(R)-1'-(3-Bromopropyl)-5'-chloro-3-((S)-1-(4-chlorophenyl)-ethyl)-4,6-dihydrospiro[[1,2,3]triazolo[4,5-b]pyridine-7,3'-indoline]-2',5(3H)-dione

ID: ALA4554332

PubChem CID: 155556178

Max Phase: Preclinical

Molecular Formula: C23H20BrCl2N5O2

Molecular Weight: 549.26

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C[C@@H](c1ccc(Cl)cc1)n1nnc2c1NC(=O)C[C@]21C(=O)N(CCCBr)c2ccc(Cl)cc21

Standard InChI:  InChI=1S/C23H20BrCl2N5O2/c1-13(14-3-5-15(25)6-4-14)31-21-20(28-29-31)23(12-19(32)27-21)17-11-16(26)7-8-18(17)30(22(23)33)10-2-9-24/h3-8,11,13H,2,9-10,12H2,1H3,(H,27,32)/t13-,23+/m0/s1

Standard InChI Key:  UJLLVCVBQJULNN-ZAMGYDSWSA-N

Molfile:  

 
     RDKit          2D

 33 37  0  0  0  0  0  0  0  0999 V2000
   35.9023  -16.1581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7011  -16.4222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6999  -17.2459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4121  -17.6590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4103  -16.0133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1230  -16.4186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1278  -17.2413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9120  -17.4939    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.3894  -16.8247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1929  -14.9323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1929  -15.7536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9023  -14.5155    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.6117  -14.9323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6162  -15.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3955  -15.9973    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.8702  -15.3323    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.3883  -14.6726    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.2107  -16.8200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.4798  -14.5217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.9891  -16.0138    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   38.0902  -14.2596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.0835  -13.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8054  -14.6623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7950  -13.0229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7886  -12.2024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.0729  -11.7988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3662  -12.2176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3761  -13.0368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.0650  -10.9775    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   35.9069  -18.3084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6120  -18.7214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3223  -18.3173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.0274  -18.7303    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  7  2  0
  6  5  2  0
  5  2  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  1  9  1  1
  1  6  1  0
 10 11  1  0
 10 12  1  0
 11  1  1  0
  1 14  1  0
 13 12  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 13  1  0
  9 18  2  0
 10 19  2  0
  2 20  1  0
 17 21  1  0
 21 22  1  0
 21 23  1  6
 22 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 22  1  0
 26 29  1  0
  8 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4554332

   ---

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: 549.26

Molecular Weight (Monoisotopic): 547.0177

AlogP: 4.95

#Rotatable Bonds: 5

Polar Surface Area: 80.12

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.06

CX Basic pKa: ┄

CX LogP: 4.54

CX LogD: 4.54

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.46

Np Likeness Score: -1.00

References

1. Xu J, Xie X, Ye N, Zou J, Chen H, White MA, Shi PY, Zhou J..  (2019)  Design, Synthesis, and Biological Evaluation of Substituted 4,6-Dihydrospiro[[1,2,3]triazolo[4,5-b]pyridine-7,3'-indoline]-2',5(3H)-dione Analogues as Potent NS4B Inhibitors for the Treatment of Dengue Virus Infection.,  62  (17): [PMID:31403780] [10.1021/acs.jmedchem.9b00698]

Source

Source(1):

• Scientific Literature