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

ID: ALA4455344

PubChem CID: 144852560

Max Phase: Preclinical

Molecular Formula: C16H14ClN5S

Molecular Weight: 343.84

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Clc1ccc(C#Cc2nc(NC3CCCC3)c3nc[nH]c3n2)s1

Standard InChI:  InChI=1S/C16H14ClN5S/c17-12-7-5-11(23-12)6-8-13-21-15-14(18-9-19-15)16(22-13)20-10-3-1-2-4-10/h5,7,9-10H,1-4H2,(H2,18,19,20,21,22)

Standard InChI Key:  XZDRDRRVIDEBHK-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
   12.5878  -24.2089    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2974  -23.7994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2946  -22.9768    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5860  -22.5715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8797  -23.7999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8764  -22.9834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0989  -22.7342    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6215  -23.3967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1042  -24.0553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5834  -21.7543    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2897  -21.3434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0042  -24.2051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7125  -24.6126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4209  -25.0200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5082  -25.8308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3079  -25.9994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7154  -25.2910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1675  -24.6847    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   17.5325  -25.2875    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   14.0379  -21.6718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5828  -21.0628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1719  -20.3563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3731  -20.5289    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  1  0
 22 23  1  0
 23 11  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4455344

   ---

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: 343.84

Molecular Weight (Monoisotopic): 343.0658

AlogP: 3.82

#Rotatable Bonds: 2

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: 3.50

CX LogP: 4.38

CX LogD: 4.37

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.69

Np Likeness Score: -0.83

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