ethyl 3-((2S,5R)-2-carbamoyl-7-oxo-1,6-diazabicyclo[3.2.1]octan-6-yloxysulfonyloxy)-2,2-dimethylpropanoate

ID: ALA4284604

PubChem CID: 135339165

Max Phase: Phase

Molecular Formula: C14H23N3O8S

Molecular Weight: 393.42

Molecule Type: Small molecule

Names and Identifiers

Synonyms: ARX-1796 | PF-07338233

Canonical SMILES:  CCOC(=O)C(C)(C)COS(=O)(=O)ON1C(=O)N2C[C@H]1CC[C@H]2C(N)=O

Standard InChI:  InChI=1S/C14H23N3O8S/c1-4-23-12(19)14(2,3)8-24-26(21,22)25-17-9-5-6-10(11(15)18)16(7-9)13(17)20/h9-10H,4-8H2,1-3H3,(H2,15,18)/t9-,10+/m1/s1

Standard InChI Key:  JHSLCXRZVJOZQZ-ZJUUUORDSA-N

Molfile:  

     RDKit          2D

 27 28  0  0  0  0  0  0  0  0999 V2000
   -2.4899   -3.7117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7466   -3.3538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6849   -2.5311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9416   -2.1731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8800   -1.3504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8183   -0.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0750   -0.1698    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0133    0.6529    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2600   -2.6379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0573   -1.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7026   -1.2888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8093    0.5913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8360    0.7146    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0483    1.4756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7916    1.8336    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7916    2.6586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4366    1.3192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2409    1.5028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5989    2.2461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2409    2.9894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4366    3.1729    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0483    3.0165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8507    2.2916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7553    3.6344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4539    4.4023    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5711    3.5114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5443    0.5012    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  4  9  2  0
  5 10  1  0
  5 11  1  0
  8 12  2  0
  8 13  2  0
  8 14  1  0
 14 15  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 16  1  0
 16 15  1  0
 15 17  1  0
 16 22  2  0
 17 23  1  0
 21 23  1  0
 20 24  1  6
 24 25  1  0
 24 26  2  0
 17 27  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4284604

   AVIBACTAM TOMILOPIL

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: 393.42

Molecular Weight (Monoisotopic): 393.1206

AlogP: -0.48

#Rotatable Bonds: 8

Polar Surface Area: 145.54

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: -0.07

CX LogD: -0.07

Aromatic Rings: ┄

Heavy Atoms: 26

QED Weighted: 0.54

Np Likeness Score: -0.30

References

1. Gordon EM, Duncton MAJ, Gallop MA..  (2018)  Orally Absorbed Derivatives of the β-Lactamase Inhibitor Avibactam. Design of Novel Prodrugs of Sulfate Containing Drugs.,  61  (22): [PMID:30296086] [10.1021/acs.jmedchem.8b01389]

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

3. International Nonproprietary Names for Pharmaceutical Substances (INN), 

Source

Source(3):

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