2-((4-(2,6-dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)bicyclo[2.2.2]octan-1-yl)(methyl)amino)acetic acid

ID: ALA384705

PubChem CID: 11995649

Max Phase: Preclinical

Molecular Formula: C24H35N5O5

Molecular Weight: 473.57

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCn1c(=O)c2nc([C@]34CC[C@](C(=O)N(C)CC(=O)OC)(CC3)CC4)[nH]c2n(CCC)c1=O

Standard InChI:  InChI=1S/C24H35N5O5/c1-5-13-28-18-17(19(31)29(14-6-2)22(28)33)25-20(26-18)23-7-10-24(11-8-23,12-9-23)21(32)27(3)15-16(30)34-4/h5-15H2,1-4H3,(H,25,26)/t23-,24+

Standard InChI Key:  BBAIDTHZIBWSIU-PSWAGMNNSA-N

Molfile:  

     RDKit          2D

 34 37  0  0  1  0  0  0  0  0999 V2000
    0.5542  -20.5208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5542  -21.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9782  -21.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9782  -20.5208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2662  -20.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2658  -22.5794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5984  -23.0644    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9332  -23.0644    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6784  -23.8490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8522  -23.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4422  -24.5619    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8539  -25.2776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6800  -25.2766    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0945  -24.5600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4412  -25.9919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9195  -24.5579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3828  -24.5618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7951  -23.8472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6201  -23.8470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0926  -25.9910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9176  -25.9909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3300  -25.2763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2643  -19.2781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9788  -18.8656    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5498  -18.8656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6708  -20.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9958  -21.0708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2625  -21.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6932  -19.2781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4077  -18.8656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1246  -19.2760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4101  -18.0385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9788  -18.0406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8376  -18.8609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0
 14 16  2  0
  7 10  1  0
 11 17  1  0
  9  8  1  0
 17 18  1  0
  8  6  2  0
 18 19  1  0
 28  6  1  1
 13 20  1  0
  9 10  2  0
 20 21  1  0
  2 28  1  0
 21 22  1  0
 28  3  1  0
  3  4  1  0
  4  5  1  0
 23 24  1  0
 23 25  2  0
  5 23  1  1
  6  7  1  0
  5 26  1  0
  1  2  1  0
 26 27  1  0
  9 14  1  0
 28 27  1  0
 10 11  1  0
 24 29  1  0
 11 12  1  0
 29 30  1  0
 12 13  1  0
 13 14  1  0
 30 31  1  0
 30 32  2  0
 24 33  1  0
 12 15  2  0
 31 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA384705

   2-((4-(2,6-dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)bicyclo[2.2.2]octan-1-yl)(methyl)amino)acetic acid

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: 473.57

Molecular Weight (Monoisotopic): 473.2638

AlogP: 1.93

#Rotatable Bonds: 8

Polar Surface Area: 119.29

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.43

CX Basic pKa: 2.47

CX LogP: 2.32

CX LogD: 2.29

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.59

Np Likeness Score: -0.61

References

1. Kiesman WF, Zhao J, Conlon PR, Dowling JE, Petter RC, Lutterodt F, Jin X, Smits G, Fure M, Jayaraj A, Kim J, Sullivan G, Linden J..  (2006)  Potent and orally bioavailable 8-bicyclo[2.2.2]octylxanthines as adenosine A1 receptor antagonists.,  49  (24): [PMID:17125264] [10.1021/jm0605381]

Source

Source(1):

• Scientific Literature