2-((5-Chlorothiophen-2-yl)ethynyl)-9-methyl-N-phenethyl-9H-purin-6-amine

ID: ALA4527909

PubChem CID: 155545399

Max Phase: Preclinical

Molecular Formula: C20H16ClN5S

Molecular Weight: 393.90

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cn1cnc2c(NCCc3ccccc3)nc(C#Cc3ccc(Cl)s3)nc21

Standard InChI:  InChI=1S/C20H16ClN5S/c1-26-13-23-18-19(22-12-11-14-5-3-2-4-6-14)24-17(25-20(18)26)10-8-15-7-9-16(21)27-15/h2-7,9,13H,11-12H2,1H3,(H,22,24,25)

Standard InChI Key:  BSQOPKHFOQKBEZ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    4.5149   -5.5125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2246   -5.1031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2217   -4.2804    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5131   -3.8752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8069   -5.1036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8036   -4.2871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0260   -4.0378    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5487   -4.7004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0313   -5.3589    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5105   -3.0580    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2169   -2.6471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9313   -5.5087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6397   -5.9162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3480   -6.3237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4354   -7.1344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2350   -7.3031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6425   -6.5947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0947   -5.9884    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.4596   -6.5912    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.9259   -3.0534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6323   -2.6425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3400   -3.0511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0459   -2.6409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0437   -1.8228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3297   -1.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6267   -1.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7820   -6.1372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  6  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9  5  1  0
  4 10  1  0
 10 11  1  0
 12 13  3  0
  2 12  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 14  1  0
 17 19  1  0
 11 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
  9 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4527909

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 393.90

Molecular Weight (Monoisotopic): 393.0815

AlogP: 4.13

#Rotatable Bonds: 4

Polar Surface Area: 55.63

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.11

CX LogP: 5.34

CX LogD: 5.34

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.53

Np Likeness Score: -0.82

References

1. Yu J, Mannes P, Jung YH, Ciancetta A, Bitant A, Lieberman DI, Khaznadar S, Auchampach JA, Gao ZG, Jacobson KA..  (2018)  Structure activity relationship of 2-arylalkynyl-adenine derivatives as human A₃ adenosine receptor antagonists.,  9  (11): [PMID:30568760] [10.1039/C8MD00317C]

2. Abel B, Murakami M, Tosh DK, Yu J, Lusvarghi S, Campbell RG, Gao ZG, Jacobson KA, Ambudkar SV..  (2022)  Interaction of A₃ adenosine receptor ligands with the human multidrug transporter ABCG2.,  231  [PMID:35152062] [10.1016/j.ejmech.2022.114103]

Source

Source(1):

• Scientific Literature