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

ID: ALA4448907

Chembl Id: CHEMBL4448907

PubChem CID: 14168143

Max Phase: Preclinical

Molecular Formula: C17H16N2O6S

Molecular Weight: 376.39

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)c3ccccc3)[C@H]2SC1

Standard InChI:  InChI=1S/C17H16N2O6S/c1-9(20)25-7-11-8-26-16-12(15(22)19(16)13(11)17(23)24)18-14(21)10-5-3-2-4-6-10/h2-6,12,16H,7-8H2,1H3,(H,18,21)(H,23,24)/t12-,16-/m1/s1

Standard InChI Key:  JEWHISMKBZQDSL-MLGOLLRUSA-N

Alternative Forms

1. Parent:

   

   ALA4448907

   (6R,7R)-3-(acetyloxymethyl)-7-benzamido-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: 376.39

Molecular Weight (Monoisotopic): 376.0729

AlogP: 0.60

#Rotatable Bonds: 5

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: 3.34

CX Basic pKa: ┄

CX LogP: 0.12

CX LogD: -3.29

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.57

Np Likeness Score: 0.21

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