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

ID: ALA302512

PubChem CID: 14556048

Max Phase: Preclinical

Molecular Formula: C10H13N5O5S2

Molecular Weight: 347.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1nnnc1SC[C@@]1(C)[C@H](C(=O)O)N2C(=O)C[C@H]2S1(=O)=O

Standard InChI:  InChI=1S/C10H13N5O5S2/c1-10(4-21-9-11-12-13-14(9)2)7(8(17)18)15-5(16)3-6(15)22(10,19)20/h6-7H,3-4H2,1-2H3,(H,17,18)/t6-,7+,10+/m1/s1

Standard InChI Key:  XQHZBWNBBIUYCN-FWWHASMVSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  1  0  0  0  0  0999 V2000
    4.4792   -1.9375    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.7000   -3.0292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9792   -2.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7000   -2.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4917   -3.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8667   -3.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9417   -1.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7125   -0.8292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8667   -2.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7667   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0500   -0.8750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3917   -0.3667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4875   -4.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5542   -2.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3625   -2.2250    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.0625   -1.2167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1917   -1.5167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2792   -3.6125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7625   -4.5167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5542   -3.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1917   -4.5292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9250   -0.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5382   -1.2132    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  9  1  0
  7 15  1  0
  8  7  1  0
  9  4  1  0
 10  7  2  0
 11 10  1  0
 12  8  1  0
  5 13  1  6
  3 14  1  0
 15 14  1  0
 16  1  2  0
 17  1  2  0
 18  6  2  0
 19 13  2  0
  3 20  1  6
 21 13  1  0
 22  8  1  0
  5  2  1  0
  6  2  1  0
 11 12  2  0
  4 23  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA302512

   (2S,3R,5R)-3-methyl-3-[(1-methyltetrazol-5-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: 347.38

Molecular Weight (Monoisotopic): 347.0358

AlogP: -1.50

#Rotatable Bonds: 4

Polar Surface Area: 135.35

Molecular Species: ACID

HBA: 9

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.82

CX Basic pKa: ┄

CX LogP: -1.01

CX LogD: -4.51

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.51

Np Likeness Score: -1.04

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