(2S,5R,6R)-6-Bromo-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid

ID: ALA73622

Cas Number: 26631-90-3

PubChem CID: 65754

Max Phase: Phase

Molecular Formula: C8H10BrNO3S

Molecular Weight: 280.14

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 6-bromopenicillanic acid | Brobactam | Sulbactam related compound d | Brobactam|26631-90-3|6-Bromopenicillanic acid|Brobactam [INN]|6I6JCF8EOE|(2S,5R,6R)-6-Bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid|(2S,5R,6R)-6-bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid|Brobactamum|4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-bromo-3,3-dimethyl-7-oxo-, (2S,5R,6R)-|Brobactamum [Latin]|UNII-6I6JCF8EOE|EINECS 247-856-3|SULBACTAM SODIUM IShow More⌵

Canonical SMILES:  CC1(C)S[C@@H]2[C@H](Br)C(=O)N2[C@H]1C(=O)O

Standard InChI:  InChI=1S/C8H10BrNO3S/c1-8(2)4(7(12)13)10-5(11)3(9)6(10)14-8/h3-4,6H,1-2H3,(H,12,13)/t3-,4+,6-/m1/s1

Standard InChI Key:  DAVPSCAAXXVSFU-ALEPSDHESA-N

Molfile:  

     RDKit          2D

 15 16  0  0  1  0  0  0  0  0999 V2000
   -0.4833    0.1458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4833   -1.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9125    0.1458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8917    0.5833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9125   -1.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8917   -1.7292    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.7375   -0.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0792    1.4208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9125    1.1750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2875   -0.9417    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.9542    2.8333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3667    0.8000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9542    0.1458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9000   -1.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6367   -2.2799    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  1  1  0
  5  3  1  0
  6  2  1  0
  7  4  1  0
  4  8  1  1
  9  3  2  0
  5 10  1  6
 11  8  2  0
 12  8  1  0
 13  7  1  0
 14  7  1  0
  6  7  1  0
  2  5  1  0
  2 15  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA73622

   BROBACTAM

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 280.14

Molecular Weight (Monoisotopic): 278.9565

AlogP: 0.90

#Rotatable Bonds: 1

Polar Surface Area: 57.61

Molecular Species: ACID

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.97

CX Basic pKa: ┄

CX LogP: 1.07

CX LogD: -2.40

Aromatic Rings: ┄

Heavy Atoms: 14

QED Weighted: 0.57

Np Likeness Score: 0.99

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]

2. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

Source

Source(2):

• Scientific Literature
• USP Dictionary of USAN and International Drug Names