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

ID: ALA70269

Chembl Id: CHEMBL70269

PubChem CID: 44311970

Max Phase: Preclinical

Molecular Formula: C15H13BrN2O4S2

Molecular Weight: 429.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@]1(CSc2nc3ccccc3o2)S[C@@H]2[C@H](Br)C(=O)N2[C@H]1C(=O)O

Standard InChI:  InChI=1S/C15H13BrN2O4S2/c1-15(6-23-14-17-7-4-2-3-5-8(7)22-14)10(13(20)21)18-11(19)9(16)12(18)24-15/h2-5,9-10,12H,6H2,1H3,(H,20,21)/t9-,10+,12-,15+/m1/s1

Standard InChI Key:  XJAMHNGKVYJQKN-HMDURAKOSA-N

Alternative Forms

1. Parent:

   

   ALA70269

   (2S,3R,5R,6R)-3-(1,3-benzoxazol-2-ylsulfanylmethyl)-6-bromo-3-methyl-7-oxo-4-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: 429.32

Molecular Weight (Monoisotopic): 427.9500

AlogP: 2.81

#Rotatable Bonds: 4

Polar Surface Area: 83.64

Molecular Species: ACID

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.38

CX Basic pKa: ┄

CX LogP: 2.92

CX LogD: -0.49

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.45

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