(+)-8-methyl-8a-phenyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-3a-ol

ID: ALA4749051

PubChem CID: 162649859

Max Phase: Preclinical

Molecular Formula: C17H18N2O

Molecular Weight: 266.34

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CN1c2ccccc2[C@@]2(O)CCN[C@@]12c1ccccc1

Standard InChI:  InChI=1S/C17H18N2O/c1-19-15-10-6-5-9-14(15)16(20)11-12-18-17(16,19)13-7-3-2-4-8-13/h2-10,18,20H,11-12H2,1H3/t16-,17-/m0/s1

Standard InChI Key:  XAIQYSJTZAPIFN-IRXDYDNUSA-N

Molfile:  

 
     RDKit          2D

 20 23  0  0  0  0  0  0  0  0999 V2000
   31.2637  -13.0554    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.7516  -12.3925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2704  -11.7249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4837  -12.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4919  -11.9821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7041  -13.0422    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.2330  -12.3758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7183  -11.7242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4001  -10.9781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5927  -10.8824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1045  -11.5389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4295  -12.2824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4837  -11.1600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.4755  -13.6199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7576  -14.0193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7490  -14.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4570  -15.2599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1750  -14.8501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1800  -14.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4437  -13.8209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0
  1  2  1  0
  2  3  1  0
  3  5  1  0
  4  5  1  0
  5  8  1  0
  7  6  1  0
  6  4  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
  5 13  1  6
  4 14  1  6
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
  6 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4749051

   ---

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: 266.34

Molecular Weight (Monoisotopic): 266.1419

AlogP: 2.17

#Rotatable Bonds: 1

Polar Surface Area: 35.50

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.82

CX Basic pKa: 7.30

CX LogP: 2.93

CX LogD: 2.68

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.83

Np Likeness Score: 0.80

References

1. Blom AEM,Su JY,Repka LM,Reisman SE,Dougherty DA.  (2020)  Synthesis and Biological Evaluation of Pyrroloindolines as Positive Allosteric Modulators of the α1β2γ2 GABA Receptor.,  11  (11): [PMID:33214830] [10.1021/acsmedchemlett.0c00340]

Source

Source(1):

• Scientific Literature