(S)-2-(3-fluoro-1-(methylsulfonyl)-10-(4-(trifluoromethyl)phenylthio)-6,7,8,9-tetrahydropyrido[1,2-a]indol-9-yl)acetic acid

ID: ALA4228478

PubChem CID: 145970031

Max Phase: Preclinical

Molecular Formula: C22H19F4NO4S2

Molecular Weight: 501.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CS(=O)(=O)c1cc(F)cc2c1c(Sc1ccc(C(F)(F)F)cc1)c1n2CCC[C@H]1CC(=O)O

Standard InChI:  InChI=1S/C22H19F4NO4S2/c1-33(30,31)17-11-14(23)10-16-19(17)21(20-12(9-18(28)29)3-2-8-27(16)20)32-15-6-4-13(5-7-15)22(24,25)26/h4-7,10-12H,2-3,8-9H2,1H3,(H,28,29)/t12-/m0/s1

Standard InChI Key:  BLIQTLNMKLWHCK-LBPRGKRZSA-N

Molfile:  

     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
   20.8168  -24.4377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2011  -24.7149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4289  -24.9767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3614  -23.9145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.8175  -25.2541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8367  -26.1542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0195  -26.1542    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   18.4281  -26.8620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0201  -25.3398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5586  -26.1329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1007  -25.5275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1506  -26.4764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5113  -25.1838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3140  -24.9312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7605  -25.9601    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   18.7292  -24.1090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3150  -24.1084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7294  -24.9312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6090  -23.7004    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   20.8079  -26.9115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6052  -27.0803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0183  -23.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8974  -25.6969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9486  -26.6440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3127  -26.5648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4940  -26.0354    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   23.2031  -27.4206    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   23.7357  -26.8517    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   19.5090  -23.8524    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.9964  -24.5235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1562  -23.6812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6687  -23.0101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8419  -23.0951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  5  1  0
  1  3  1  1
  2  4  2  0
  7  6  2  0
  8  7  2  0
 29 16  1  0
 17 14  2  0
 10 20  2  0
 18 13  1  0
 16 18  1  0
 21 12  2  0
 13 15  1  0
 22 17  1  0
 23 11  2  0
 13 30  2  0
 11 10  1  0
  9 18  2  0
 17 19  1  0
 12 23  1  0
 20 21  1  0
  9  7  1  0
 14  9  1  0
 15 10  1  0
 12 24  1  0
 16 22  2  0
  7 25  1  0
 24 26  1  0
 24 27  1  0
 24 28  1  0
 29 30  1  0
 29 33  1  0
 30  1  1  0
  1 31  1  0
 31 32  1  0
 32 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4228478

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 501.52

Molecular Weight (Monoisotopic): 501.0692

AlogP: 5.71

#Rotatable Bonds: 5

Polar Surface Area: 76.37

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.83

CX Basic pKa: ┄

CX LogP: 4.53

CX LogD: 1.28

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.45

Np Likeness Score: -1.07

References

1. Stachel SJ, Egbertson MS, Wai J, Machacek M, Toolan DM, Swestock J, Eddins DM, Puri V, McGaughey G, Su HP, Perlow D, Wang D, Ma L, Parthasarathy G, Reid JC, Abeywickrema PD, Smith SM, Uslaner JM..  (2018)  Indole acids as a novel PDE2 inhibitor chemotype that demonstrate pro-cognitive activity in multiple species.,  28  (6): [PMID:29534798] [10.1016/j.bmcl.2018.01.039]

Source

Source(1):

• Scientific Literature