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

ID: ALA3291308

PubChem CID: 57344115

Max Phase: Preclinical

Molecular Formula: C16H16BrN5O

Molecular Weight: 374.24

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C16H16BrN5O/c1-2-10-22-14-12(21-15(22)17)13(18)19-11(20-14)6-9-16(23)7-4-3-5-8-16/h1,23H,3-5,7-8,10H2,(H2,18,19,20)

Standard InChI Key:  UYYNNRWFLVQUKF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  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
    7.0291  -11.6214    0.0000 Br  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
 15 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3291308

   1-[2-(6-Amino-8-bromo-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: 374.24

Molecular Weight (Monoisotopic): 373.0538

AlogP: 1.85

#Rotatable Bonds: 1

Polar Surface Area: 89.85

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.97

CX Basic pKa: 2.93

CX LogP: 3.03

CX LogD: 3.03

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.59

Np Likeness Score: -0.56

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