5-(3-hydropropyl)-1-isobutyl-3-methyl-7-(naphthalene-1-ylmethyl)-1,5-dihydropteridine-2,4,6(3H)-trione

ID: ALA3326257

Max Phase: Preclinical

Molecular Formula: C25H28N4O3

Molecular Weight: 432.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCn1c(=O)c(Cc2cccc3ccccc23)nc2c1c(=O)n(C)c(=O)n2CC(C)C

Standard InChI:  InChI=1S/C25H28N4O3/c1-5-13-28-21-22(29(15-16(2)3)25(32)27(4)24(21)31)26-20(23(28)30)14-18-11-8-10-17-9-6-7-12-19(17)18/h6-12,16H,5,13-15H2,1-4H3

Standard InChI Key:  IZRLGBMJKWZZDY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   11.6576   -3.8583    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9417   -3.4499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9417   -2.6208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6576   -2.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3693   -2.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0852   -2.2083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.7968   -2.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7968   -3.4458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0852   -3.8583    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3693   -3.4458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2259   -3.8583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6576   -1.3833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5127   -2.2083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5127   -3.8624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2286   -3.4499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2286   -2.6208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9403   -2.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6561   -2.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6561   -3.4458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3719   -3.8624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3719   -4.6833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6561   -5.0958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9403   -4.6833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9403   -3.8583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2259   -2.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6576   -4.6833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9417   -5.0958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9417   -5.9208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2259   -4.6833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0852   -1.3833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7968   -0.9708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7968   -0.1459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  1 10  1  0
  5 10  2  0
  2 11  2  0
  4 12  2  0
  7 13  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 15 24  2  0
 19 24  1  0
 14 15  1  0
  8 14  1  0
  3 25  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  0
  1 26  1  0
 30 31  1  0
 31 32  1  0
  6 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3326257

   ---

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: 432.52

Molecular Weight (Monoisotopic): 432.2161

AlogP: 3.07

#Rotatable Bonds: 6

Polar Surface Area: 78.89

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.12

CX LogD: 4.12

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.47

Np Likeness Score: -0.96

References

1. Wang H, Yang C, Doherty JR, Roush WR, Cleveland JL, Bannister TD..  (2014)  Synthesis and structure-activity relationships of pteridine dione and trione monocarboxylate transporter 1 inhibitors.,  57  (17): [PMID:25068893] [10.1021/jm500640x]

2. Murray, Clare M CM and 26 more authors.  2005-12  Monocarboxylate transporter MCT1 is a target for immunosuppression.  [PMID:16370372]

3. Wang, Hui H and 5 more authors.  2014-09-11  Synthesis and structure-activity relationships of pteridine dione and trione monocarboxylate transporter 1 inhibitors.  [PMID:25068893]

4. Nair, Reji N and 9 more authors.  2016-05-01  Exploiting the co-reliance of tumours upon transport of amino acids and lactate: Gln and Tyr conjugates of MCT1 inhibitors.  [PMID:27347360]

Source

Source(1):

• Scientific Literature