N-(3-Chlorobenzyl)-2-((5-chlorothiophen-2-yl)ethynyl)-9H-purin-6-amine

ID: ALA4530091

PubChem CID: 155545843

Max Phase: Preclinical

Molecular Formula: C18H11Cl2N5S

Molecular Weight: 400.29

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Clc1cccc(CNc2nc(C#Cc3ccc(Cl)s3)nc3[nH]cnc23)c1

Standard InChI:  InChI=1S/C18H11Cl2N5S/c19-12-3-1-2-11(8-12)9-21-17-16-18(23-10-22-16)25-15(24-17)7-5-13-4-6-14(20)26-13/h1-4,6,8,10H,9H2,(H2,21,22,23,24,25)

Standard InChI Key:  YLUPQKCHATVQQM-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   11.6419  -30.8123    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3584  -30.3990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3555  -29.5684    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6401  -29.1592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9271  -30.3994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9238  -29.5751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1387  -29.3235    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6568  -29.9924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1440  -30.6573    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6374  -28.3343    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3506  -27.9194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0719  -30.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7871  -31.2199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5022  -31.6313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5904  -32.4498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3977  -32.6201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8091  -31.9049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2560  -31.2927    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   16.6340  -31.9014    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   13.0664  -28.3296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0671  -29.1524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7821  -29.5624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4962  -29.1476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4909  -28.3183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7754  -27.9119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2026  -27.9010    0.0000 Cl  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  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 24 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4530091

   ---

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: 400.29

Molecular Weight (Monoisotopic): 399.0112

AlogP: 4.73

#Rotatable Bonds: 3

Polar Surface Area: 66.49

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.68

CX Basic pKa: 3.48

CX LogP: 5.39

CX LogD: 5.39

Aromatic Rings: 4

Heavy Atoms: 26

QED Weighted: 0.49

Np Likeness Score: -1.17

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]

Source

Source(1):

• Scientific Literature