1'-[[1-(2-methylsulfonylethyl)indol-2-yl]methyl]spiro[cyclopropane-1,3'-pyrrolo[2,3-c]pyridine]-2'-one

ID: ALA4526386

PubChem CID: 86292718

Max Phase: Preclinical

Molecular Formula: C21H21N3O3S

Molecular Weight: 395.48

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CS(=O)(=O)CCn1c(CN2C(=O)C3(CC3)c3ccncc32)cc2ccccc21

Standard InChI:  InChI=1S/C21H21N3O3S/c1-28(26,27)11-10-23-16(12-15-4-2-3-5-18(15)23)14-24-19-13-22-9-6-17(19)21(7-8-21)20(24)25/h2-6,9,12-13H,7-8,10-11,14H2,1H3

Standard InChI Key:  KHHLCYXJSGSSBR-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 28 32  0  0  0  0  0  0  0  0999 V2000
    7.4461   -6.1672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6248   -6.1672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0333   -6.8749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4565   -5.3683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6447   -5.2862    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2358   -4.5787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4186   -4.5790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9376   -5.2415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1590   -4.9887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4519   -5.4022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7397   -4.9932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7408   -4.1737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4501   -3.7648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1587   -4.1701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9372   -3.9169    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1894   -3.1396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9887   -2.9695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2380   -2.1885    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.5281   -1.7799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2369   -1.3694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0402   -2.0220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3136   -6.0288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9192   -6.5764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7513   -7.3710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9787   -7.6249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3681   -7.0782    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5386   -6.2799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0027   -4.7605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  1  3  1  0
  2  4  1  0
  4  5  1  0
  6  5  1  0
  7  6  1  0
  8  7  2  0
  9  8  1  0
 10  9  2  0
 11 10  1  0
 12 11  2  0
 13 12  1  0
 14 13  2  0
 14  9  1  0
 15 14  1  0
  7 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 20 18  2  0
 18 21  1  0
  5 22  1  0
 23 22  2  0
 23  2  1  0
 24 23  1  0
 25 24  2  0
 26 25  1  0
 27 26  2  0
 22 27  1  0
  4 28  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4526386

   US10189838, Example 1-1

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: 395.48

Molecular Weight (Monoisotopic): 395.1304

AlogP: 2.66

#Rotatable Bonds: 5

Polar Surface Area: 72.27

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.23

CX LogP: 1.00

CX LogD: 1.00

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.67

Np Likeness Score: -0.78

References

1. Zheng X, Liang C, Wang L, Miao K, Wang B, Zhang W, Chen D, Wu G, Zhu W, Guo L, Feng S, Gao L, Shen HC, Yun H..  (2019)  Discovery of (aza)indole derivatives as novel respiratory syncytial virus fusion inhibitors.,  10  (6): [PMID:31303995] [10.1039/C9MD00178F]

Source

Source(1):

• Scientific Literature