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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (7) Show 7 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:48 UTC

HMDB ID

HMDB0014944

Secondary Accession Numbers

HMDB14944

Metabolite Identification

Common Name

Pentoxifylline

Description

Pentoxifylline, also known as pentoxil or trental, belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety. Contraindications include intolerance to pentoxifylline or other xanthine derivatives, recent retinal or cerebral haemorrhage, and risk factors for haemorrhage. In addition, pentoxifylline improves red blood cell deformability (known as a haemorrheologic effect), reduces blood viscosity and decreases the potential for platelet aggregation and blood clot formation. Pentoxifylline is a drug which is used for the treatment of patients with intermittent lameness or immobility arising from chronic occlusive arterial disease of the limbs. There is some evidence that pentoxifylline can lower the levels of some biomarkers in non-alcoholic steatohepatitis but evidence is insufficient to determine if the drug is safe and effective for this use. However, pentoxifylline is also recommended for off-label use as an adjunct to compression bandaging for the treatment of chronic venous leg ulcers by the Scottish Intercollegiate Guidelines Network) (SIGN) as this has been shown to improve healing rates. Pentoxifylline, in combination with tocopherol and clodronate, has been found to heal refractory osteoradionecrosis of the jaw,and to be prophylactic against osteoradionecrosis. Like other methylated xanthine derivatives, pentoxifylline is a competitive nonselective phosphodiesterase inhibitor which raises intracellular cAMP, activates PKA, inhibits TNF and leukotriene synthesis, and reduces inflammation and innate immunity. Human studies have been conducted for Peyronie's disease. Pentoxifylline is an extremely weak basic (essentially neutral) compound (based on its pKa). This is its only FDA, MHRA and TGA-labelled indication. Pentoxifylline has also been shown to be of benefit in alcoholic hepatitis, with some studies demonstrating a reduction in risk of hepatorenal syndrome. In a Cochrane systematic review on the use of Pentoxifylline for intermittent claudication in 2015, the following was concluded "The quality of included studies was generally low, and very large variability between studies was noted in reported findings including duration of trials, doses of pentoxifylline and distances participants could walk at the start of trials. Most included studies did not report on randomisation techniques or how treatment allocation was concealed, did not provide adequate information to permit judgement of selective reporting and did not report blinding of outcome assessors. Given all these factors, the role of pentoxifylline in intermittent claudication remains uncertain, although this medication was generally well tolerated by participants". It is generic and sold under many brand names worldwide. Animal studies have been conducted exploring the use of pentoxifylline for erectile dysfunction and hearing loss.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0014944
     RDKit          3D
Pentoxifylline
 38 39  0  0  0  0  0  0  0  0999 V2000
    5.0859   -1.3859   -0.0757 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1388   -0.2735   -0.4417 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7124   -0.3240   -1.5836 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7764    0.7854    0.5400 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8299    1.7847    0.0016 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5076    1.2730   -0.4537 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7553    0.6117    0.6361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5130    0.0840    0.3338 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6684    0.7662    0.4360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5622    1.9512    0.8320 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8994    0.2411    0.1382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9658   -1.0821   -0.2986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2588   -1.3477   -0.5185 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9808   -0.2232   -0.2277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1429    0.7397    0.1717 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4794    2.0823    0.5732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8027   -1.7562   -0.3974 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8750   -3.1341   -0.8526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6217   -1.1965   -0.0935 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4001   -1.9325   -0.2270 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6421   -1.7266   -0.9469 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4442   -2.2177    0.3120 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7665   -0.9914    0.7343 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4671    0.3448    1.5213 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7334    1.3197    0.7747 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3251    2.2318   -0.9137 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7506    2.6486    0.6992 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5901    0.5893   -1.3183 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9641    2.1788   -0.8560 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3784   -0.2207    1.0278 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6396    1.3526    1.4711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0652   -0.1216   -0.3068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5532    2.2879    0.5594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9823    2.8141   -0.1177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0448    2.3254    1.5863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8097   -3.8199    0.0244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9352   -3.3175   -1.4443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7471   -3.3410   -1.4809 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 12 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 19  8  1  0
 15 11  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
 14 32  1  0
 16 33  1  0
 16 34  1  0
 16 35  1  0
 18 36  1  0
 18 37  1  0
 18 38  1  0
M  END

