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

ID: ALA72046

PubChem CID: 44311932

Max Phase: Preclinical

Molecular Formula: C11H14N2O5S3

Molecular Weight: 350.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@]1(CSC2=NCCS2)[C@H](C(=O)O)N2C(=O)C[C@H]2S1(=O)=O

Standard InChI:  InChI=1S/C11H14N2O5S3/c1-11(5-20-10-12-2-3-19-10)8(9(15)16)13-6(14)4-7(13)21(11,17)18/h7-8H,2-5H2,1H3,(H,15,16)/t7-,8+,11+/m1/s1

Standard InChI Key:  MXCGPVVSKSQZRV-FYBVGQRMSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  1  0  0  0  0  0999 V2000
    4.6167   -1.6167    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.8417   -2.7042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1167   -2.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8417   -1.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6292   -2.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0125   -2.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0125   -1.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0792   -1.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6292   -3.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7000   -1.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9125   -1.3292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0292   -1.0250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2042   -1.0250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5042   -1.9042    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.8542   -0.5125    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.4250   -3.2917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9042   -4.1917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7000   -2.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3375   -4.2042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1917   -0.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5375   -0.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6791   -0.8925    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0
  3  1  1  0
  4  1  1  0
  5  3  1  0
  6  7  1  0
  7  4  1  0
  8 14  1  0
  5  9  1  6
  3 10  1  0
 11  8  2  0
 12  1  2  0
 13  1  2  0
 14 10  1  0
 15  8  1  0
 16  6  2  0
 17  9  2  0
  3 18  1  6
 19  9  1  0
 20 11  1  0
 21 15  1  0
  5  2  1  0
  6  2  1  0
 20 21  1  0
  4 22  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA72046

   (2S,3R,5R)-3-(4,5-dihydro-1,3-thiazol-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: 350.44

Molecular Weight (Monoisotopic): 350.0065

AlogP: 0.02

#Rotatable Bonds: 3

Polar Surface Area: 104.11

Molecular Species: ACID

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.91

CX Basic pKa: 3.68

CX LogP: -0.69

CX LogD: -3.28

Aromatic Rings: ┄

Heavy Atoms: 21

QED Weighted: 0.72

Np Likeness Score: -0.05

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