Rac-methyl 2-(4-chlorophenyl)-3-cyano-2-[4-(methanesulfonamido)indol-1-yl]propanoate

ID: ALA4777170

PubChem CID: 57524935

Max Phase: Preclinical

Molecular Formula: C20H18ClN3O4S

Molecular Weight: 431.90

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COC(=O)C(CC#N)(c1ccc(Cl)cc1)n1ccc2c(NS(C)(=O)=O)cccc21

Standard InChI:  InChI=1S/C20H18ClN3O4S/c1-28-19(25)20(11-12-22,14-6-8-15(21)9-7-14)24-13-10-16-17(23-29(2,26)27)4-3-5-18(16)24/h3-10,13,23H,11H2,1-2H3

Standard InChI Key:  TYRNKDZXXKSBNZ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   -1.9535   -2.2902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1363   -2.2902    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5449   -1.5825    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1336    0.1614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1348   -0.6581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4267   -1.0671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4285    0.5703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2801    0.1650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2804   -0.6582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0634   -0.9124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5471   -0.2462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0629    0.4195    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4265   -1.8843    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1339   -3.1103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0552    1.2386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3437    1.6405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3360    2.4576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3601    1.2253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0716    1.6272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2657    2.0310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8435    1.0281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0530    0.2384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8405    0.0278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4179    0.6055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2024    1.3968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4153    1.6038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2077    0.3957    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.0546    2.2442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8425    2.4587    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  2  0
  5  6  1  0
  6  9  2  0
  8  7  2  0
  7  4  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12  8  1  0
  6 13  1  0
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  2 14  1  0
 12 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 15 20  1  0
 15 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 24 27  1  0
 20 28  1  0
 28 29  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA4777170

   Methyl 2-(4-chlorophenyl)-3-cyano-2-[4-(methanesulfonamido)indol-1-yl]propanoate

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: 431.90

Molecular Weight (Monoisotopic): 431.0707

AlogP: 3.50

#Rotatable Bonds: 6

Polar Surface Area: 101.19

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.57

CX Basic pKa: ┄

CX LogP: 2.68

CX LogD: 2.66

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.60

Np Likeness Score: -1.16

References

1. Ogawa AK,Bunte EV,Mal R,Lan P,Sun Z,Crespo A,Wiltsie J,Clemas J,Gibson J,Contino L,Lisnock J,Zhou G,Garcia-Calvo M,Jochnowitz N,Ma X,Pan Y,Brown P,Zamlynny B,Bateman T,Leung D,Xu L,Tong X,Liu K,Crook M,Sinclair P.  (2016)  Discovery of novel non-steroidal reverse indole mineralocorticoid receptor antagonists.,  26  (12.0): [PMID:27161805] [10.1016/j.bmcl.2016.04.052]

Source

Source(1):

• Scientific Literature