(2S,3R,5R,6R)-6-Bromo-3-methyl-3-(1-methyl-1H-imidazol-2-ylsulfanylmethyl)-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid

ID: ALA73450

Chembl Id: CHEMBL73450

PubChem CID: 44312320

Max Phase: Preclinical

Molecular Formula: C12H14BrN3O3S2

Molecular Weight: 392.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1ccnc1SC[C@]1(C)S[C@@H]2[C@H](Br)C(=O)N2[C@H]1C(=O)O

Standard InChI:  InChI=1S/C12H14BrN3O3S2/c1-12(5-20-11-14-3-4-15(11)2)7(10(18)19)16-8(17)6(13)9(16)21-12/h3-4,6-7,9H,5H2,1-2H3,(H,18,19)/t6-,7+,9-,12+/m1/s1

Standard InChI Key:  FEKDJDOMDQNFAM-GUKKNSHRSA-N

Alternative Forms

1. Parent:

   

   ALA73450

   (2S,3R,5R,6R)-6-bromo-3-methyl-3-[(1-methylimidazol-2-yl)sulfanylmethyl]-7-oxo-4-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: 392.30

Molecular Weight (Monoisotopic): 390.9660

AlogP: 1.40

#Rotatable Bonds: 4

Polar Surface Area: 75.43

Molecular Species: ACID

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.91

CX Basic pKa: 5.03

CX LogP: 0.41

CX LogD: -1.59

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.47

Np Likeness Score: -0.57

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