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

ID: ALA314095

PubChem CID: 10042972

Max Phase: Preclinical

Molecular Formula: C19H16ClNO3

Molecular Weight: 341.79

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1oc2cc(O)ccc2c2c1CN(Cc1ccc(Cl)cc1)CC2

Standard InChI:  InChI=1S/C19H16ClNO3/c20-13-3-1-12(2-4-13)10-21-8-7-15-16-6-5-14(22)9-18(16)24-19(23)17(15)11-21/h1-6,9,22H,7-8,10-11H2

Standard InChI Key:  DTSBUYTYJIUAIH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 27  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
    6.2875   -6.9917    0.0000 O   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
    7.0042   -4.0792    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
    2.7042   -5.7417    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
    7.0125   -1.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0125   -0.7667    0.0000 Cl  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
    7.7292   -2.0042    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
    7.7292   -2.8375    0.0000 C   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
  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  3  2  0
 13  7  1  0
 14  7  1  0
 15 10  1  0
 16 11  1  0
 17 14  1  0
 18 21  2  0
 19 18  1  0
 20 22  2  0
 21 23  1  0
 22 17  1  0
 23 17  2  0
 24 15  1  0
  5  6  1  0
 13  9  1  0
 15 16  2  0
 18 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA314095

   3-(4-Chloro-benzyl)-8-hydroxy-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: 341.79

Molecular Weight (Monoisotopic): 341.0819

AlogP: 3.71

#Rotatable Bonds: 2

Polar Surface Area: 53.68

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.79

CX Basic pKa: 6.66

CX LogP: 3.20

CX LogD: 3.21

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.72

Np Likeness Score: -0.42

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