(3R)-7-(cyclopropylmethoxy)-2-hydroxy-3-(1,3,4-thiadiazol-2-ylsulfanyl)-3,4-dihydro-1,2-benzoxaborinine-8-carboxylic acid

ID: ALA4649813

PubChem CID: 140786594

Max Phase: Preclinical

Molecular Formula: C15H15BN2O5S2

Molecular Weight: 378.24

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)c1c(OCC2CC2)ccc2c1OB(O)[C@@H](Sc1nncs1)C2

Standard InChI:  InChI=1S/C15H15BN2O5S2/c19-14(20)12-10(22-6-8-1-2-8)4-3-9-5-11(16(21)23-13(9)12)25-15-18-17-7-24-15/h3-4,7-8,11,21H,1-2,5-6H2,(H,19,20)/t11-/m0/s1

Standard InChI Key:  KMEJHJKNWMYMEG-NSHDSACASA-N

Molfile:  

 
     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
   15.0847   -2.8340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7944   -2.4245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7916   -1.6019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0830   -1.1966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3767   -2.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3808   -1.6054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6770   -1.1944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9646   -1.5983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9605   -2.4179    0.0000 B   0  0  0  0  0  0  0  0  0  0  0  0
   13.6688   -2.8335    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0845   -3.6511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3767   -4.0596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7922   -4.0599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2503   -2.8222    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2595   -1.1852    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.5492   -1.5892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8079   -1.2488    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.2572   -1.8526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6613   -2.5629    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4616   -2.3980    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.5028   -2.8320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2098   -2.4223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9182   -2.8298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3254   -3.5359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7329   -2.8275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  6  1  0
  5  6  2  0
  5 10  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  1 11  1  0
 11 12  1  0
 11 13  2  0
  9 14  1  0
  8 15  1  1
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 16  2  0
  2 21  1  0
 21 22  1  0
 22 23  1  0
 24 23  1  0
 25 24  1  0
 23 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4649813

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 378.24

Molecular Weight (Monoisotopic): 378.0515

AlogP: ┄

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#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

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CX LogD: ┄

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QED Weighted: ┄

Np Likeness Score: ┄

References

1. Hecker SJ, Reddy KR, Lomovskaya O, Griffith DC, Rubio-Aparicio D, Nelson K, Tsivkovski R, Sun D, Sabet M, Tarazi Z, Parkinson J, Totrov M, Boyer SH, Glinka TW, Pemberton OA, Chen Y, Dudley MN..  (2020)  Discovery of Cyclic Boronic Acid QPX7728, an Ultrabroad-Spectrum Inhibitor of Serine and Metallo-β-lactamases.,  63  (14): [PMID:32150407] [10.1021/acs.jmedchem.9b01976]

Source

Source(1):

• Scientific Literature