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

ID: ALA91658

PubChem CID: 10689266

Max Phase: Preclinical

Molecular Formula: C21H21NO4

Molecular Weight: 351.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(CN2CCc3c(c(=O)oc4cc(OC)ccc34)C2)cc1

Standard InChI:  InChI=1S/C21H21NO4/c1-24-15-5-3-14(4-6-15)12-22-10-9-17-18-8-7-16(25-2)11-20(18)26-21(23)19(17)13-22/h3-8,11H,9-10,12-13H2,1-2H3

Standard InChI Key:  STNPHZVHYQRIIW-UHFFFAOYSA-N

Molfile:  

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    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
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    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
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    7.0042   -4.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.7292   -2.8375    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
    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
    1.9917   -6.9792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0125   -0.7667    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
    7.7250   -0.3542    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
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  7  8  1  0
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 16 11  1  0
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 19 17  2  0
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 26 24  1  0
  5  6  1  0
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 15 16  2  0
 18 22  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA91658

   8-Methoxy-3-(4-methoxy-benzyl)-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: 351.40

Molecular Weight (Monoisotopic): 351.1471

AlogP: 3.37

#Rotatable Bonds: 4

Polar Surface Area: 51.91

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.21

CX LogP: 2.84

CX LogD: 2.63

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.67

Np Likeness Score: -0.46

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