6-((4-bromonaphthalen-1-yl)methyl)-7-(3-hydroxypropylthio)-4-isobutyl-2-methyl-2,6-dihydro-1H-pyrrolo[3,4-d]pyridazin-1-one

ID: ALA3817902

PubChem CID: 127049085

Max Phase: Preclinical

Molecular Formula: C25H28BrN3O2S

Molecular Weight: 514.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)Cc1nn(C)c(=O)c2c(SCCCO)n(Cc3ccc(Br)c4ccccc34)cc12

Standard InChI:  InChI=1S/C25H28BrN3O2S/c1-16(2)13-22-20-15-29(14-17-9-10-21(26)19-8-5-4-7-18(17)19)25(32-12-6-11-30)23(20)24(31)28(3)27-22/h4-5,7-10,15-16,30H,6,11-14H2,1-3H3

Standard InChI Key:  YCYDUTCGYOKSNL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   -6.4133   -6.8760    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1764   -5.5904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4385   -4.2619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8936   -6.8644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1714   -5.5451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9345   -4.2596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9443   -3.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5870   -3.7544    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7158   -5.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2779   -7.8944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1996   -2.9687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7004   -2.9802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3090   -1.9460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2921   -4.0242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0029   -7.9211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5797   -6.1883    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1630   -5.6929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9749   -6.6715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3917   -6.1761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3015   -6.9585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2907   -2.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964   -1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964    1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964   -1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964    1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2928    2.6973    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  4  1  0
  2  3  2  0
  3  6  1  0
  5  4  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9  5  2  0
  4 10  2  0
  3 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
  1 15  1  0
  9 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
  8 21  1  0
 21 22  1  0
 22 27  1  0
 26 23  1  0
 23 24  2  0
 24 25  1  0
 25 22  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 26  2  0
 23 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3817902

   ---

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: 514.49

Molecular Weight (Monoisotopic): 513.1086

AlogP: 5.37

#Rotatable Bonds: 8

Polar Surface Area: 60.05

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.26

CX LogD: 5.26

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.25

Np Likeness Score: -0.75

References

1. Nair RN, Mishra JK, Li F, Tortosa M, Yang C, Doherty JR, Cameron M, Cleveland JL, Roush WR, Bannister TD..  (2016)  Exploiting the co-reliance of tumours upon transport of amino acids and lactate: Gln and Tyr conjugates of MCT1 inhibitors.,  7  (5): [PMID:27347360] [10.1039/c5md00579e]

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