3-(3,4-Dichloro-benzyl)-8-methoxy-1,2,3,4-tetrahydro-chromeno[3,4-c]pyridin-5-one

ID: ALA89913

PubChem CID: 10786591

Max Phase: Preclinical

Molecular Formula: C20H17Cl2NO3

Molecular Weight: 390.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc2c3c(c(=O)oc2c1)CN(Cc1ccc(Cl)c(Cl)c1)CC3

Standard InChI:  InChI=1S/C20H17Cl2NO3/c1-25-13-3-4-15-14-6-7-23(10-12-2-5-17(21)18(22)8-12)11-16(14)20(24)26-19(15)9-13/h2-5,8-9H,6-7,10-11H2,1H3

Standard InChI Key:  CDPWDOLVSDDBEM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    5.5667   -5.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8500   -5.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5667   -6.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8500   -6.9792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1375   -6.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1375   -5.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2792   -4.5000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2792   -5.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8500   -4.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4250   -6.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4250   -5.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7292   -2.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2875   -6.9917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0125   -1.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7292   -2.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0125   -3.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0042   -4.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5625   -4.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3000   -2.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7042   -6.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4417   -1.5917    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.7042   -5.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3000   -2.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0042   -0.7667    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.9917   -6.9792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2792   -6.5667    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  5  2  0
 11  6  2  0
 12 15  1  0
 13  3  2  0
 14 19  1  0
 15 16  2  0
 16 17  1  0
 17  7  1  0
 18  7  1  0
 19 23  2  0
 20 10  1  0
 21 12  1  0
 22 11  1  0
 23 16  1  0
 24 14  1  0
 25 20  1  0
 26 25  1  0
  5  6  1  0
 18  9  1  0
 20 22  2  0
 14 12  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA89913

   3-(3,4-Dichloro-benzyl)-8-methoxy-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: 390.27

Molecular Weight (Monoisotopic): 389.0585

AlogP: 4.67

#Rotatable Bonds: 3

Polar Surface Area: 42.68

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.04

CX LogP: 4.21

CX LogD: 4.19

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.61

Np Likeness Score: -0.85

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