2-{4-[(1R)-1-[(4-chloro-5-fluoro-1,6-dimethyl-1H-indol-2-yl)formamido]ethyl]benzenesulfonyl}acetic acid

ID: ALA4548014

PubChem CID: 142427709

Max Phase: Preclinical

Molecular Formula: C21H20ClFN2O5S

Molecular Weight: 466.92

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1cc2c(cc(C(=O)N[C@H](C)c3ccc(S(=O)(=O)CC(=O)O)cc3)n2C)c(Cl)c1F

Standard InChI:  InChI=1S/C21H20ClFN2O5S/c1-11-8-16-15(19(22)20(11)23)9-17(25(16)3)21(28)24-12(2)13-4-6-14(7-5-13)31(29,30)10-18(26)27/h4-9,12H,10H2,1-3H3,(H,24,28)(H,26,27)/t12-/m1/s1

Standard InChI Key:  XUHCJICQDVKJTB-GFCCVEGCSA-N

Molfile:  

 
     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
   16.0036   -6.5705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0077   -5.7456    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.2912   -6.1545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5857   -3.2248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5846   -4.0522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2993   -4.4650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2975   -2.8121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0129   -3.2212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0178   -4.0476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8052   -4.2984    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2871   -3.6270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7973   -2.9613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1120   -3.6221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5287   -4.3341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5203   -2.9053    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.3452   -2.9003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7535   -2.1835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7620   -3.6124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3507   -4.3288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7667   -5.0403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5926   -5.0359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0007   -4.3140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5823   -3.6054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8351   -5.7413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2528   -6.4528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0777   -6.4469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8455   -7.1702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0646   -5.0815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2951   -1.9871    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.8698   -4.4641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8711   -2.8125    0.0000 F   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  1  0
 11 12  2  0
 12  8  1  0
 11 13  1  0
 13 14  2  0
 13 15  1  0
 16 15  1  6
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 21  2  1  0
  2 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  2  0
 10 28  1  0
  7 29  1  0
  5 30  1  0
  4 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4548014

   ---

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: 466.92

Molecular Weight (Monoisotopic): 466.0765

AlogP: 3.63

#Rotatable Bonds: 6

Polar Surface Area: 105.47

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.22

CX Basic pKa: ┄

CX LogP: 3.47

CX LogD: 0.02

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.58

Np Likeness Score: -1.33

References

1.  (2018)  Tosylacetate based compounds and derivatives thereof as phgdh inhibitors, 

Source

Source(1):

• Patent Bioactivity Data