5-((1-(1-naphthoyl)-1H-indol-3-yl)methylene)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione

ID: ALA2326877

PubChem CID: 71562017

Max Phase: Preclinical

Molecular Formula: C24H15N3O3S

Molecular Weight: 425.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1NC(=S)NC(=O)C1=Cc1cn(C(=O)c2cccc3ccccc23)c2ccccc12

Standard InChI:  InChI=1S/C24H15N3O3S/c28-21-19(22(29)26-24(31)25-21)12-15-13-27(20-11-4-3-9-17(15)20)23(30)18-10-5-7-14-6-1-2-8-16(14)18/h1-13H,(H2,25,26,28,29,31)

Standard InChI Key:  RWECERWMOSPKHW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   12.6958   -5.6270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4106   -6.0398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4088   -4.3868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1242   -4.7960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1245   -5.6270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9150   -5.8827    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.4033   -5.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9149   -4.5378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3430   -6.5880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   14.1548   -8.7533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9220   -3.7128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   17.0677   -3.3232    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.0790   -2.4980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3683   -2.0772    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.6462   -2.4817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3437   -4.5511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7985   -2.0943    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   14.9361   -2.0618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3768   -8.0096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9841   -8.7311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4124   -9.4299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2334   -9.4084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6241   -8.6822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1935   -7.9864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
  7 10  1  0
 10 11  1  0
 10 12  2  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
 15 27  1  0
 26 11  1  0
  9 16  1  0
 16 17  2  0
 17 18  1  0
 17 22  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 18 23  2  0
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 22 25  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 26  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2326877

   5-[[1-(Naphthalene-1-carbonyl)indol-3-yl]methylidene]-2-sulfanylidene-1,3-diazinane-4,6-dione

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: 425.47

Molecular Weight (Monoisotopic): 425.0834

AlogP: 3.40

#Rotatable Bonds: 2

Polar Surface Area: 80.20

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.44

CX Basic pKa: ┄

CX LogP: 3.94

CX LogD: 3.66

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.29

Np Likeness Score: -1.07

References

1. Penthala NR, Ponugoti PR, Kasam V, Crooks PA..  (2013)  5-((1-Aroyl-1H-indol-3-yl)methylene)-2-thioxodihydropyrimidine-4,6(1H,5H)-diones as potential anticancer agents with anti-inflammatory properties.,  23  (5): [PMID:23339966] [10.1016/j.bmcl.2012.12.053]

Source

Source(1):

• Scientific Literature