806
  Mrv0541 02231215012D          

 20 21  0  0  0  0            999 V2000
    6.6515    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1466    0.6639    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1466   -0.6639    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6280    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4029    1.4482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 12  2  0  0  0  0
  2 14  2  0  0  0  0
  3 19  2  0  0  0  0
  4  8  1  0  0  0  0
  4 12  1  0  0  0  0
  4 14  1  0  0  0  0
  5 13  1  0  0  0  0
  5 14  1  0  0  0  0
  5 17  1  0  0  0  0
  6 11  1  0  0  0  0
  6 16  1  0  0  0  0
  6 18  1  0  0  0  0
  7 13  1  0  0  0  0
  7 16  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 15  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 15 19  1  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014944

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1C=NC2=C1C(=O)N(CCCCC(C)=O)C(=O)N2C

> <INCHI_IDENTIFIER>
InChI=1S/C13H18N4O3/c1-9(18)6-4-5-7-17-12(19)10-11(14-8-15(10)2)16(3)13(17)20/h8H,4-7H2,1-3H3

> <INCHI_KEY>
BYPFEZZEUUWMEJ-UHFFFAOYSA-N

> <FORMULA>
C13H18N4O3

> <MOLECULAR_WEIGHT>
278.307

> <EXACT_MASS>
278.137890462

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
29.269593476836803

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,7-dimethyl-1-(5-oxohexyl)-2,3,6,7-tetrahydro-1H-purine-2,6-dione

> <ALOGPS_LOGP>
0.08

> <JCHEM_LOGP>
0.23220584566666638

> <ALOGPS_LOGS>
-1.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.64286715835779

> <JCHEM_PKA_STRONGEST_BASIC>
-0.9270915732483686

> <JCHEM_POLAR_SURFACE_AREA>
75.51

> <JCHEM_REFRACTIVITY>
73.52229999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.17e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pentoxifylline

