(E)-3-[4-(2,6-dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]oct-1-yl]-acrylic acid

ID: ALA217076

PubChem CID: 9844693

Max Phase: Preclinical

Molecular Formula: C22H30N4O4

Molecular Weight: 414.51

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C22H30N4O4/c1-3-13-25-17-16(18(29)26(14-4-2)20(25)30)23-19(24-17)22-10-7-21(8-11-22,9-12-22)6-5-15(27)28/h5-6H,3-4,7-14H2,1-2H3,(H,23,24)(H,27,28)/b6-5+/t21-,22-

Standard InChI Key:  VPQZQQILWCCMPS-UYGKQXMSSA-N

Molfile:  

     RDKit          2D

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   -3.8559   -9.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4740  -10.5090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2202  -10.6955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1408   -8.5896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1408   -7.7647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4247   -7.3512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8505   -7.3512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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 13 14  1  0
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  9  7  2  0
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  3  7  1  1
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  2  3  1  0
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  3  4  1  0
  6 24  1  1
  4  5  1  0
  6 25  1  0
  5  6  1  0
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  3 26  1  0
  7  8  1  0
 24 27  2  0
 27 28  1  0
 10 15  1  0
 11 12  1  0
 28 29  1  0
 28 30  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA217076

   (E)-3-[4-(2,6-dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]oct-1-yl]-acrylic 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: 414.51

Molecular Weight (Monoisotopic): 414.2267

AlogP: 2.94

#Rotatable Bonds: 7

Polar Surface Area: 109.98

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.07

CX Basic pKa: 2.44

CX LogP: 3.28

CX LogD: 0.26

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.68

Np Likeness Score: -0.06

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