(R)-4-benzyl-6,6a,7,8,9,10-hexahydro-5H-pyrazino[1,2-a][1,7]naphthyridine

ID: ALA4778570

PubChem CID: 134265735

Max Phase: Preclinical

Molecular Formula: C18H21N3

Molecular Weight: 279.39

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  c1ccc(Cc2cncc3c2CC[C@@H]2CNCCN32)cc1

Standard InChI:  InChI=1S/C18H21N3/c1-2-4-14(5-3-1)10-15-11-20-13-18-17(15)7-6-16-12-19-8-9-21(16)18/h1-5,11,13,16,19H,6-10,12H2/t16-/m1/s1

Standard InChI Key:  YEAATRDZIJRTNR-MRXNPFEDSA-N

Molfile:  

 
     RDKit          2D

 22 25  0  0  0  0  0  0  0  0999 V2000
   40.8870  -20.5866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.8859  -21.4061    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.5939  -21.8151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.5921  -20.1777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.3008  -20.5830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.3042  -21.4082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.7267  -20.5771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.0098  -20.1652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.7301  -21.4023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.0142  -21.8137    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   43.0125  -22.6347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.7250  -23.0507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.4409  -22.6394    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   44.4443  -21.8121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.4337  -20.9870    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   41.5897  -19.3605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.2962  -18.9498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.0030  -19.3587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.7090  -18.9487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.7070  -18.1306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.9931  -17.7243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.2900  -18.1367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5  8  1  0
  6 10  1  0
  9  7  1  0
  7  8  1  0
  9 10  1  0
  9 14  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
  9 15  1  1
  4 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4778570

   ---

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: 279.39

Molecular Weight (Monoisotopic): 279.1735

AlogP: 2.40

#Rotatable Bonds: 2

Polar Surface Area: 28.16

Molecular Species: BASE

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.97

CX LogP: 2.96

CX LogD: 1.36

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.91

Np Likeness Score: -0.29

References

1. Schrader TO,Zhu X,Kasem M,Ren A,Liu C,Wu C,Dang H,Le M,Gatlin J,Chase K,Frazer J,Whelan KT,Grottick AJ,Hutton C,Barden J,Chen C,Ortiz A,Feichtinger K,Semple G.  (2021)  Novel (R)-6,6a,7,8,9,10-hexahydro-5H-pyrazino[1,2-a][1,n]naphthyridines as potent and selective agonists of the 5-HT receptor.,  38  [PMID:33636307] [10.1016/j.bmcl.2021.127872]

Source

Source(1):

• Scientific Literature