2-((5-Chlorothiophen-2-yl)ethynyl)-N-(3,4-dihydroxyphenethyl)-9H-purin-6-amine

ID: ALA4581568

PubChem CID: 155561439

Max Phase: Preclinical

Molecular Formula: C19H14ClN5O2S

Molecular Weight: 411.87

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Oc1ccc(CCNc2nc(C#Cc3ccc(Cl)s3)nc3[nH]cnc23)cc1O

Standard InChI:  InChI=1S/C19H14ClN5O2S/c20-15-5-2-12(28-15)3-6-16-24-18(17-19(25-16)23-10-22-17)21-8-7-11-1-4-13(26)14(27)9-11/h1-2,4-5,9-10,26-27H,7-8H2,(H2,21,22,23,24,25)

Standard InChI Key:  OUDNABXHAKYWLX-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   28.1970  -31.3944    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.9066  -30.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9038  -30.1623    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.1952  -29.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4889  -30.9854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4856  -30.1689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7080  -29.9197    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.2307  -30.5822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7134  -31.2408    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.1925  -28.9398    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.8989  -28.5290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6134  -31.3906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3217  -31.7981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0301  -32.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1174  -33.0163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9170  -33.1849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3245  -32.4765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7767  -31.8702    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   33.1416  -32.4730    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   29.6079  -28.9353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3143  -28.5244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0220  -28.9329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7279  -28.5227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7257  -27.7047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0117  -27.2985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3088  -27.7111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0062  -26.4814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.4316  -27.2928    0.0000 O   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
 25 27  1  0
 24 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4581568

   ---

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: 411.87

Molecular Weight (Monoisotopic): 411.0557

AlogP: 3.53

#Rotatable Bonds: 4

Polar Surface Area: 106.95

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.27

CX Basic pKa: 3.53

CX LogP: 4.54

CX LogD: 4.54

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.30

Np Likeness Score: -0.34

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