2-(2-ethylbutyl)-7-hydroxy-1,2,3,4-tetrahydro-8H-pyrido[1,2-a]pyrazin-8-one

ID: ALA4551380

PubChem CID: 129165444

Max Phase: Preclinical

Molecular Formula: C14H22N2O2

Molecular Weight: 250.34

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCC(CC)CN1CCn2cc(O)c(=O)cc2C1

Standard InChI:  InChI=1S/C14H22N2O2/c1-3-11(4-2)8-15-5-6-16-10-14(18)13(17)7-12(16)9-15/h7,10-11,18H,3-6,8-9H2,1-2H3

Standard InChI Key:  DEXWPQYWPXPZTH-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 18 19  0  0  0  0  0  0  0  0999 V2000
   26.8930   -1.8284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8930   -2.6456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3036   -1.8284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5983   -1.4156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3036   -2.6456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5963   -3.0466    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.5900   -3.8551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2893   -4.2687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9965   -3.8677    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.0045   -3.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5983   -0.5984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.1841   -1.4218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.7006   -4.2825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4119   -3.8801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1160   -4.2949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4191   -3.0630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1304   -2.6606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8273   -3.8926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  1  4  1  0
  2  6  1  0
  5  3  2  0
  3  4  1  0
  5  6  1  0
  5 10  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  4 11  2  0
  1 12  1  0
  9 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 15 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4551380

   ---

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: 250.34

Molecular Weight (Monoisotopic): 250.1681

AlogP: 1.81

#Rotatable Bonds: 4

Polar Surface Area: 45.47

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.73

CX Basic pKa: 7.93

CX LogP: 2.24

CX LogD: 1.59

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.89

Np Likeness Score: -0.17

References

1. Ernst G, Akuma D, Au V, Buchler IP, Byers S, Carr GV, Defays S, de León P, Demaude T, DePasquale M, Durieu V, Huang Y, Jigorel E, Kimos M, Kolobova A, Montel F, Moureau F, Poslusney M, Swinnen D, Vandergeten MC, Van Houtvin N, Wei H, White N, Wood M, Barrow JC..  (2019)  Synthesis and Evaluation of Bicyclic Hydroxypyridones as Inhibitors of Catechol O-Methyltransferase.,  10  (11): [PMID:32038769] [10.1021/acsmedchemlett.9b00345]

Source

Source(1):

• Scientific Literature