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

ID: ALA4582621

Chembl Id: CHEMBL4582621

Cas Number: 3432-90-4

PubChem CID: 22818307

Max Phase: Preclinical

Molecular Formula: C16H16N2O6S2

Molecular Weight: 396.45

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)Cc3ccsc3)[C@H]2SC1

Standard InChI:  InChI=1S/C16H16N2O6S2/c1-8(19)24-5-10-7-26-15-12(14(21)18(15)13(10)16(22)23)17-11(20)4-9-2-3-25-6-9/h2-3,6,12,15H,4-5,7H2,1H3,(H,17,20)(H,22,23)/t12-,15-/m1/s1

Standard InChI Key:  KRXLKROAQPXHBK-IUODEOHRSA-N

Alternative Forms

1. Parent:

   

   ALA4582621

   (6R,7R)-3-[(acetyloxy)methyl]-8-oxo-7-[2-(thiophen-3-yl)acetamido]-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: 396.45

Molecular Weight (Monoisotopic): 396.0450

AlogP: 0.59

#Rotatable Bonds: 6

Polar Surface Area: 113.01

Molecular Species: ACID

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.31

CX Basic pKa: ┄

CX LogP: -0.12

CX LogD: -3.54

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.53

Np Likeness Score: -0.43

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