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

ID: ALA302241

PubChem CID: 44311971

Max Phase: Preclinical

Molecular Formula: C12H15N3O5S2

Molecular Weight: 345.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1ccnc1SC[C@@]1(C)[C@H](C(=O)O)N2C(=O)C[C@H]2S1(=O)=O

Standard InChI:  InChI=1S/C12H15N3O5S2/c1-12(6-21-11-13-3-4-14(11)2)9(10(17)18)15-7(16)5-8(15)22(12,19)20/h3-4,8-9H,5-6H2,1-2H3,(H,17,18)/t8-,9+,12+/m1/s1

Standard InChI Key:  RROHCWIBSPHGHX-PTRXPTGYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  1  0  0  0  0  0999 V2000
    3.4375   -0.2375    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.6542   -1.3292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9375   -0.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6542   -0.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4500   -1.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8292   -1.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8292   -0.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9000    0.0708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6667    0.8708    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4417   -2.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7292    0.0500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5167   -0.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3167   -0.5250    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.7167    0.1833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1542    0.1833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0042    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2417   -1.9125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3542    1.3333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7167   -2.8167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5167   -1.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1542   -2.8292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8792    1.1458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4932    0.4870    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 13  1  0
  9  8  1  0
  5 10  1  6
 11  8  2  0
  3 12  1  0
 13 12  1  0
 14  1  2  0
 15  1  2  0
 16 11  1  0
 17  6  2  0
 18  9  1  0
 19 10  2  0
  3 20  1  6
 21 10  1  0
 22  9  1  0
  5  2  1  0
  6  2  1  0
 16 18  2  0
  4 23  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA302241

   (2S,3R,5R)-3-methyl-3-[(1-methylimidazol-2-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: 345.40

Molecular Weight (Monoisotopic): 345.0453

AlogP: -0.29

#Rotatable Bonds: 4

Polar Surface Area: 109.57

Molecular Species: ACID

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.05

CX Basic pKa: 5.03

CX LogP: -1.53

CX LogD: -3.55

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.59

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