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

ID: ALA310221

PubChem CID: 44312261

Max Phase: Preclinical

Molecular Formula: C11H13BrN2O3S3

Molecular Weight: 397.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@]1(CSC2=NCCS2)S[C@@H]2[C@H](Br)C(=O)N2[C@H]1C(=O)O

Standard InChI:  InChI=1S/C11H13BrN2O3S3/c1-11(4-19-10-13-2-3-18-10)6(9(16)17)14-7(15)5(12)8(14)20-11/h5-6,8H,2-4H2,1H3,(H,16,17)/t5-,6+,8-,11+/m1/s1

Standard InChI Key:  SIVNUZUWNGEGKW-AGNDVQSCSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  1  0  0  0  0  0999 V2000
    4.1000   -3.7542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0917   -2.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2667   -3.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8792   -4.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3625   -3.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8750   -2.6667    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.2667   -2.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3250   -2.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8750   -4.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1417   -2.3917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9500   -2.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0875   -1.5792    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.6792   -4.3417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7417   -2.9542    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.6792   -2.3417    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    4.1542   -5.2417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9500   -3.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5875   -5.2542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4167   -1.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7667   -1.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9307   -1.9422    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  1  1  0
  5  4  1  0
  2  6  1  0
  7  3  1  0
  8 14  1  0
  4  9  1  6
 10  8  2  0
  5 11  1  0
 12  8  1  0
 13  3  2  0
 14 11  1  0
  7 15  1  1
 16  9  2  0
  5 17  1  6
 18  9  1  0
 19 10  1  0
 20 12  1  0
  2  7  1  0
  5  6  1  0
 20 19  1  0
  2 21  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA310221

   (2S,3R,5R,6R)-6-bromo-3-(4,5-dihydro-1,3-thiazol-2-ylsulfanylmethyl)-3-methyl-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: 397.34

Molecular Weight (Monoisotopic): 395.9272

AlogP: 1.71

#Rotatable Bonds: 3

Polar Surface Area: 69.97

Molecular Species: ACID

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.83

CX Basic pKa: 3.67

CX LogP: 1.19

CX LogD: -1.33

Aromatic Rings: ┄

Heavy Atoms: 20

QED Weighted: 0.58

Np Likeness Score: 0.03

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