(R)-7,9-dimethyl-3,4,11,11a-tetrahydro-1H-pyrazino[1,2-b]isoquinolin-6(2H)-one

ID: ALA2397910

PubChem CID: 24826963

Max Phase: Preclinical

Molecular Formula: C14H18N2O

Molecular Weight: 230.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(C)c2c(c1)C[C@@H]1CNCCN1C2=O

Standard InChI:  InChI=1S/C14H18N2O/c1-9-5-10(2)13-11(6-9)7-12-8-15-3-4-16(12)14(13)17/h5-6,12,15H,3-4,7-8H2,1-2H3/t12-/m1/s1

Standard InChI Key:  VXTVXKNGQJWYSP-GFCCVEGCSA-N

Molfile:  

     RDKit          2D

 18 20  0  0  0  0  0  0  0  0999 V2000
   10.5867   -3.8322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5867   -4.6572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3025   -5.0697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0142   -4.6572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0142   -3.8322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3025   -3.4197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7301   -5.0697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4460   -4.6572    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4460   -3.8322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7301   -3.4197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1577   -5.0697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8735   -4.6572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8735   -3.8322    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1577   -3.4197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7301   -5.8947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4460   -3.0072    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3036   -5.8947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8724   -3.4194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  4  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10  5  1  0
  8 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14  9  1  0
  7 15  2  0
  9 16  1  1
  3 17  1  0
  1 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2397910

   (11aR)-7,9-dimethyl-1,2,3,4,11,11a-hexahydropyrazino[1,2-b]isoquinolin-6-one

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 230.31

Molecular Weight (Monoisotopic): 230.1419

AlogP: 1.27

#Rotatable Bonds: ┄

Polar Surface Area: 32.34

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.61

CX LogP: 1.86

CX LogD: 1.44

Aromatic Rings: 1

Heavy Atoms: 17

QED Weighted: 0.73

Np Likeness Score: -0.13

References

1. Zhao G, Kwon C, Bisaha SN, Stein PD, Rossi KA, Cao X, Ung T, Wu G, Hung CP, Malmstrom SE, Zhang G, Qu Q, Gan J, Keim WJ, Cullen MJ, Rohrbach KW, Devenny J, Pelleymounter MA, Miller KJ, Robl JA..  (2013)  Synthesis and SAR of potent and selective tetrahydropyrazinoisoquinolinone 5-HT(2C) receptor agonists.,  23  (13): [PMID:23683593] [10.1016/j.bmcl.2013.04.061]

Source

Source(1):

• Scientific Literature