2-Methylsulfinyl-4-methyl-6-[(3-hydroxyphenyl)methyl]-4H-thieno[3,2-b]pyrrole[3,2-d]pyridazinone

ID: ALA1082815

Cas Number: 1222535-34-3

PubChem CID: 44543627

Max Phase: Preclinical

Molecular Formula: C17H15N3O3S2

Molecular Weight: 373.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1c2cc([S+](C)[O-])sc2c2cnn(Cc3cccc(O)c3)c(=O)c21

Standard InChI:  InChI=1S/C17H15N3O3S2/c1-19-13-7-14(25(2)23)24-16(13)12-8-18-20(17(22)15(12)19)9-10-4-3-5-11(21)6-10/h3-8,21H,9H2,1-2H3

Standard InChI Key:  PTQIMFRZBDFMMQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
    9.3956   -5.2426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1068   -4.8152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8332   -5.2161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5402   -4.7887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5249   -3.9603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8026   -3.5593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0915   -3.9867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9605   -5.2721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6735   -4.8440    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6538   -4.0127    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9271   -3.6134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2347   -4.8713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2212   -4.0381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4507   -5.1393    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9503   -4.4753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4274   -3.7938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9261   -3.1265    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.1388   -3.3987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1512   -4.2307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9755   -6.0992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2056   -5.9301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4134   -2.9850    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.4121   -2.1579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6983   -3.4002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2656   -5.1891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  2  1  0
 12  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 13  1  0
 12 13  2  0
 13 16  1  0
 15 14  1  0
 14 12  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 15  1  0
  8 20  2  0
 14 21  1  0
  9  1  1  0
 18 22  1  0
 22 23  1  0
 22 24  1  0
  4 25  1  0
M  CHG  2  22   1  23  -1
M  END

Alternative Forms

1. Parent:

   

   ALA1082815

   6-(3-Hydroxybenzyl)-4-methyl-2-(methylsulfinyl)-4H-thieno[2',3':4,5]pyrrolo[2,3-d]pyridazin-5(6H)-one

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: 373.46

Molecular Weight (Monoisotopic): 373.0555

AlogP: 2.44

#Rotatable Bonds: 3

Polar Surface Area: 83.11

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.41

CX Basic pKa: ┄

CX LogP: 1.66

CX LogD: 1.66

Aromatic Rings: 4

Heavy Atoms: 25

QED Weighted: 0.56

Np Likeness Score: -1.05

References

1. Jiang JK, Boxer MB, Vander Heiden MG, Shen M, Skoumbourdis AP, Southall N, Veith H, Leister W, Austin CP, Park HW, Inglese J, Cantley LC, Auld DS, Thomas CJ..  (2010)  Evaluation of thieno[3,2-b]pyrrole[3,2-d]pyridazinones as activators of the tumor cell specific M2 isoform of pyruvate kinase.,  20  (11): [PMID:20451379] [10.1016/j.bmcl.2010.04.015]

2. PubChem BioAssay data set, 

Source

Source(2):

• Scientific Literature
• PubChem BioAssays