3-Benzyl-8-methyl-1,2,3,4-tetrahydro-chromeno[3,4-c]pyridin-5-one

ID: ALA92489

PubChem CID: 9995264

Max Phase: Preclinical

Molecular Formula: C20H19NO2

Molecular Weight: 305.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc2c3c(c(=O)oc2c1)CN(Cc1ccccc1)CC3

Standard InChI:  InChI=1S/C20H19NO2/c1-14-7-8-17-16-9-10-21(12-15-5-3-2-4-6-15)13-18(16)20(22)23-19(17)11-14/h2-8,11H,9-10,12-13H2,1H3

Standard InChI Key:  JYTBEUORVGHEBI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    5.4417   -5.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7250   -5.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4417   -6.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7250   -6.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0125   -6.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0125   -5.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1542   -4.4667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1542   -5.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7250   -4.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000   -5.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1625   -6.9542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000   -6.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4375   -4.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8792   -4.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5792   -5.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5792   -6.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8875   -3.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8667   -6.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1750   -2.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6042   -2.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6042   -1.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1750   -1.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8875   -1.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  1  0
  4  3  1  0
  5  4  1  0
  6  2  1  0
  7  8  1  0
  8  1  1  0
  9  2  1  0
 10  6  2  0
 11  3  2  0
 12  5  2  0
 13  7  1  0
 14  7  1  0
 15 10  1  0
 16 12  1  0
 17 14  1  0
 18 16  1  0
 19 17  1  0
 20 17  2  0
 21 20  1  0
 22 19  2  0
 23 21  2  0
  5  6  1  0
 13  9  1  0
 16 15  2  0
 23 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA92489

   3-Benzyl-8-methyl-1,2,3,4-tetrahydro-chromeno[3,4-c]pyridin-5-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: 305.38

Molecular Weight (Monoisotopic): 305.1416

AlogP: 3.66

#Rotatable Bonds: 2

Polar Surface Area: 33.45

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.67

CX LogP: 3.67

CX LogD: 3.21

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.68

Np Likeness Score: -0.68

References

1. Unangst PC, Capiris T, Connor DT, Heffner TG, MacKenzie RG, Miller SR, Pugsley TA, Wise LD..  (1997)  Chromeno[3,4-c]pyridin-5-ones: selective human dopamine D4 receptor antagonists as potential antipsychotic agents.,  40  (17): [PMID:9276014] [10.1021/jm970170v]

2. Salehian F, Nadri H, Jalili-Baleh L, Youseftabar-Miri L, Abbas Bukhari SN, Foroumadi A, Tüylü Küçükkilinç T, Sharifzadeh M, Khoobi M..  (2021)  A review: Biologically active 3,4-heterocycle-fused coumarins.,  212  [PMID:33276991] [10.1016/j.ejmech.2020.113034]

Source

Source(1):

• Scientific Literature