2-[(2,3-dimethylphenyl)methyl]-7-hydroxy-3,4-dihydro-1H-pyrido[1,2-a]pyrazin-8-one

ID: ALA4583818

PubChem CID: 129165556

Max Phase: Preclinical

Molecular Formula: C17H20N2O2

Molecular Weight: 284.36

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1cccc(CN2CCn3cc(O)c(=O)cc3C2)c1C

Standard InChI:  InChI=1S/C17H20N2O2/c1-12-4-3-5-14(13(12)2)9-18-6-7-19-11-17(21)16(20)8-15(19)10-18/h3-5,8,11,21H,6-7,9-10H2,1-2H3

Standard InChI Key:  PUYUJSHHBWWWRE-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
    3.3926   -2.2328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3926   -3.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8031   -2.2328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0979   -1.8201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8031   -3.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0959   -3.4510    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0896   -4.2595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7889   -4.6731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4961   -4.2721    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5041   -3.4575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0979   -1.0029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6837   -1.8263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2002   -4.6869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9115   -4.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6134   -4.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3241   -4.3025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3318   -3.4845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6227   -3.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9148   -3.4738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6034   -5.5213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0280   -4.7176    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  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 15 20  1  0
 16 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4583818

   ---

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: 284.36

Molecular Weight (Monoisotopic): 284.1525

AlogP: 2.19

#Rotatable Bonds: 2

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: 11.64

CX Basic pKa: 7.00

CX LogP: 2.85

CX LogD: 2.71

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.92

Np Likeness Score: -0.74

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