1-(4-chlorophenyl)-5-(3,4-dihydroxybenzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione

ID: ALA1668297

PubChem CID: 5557305

Max Phase: Preclinical

Molecular Formula: C17H11ClN2O5

Molecular Weight: 358.74

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1NC(=O)N(c2ccc(Cl)cc2)C(=O)/C1=C/c1ccc(O)c(O)c1

Standard InChI:  InChI=1S/C17H11ClN2O5/c18-10-2-4-11(5-3-10)20-16(24)12(15(23)19-17(20)25)7-9-1-6-13(21)14(22)8-9/h1-8,21-22H,(H,19,23,25)/b12-7+

Standard InChI Key:  DCBWSCLMCVJGBP-KPKJPENVSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   15.0861  -14.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0849  -15.3607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7997  -15.7735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5162  -15.3602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5133  -14.5297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7979  -14.1205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2313  -15.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9451  -15.3579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6546  -15.7727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3663  -15.3626    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.3693  -14.5373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6543  -14.1237    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.9364  -14.5355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2203  -14.1257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6520  -16.5977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0846  -14.1263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0777  -15.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0746  -16.6011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7873  -17.0151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5036  -16.6041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5028  -15.7748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7895  -15.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2178  -17.0172    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   15.7955  -13.2955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3715  -14.1210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
  1  2  2  0
 13 14  2  0
  4  7  1  0
  9 15  2  0
  3  4  2  0
 11 16  2  0
  7  8  2  0
  8  9  1  0
 17 18  2  0
 18 19  1  0
  4  5  1  0
 19 20  2  0
  2  3  1  0
 20 21  1  0
  5  6  2  0
 21 22  2  0
 22 17  1  0
 10 17  1  0
  6  1  1  0
 20 23  1  0
  8 13  1  0
  6 24  1  0
  9 10  1  0
  1 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1668297

   1-(4-chlorophenyl)-5-(3,4-dihydroxybenzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione

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: 358.74

Molecular Weight (Monoisotopic): 358.0356

AlogP: 2.42

#Rotatable Bonds: 2

Polar Surface Area: 106.94

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.71

CX Basic pKa: ┄

CX LogP: 2.66

CX LogD: 1.91

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.43

Np Likeness Score: -0.85

References

1. Chu Y, Chen X, Yang Y, Tang Y..  (2011)  Identification of small molecular inhibitors for Ero1p by structure-based virtual screening.,  21  (4): [PMID:21269829] [10.1016/j.bmcl.2010.12.129]

Source

Source(1):

• Scientific Literature