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

ID: ALA3326255

PubChem CID: 118711516

Max Phase: Preclinical

Molecular Formula: C27H32N4O4

Molecular Weight: 476.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)Cn1c(=O)n(C)c(=O)c2c1nc(Cc1cccc3ccccc13)c(=O)n2CCCCCO

Standard InChI:  InChI=1S/C27H32N4O4/c1-18(2)17-31-24-23(26(34)29(3)27(31)35)30(14-7-4-8-15-32)25(33)22(28-24)16-20-12-9-11-19-10-5-6-13-21(19)20/h5-6,9-13,18,32H,4,7-8,14-17H2,1-3H3

Standard InChI Key:  RFIWALSGOQSCAD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   27.9061   -3.3312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9061   -2.5062    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.6179   -2.0937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   32.9047   -3.7437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1903   -2.0937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6179   -4.5687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   27.1903   -4.5687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9061   -5.8062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0496   -1.2687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   31.4771   -1.2687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   32.9047   -1.2687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6206   -0.8562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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 34 35  1  0
  6 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3326255

   ---

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: 476.58

Molecular Weight (Monoisotopic): 476.2424

AlogP: 2.82

#Rotatable Bonds: 9

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: 3.57

CX LogD: 3.57

Aromatic Rings: 4

Heavy Atoms: 35

QED Weighted: 0.37

Np Likeness Score: -0.70

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