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

ID: ALA4790021

PubChem CID: 57524865

Max Phase: Preclinical

Molecular Formula: C19H19ClN2O4S

Molecular Weight: 406.89

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C19H19ClN2O4S/c1-19(18(23)26-2,13-7-9-14(20)10-8-13)22-12-11-15-16(21-27(3,24)25)5-4-6-17(15)22/h4-12,21H,1-3H3

Standard InChI Key:  RREBBWCGJCVMTA-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   18.7417   -6.9461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.5589   -6.9461    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   19.1503   -6.2384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.5616   -4.4945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5605   -5.3141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2685   -5.7230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2668   -4.0857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9754   -4.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9756   -5.3141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7586   -5.5683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2423   -4.9021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7582   -4.2364    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.0105   -3.4591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8097   -3.2889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4635   -2.8520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7157   -2.0747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6642   -3.0221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.1172   -2.4150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3537   -3.9008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1524   -3.7312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4053   -2.9532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8535   -2.3447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0570   -2.5175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2688   -6.5402    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.5614   -7.7662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2044   -2.7820    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   22.5842   -4.0364    0.0000 C   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
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 14 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 14  1  0
  6 24  1  0
 24  2  1  0
  2 25  1  0
 21 26  1  0
 13 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4790021

   Methyl 2-(4-chlorophenyl)-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: 406.89

Molecular Weight (Monoisotopic): 406.0754

AlogP: 3.60

#Rotatable Bonds: 5

Polar Surface Area: 77.40

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.57

CX Basic pKa: ┄

CX LogP: 3.27

CX LogD: 3.24

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.66

Np Likeness Score: -1.08

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