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Rac-4-(2-(2,4-dichlorophenyl)-4-(4-iodophenylimino)azetidin-1-yl)benzoic acid ID: ALA4853896
PubChem CID: 164613453
Max Phase: Preclinical
Molecular Formula: C22H15Cl2IN2O2
Molecular Weight: 537.18
Molecule Type: Unknown
Associated Items:
Names and Identifiers Canonical SMILES: O=C(O)c1ccc(N2/C(=N/c3ccc(I)cc3)CC2c2ccc(Cl)cc2Cl)cc1
Standard InChI: InChI=1S/C22H15Cl2IN2O2/c23-14-3-10-18(19(24)11-14)20-12-21(26-16-6-4-15(25)5-7-16)27(20)17-8-1-13(2-9-17)22(28)29/h1-11,20H,12H2,(H,28,29)/b26-21+
Standard InChI Key: VLFLKWDYQOWAGM-YYADALCUSA-N
Molfile:
RDKit 2D
29 32 0 0 0 0 0 0 0 0999 V2000
22.7053 -11.8901 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
22.7053 -12.7160 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
23.5312 -12.7160 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
23.5312 -11.8901 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
24.1151 -13.3008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
23.9008 -14.0994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
24.4810 -14.6842 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
25.2799 -14.4676 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
25.4911 -13.6650 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
24.9093 -13.0876 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
24.1121 -11.3051 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
24.9106 -11.5236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
25.4914 -10.9392 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
23.8990 -10.5150 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
22.1201 -13.3012 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
21.3223 -13.0885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
21.1117 -12.2921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
20.3147 -12.0752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
19.7286 -12.6607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
19.9490 -13.4620 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
20.7457 -13.6710 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
24.4763 -9.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
25.2749 -10.1424 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
18.9341 -12.4505 0.0000 I 0 0 0 0 0 0 0 0 0 0 0 0
25.8546 -9.5602 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0
23.1043 -10.3060 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0
25.8631 -15.0465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
25.6534 -15.8410 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
26.6560 -14.8308 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
1 2 1 0
2 3 1 0
3 4 1 0
4 1 1 0
5 6 2 0
6 7 1 0
7 8 2 0
8 9 1 0
9 10 2 0
10 5 1 0
3 5 1 0
11 12 2 0
12 13 1 0
13 23 2 0
22 14 2 0
14 11 1 0
4 11 1 0
2 15 2 0
15 16 1 0
16 17 2 0
17 18 1 0
18 19 2 0
19 20 1 0
20 21 2 0
21 16 1 0
22 23 1 0
19 24 1 0
23 25 1 0
14 26 1 0
8 27 1 0
27 28 1 0
27 29 2 0
M END Associated Targets(non-human) Molecule Features Natural Product: NoOral: NoChemical Probe: NoParenteral: NoMolecule Type: UnknownTopical: NoFirst In Class: NoBlack Box: NoChirality: NoAvailability: NoProdrug: 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
Calculated Properties Molecular Weight: 537.18Molecular Weight (Monoisotopic): 535.9555AlogP: 6.98#Rotatable Bonds: 4Polar Surface Area: 52.90Molecular Species: ACIDHBA: 2HBD: 1#RO5 Violations: 2HBA (Lipinski): 4HBD (Lipinski): 1#RO5 Violations (Lipinski): 2CX Acidic pKa: 4.48CX Basic pKa: 6.85CX LogP: 5.90CX LogD: 5.32Aromatic Rings: 3Heavy Atoms: 29QED Weighted: 0.37Np Likeness Score: -1.04
References 1. Romero E, Oueslati S, Benchekroun M, D'Hollander ACA, Ventre S, Vijayakumar K, Minard C, Exilie C, Tlili L, Retailleau P, Zavala A, Elisée E, Selwa E, Nguyen LA, Pruvost A, Naas T, Iorga BI, Dodd RH, Cariou K.. (2021) Azetidinimines as a novel series of non-covalent broad-spectrum inhibitors of β-lactamases with submicromolar activities against carbapenemases KPC-2 (class A), NDM-1 (class B) and OXA-48 (class D)., 219 [PMID:33862516 ] [10.1016/j.ejmech.2021.113418 ]