutamate ligase 81 Activities
Molecule Features
| Natural Product: Yes | 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 |
Drug Indications
| MESH ID | MESH Heading | EFO IDs | EFO Terms | Max Phase for Indication | References |
|---|
Mechanisms of Action
| Mechanism of Action | Action Type | target ID | Target Name | Target Type | Target Organism | Binding Site Name | References |
|---|
Properties
| Molecular Weight: 409.46 | Molecular Weight (Monoisotopic): 409.1195 | AlogP: 2.62 | #Rotatable Bonds: 11 |
| Polar Surface Area: 130.00 | Molecular Species: ACID | HBA: 5 | HBD: 3 |
| #RO5 Violations: 0 | HBA (Lipinski): 8 | HBD (Lipinski): 3 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: 2.97 | CX Basic pKa: | CX LogP: 2.65 | CX LogD: -4.14 |
| Aromatic Rings: 2 | Heavy Atoms: 28 | QED Weighted: 0.49 | Np Likeness Score: -0.63 |
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. Simcic M, Hodoscek M, Humljan J, Kristan K, Urleb U, Kocjan D, Grdadolnik SG.. (2009) NMR and molecular dynamics study of the binding mode of naphthalene-N-sulfonyl-D-glutamic acid derivatives: novel MurD ligase inhibitors., 52 (9): [PMID:19358612] [10.1021/jm900117n] |
| 3. Perdih A, Kovac A, Wolber G, Blanot D, Gobec S, Solmajer T.. (2009) Discovery of novel benzene 1,3-dicarboxylic acid inhibitors of bacterial MurD and MurE ligases by structure-based virtual screening approach., 19 (10): [PMID:19369074] [10.1016/j.bmcl.2009.03.141] |
| 4. 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] |
| 5. 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):