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

ID: ALA4526748

PubChem CID: 155544173

Max Phase: Preclinical

Molecular Formula: C20H16ClN5O2S

Molecular Weight: 425.90

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc(CCNc2nc(C#Cc3ccc(Cl)s3)nc3[nH]cnc23)ccc1O

Standard InChI:  InChI=1S/C20H16ClN5O2S/c1-28-15-10-12(2-5-14(15)27)8-9-22-19-18-20(24-11-23-18)26-17(25-19)7-4-13-3-6-16(21)29-13/h2-3,5-6,10-11,27H,8-9H2,1H3,(H2,22,23,24,25,26)

Standard InChI Key:  YFYHPWYFTLJMAL-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   38.0528  -31.0518    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.7624  -30.6424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7596  -29.8197    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.0510  -29.4145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3447  -30.6429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3414  -29.8263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5639  -29.5771    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.0865  -30.2397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5692  -30.8982    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.0484  -28.5973    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.7547  -28.1864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.4692  -31.0480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.1775  -31.4555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.8859  -31.8630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.9732  -32.6737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.7729  -32.8424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.1804  -32.1340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.6325  -31.5277    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   42.9975  -32.1305    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   39.4638  -28.5927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.1701  -28.1818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.8778  -28.5904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.5838  -28.1802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.5816  -27.3621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.8676  -26.9560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.1646  -27.3685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.2926  -28.5868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   42.2948  -29.4040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.2874  -26.9503    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
 23 27  1  0
 27 28  1  0
 24 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4526748

   ---

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: 425.90

Molecular Weight (Monoisotopic): 425.0713

AlogP: 3.84

#Rotatable Bonds: 5

Polar Surface Area: 95.95

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.58

CX Basic pKa: 3.53

CX LogP: 4.62

CX LogD: 4.62

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.42

Np Likeness Score: -0.37

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