8-(2-Furyl)-2-[2-(1-hydroxycyclohexyl)ethyn-1-yl]-N9-propargyladenine

ID: ALA3291310

PubChem CID: 89805044

Max Phase: Preclinical

Molecular Formula: C20H19N5O2

Molecular Weight: 361.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C#CCn1c(-c2ccco2)nc2c(N)nc(C#CC3(O)CCCCC3)nc21

Standard InChI:  InChI=1S/C20H19N5O2/c1-2-12-25-18(14-7-6-13-27-14)24-16-17(21)22-15(23-19(16)25)8-11-20(26)9-4-3-5-10-20/h1,6-7,13,26H,3-5,9-10,12H2,(H2,21,22,23)

Standard InChI Key:  GTGGDWUGNLGPSN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   12.6656  -13.2594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2460  -13.9617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6423  -14.6723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4597  -14.6868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8793  -13.9844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4815  -13.2676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5194  -11.2187    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5204  -12.0373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8070  -12.4470    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1043  -12.0360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1027  -11.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8084  -10.8119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8110   -9.9953    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3291  -12.2916    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8477  -11.6247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3263  -10.9686    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0741  -13.0680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2812  -13.2439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4779  -13.4152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2314  -12.4483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9465  -12.8552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0803  -12.5604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0314  -11.6245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5527  -10.9622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7749  -11.2128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7729  -12.0300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5494  -12.2844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
  7 12  2  0
 10 14  1  0
 14 15  1  0
 15 16  2  0
 11 16  1  0
 17 18  1  0
 18 19  3  0
 14 17  1  0
 20 21  3  0
 21  1  1  0
  1 22  1  0
  8 20  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 23  2  0
 15 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3291310

   1-[2-[6-Amino-8-(furan-2-yl)-9-prop-2-ynylpurin-2-yl]ethynyl]cyclohexan-1-ol

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 361.41

Molecular Weight (Monoisotopic): 361.1539

AlogP: 2.35

#Rotatable Bonds: 2

Polar Surface Area: 102.99

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.97

CX Basic pKa: 3.77

CX LogP: 2.98

CX LogD: 2.98

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.68

Np Likeness Score: -0.79

References

1. Endo K, Deguchi K, Matsunaga H, Tomaya K, Yamada K..  (2014)  8-Substituted 2-alkynyl-N(9)-propargyladenines as A2A adenosine receptor antagonists.,  22  (12): [PMID:24815000] [10.1016/j.bmc.2014.04.041]

Source

Source(1):

• Scientific Literature