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

ID: ALA423309

PubChem CID: 44311943

Max Phase: Preclinical

Molecular Formula: C11H14N4O5S2

Molecular Weight: 346.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1cnnc1SC[C@@]1(C)[C@H](C(=O)O)N2C(=O)C[C@H]2S1(=O)=O

Standard InChI:  InChI=1S/C11H14N4O5S2/c1-11(4-21-10-13-12-5-14(10)2)8(9(17)18)15-6(16)3-7(15)22(11,19)20/h5,7-8H,3-4H2,1-2H3,(H,17,18)/t7-,8+,11+/m1/s1

Standard InChI Key:  QDJWMEGFGPTSBD-FYBVGQRMSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  1  0  0  0  0  0999 V2000
    4.4292   -1.9250    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.6542   -3.0167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9292   -2.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6542   -2.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4417   -3.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8250   -3.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8250   -2.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6667   -0.8167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8917   -1.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7250   -1.6375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0042   -0.8625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4417   -4.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5125   -2.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3500   -0.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3167   -2.2125    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.8417   -1.3292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1500   -1.5042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2375   -3.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7167   -4.5042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5125   -3.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1500   -4.5167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8792   -0.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4916   -1.2008    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  9  1  0
  9 15  1  0
 10  9  2  0
 11 10  1  0
  5 12  1  6
  3 13  1  0
 14  8  1  0
 15 13  1  0
 16  1  2  0
 17  1  2  0
 18  6  2  0
 19 12  2  0
  3 20  1  6
 21 12  1  0
 22  8  1  0
  5  2  1  0
  6  2  1  0
 11 14  2  0
  4 23  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA423309

   (2S,3R,5R)-3-methyl-3-[(4-methyl-1,2,4-triazol-3-yl)sulfanylmethyl]-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: 346.39

Molecular Weight (Monoisotopic): 346.0406

AlogP: -0.89

#Rotatable Bonds: 4

Polar Surface Area: 122.46

Molecular Species: ACID

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.95

CX Basic pKa: 1.74

CX LogP: -1.51

CX LogD: -4.73

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.55

Np Likeness Score: -0.81

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