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

ID: ALA4442878

Chembl Id: CHEMBL4442878

PubChem CID: 14168087

Max Phase: Preclinical

Molecular Formula: C14H18N2O6S

Molecular Weight: 342.37

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCCC(=O)N[C@@H]1C(=O)N2C(C(=O)O)=C(COC(C)=O)CS[C@H]12

Standard InChI:  InChI=1S/C14H18N2O6S/c1-3-4-9(18)15-10-12(19)16-11(14(20)21)8(5-22-7(2)17)6-23-13(10)16/h10,13H,3-6H2,1-2H3,(H,15,18)(H,20,21)/t10-,13-/m1/s1

Standard InChI Key:  DJLOKMQBWZXCBH-ZWNOBZJWSA-N

Alternative Forms

1. Parent:

   

   ALA4442878

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

Molecule Features

Natural Product: Yes

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: 342.37

Molecular Weight (Monoisotopic): 342.0886

AlogP: 0.09

#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: 3.49

CX Basic pKa: ┄

CX LogP: -0.59

CX LogD: -3.96

Aromatic Rings: ┄

Heavy Atoms: 23

QED Weighted: 0.52

Np Likeness Score: 0.34

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