(+)-benzyl 3a-hydroxy-8-methyl-8a-phenyl-3,3a,8,8a-tetrahydropyrrolo[2,3-b]indole-1(2H)-carboxylate

ID: ALA4785192

PubChem CID: 162666398

Max Phase: Preclinical

Molecular Formula: C25H24N2O3

Molecular Weight: 400.48

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CN1c2ccccc2[C@@]2(O)CCN(C(=O)OCc3ccccc3)[C@@]12c1ccccc1

Standard InChI:  InChI=1S/C25H24N2O3/c1-26-22-15-9-8-14-21(22)24(29)16-17-27(25(24,26)20-12-6-3-7-13-20)23(28)30-18-19-10-4-2-5-11-19/h2-15,29H,16-18H2,1H3/t24-,25+/m0/s1

Standard InChI Key:  XABPYSFEEZDJSP-LOSJGSFVSA-N

Molfile:  

 
     RDKit          2D

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   18.4908   -2.8009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   17.2229   -3.2072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2311   -2.3904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4433   -3.4505    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.9722   -2.7841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   19.2205   -4.1742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1887   -4.9568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6241   -4.8847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4413   -4.8904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8420   -5.5995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6584   -5.6056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0727   -4.9002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6647   -4.1873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8496   -4.1847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 30 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4785192

   ---

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: 400.48

Molecular Weight (Monoisotopic): 400.1787

AlogP: 4.22

#Rotatable Bonds: 3

Polar Surface Area: 53.01

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.79

CX Basic pKa: ┄

CX LogP: 4.89

CX LogD: 4.89

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.72

Np Likeness Score: 0.31

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