Dipropylcyclopentylxanthine

ID: ALA4177295

PubChem CID: 69612603

Max Phase: Preclinical

Molecular Formula: C16H24N4O2

Molecular Weight: 304.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCC1CCC(CCC)(n2c(=O)[nH]c3nc[nH]c3c2=O)C1

Standard InChI:  InChI=1S/C16H24N4O2/c1-3-5-11-6-8-16(9-11,7-4-2)20-14(21)12-13(18-10-17-12)19-15(20)22/h10-11H,3-9H2,1-2H3,(H,17,18)(H,19,22)

Standard InChI Key:  KDVDHEFNRCQNIQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
    5.0682  -20.4174    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0682  -21.2346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7735  -21.6391    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7735  -20.0047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4788  -20.4174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4833  -21.2356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2628  -21.4842    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7402  -20.8195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2555  -20.1603    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3567  -20.0077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6869  -19.2602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0780  -18.7152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3714  -19.1259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5438  -19.9246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7735  -19.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3611  -21.6442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1396  -20.7930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3486  -20.9982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1308  -21.7858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1610  -17.9022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9066  -17.5676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9896  -16.7547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  4  1  0
  2  3  1  0
  3  6  1  0
  5  4  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9  5  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 10  1  0
  1 10  1  0
  4 15  2  0
  2 16  2  0
 10 17  1  0
 17 18  1  0
 18 19  1  0
 12 20  1  0
 20 21  1  0
 21 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4177295

   1,3-Dipropyl-cyclopentyl-xanthine

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: 304.39

Molecular Weight (Monoisotopic): 304.1899

AlogP: 2.51

#Rotatable Bonds: 5

Polar Surface Area: 83.54

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.89

CX Basic pKa: ┄

CX LogP: 3.80

CX LogD: 3.69

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.89

Np Likeness Score: 0.44

References

1. Lambertucci C, Marucci G, Dal Ben D, Buccioni M, Spinaci A, Kachler S, Klotz KN, Volpini R..  (2018)  New potent and selective A1 adenosine receptor antagonists as potential tools for the treatment of gastrointestinal diseases.,  151  [PMID:29614417] [10.1016/j.ejmech.2018.03.067]

Source

Source(1):

• Scientific Literature