(R)-3-(2-(5-amino-1,3,4-thiadiazol-2-ylthio)acetamido)-2-hydroxy-3,4-dihydro-2H-benzo[e][1,2]oxaborinine-8-carboxylic acid

ID: ALA4636953

PubChem CID: 76900728

Max Phase: Preclinical

Molecular Formula: C13H13BN4O5S2

Molecular Weight: 380.22

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Nc1nnc(SCC(=O)N[C@H]2Cc3cccc(C(=O)O)c3OB2O)s1

Standard InChI:  InChI=1S/C13H13BN4O5S2/c15-12-17-18-13(25-12)24-5-9(19)16-8-4-6-2-1-3-7(11(20)21)10(6)23-14(8)22/h1-3,8,22H,4-5H2,(H2,15,17)(H,16,19)(H,20,21)/t8-/m0/s1

Standard InChI Key:  IUNQEXJRZWMEMG-QMMMGPOBSA-N

Molfile:  

 
     RDKit          2D

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    8.8856   -3.7997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5953   -3.3903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5925   -2.5676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8839   -2.1624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1776   -3.3908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1817   -2.5712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4779   -2.1601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7655   -2.5641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7614   -3.3836    0.0000 B   0  0  0  0  0  0  0  0  0  0  0  0
    7.4697   -3.7993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0604   -2.1510    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3501   -2.5550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6450   -2.1419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3449   -3.3722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9347   -2.5460    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.2297   -2.1328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8854   -4.6169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1776   -5.0253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5931   -5.0257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0512   -3.7880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1503   -1.3174    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3520   -1.1424    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9389   -1.8475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4819   -2.4582    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.1257   -1.9278    0.0000 N   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
  8 11  1  1
 11 12  1  0
 12 13  1  0
 12 14  2  0
 13 15  1  0
 15 16  1  0
  1 17  1  0
 17 18  1  0
 17 19  2  0
  9 20  1  0
 16 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 16  1  0
 23 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4636953

   (3R)-3-[[2-[(5-amino-1,3,4-thiadiazol-2-yl)sulfanyl]acetyl]amino]-2-hydroxy-3,4-dihydro-1,2-benzoxaborinine-8-carboxylic acid

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: 380.22

Molecular Weight (Monoisotopic): 380.0420

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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