(S)-3a-hydroxy-5-methyl-1-phenyl-3,3a-dihydro-1H-pyrrolo[2,3-b]quinolin-4(2H)-one

ID: ALA1231375

PubChem CID: 24178119

Max Phase: Preclinical

Molecular Formula: C18H16N2O2

Molecular Weight: 292.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cccc2c1C(=O)[C@]1(O)CCN(c3ccccc3)C1=N2

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

Standard InChI Key:  NJBBBRZNBVLTRZ-GOSISDBHSA-N

Molfile:  

     RDKit          2D

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   -0.4026   -1.1974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3118   -0.7849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3981   -1.6054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0965   -1.0398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5814   -0.3724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0965    0.2951    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3514    1.0797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7994    1.6928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0543    2.4774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8613    2.6489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4133    2.0358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1584    1.2512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3118    0.0401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4026    0.4526    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1171    0.0401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1171   -0.7849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8316    0.4526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5461    0.0401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5461   -0.7849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8316   -1.1974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8316   -2.0224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  5  3  1  0
  3  4  1  6
  6  5  1  0
  6  7  1  0
 14  7  1  0
  8  7  1  0
  8  9  1  0
 10  9  2  0
 11 10  1  0
 12 11  2  0
 13 12  1  0
  8 13  2  0
 14  3  1  0
 14 15  2  0
 16 15  1  0
 16 17  1  0
  2 17  1  0
 17 21  2  0
 16 18  2  0
 19 18  1  0
 20 19  2  0
 21 20  1  0
 22 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1231375

   (3aS)-3a-hydroxy-5-methyl-1-phenyl-1,2,3,3a-tetrahydro-4H-pyrrolo[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: 11.55

CX Basic pKa: 2.38

CX LogP: 2.88

CX LogD: 2.88

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.88

Np Likeness Score: 0.31

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