4-(5-(3,5-Dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-((1-hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborol-5-yl)methyl)-2-methylbenzamide

ID: ALA3637905

PubChem CID: 71575882

Max Phase: Preclinical

Molecular Formula: C28H23BCl2F4N2O4

Molecular Weight: 609.21

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(C2=NOC(c3cc(Cl)c(F)c(Cl)c3)(C(F)(F)F)C2)ccc1C(=O)NCc1ccc2c(c1)C(C)(C)OB2O

Standard InChI:  InChI=1S/C28H23BCl2F4N2O4/c1-14-8-16(23-12-27(41-37-23,28(33,34)35)17-10-21(30)24(32)22(31)11-17)5-6-18(14)25(38)36-13-15-4-7-20-19(9-15)26(2,3)40-29(20)39/h4-11,39H,12-13H2,1-3H3,(H,36,38)

Standard InChI Key:  VXKBOWDIIISNFX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 41 45  0  0  0  0  0  0  0  0999 V2000
   -7.2768    5.3801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2396    5.9835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2445    7.4835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9480    8.2378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6465    7.4922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6415    5.9922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9380    5.2378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9300    3.7369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9662    3.1317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6267    2.9927    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6187    1.4919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028   -1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138   -1.2033    0.0000 B   0  0  0  0  0  0  0  0  0  0  0  0
    2.0907   -2.3426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5889    0.0182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138    1.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8955    2.0810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8908    1.4370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028    1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9530    9.7386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1680   10.5963    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7070   12.0237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2070   12.0263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7410   10.6005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8360   13.3747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3303   13.5052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9644   14.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1598   14.9690    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -6.1042   16.0934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6115   17.1809    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6099   15.9629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9217   16.9460    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.9758   14.6035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7300   11.8497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2396   10.7545    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5363   11.7267    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0264   12.8218    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  2  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
 15 22  1  0
 22 23  2  0
 12 23  1  0
  4 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 24 28  1  0
 27 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  1  0
 31 33  2  0
 33 34  1  0
 33 35  1  0
 35 36  1  0
 35 37  2  0
 29 37  1  0
 27 38  1  0
 38 39  1  0
 38 40  1  0
 38 41  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3637905

   4-(5-(3,5-Dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-((1-hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborol-5-yl)methyl)-2-methylbenzamide

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: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 609.21

Molecular Weight (Monoisotopic): 608.1064

AlogP: ┄

#Rotatable Bonds: ┄

Polar Surface Area: ┄

Molecular Species: ┄

HBA: ┄

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): ┄

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: ┄

CX LogD: ┄

Aromatic Rings: ┄

Heavy Atoms: ┄

QED Weighted: ┄

Np Likeness Score: ┄

References

1. MMV Pathogen Box,  [10.6019/CHEMBL3637841]

2. Nathan group, Weill Cornell Medical College; Barry Lab, NIAID NIH; Winzeler lab, UCSD; Laboratory of Microbiology, Parasitology and Hygiene (LMPH), Univ. of Antwerp; London School of Hygiene and Tropical Medicine; Parasite Chemotherapy Unit at Swiss Tropical and Public Health Institute; Huston group at the University of Vermont; Castellanos group at UTMB, Galveston, Texas; Sakanari Lab, Univ. of Calif. San Francisco; Townson (Simon) Lab, Imperial College London; Fidelis Cho-Ngwa Lab, University of Buea, Buea, Cameroon; Laboratory of Molecular Parasitology at the New York Blood Center; Bickle Lab, London School of Hygiene and Tropical Medicine; Keiser Lab, Swiss Tropical and Public Health Institute; Caffrey group at the Center for Discovery and Innovation in Parasitic Diseases, Skaggs School of Pharmacy and Pharmaceutical Sciences, UC San Diego; University of Cape Town; Shanmugam group at CSIR-National Chemical Laboratory, Pune (India); Novartis Institute for Tropical Disease-Singapore; Abbvie. MMV Pathogen Box Bioactivity Data,  [10.6019/CHEMBL3832761]

3. Anna Ehmann. The Australian National University Dept Of Immunology Pathogen Box Compounds Screened,  [10.6019/CHEMBL3987221]

4. Veale CGL, Hoppe HC..  (2018)  Screening of the Pathogen Box reveals new starting points for anti-trypanosomal drug discovery.,  9  (12): [PMID:30647879] [10.1039/C8MD00319J]

5. Sarink, M; Mykytyn, A; Tielens, A; van Hellemond, J. Naegleria gruberi Pathogen Box compounds screening,  [10.6019/CHEMBL4513101]

6. Johannes Zuegg, Alysha Elliott, Maite Amado, Emma Cowie, Ali Hinton, Geraldine Kaeslin, Angela Kavanagh, Anne Kunert, Gabriell Lowe, Soumya Ramu, Janet Reid, Robin Trauer, Mathilde Desselle, Ruth Neale, Karl Hansford, Mark Blascovich, Matthew Cooper. CO-ADD screening of MMV (CH) - MMV compounds,  [10.6019/CHEMBL4513149]

Source

Source(3):

• Scientific Literature
• MMV Pathogen Box
• CO-ADD antimicrobial screening data