(3aS,9bS)-2-(Benzo[d][1,3]dioxol-5-ylsulfonyl)-5-methyl-3,3a,5,9b-tetrahydro-1H-pyrrolo[3,4-c]quinolin-4(2H)-one

ID: ALA4083687

PubChem CID: 137647959

Max Phase: Preclinical

Molecular Formula: C19H18N2O5S

Molecular Weight: 386.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1C(=O)[C@@H]2CN(S(=O)(=O)c3ccc4c(c3)OCO4)C[C@@H]2c2ccccc21

Standard InChI:  InChI=1S/C19H18N2O5S/c1-20-16-5-3-2-4-13(16)14-9-21(10-15(14)19(20)22)27(23,24)12-6-7-17-18(8-12)26-11-25-17/h2-8,14-15H,9-11H2,1H3/t14-,15-/m1/s1

Standard InChI Key:  FQODOKMLFCFEMH-HUUCEWRRSA-N

Molfile:  

     RDKit          2D

 29 33  0  0  0  0  0  0  0  0999 V2000
   18.9192   -4.6638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6291   -5.0724    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   19.6280   -4.2533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1113   -7.0947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1101   -7.9142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8182   -8.3232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8164   -6.6858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5250   -7.0911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5284   -7.9163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2340   -6.6733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9475   -7.0848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5594   -6.5335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2241   -5.7811    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.4050   -5.8676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9543   -7.9104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2387   -8.3236    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.6497   -7.4909    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.5201   -6.2610    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.4496   -5.0728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8581   -5.7851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6750   -4.3619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8566   -4.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0893   -5.0751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6783   -5.7841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2256   -6.3942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.9750   -6.0621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8906   -5.2469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2400   -9.1408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6637   -8.3161    0.0000 O   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
  8 10  1  0
  9 16  1  0
 15 11  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 10  1  0
 15 16  1  0
 11 17  1  6
 10 18  1  6
 13  2  1  0
  2 19  1  0
 19 20  2  0
 20 24  1  0
 23 21  1  0
 21 22  2  0
 22 19  1  0
 23 24  2  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 23  1  0
 16 28  1  0
 15 29  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4083687

   ---

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: 386.43

Molecular Weight (Monoisotopic): 386.0936

AlogP: 1.80

#Rotatable Bonds: 2

Polar Surface Area: 76.15

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 1.26

CX LogD: 1.26

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.79

Np Likeness Score: -0.71

References

1. Bregman H, Simard JR, Andrews KL, Ayube S, Chen H, Gunaydin H, Guzman-Perez A, Hu J, Huang L, Huang X, Krolikowski PH, Lehto SG, Lewis RT, Michelsen K, Pegman P, Plant MH, Shaffer PL, Teffera Y, Yi S, Zhang M, Gingras J, DiMauro EF..  (2017)  The Discovery and Hit-to-Lead Optimization of Tricyclic Sulfonamides as Potent and Efficacious Potentiators of Glycine Receptors.,  60  (3): [PMID:28001399] [10.1021/acs.jmedchem.6b01496]

2. Chakka N, Andrews KL, Berry LM, Bregman H, Gunaydin H, Huang L, Guzman-Perez A, Plant MH, Simard JR, Gingras J, DiMauro EF..  (2017)  Applications of parallel synthetic lead hopping and pharmacophore-based virtual screening in the discovery of efficient glycine receptor potentiators.,  137  [PMID:28575722] [10.1016/j.ejmech.2017.05.036]

Source

Source(1):

• Scientific Literature