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(R)-2-(3-tert-butyloxycarbonylamidophenyl)-4,5-dihydrothiazole-4-carboxylic acid

ID: ALA2087635

PubChem CID: 70689034

Max Phase: Preclinical

Molecular Formula: C15H18N2O4S

Molecular Weight: 322.39

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  CC(C)(C)OC(=O)Nc1cccc(C2=N[C@H](C(=O)O)CS2)c1

Standard InChI:  InChI=1S/C15H18N2O4S/c1-15(2,3)21-14(20)16-10-6-4-5-9(7-10)12-17-11(8-22-12)13(18)19/h4-7,11H,8H2,1-3H3,(H,16,20)(H,18,19)/t11-/m0/s1

Standard InChI Key:  YROWLKPEUPIUAV-NSHDSACASA-N

Molfile:  

     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
   -4.5056  -15.5541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5068  -16.3815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7919  -16.7944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0755  -16.3810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0784  -15.5505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7937  -15.1414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3644  -16.7904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2769  -17.6108    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4696  -17.7810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0582  -17.0659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6113  -16.4538    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1329  -18.5342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6168  -19.2024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3123  -18.6191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7962  -14.3164    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0830  -13.9017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0854  -13.0767    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3673  -14.3121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6540  -13.8975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9383  -14.3078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6565  -13.0725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9417  -13.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 11  7  1  0
  4  7  1  0
  5  6  2  0
  9 12  1  1
  6  1  1  0
 12 13  1  0
  7  8  2  0
 12 14  2  0
  1  2  2  0
  6 15  1  0
  3  4  2  0
 15 16  1  0
 16 17  2  0
  4  5  1  0
 16 18  1  0
  2  3  1  0
 18 19  1  0
  8  9  1  0
 19 20  1  0
  9 10  1  0
 19 21  1  0
 10 11  1  0
 19 22  1  0
M  END

Associated Targets(non-human)

blaIMP-1 Beta-lactamase (551 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
bla2 Beta-lactamase II (21 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Biocomponents

Calculated Properties

Molecular Weight: 322.39Molecular Weight (Monoisotopic): 322.0987AlogP: 2.98#Rotatable Bonds: 3
Polar Surface Area: 87.99Molecular Species: ACIDHBA: 5HBD: 2
#RO5 Violations: HBA (Lipinski): 6HBD (Lipinski): 2#RO5 Violations (Lipinski):
CX Acidic pKa: 3.26CX Basic pKa: 1.46CX LogP: 2.78CX LogD: -0.50
Aromatic Rings: 1Heavy Atoms: 22QED Weighted: 0.89Np Likeness Score: -0.52

References

1. Chen P, Horton LB, Mikulski RL, Deng L, Sundriyal S, Palzkill T, Song Y..  (2012)  2-Substituted 4,5-dihydrothiazole-4-carboxylic acids are novel inhibitors of metallo-β-lactamases.,  22  (19): [PMID:22921080] [10.1016/j.bmcl.2012.08.012]

Source