4-((2S,3S)-1-Benzylcarbamoyl-3-ethyl-4-oxo-azetidin-2-yloxy)-benzoic acid

ID: ALA308040

Chembl Id: CHEMBL308040

PubChem CID: 15934701

Max Phase: Preclinical

Molecular Formula: C20H20N2O5

Molecular Weight: 368.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@@H]1C(=O)N(C(=O)NCc2ccccc2)[C@H]1Oc1ccc(C(=O)O)cc1

Standard InChI:  InChI=1S/C20H20N2O5/c1-2-16-17(23)22(20(26)21-12-13-6-4-3-5-7-13)18(16)27-15-10-8-14(9-11-15)19(24)25/h3-11,16,18H,2,12H2,1H3,(H,21,26)(H,24,25)/t16-,18+/m1/s1

Standard InChI Key:  LPVMGHAIQBNBCR-AEFFLSMTSA-N

Alternative Forms

1. Parent:

   

   ALA308040

   4-[(2S,3S)-1-(benzylcarbamoyl)-3-ethyl-4-oxoazetidin-2-yl]oxybenzoic acid

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: 368.39

Molecular Weight (Monoisotopic): 368.1372

AlogP: 2.87

#Rotatable Bonds: 6

Polar Surface Area: 95.94

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.34

CX Basic pKa: ┄

CX LogP: 3.35

CX LogD: 0.41

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.76

Np Likeness Score: -0.36

References

1. Shah SK, Finke PE, Brause KA, Chandler GO, Ashe BM, Weston H, Maycock AL, Mumford RA, Doherty JB.  (1993)  Monocyclic -lactam inhibitors of human leukocyte elastase. Stereospecific synthesis and activity of 3,4-disubstituted-2-azetidinones.,  3  (11): [10.1016/S0960-894X(01)80942-2]

2. Hagmann WK, Shah SK, Dorn CP, O'Grady LA, Hale JJ, Finke P, Thompson KR, Brause Ka, Ash BM, Weston H, Dahlgren M, Maycock AL, Dellea PS, Hand KM, Osinga DG, Bonney RJ, Davies P, Fletcher DS, Doherty JB.  (1991)  Prevention of human leukocyte elastase-mediated lung damage by 3-alkyl-4-azetidinones,  1  (10): [10.1016/S0960-894X(01)80463-7]

3. Hagmann WK, Thompson KR, Shah SK, Finke PE, Ashe BM, Weston H, Maycock AL, Doherty JB.  (1992)  The effect of N-acyl substituents on the stability of monocyclic -lactam inhibitors of human leukocyte elastase,  2  (7): [10.1016/S0960-894X(00)80390-X]

4. Wu YJ, Meanwell NA..  (2021)  Geminal Diheteroatomic Motifs: Some Applications of Acetals, Ketals, and Their Sulfur and Nitrogen Homologues in Medicinal Chemistry and Drug Design.,  64  (14.0): [PMID:34213340] [10.1021/acs.jmedchem.1c00790]

Source

Source(1):

• Scientific Literature