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014944
     RDKit          3D
Pentoxifylline
 38 39  0  0  0  0  0  0  0  0999 V2000
    5.0859   -1.3859   -0.0757 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1388   -0.2735   -0.4417 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7124   -0.3240   -1.5836 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7764    0.7854    0.5400 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8299    1.7847    0.0016 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5076    1.2730   -0.4537 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7553    0.6117    0.6361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5130    0.0840    0.3338 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6684    0.7662    0.4360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5622    1.9512    0.8320 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8994    0.2411    0.1382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9658   -1.0821   -0.2986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2588   -1.3477   -0.5185 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9808   -0.2232   -0.2277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1429    0.7397    0.1717 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4794    2.0823    0.5732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8027   -1.7562   -0.3974 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8750   -3.1341   -0.8526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6217   -1.1965   -0.0935 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4001   -1.9325   -0.2270 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6421   -1.7266   -0.9469 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4442   -2.2177    0.3120 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7665   -0.9914    0.7343 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4671    0.3448    1.5213 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7334    1.3197    0.7747 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3251    2.2318   -0.9137 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7506    2.6486    0.6992 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5901    0.5893   -1.3183 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9641    2.1788   -0.8560 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3784   -0.2207    1.0278 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6396    1.3526    1.4711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0652   -0.1216   -0.3068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5532    2.2879    0.5594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9823    2.8141   -0.1177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0448    2.3254    1.5863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8097   -3.8199    0.0244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9352   -3.3175   -1.4443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7471   -3.3410   -1.4809 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 12 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 19  8  1  0
 15 11  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
 14 32  1  0
 16 33  1  0
 16 34  1  0
 16 35  1  0
 18 36  1  0
 18 37  1  0
 18 38  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 806                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      12.416   3.080   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       9.748  -1.540   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       4.414   3.080   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0      11.082   0.770   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0      12.416  -1.540   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0      15.207   1.239   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0      15.207  -1.239   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       9.748   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.415   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.081   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.750   0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.416   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.750  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.082  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.748   0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      16.106   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.416  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      15.685   2.703   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.414   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.080   0.770   0.000  0.00  0.00           C+0
CONECT    1   12                                                            
CONECT    2   14                                                            
CONECT    3   19                                                            
CONECT    4    8   12   14                                                  
CONECT    5   13   14   17                                                  
CONECT    6   11   16   18                                                  
CONECT    7   13   16                                                       
CONECT    8    4    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   15                                                       
CONECT   11    6   12   13                                                  
CONECT   12    1    4   11                                                  
CONECT   13    5    7   11                                                  
CONECT   14    2    4    5                                                  
CONECT   15   10   19                                                       
CONECT   16    6    7                                                       
CONECT   17    5                                                            
CONECT   18    6                                                            
CONECT   19    3   15   20                                                  
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0014944
HETATM    1  C1  UNL     1       5.086  -1.386  -0.076  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.139  -0.273  -0.442  1.00  0.00           C  
HETATM    3  O1  UNL     1       3.712  -0.324  -1.584  1.00  0.00           O  
HETATM    4  C3  UNL     1       3.776   0.785   0.540  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.830   1.785   0.002  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.508   1.273  -0.454  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.755   0.612   0.636  1.00  0.00           C  
HETATM    8  N1  UNL     1      -0.513   0.084   0.334  1.00  0.00           N  
HETATM    9  C7  UNL     1      -1.668   0.766   0.436  1.00  0.00           C  
HETATM   10  O2  UNL     1      -1.562   1.951   0.832  1.00  0.00           O  
HETATM   11  C8  UNL     1      -2.899   0.241   0.138  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.966  -1.082  -0.299  1.00  0.00           C  
HETATM   13  N2  UNL     1      -4.259  -1.348  -0.518  1.00  0.00           N  
HETATM   14  C10 UNL     1      -4.981  -0.223  -0.228  1.00  0.00           C  
HETATM   15  N3  UNL     1      -4.143   0.740   0.172  1.00  0.00           N  
HETATM   16  C11 UNL     1      -4.479   2.082   0.573  1.00  0.00           C  
HETATM   17  N4  UNL     1      -1.803  -1.756  -0.397  1.00  0.00           N  
HETATM   18  C12 UNL     1      -1.875  -3.134  -0.853  1.00  0.00           C  
HETATM   19  C13 UNL     1      -0.622  -1.197  -0.093  1.00  0.00           C  
HETATM   20  O3  UNL     1       0.400  -1.933  -0.227  1.00  0.00           O  
HETATM   21  H1  UNL     1       5.642  -1.727  -0.947  1.00  0.00           H  
HETATM   22  H2  UNL     1       4.444  -2.218   0.312  1.00  0.00           H  
HETATM   23  H3  UNL     1       5.766  -0.991   0.734  1.00  0.00           H  
HETATM   24  H4  UNL     1       3.467   0.345   1.521  1.00  0.00           H  
HETATM   25  H5  UNL     1       4.733   1.320   0.775  1.00  0.00           H  
HETATM   26  H6  UNL     1       3.325   2.232  -0.914  1.00  0.00           H  
HETATM   27  H7  UNL     1       2.751   2.649   0.699  1.00  0.00           H  
HETATM   28  H8  UNL     1       1.590   0.589  -1.318  1.00  0.00           H  
HETATM   29  H9  UNL     1       0.964   2.179  -0.856  1.00  0.00           H  
HETATM   30  H10 UNL     1       1.378  -0.221   1.028  1.00  0.00           H  
HETATM   31  H11 UNL     1       0.640   1.353   1.471  1.00  0.00           H  
HETATM   32  H12 UNL     1      -6.065  -0.122  -0.307  1.00  0.00           H  
HETATM   33  H13 UNL     1      -5.553   2.288   0.559  1.00  0.00           H  
HETATM   34  H14 UNL     1      -3.982   2.814  -0.118  1.00  0.00           H  
HETATM   35  H15 UNL     1      -4.045   2.325   1.586  1.00  0.00           H  
HETATM   36  H16 UNL     1      -1.810  -3.820   0.024  1.00  0.00           H  
HETATM   37  H17 UNL     1      -0.935  -3.317  -1.444  1.00  0.00           H  
HETATM   38  H18 UNL     1      -2.747  -3.341  -1.481  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3    3    4
CONECT    4    5   24   25
CONECT    5    6   26   27
CONECT    6    7   28   29
CONECT    7    8   30   31
CONECT    8    9   19
CONECT    9   10   10   11
CONECT   11   12   12   15
CONECT   12   13   17
CONECT   13   14   14
CONECT   14   15   32
CONECT   15   16
CONECT   16   33   34   35
CONECT   17   18   19
CONECT   18   36   37   38
CONECT   19   20   20
END

