(6R,7R)-3-((3-carboxy-4-nitrophenylthio)methyl)-8-oxo-7-(2-(thiophen-2-yl)acetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

ID: ALA1650032

Chembl Id: CHEMBL1650032

Cas Number: 9073-60-3

PubChem CID: 133358

Product Number: L105715

Max Phase: Preclinical

Molecular Formula: C21H17N3O8S3

Molecular Weight: 535.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Cc1cccs1)N[C@@H]1C(=O)N2C(C(=O)O)=C(CSc3ccc([N+](=O)[O-])c(C(=O)O)c3)CS[C@H]12

Standard InChI:  InChI=1S/C21H17N3O8S3/c25-15(7-11-2-1-5-33-11)22-16-18(26)23-17(21(29)30)10(9-35-19(16)23)8-34-12-3-4-14(24(31)32)13(6-12)20(27)28/h1-6,16,19H,7-9H2,(H,22,25)(H,27,28)(H,29,30)/t16-,19-/m1/s1

Standard InChI Key:  PFVWVVUSAORMBB-VQIMIIECSA-N

Alternative Forms

1. Parent:

   

   ALA1650032

   Centa

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 535.58

Molecular Weight (Monoisotopic): 535.0178

AlogP: 2.43

#Rotatable Bonds: 9

Polar Surface Area: 167.15

Molecular Species: ACID

HBA: 9

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 1.02

CX Basic pKa: ┄

CX LogP: 2.19

CX LogD: -4.80

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.19

Np Likeness Score: -1.19

References

1. Bebrone C, Delbrück H, Kupper MB, Schlömer P, Willmann C, Frère JM, Fischer R, Galleni M, Hoffmann KM..  (2009)  The structure of the dizinc subclass B2 metallo-beta-lactamase CphA reveals that the second inhibitory zinc ion binds in the histidine site.,  53  (10): [PMID:19651913] [10.1128/aac.00288-09]

2. van Berkel SS, Brem J, Rydzik AM, Salimraj R, Cain R, Verma A, Owens RJ, Fishwick CW, Spencer J, Schofield CJ..  (2013)  Assay platform for clinically relevant metallo-β-lactamases.,  56  (17): [PMID:23898798] [10.1021/jm400769b]

3. Lund BA, Christopeit T, Guttormsen Y, Bayer A, Leiros HK..  (2016)  Screening and Design of Inhibitor Scaffolds for the Antibiotic Resistance Oxacillinase-48 (OXA-48) through Surface Plasmon Resonance Screening.,  59  (11): [PMID:27165692] [10.1021/acs.jmedchem.6b00660]

Source

Source(1):

• Scientific Literature