3-(4-amino-5-(4-chlorophenyl)-2-thioxo-2,5-dihydro-1H-pyrano[2,3-d]pyrimidin-7-yl)-2H-chromen-2-one

ID: ALA5287867

Max Phase: Preclinical

Molecular Formula: C22H14ClN3O3S

Molecular Weight: 435.89

Names and Identifiers

Canonical SMILES:  Nc1nc(=S)[nH]c2c1C(c1ccc(Cl)cc1)C=C(c1cc3ccccc3oc1=O)O2

Standard InChI:  InChI=1S/C22H14ClN3O3S/c23-13-7-5-11(6-8-13)14-10-17(28-20-18(14)19(24)25-22(30)26-20)15-9-12-3-1-2-4-16(12)29-21(15)27/h1-10,14H,(H3,24,25,26,30)

Standard InChI Key:  GYAPFWUJHNYJOH-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    0.7147    0.6196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0010    1.0322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0010    1.8547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4288   -0.6177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1431   -0.2053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1431    0.6196    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5718   -1.8549    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.1431   -1.8548    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4288   -1.4424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7147   -1.8548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8604   -1.4409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5718   -1.8574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5718   -2.6782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8553   -3.0906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1428   -2.6798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4284   -3.0923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7139   -2.6799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0005   -3.0923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0005   -0.6177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

Alternative Forms

1. Parent:

   

   ALA5287867

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 435.89

Molecular Weight (Monoisotopic): 435.0444

AlogP: 5.05

#Rotatable Bonds: 2

Polar Surface Area: 94.14

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.84

CX Basic pKa: 0.10

CX LogP: 3.44

CX LogD: 3.32

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.34

Np Likeness Score: -0.31

References

1. Elattar KM, El-Khateeb AY, Hamed SE..  (2022)  Insights into the recent progress in the medicinal chemistry of pyranopyrimidine analogs.,  13  (5.0): [PMID:35694689] [10.1039/d2md00076h]

Source

Source(1):

• Scientific Literature