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

ID: ALA4520258

Chembl Id: CHEMBL4520258

PubChem CID: 14168175

Max Phase: Preclinical

Molecular Formula: C24H22N2O6S

Molecular Weight: 466.52

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)Cc3ccc(-c4ccccc4)cc3)[C@H]2SC1

Standard InChI:  InChI=1S/C24H22N2O6S/c1-14(27)32-12-18-13-33-23-20(22(29)26(23)21(18)24(30)31)25-19(28)11-15-7-9-17(10-8-15)16-5-3-2-4-6-16/h2-10,20,23H,11-13H2,1H3,(H,25,28)(H,30,31)/t20-,23-/m1/s1

Standard InChI Key:  KWHMGICVRLIAHY-NFBKMPQASA-N

Alternative Forms

1. Parent:

   

   ALA4520258

   (6R,7R)-3-(acetyloxymethyl)-8-oxo-7-[[2-(4-phenylphenyl)acetyl]amino]-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: 466.52

Molecular Weight (Monoisotopic): 466.1199

AlogP: 2.20

#Rotatable Bonds: 7

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: 3.42

CX Basic pKa: ┄

CX LogP: 1.75

CX LogD: -1.65

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.48

Np Likeness Score: 0.07

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