2-benzyl-8-methoxy-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

ID: ALA4849640

Cas Number: 69069-65-4

PubChem CID: 132599

Max Phase: Preclinical

Molecular Formula: C19H20N2O

Molecular Weight: 292.38

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc2[nH]c3c(c2c1)CN(Cc1ccccc1)CC3

Standard InChI:  InChI=1S/C19H20N2O/c1-22-15-7-8-18-16(11-15)17-13-21(10-9-19(17)20-18)12-14-5-3-2-4-6-14/h2-8,11,20H,9-10,12-13H2,1H3

Standard InChI Key:  FCUJMVMWOLCXGK-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 22 25  0  0  0  0  0  0  0  0999 V2000
   23.0902  -17.7336    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.4245  -17.2531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6790  -16.4769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1346  -15.8704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3355  -16.0389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0837  -16.8193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6299  -17.4225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4945  -16.4764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7442  -17.2508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5353  -17.4208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0824  -16.8193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8326  -16.0449    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.0359  -15.8720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3814  -15.4394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1802  -15.6118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4260  -16.3895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2240  -16.5622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7736  -15.9563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5198  -15.1751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7224  -15.0061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7885  -15.4317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.0409  -14.6544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0
  8  3  1  0
  2  1  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  2  1  0
  8  9  2  0
  8 13  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 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
  5 21  1  0
 21 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4849640

   2-benzyl-8-methoxy-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

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: 292.38

Molecular Weight (Monoisotopic): 292.1576

AlogP: 3.73

#Rotatable Bonds: 3

Polar Surface Area: 28.26

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.91

CX LogP: 3.31

CX LogD: 3.19

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.80

Np Likeness Score: -1.00

References

1. Schwarthoff S, Tischer N, Sager H, Schätz B, Rohrbach MM, Raztsou I, Robaa D, Gaube F, Arndt HD, Winckler T..  (2021)  Evaluation of γ-carboline-phenothiazine conjugates as simultaneous NMDA receptor blockers and cholinesterase inhibitors.,  46  [PMID:34391122] [10.1016/j.bmc.2021.116355]

Source

Source(1):

• Scientific Literature