(+)-1,8-dimethyl-5-morpholino-8a-phenyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-3a-ol

ID: ALA4752827

PubChem CID: 162653305

Max Phase: Preclinical

Molecular Formula: C22H27N3O2

Molecular Weight: 365.48

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CN1CC[C@@]2(O)c3cc(N4CCOCC4)ccc3N(C)[C@@]12c1ccccc1

Standard InChI:  InChI=1S/C22H27N3O2/c1-23-11-10-21(26)19-16-18(25-12-14-27-15-13-25)8-9-20(19)24(2)22(21,23)17-6-4-3-5-7-17/h3-9,16,26H,10-15H2,1-2H3/t21-,22-/m1/s1

Standard InChI Key:  DBWPOSGITJRQNX-FGZHOGPDSA-N

Molfile:  

 
     RDKit          2D

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    8.9321  -24.8526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4509  -24.1850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6642  -25.2590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.7732  -23.3425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.6101  -24.7425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6643  -23.6201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6560  -26.0800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9381  -26.4794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9296  -27.2996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.6243  -26.2810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6930  -26.2939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4499  -22.5920    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9383  -21.9368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6383  -22.4967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3151  -21.7462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8034  -21.0909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6150  -21.1862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1 21  1  0
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 25 26  1  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4752827

   ---

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: 365.48

Molecular Weight (Monoisotopic): 365.2103

AlogP: 2.35

#Rotatable Bonds: 2

Polar Surface Area: 39.18

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.84

CX Basic pKa: 6.98

CX LogP: 3.21

CX LogD: 3.07

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.88

Np Likeness Score: -0.09

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