(S)-3a-hydroxy-8-methyl-1-phenyl-3,3a-dihydro-1H-pyrrolo[2,3-b]quinolin-4(2H)-one

ID: ALA4172286

PubChem CID: 24887899

Max Phase: Preclinical

Molecular Formula: C18H16N2O2

Molecular Weight: 292.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cccc2c1N=C1N(c3ccccc3)CC[C@@]1(O)C2=O

Standard InChI:  InChI=1S/C18H16N2O2/c1-12-6-5-9-14-15(12)19-17-18(22,16(14)21)10-11-20(17)13-7-3-2-4-8-13/h2-9,22H,10-11H2,1H3/t18-/m1/s1

Standard InChI Key:  PGAGXFLEDIYPCD-GOSISDBHSA-N

Molfile:  

     RDKit          2D

 22 25  0  0  0  0  0  0  0  0999 V2000
   34.0523   -2.4804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0512   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7592   -3.7089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7575   -2.0716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4661   -2.4768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4649   -3.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1750   -3.7134    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.1774   -2.0630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1774   -1.2458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.8920   -2.4789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8888   -3.3022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6708   -3.5597    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.1574   -2.8955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6760   -2.2276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9202   -4.3379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3689   -4.9423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6178   -5.7199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4172   -5.8936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.9673   -5.2836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7156   -4.5084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8850   -1.6591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.7590   -4.5261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5  8  1  0
  6  7  1  0
  7 11  2  0
 10  8  1  0
  8  9  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 10  1  0
 12 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 10 21  1  1
  3 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4172286

   (3aS)-3a-hydroxy-8-methyl-1-phenyl-2,3-dihydropyrrolo[2,3-b]quinolin-4-one

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: 292.34

Molecular Weight (Monoisotopic): 292.1212

AlogP: 2.86

#Rotatable Bonds: 1

Polar Surface Area: 52.90

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.54

CX Basic pKa: 2.46

CX LogP: 2.88

CX LogD: 2.88

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.88

Np Likeness Score: 0.13

References

1. Roman BI, Verhasselt S, Stevens CV..  (2018)  Medicinal Chemistry and Use of Myosin II Inhibitor ( S)-Blebbistatin and Its Derivatives.,  61  (21): [PMID:29878759] [10.1021/acs.jmedchem.8b00503]

Source

Source(1):

• Scientific Literature