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

ID: ALA3818005

PubChem CID: 122212031

Max Phase: Preclinical

Molecular Formula: C20H25ClN4O2S

Molecular Weight: 420.97

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)Cc1nn(C)c(=O)c2c(SCCCO)n(Cc3ccnc(Cl)c3)cc12

Standard InChI:  InChI=1S/C20H25ClN4O2S/c1-13(2)9-16-15-12-25(11-14-5-6-22-17(21)10-14)20(28-8-4-7-26)18(15)19(27)24(3)23-16/h5-6,10,12-13,26H,4,7-9,11H2,1-3H3

Standard InChI Key:  IEEHXVUFVDOULN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   -2.3155    0.7475    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155   -0.7475    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028   -1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028    1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138   -1.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5889    0.0182    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138    1.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9991    2.7132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9971   -3.0138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2935   -3.7700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2889   -4.9699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3352   -3.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3560    1.3452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1812    2.6271    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.6500    2.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1182    4.3614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5870    4.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9614    5.8100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0872    0.0320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8506   -1.2602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3709   -3.8465    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8709   -3.8583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1108   -2.5652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1107   -2.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3505   -1.2485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2791   -4.9022    0.0000 Cl  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  2  0
 24 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3818005

   ---

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: 420.97

Molecular Weight (Monoisotopic): 420.1387

AlogP: 3.50

#Rotatable Bonds: 8

Polar Surface Area: 72.94

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.56

CX LogP: 3.11

CX LogD: 3.11

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.34

Np Likeness Score: -0.98

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