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

ID: ALA4536890

PubChem CID: 155548509

Max Phase: Preclinical

Molecular Formula: C22H18Cl2FN5O2

Molecular Weight: 474.32

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C22H18Cl2FN5O2/c1-12(13-2-4-14(23)5-3-13)30-20-19(27-28-30)22(11-18(31)26-20)16-10-15(24)6-7-17(16)29(9-8-25)21(22)32/h2-7,10,12H,8-9,11H2,1H3,(H,26,31)/t12-,22+/m0/s1

Standard InChI Key:  JZSKZJDKCGXEOZ-AMXDTQDGSA-N

Molfile:  

 
     RDKit          2D

 32 36  0  0  0  0  0  0  0  0999 V2000
   28.7581  -16.0632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5568  -16.3273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5557  -17.1509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2678  -17.5640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2661  -15.9184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9788  -16.3237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9836  -17.1464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7678  -17.3990    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.2451  -16.7297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0486  -14.8374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0486  -15.6587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7581  -14.4205    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.4675  -14.8374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4719  -15.6552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2513  -15.9024    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.7260  -15.2373    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.2440  -14.5776    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.0664  -16.7250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.3356  -14.4267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.8449  -15.9189    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   30.9460  -14.1646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9392  -13.3434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6611  -14.5674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6507  -12.9280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6443  -12.1074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9286  -11.7039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2220  -12.1227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2319  -12.9419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9208  -10.8826    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   28.7627  -18.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4678  -18.6265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4627  -19.4437    0.0000 F   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
M  END

Alternative Forms

1. Parent:

   

   ALA4536890

   ---

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: 474.32

Molecular Weight (Monoisotopic): 473.0822

AlogP: 4.14

#Rotatable Bonds: 4

Polar Surface Area: 80.12

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.06

CX Basic pKa: ┄

CX LogP: 3.83

CX LogD: 3.83

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.62

Np Likeness Score: -1.08

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