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

ID: ALA3326258

PubChem CID: 118711518

Max Phase: Preclinical

Molecular Formula: C22H22N4O3

Molecular Weight: 390.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)Cn1c(=O)n(C)c(=O)c2[nH]c(=O)c(Cc3cccc4ccccc34)nc21

Standard InChI:  InChI=1S/C22H22N4O3/c1-13(2)12-26-19-18(21(28)25(3)22(26)29)24-20(27)17(23-19)11-15-9-6-8-14-7-4-5-10-16(14)15/h4-10,13H,11-12H2,1-3H3,(H,24,27)

Standard InChI Key:  BTUSRASQSIYIRD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
    6.8005   -2.4650    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5095   -2.8736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5095   -3.6908    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8005   -4.0994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0955   -3.6908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3864   -4.0994    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6773   -3.6908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6773   -2.8736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3864   -2.4650    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0955   -2.8736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2145   -2.4650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8005   -4.9166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9682   -4.0994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9682   -2.4650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2633   -2.8736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2633   -3.6908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5542   -4.0994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8451   -3.6908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8451   -2.8736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1401   -2.4650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1401   -1.6478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8451   -1.2392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5542   -1.6478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5542   -2.4650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2145   -4.0994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8005   -1.6478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5095   -1.2392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5095   -0.4220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2145   -1.6478    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
M  END

Alternative Forms

1. Parent:

   

   ALA3326258

   ---

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: 390.44

Molecular Weight (Monoisotopic): 390.1692

AlogP: 2.18

#Rotatable Bonds: 4

Polar Surface Area: 89.75

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.56

CX Basic pKa: ┄

CX LogP: 3.01

CX LogD: 2.82

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.58

Np Likeness Score: -0.88

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