2-((R)-5'-Chloro-3-((S)-1-(4-chlorophenyl)ethyl)-2',5-dioxo-3,4,5,6-tetrahydrospiro[[1,2,3]triazolo[4,5-b]pyridine-7,3'-indolin]-1'-yl)acetic acid

ID: ALA4532280

PubChem CID: 155546476

Max Phase: Preclinical

Molecular Formula: C22H17Cl2N5O4

Molecular Weight: 486.32

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C22H17Cl2N5O4/c1-11(12-2-4-13(23)5-3-12)29-20-19(26-27-29)22(9-17(30)25-20)15-8-14(24)6-7-16(15)28(21(22)33)10-18(31)32/h2-8,11H,9-10H2,1H3,(H,25,30)(H,31,32)/t11-,22+/m0/s1

Standard InChI Key:  HCCBGDROFJNASJ-KPWVOAKYSA-N

Molfile:  

 
     RDKit          2D

 33 37  0  0  0  0  0  0  0  0999 V2000
   20.6522  -16.2860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4509  -16.5501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4498  -17.3738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1620  -17.7869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1602  -16.1413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8729  -16.5465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8777  -17.3693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6619  -17.6219    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.1392  -16.9526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9428  -15.0603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9428  -15.8816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6522  -14.6434    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.3616  -15.0603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3660  -15.8780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1454  -16.1253    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.6201  -15.4602    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.1382  -14.8005    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.9605  -16.9479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2297  -14.6496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7390  -16.1417    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   22.8401  -14.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8333  -13.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5553  -14.7903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5449  -13.1508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5385  -12.3303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8228  -11.9267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1161  -12.3456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1260  -13.1647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8149  -11.1055    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   20.6568  -18.4363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3619  -18.8494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3568  -19.6665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0722  -18.4452    0.0000 O   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  2  0
 31 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4532280

   ---

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: 486.32

Molecular Weight (Monoisotopic): 485.0658

AlogP: 3.25

#Rotatable Bonds: 4

Polar Surface Area: 117.42

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.27

CX Basic pKa: ┄

CX LogP: 3.10

CX LogD: -0.33

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.58

Np Likeness Score: -0.95

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