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

ID: ALA4446739

Chembl Id: CHEMBL4446739

PubChem CID: 14168226

Max Phase: Preclinical

Molecular Formula: C15H14N2O7S

Molecular Weight: 366.35

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)c3ccco3)[C@H]2SC1

Standard InChI:  InChI=1S/C15H14N2O7S/c1-7(18)24-5-8-6-25-14-10(13(20)17(14)11(8)15(21)22)16-12(19)9-3-2-4-23-9/h2-4,10,14H,5-6H2,1H3,(H,16,19)(H,21,22)/t10-,14-/m1/s1

Standard InChI Key:  XVQBJKJRDYUPPJ-QMTHXVAHSA-N

Alternative Forms

1. Parent:

   

   ALA4446739

   (6R,7R)-3-(acetyloxymethyl)-7-(furan-2-carbonylamino)-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: 366.35

Molecular Weight (Monoisotopic): 366.0522

AlogP: 0.19

#Rotatable Bonds: 5

Polar Surface Area: 126.15

Molecular Species: ACID

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.96

CX Basic pKa: ┄

CX LogP: -0.82

CX LogD: -4.30

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.56

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