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

ID: ALA3326256

Max Phase: Preclinical

Molecular Formula: C26H30N4O4

Molecular Weight: 462.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)Cn1c(=O)n(C)c(=O)c2c1nc(Cc1cccc3ccccc13)c(=O)n2CCCCO

Standard InChI:  InChI=1S/C26H30N4O4/c1-17(2)16-30-23-22(25(33)28(3)26(30)34)29(13-6-7-14-31)24(32)21(27-23)15-19-11-8-10-18-9-4-5-12-20(18)19/h4-5,8-12,17,31H,6-7,13-16H2,1-3H3

Standard InChI Key:  QIZKRTHTRIGWIC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 37  0  0  0  0  0  0  0  0999 V2000
   19.9367   -3.5537    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.2208   -3.1412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2208   -2.3162    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.9367   -1.9037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6484   -2.3162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3643   -1.9037    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.0759   -2.3162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0759   -3.1412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3643   -3.5537    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.6484   -3.1412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5050   -3.5537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9367   -1.0787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.7918   -1.9037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.7918   -3.5537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5077   -3.1412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5077   -2.3162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2194   -1.9037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9352   -2.3162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9352   -3.1412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6510   -3.5537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6510   -4.3786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9352   -4.7911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2194   -4.3786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2194   -3.5537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5050   -1.9037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9367   -4.3786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2208   -4.7911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2208   -5.6161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5050   -4.3786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3643   -1.0787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0759   -0.6662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7918   -1.0787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5077   -0.6662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2194   -1.0787    0.0000 O   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
 32 33  1  0
 33 34  1  0
  6 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3326256

   ---

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: 462.55

Molecular Weight (Monoisotopic): 462.2267

AlogP: 2.43

#Rotatable Bonds: 8

Polar Surface Area: 99.12

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.12

CX LogD: 3.12

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.41

Np Likeness Score: -0.75

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