(6R,7R)-3-(Acetoxymethyl)-7-(2-(4-chlorophenyl)-acetamido)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

ID: ALA4443633

Chembl Id: CHEMBL4443633

PubChem CID: 68239195

Max Phase: Preclinical

Molecular Formula: C18H17ClN2O6S

Molecular Weight: 424.86

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)Cc3ccc(Cl)cc3)[C@H]2SC1

Standard InChI:  InChI=1S/C18H17ClN2O6S/c1-9(22)27-7-11-8-28-17-14(16(24)21(17)15(11)18(25)26)20-13(23)6-10-2-4-12(19)5-3-10/h2-5,14,17H,6-8H2,1H3,(H,20,23)(H,25,26)/t14-,17-/m1/s1

Standard InChI Key:  PBAXHVPFTLYIOL-RHSMWYFYSA-N

Alternative Forms

1. Parent:

   

   ALA4443633

   (6R,7R)-3-(acetyloxymethyl)-7-[[2-(4-chlorophenyl)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 424.86

Molecular Weight (Monoisotopic): 424.0496

AlogP: 1.18

#Rotatable Bonds: 6

Polar Surface Area: 113.01

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.41

CX Basic pKa: ┄

CX LogP: 0.71

CX LogD: -2.69

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.52

Np Likeness Score: -0.04

References

1. Evans LE, Krishna A, Ma Y, Webb TE, Marshall DC, Tooke CL, Spencer J, Clarke TB, Armstrong A, Edwards AM..  (2019)  Exploitation of Antibiotic Resistance as a Novel Drug Target: Development of a β-Lactamase-Activated Antibacterial Prodrug.,  62  (9): [PMID:31009558] [10.1021/acs.jmedchem.8b01923]

Source

Source(1):

• Scientific Literature