(R)-1-((S,Z)-2-(2-(benzyloxy)-2-oxoethylidene)-4-oxoazetidin-3-yl)ethyl 4-hydroxy-3,5-dimethoxybenzoate

ID: ALA425595

Chembl Id: CHEMBL425595

PubChem CID: 11611949

Max Phase: Preclinical

Molecular Formula: C23H23NO8

Molecular Weight: 441.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(C(=O)O[C@H](C)[C@H]2C(=O)N/C2=C\C(=O)OCc2ccccc2)cc(OC)c1O

Standard InChI:  InChI=1S/C23H23NO8/c1-13(32-23(28)15-9-17(29-2)21(26)18(10-15)30-3)20-16(24-22(20)27)11-19(25)31-12-14-7-5-4-6-8-14/h4-11,13,20,26H,12H2,1-3H3,(H,24,27)/b16-11-/t13-,20-/m1/s1

Standard InChI Key:  TUYATMIGLCAYDA-WAQFEYKTSA-N

Alternative Forms

1. Parent:

   

   ALA425595

   [(1R)-1-[(3S,4Z)-2-oxo-4-(2-oxo-2-phenylmethoxyethylidene)azetidin-3-yl]ethyl] 4-hydroxy-3,5-dimethoxybenzoate

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: 441.44

Molecular Weight (Monoisotopic): 441.1424

AlogP: 2.33

#Rotatable Bonds: 8

Polar Surface Area: 120.39

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.43

CX Basic pKa: ┄

CX LogP: 2.44

CX LogD: 2.40

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.36

Np Likeness Score: 0.19

References

1. Broccolo F, Cainelli G, Caltabiano G, Cocuzza CE, Fortuna CG, Galletti P, Giacomini D, Musumarra G, Musumeci R, Quintavalla A..  (2006)  Design, synthesis, and biological evaluation of 4-alkyliden-beta lactams: new products with promising antibiotic activity against resistant bacteria.,  49  (9): [PMID:16640341] [10.1021/jm0580510]

Source

Source(1):

• Scientific Literature