8-Methoxy-3-phenethyl-1,2,3,4-tetrahydro-chromeno[3,4-c]pyridin-5-one

ID: ALA440506

PubChem CID: 10568805

Max Phase: Preclinical

Molecular Formula: C21H21NO3

Molecular Weight: 335.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc2c3c(c(=O)oc2c1)CN(CCc1ccccc1)CC3

Standard InChI:  InChI=1S/C21H21NO3/c1-24-16-7-8-18-17-10-12-22(11-9-15-5-3-2-4-6-15)14-19(17)21(23)25-20(18)13-16/h2-8,13H,9-12,14H2,1H3

Standard InChI Key:  IAWWLCSYFAOUES-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    4.6542   -5.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3750   -6.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6542   -6.7792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.0917   -4.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6542   -4.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2292   -5.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0917   -6.7917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5167   -6.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5167   -5.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4667   -4.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2667   -4.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8000   -6.7792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8500   -5.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4667   -3.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0875   -6.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2625   -3.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6417   -4.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8542   -4.0042    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
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  7  1  1  0
  8  7  1  0
  9  2  1  0
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 16 11  1  0
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 18 17  1  0
 19 14  1  0
 20 18  2  0
 21 18  1  0
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 24 20  1  0
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  5  6  1  0
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 14 16  2  0
 25 24  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA440506

   8-Methoxy-3-phenethyl-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: 335.40

Molecular Weight (Monoisotopic): 335.1521

AlogP: 3.40

#Rotatable Bonds: 4

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: 8.45

CX LogP: 3.29

CX LogD: 2.20

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.69

Np Likeness Score: -0.41

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