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

ID: ALA309009

Chembl Id: CHEMBL309009

PubChem CID: 44311630

Max Phase: Preclinical

Molecular Formula: C15H14N2O6S2

Molecular Weight: 382.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@]1(CSc2nc3ccccc3o2)[C@H](C(=O)O)N2C(=O)C[C@H]2S1(=O)=O

Standard InChI:  InChI=1S/C15H14N2O6S2/c1-15(7-24-14-16-8-4-2-3-5-9(8)23-14)12(13(19)20)17-10(18)6-11(17)25(15,21)22/h2-5,11-12H,6-7H2,1H3,(H,19,20)/t11-,12+,15+/m1/s1

Standard InChI Key:  QOMLCKUMUUKMOX-XUJVJEKNSA-N

Alternative Forms

1. Parent:

   

   ALA309009

   (2S,3R,5R)-3-(1,3-benzoxazol-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: 382.42

Molecular Weight (Monoisotopic): 382.0293

AlogP: 1.12

#Rotatable Bonds: 4

Polar Surface Area: 117.78

Molecular Species: ACID

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.53

CX Basic pKa: ┄

CX LogP: 0.95

CX LogD: -2.41

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.62

Np Likeness Score: -0.44

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