(2S,3R,5R)-3-(1H-Benzoimidazol-2-ylsulfanylmethyl)-3-methyl-4,4,7-trioxo-4lambda*6*-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid

ID: ALA72972

Chembl Id: CHEMBL72972

PubChem CID: 44311985

Max Phase: Preclinical

Molecular Formula: C15H15N3O5S2

Molecular Weight: 381.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@]1(CSc2nc3ccccc3[nH]2)[C@H](C(=O)O)N2C(=O)C[C@H]2S1(=O)=O

Standard InChI:  InChI=1S/C15H15N3O5S2/c1-15(7-24-14-16-8-4-2-3-5-9(8)17-14)12(13(20)21)18-10(19)6-11(18)25(15,22)23/h2-5,11-12H,6-7H2,1H3,(H,16,17)(H,20,21)/t11-,12+,15+/m1/s1

Standard InChI Key:  ANZJFEYHQKFAQH-XUJVJEKNSA-N

Alternative Forms

1. Parent:

   

   ALA72972

   (2S,3R,5R)-3-(1H-benzimidazol-2-ylsulfanylmethyl)-3-methyl-4,4,7-trioxo-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

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: 381.44

Molecular Weight (Monoisotopic): 381.0453

AlogP: 0.85

#Rotatable Bonds: 4

Polar Surface Area: 120.43

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.13

CX Basic pKa: 4.28

CX LogP: -0.32

CX LogD: -2.54

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.59

Np Likeness Score: -0.54

References

1. von Daehne W, Hoffmeyer L, Keiding J.  (1993)  Rearrangement of unsymmetrical azetidinone disulfides to 2-(heterocyclylthiomethyl)penams, a synthetic approach to new -lactamase inhibitors,  3  (11): [10.1016/S0960-894X(01)80933-1]

Source

Source(1):

• Scientific Literature