1,3-Dibutyl-7-(2-oxo-propyl)-3,7-dihydro-purine-2,6-dione (Denbufyllene)

ID: ALA277465

Cas Number: 57076-71-8

PubChem CID: 2984

Product Number: D341180, Order Now?

Max Phase: Phase

Molecular Formula: C16H24N4O3

Molecular Weight: 320.39

Molecule Type: Small molecule

Names and Identifiers

Synonyms: BRL 30892 | BRL-30892 | denbufylline|57076-71-8|BRL 30892|BRL-30892|7-Acetonyl-1,3-dibutylxanthine|1,3-dibutyl-7-(2-oxopropyl)purine-2,6-dione|CHEMBL277465|04B949KO6F|Denbufilina [Spanish]|Denbufyllinum [Latin]|Denbufilina|Denbufyllinum|Denbufylline [INN:BAN]|1,3-Di-n-butyl-7-(2-oxopropyl)xanthine|UNII-04B949KO6F|3,7-Dihydro-1,3-dibutyl-7-(2-oxopropyl)-1H-purine-2,6-dione|DENBUFYLLINE [INN]|DENBUFYLLINE [MART.]|SCHEMBL127152|CHEBI:92669|DTXSID30205687|HMS2089J13|1H-Purine-2,6-dione, 3,7-dihydro-Show More⌵

Canonical SMILES:  CCCCn1c(=O)c2c(ncn2CC(C)=O)n(CCCC)c1=O

Standard InChI:  InChI=1S/C16H24N4O3/c1-4-6-8-19-14-13(18(11-17-14)10-12(3)21)15(22)20(16(19)23)9-7-5-2/h11H,4-10H2,1-3H3

Standard InChI Key:  HJPRDDKCXVCFOH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
    1.1542   -0.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1542    0.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -0.5542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5958    0.9625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5958   -0.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    1.4708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1125   -0.3750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1125    1.2958    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6792    0.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4375    2.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4875   -0.5542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    2.4833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -1.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4875    1.4708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4167    2.4833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7167    3.4375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1042    1.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1542   -2.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3583    0.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1292   -3.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2208    1.4708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9917   -3.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1083    0.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  1  0
  4  5  1  0
  5  3  1  0
  6  2  1  0
  7  1  1  0
  8  2  1  0
  9  7  2  0
 10  8  1  0
 11  5  2  0
 12  6  2  0
 13  3  1  0
 14  4  1  0
 15 10  1  0
 16 15  2  0
 17 15  1  0
 18 13  1  0
 19 14  1  0
 20 18  1  0
 21 19  1  0
 22 20  1  0
 23 21  1  0
  8  9  1  0
  6  4  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA277465

   Denbufylline

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: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 320.39

Molecular Weight (Monoisotopic): 320.1848

AlogP: 1.55

#Rotatable Bonds: 8

Polar Surface Area: 78.89

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 1.91

CX LogD: 1.91

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.74

Np Likeness Score: -1.17

References

1. Gilbert AM, Caltabiano S, Roberts D, Sum SF, Francisco GD, Lim K, Asselin M, Ellingboe JW, Kharode Y, Cannistraci A, Francis R, TrailSmith M, Gralnick D..  (2000)  Novel and selective calcitonin-inducing agents.,  43  (6): [PMID:10737755] [10.1021/jm990558l]

2. Miyamoto K, Yamamoto Y, Kurita M, Sakai R, Konno K, Sanae F, Ohshima T, Takagi K, Hasegawa T, Iwasaki N..  (1993)  Bronchodilator activity of xanthine derivatives substituted with functional groups at the 1- or 7-position.,  36  (10): [PMID:8496906] [10.1021/jm00062a010]

3. Gilbert AM, Caltabiano S, Koehn FE, Chen ZJ, Francisco GD, Ellingboe JW, Kharode Y, Mangine A, Francis R, TrailSmith M, Gralnick D..  (2002)  Pyrazolopyrimidine-2,4-dione sulfonamides: novel and selective calcitonin inducers.,  45  (11): [PMID:12014973] [10.1021/jm010554s]

4. Sawanishi H, Suzuki H, Yamamoto S, Waki Y, Kasugai S, Ohya K, Suzuki N, Miyamoto K, Takagi K..  (1997)  Selective inhibitors of cyclic AMP-specific phosphodiesterase: heterocycle-condensed purines.,  40  (20): [PMID:9379444] [10.1021/jm970089s]

5. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

Source

Source(2):

• Scientific Literature
• USP Dictionary of USAN and International Drug Names