1,3-dipropyl-8-[2-(5,6-exo-epoxy-(1S,2S)-norborn-2-yl)]-xanthine

ID: ALA216750

PubChem CID: 44417680

Max Phase: Preclinical

Molecular Formula: C18H24N4O3

Molecular Weight: 344.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCn1c(=O)c2nc([C@H]3CC4C[C@@H]3[C@H]3O[C@@H]43)[nH]c2n(CCC)c1=O

Standard InChI:  InChI=1S/C18H24N4O3/c1-3-5-21-16-12(17(23)22(6-4-2)18(21)24)19-15(20-16)11-8-9-7-10(11)14-13(9)25-14/h9-11,13-14H,3-8H2,1-2H3,(H,19,20)/t9?,10-,11-,13-,14+/m0/s1

Standard InChI Key:  OQCJPFYWFGUHIN-KAELQNTISA-N

Molfile:  

     RDKit          2D

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   15.2763   -3.2224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0840   -3.8243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1425   -2.5411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9409   -3.6111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6942   -4.1336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6933   -4.9641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0221   -5.4511    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.1086   -6.2413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2807   -6.2385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8695   -6.9520    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.2791   -7.6712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1111   -7.6698    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.5252   -6.9534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8679   -8.3884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3512   -6.9501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0393   -6.9560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6285   -6.2385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8057   -6.2382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5223   -8.3870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3524   -8.3868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7633   -7.6694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3610   -5.4531    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4362   -4.1503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7413   -3.5986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1109   -3.6102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4309   -2.6480    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.7137   -3.1896    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.0825   -4.8243    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  2  1  0
  6  7  1  0
  7  9  1  0
  5  6  1  6
  8  9  2  0
  8 13  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 11 14  2  0
 13 15  2  0
 10 16  1  0
 16 17  1  0
 17 18  1  0
 12 19  1  0
 19 20  1  0
 20 21  1  0
  8 22  1  0
 22  6  2  0
 24 23  1  0
 24 25  1  0
 23 25  1  0
 24  1  1  0
 23  2  1  0
  2  3  1  0
  3  1  1  0
  1  4  1  0
  4  5  1  0
 24 26  1  6
 23 27  1  6
  2 28  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA216750

   8-[(2S,4R,5S,6S)-3-oxatricyclo[3.2.1.02,4]octan-6-yl]-1,3-dipropyl-7H-purine-2,6-dione

Molecule Features

Natural Product: Yes

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: 344.42

Molecular Weight (Monoisotopic): 344.1848

AlogP: 1.60

#Rotatable Bonds: 5

Polar Surface Area: 85.21

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.53

CX Basic pKa: 2.57

CX LogP: 1.71

CX LogD: 1.68

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.83

Np Likeness Score: -0.02

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