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

ID: ALA308516

PubChem CID: 44311944

Max Phase: Preclinical

Molecular Formula: C15H13BrN2O3S3

Molecular Weight: 445.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@]1(CSc2nc3ccccc3s2)S[C@@H]2[C@H](Br)C(=O)N2[C@H]1C(=O)O

Standard InChI:  InChI=1S/C15H13BrN2O3S3/c1-15(6-22-14-17-7-4-2-3-5-8(7)23-14)10(13(20)21)18-11(19)9(16)12(18)24-15/h2-5,9-10,12H,6H2,1H3,(H,20,21)/t9-,10+,12-,15+/m1/s1

Standard InChI Key:  WOFAABWEQYFPBT-HMDURAKOSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  1  0  0  0  0  0999 V2000
    3.6667   -4.3167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6625   -3.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8375   -4.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4500   -4.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9292   -3.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4417   -3.2292    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.8375   -3.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8917   -2.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7125   -2.9542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6542   -2.1375    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.4417   -5.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9875   -2.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3375   -1.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5167   -3.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2500   -4.9042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3125   -3.5167    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.2500   -2.9042    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.7250   -5.8000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5167   -4.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1542   -5.8125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7417   -1.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4417   -0.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8542   -1.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2042   -0.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5007   -2.5049    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 16  1  0
  9  8  2  0
 10  8  1  0
  4 11  1  6
 12  9  1  0
 13 10  1  0
  5 14  1  0
 15  3  2  0
 16 14  1  0
  7 17  1  1
 18 11  2  0
  5 19  1  6
 20 11  1  0
 21 12  1  0
 22 13  1  0
 23 21  2  0
 24 22  2  0
  2  7  1  0
  5  6  1  0
 13 12  2  0
 23 24  1  0
  2 25  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA308516

   (2S,3R,5R,6R)-3-(1,3-benzothiazol-2-ylsulfanylmethyl)-6-bromo-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: 445.39

Molecular Weight (Monoisotopic): 443.9272

AlogP: 3.28

#Rotatable Bonds: 4

Polar Surface Area: 70.50

Molecular Species: ACID

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.37

CX Basic pKa: 1.09

CX LogP: 3.71

CX LogD: 0.30

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.44

Np Likeness Score: -0.72

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