(R)-10-methoxy-9-methyl-3,4,11,11a-tetrahydro-1H-pyrazino[1,2-b]isoquinolin-6(2H)-one

ID: ALA2397913

PubChem CID: 71682217

Max Phase: Preclinical

Molecular Formula: C14H18N2O2

Molecular Weight: 246.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1c(C)ccc2c1C[C@@H]1CNCCN1C2=O

Standard InChI:  InChI=1S/C14H18N2O2/c1-9-3-4-11-12(13(9)18-2)7-10-8-15-5-6-16(10)14(11)17/h3-4,10,15H,5-8H2,1-2H3/t10-/m1/s1

Standard InChI Key:  ZYDTYBMBYADEAB-SNVBAGLBSA-N

Molfile:  

     RDKit          2D

 19 21  0  0  0  0  0  0  0  0999 V2000
    8.1479   -4.9452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1479   -5.7702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8638   -6.1827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5755   -5.7702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5755   -4.9452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8638   -4.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2914   -6.1827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0072   -5.7702    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0072   -4.9452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2914   -4.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7189   -6.1827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4348   -5.7702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4348   -4.9452    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7189   -4.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2914   -7.0077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0072   -4.1202    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4336   -4.5324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8648   -3.7077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1509   -3.2942    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
  1 17  1  0
  6 18  1  0
 18 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2397913

   (11aR)-10-methoxy-9-methyl-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: 246.31

Molecular Weight (Monoisotopic): 246.1368

AlogP: 0.97

#Rotatable Bonds: 1

Polar Surface Area: 41.57

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.56

CX LogP: 1.19

CX LogD: 0.80

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.80

Np Likeness Score: 0.11

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