6-((1-(5-aminopentylamino)isoquinolin-4-yl)methyl)-7-(3-hydroxypropylthio)-4-isobutyl-2-methyl-2,6-dihydro-1H-pyrrolo[3,4-d]pyridazin-1-one

ID: ALA3818311

PubChem CID: 127052807

Max Phase: Preclinical

Molecular Formula: C29H40N6O2S

Molecular Weight: 536.75

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)Cc1nn(C)c(=O)c2c(SCCCO)n(Cc3cnc(NCCCCCN)c4ccccc34)cc12

Standard InChI:  InChI=1S/C29H40N6O2S/c1-20(2)16-25-24-19-35(29(38-15-9-14-36)26(24)28(37)34(3)33-25)18-21-17-32-27(31-13-8-4-7-12-30)23-11-6-5-10-22(21)23/h5-6,10-11,17,19-20,36H,4,7-9,12-16,18,30H2,1-3H3,(H,31,32)

Standard InChI Key:  UKBMJQCYJYSUFI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -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
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   -7.0029   -7.9211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3015   -6.9585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -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 N   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
   -1.2907    2.9981    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5870    3.7544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5812    5.2552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8775    6.0115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8717    7.5123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1681    8.2686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1634    9.4686    0.0000 N   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
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3818311

   ---

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: 536.75

Molecular Weight (Monoisotopic): 536.2933

AlogP: 4.55

#Rotatable Bonds: 14

Polar Surface Area: 110.99

Molecular Species: BASE

HBA: 9

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 10.21

CX LogP: 3.57

CX LogD: 0.84

Aromatic Rings: 4

Heavy Atoms: 38

QED Weighted: 0.16

Np Likeness Score: -0.63

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. Wang Y, Qin L, Chen W, Chen Q, Sun J, Wang G..  (2021)  Novel strategies to improve tumour therapy by targeting the proteins MCT1, MCT4 and LAT1.,  226  [PMID:34517305] [10.1016/j.ejmech.2021.113806]

3. Murray, Clare M CM and 26 more authors.  2005-12  Monocarboxylate transporter MCT1 is a target for immunosuppression.  [PMID:16370372]

4. 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]

5. 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