(R)-3-(4-(8-ethyl-5-oxo-4-propyl-4,5,7,8-tetrahydro-1H-imidazo[1,2-g]purin-2-yl)bicyclo[2.2.2]octan-1-yl)propanoic acid

ID: ALA217268

PubChem CID: 135404340

Max Phase: Preclinical

Molecular Formula: C23H33N5O3

Molecular Weight: 427.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCN1C(=O)N2C[C@@H](CC)N=C2c2[nH]c(C34CCC(CCC(=O)O)(CC3)CC4)nc21

Standard InChI:  InChI=1S/C23H33N5O3/c1-3-13-27-19-17(18-24-15(4-2)14-28(18)21(27)31)25-20(26-19)23-10-7-22(8-11-23,9-12-23)6-5-16(29)30/h15H,3-14H2,1-2H3,(H,25,26)(H,29,30)/t15-,22?,23?/m1/s1

Standard InChI Key:  UFPMVCAGTVEGMT-CGDGTSQQSA-N

Molfile:  

     RDKit          2D

 31 35  0  0  1  0  0  0  0  0999 V2000
   -3.4875   -7.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7755   -7.9375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0635   -6.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0635   -7.5302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2779   -7.7855    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7923   -7.1172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2778   -6.4490    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7759   -8.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4906   -9.1746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2049   -8.7617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0327   -7.1172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4426   -7.8389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2640   -7.8409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6803   -7.1282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2691   -6.4119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4414   -6.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8792   -6.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8792   -7.4208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2023   -7.9410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5042   -7.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9195   -7.8379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7445   -7.8346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1614   -8.5467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1558   -7.1178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4844   -6.7000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7755   -6.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9487   -5.4858    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7648   -5.4028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0958   -6.1532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1797   -4.6897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0047   -4.6925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 11 16  1  0
 12 13  1  0
 13 14  1  0
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 15 16  1  0
  7  3  1  0
 11 17  1  0
  3  4  2  0
 17 18  1  0
 18 14  1  0
  2  8  1  0
  1 19  2  0
 14 20  1  0
  8  9  1  0
 20 21  1  0
 25  1  1  0
 21 22  1  0
  9 10  1  0
  1  2  1  0
 22 23  1  0
 22 24  2  0
 25 26  1  0
  6 11  1  0
 11 12  1  0
  2  4  1  0
  3 26  1  0
  4  5  1  0
 26 27  2  0
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 28 29  1  0
 29 25  1  0
  5  6  2  0
 28 30  1  1
  6  7  1  0
 30 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA217268

   ---

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: 427.55

Molecular Weight (Monoisotopic): 427.2583

AlogP: 4.06

#Rotatable Bonds: 7

Polar Surface Area: 101.89

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.87

CX Basic pKa: 5.14

CX LogP: 2.24

CX LogD: 0.45

Aromatic Rings: 1

Heavy Atoms: 31

QED Weighted: 0.68

Np Likeness Score: 0.10

References

1. Vu CB, Kiesman WF, Conlon PR, Lin KC, Tam M, Petter RC, Smits G, Lutterodt F, Jin X, Chen L, Zhang J..  (2006)  Tricyclic imidazoline derivatives as potent and selective adenosine A1 receptor antagonists.,  49  (24): [PMID:17125265] [10.1021/jm060539t]

Source

Source(1):

• Scientific Literature