HMDB0014944
     RDKit          3D
Pentoxifylline
 38 39  0  0  0  0  0  0  0  0999 V2000
    5.0859   -1.3859   -0.0757 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1388   -0.2735   -0.4417 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7124   -0.3240   -1.5836 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7764    0.7854    0.5400 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8299    1.7847    0.0016 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5076    1.2730   -0.4537 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7553    0.6117    0.6361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5130    0.0840    0.3338 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6684    0.7662    0.4360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5622    1.9512    0.8320 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8994    0.2411    0.1382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9658   -1.0821   -0.2986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2588   -1.3477   -0.5185 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9808   -0.2232   -0.2277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1429    0.7397    0.1717 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4794    2.0823    0.5732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8027   -1.7562   -0.3974 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8750   -3.1341   -0.8526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6217   -1.1965   -0.0935 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4001   -1.9325   -0.2270 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6421   -1.7266   -0.9469 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4442   -2.2177    0.3120 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7665   -0.9914    0.7343 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4671    0.3448    1.5213 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7334    1.3197    0.7747 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3251    2.2318   -0.9137 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7506    2.6486    0.6992 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5901    0.5893   -1.3183 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9641    2.1788   -0.8560 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3784   -0.2207    1.0278 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6396    1.3526    1.4711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0652   -0.1216   -0.3068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5532    2.2879    0.5594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9823    2.8141   -0.1177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0448    2.3254    1.5863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8097   -3.8199    0.0244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9352   -3.3175   -1.4443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7471   -3.3410   -1.4809 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 12 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 19  8  1  0
 15 11  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
 14 32  1  0
 16 33  1  0
 16 34  1  0
 16 35  1  0
 18 36  1  0
 18 37  1  0
 18 38  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Pentoxil	Kegg
Trental	Kegg
EHT0201	HMDB
Agapurin	HMDB
Torental	HMDB
Oxpentifylline	HMDB

Chemical Formula

C₁₃H₁₈N₄O₃

Average Molecular Weight

278.307

Monoisotopic Molecular Weight

278.137890462

IUPAC Name

3,7-dimethyl-1-(5-oxohexyl)-2,3,6,7-tetrahydro-1H-purine-2,6-dione

Traditional Name

pentoxifylline

CAS Registry Number

6493-05-6

SMILES

CN1C=NC2=C1C(=O)N(CCCCC(C)=O)C(=O)N2C

InChI Identifier

InChI=1S/C13H18N4O3/c1-9(18)6-4-5-7-17-12(19)10-11(14-8-15(10)2)16(3)13(17)20/h8H,4-7H2,1-3H3

InChI Key

BYPFEZZEUUWMEJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Imidazopyrimidines

Sub Class

Purines and purine derivatives

Direct Parent

Xanthines

Alternative Parents

Substituents

Xanthine
6-oxopurine
Purinone
Alkaloid or derivatives
Pyrimidone
N-substituted imidazole
Pyrimidine
Azole
Imidazole
Heteroaromatic compound
Vinylogous amide
Lactam
Ketone
Urea
Azacycle
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

oxopurine (CHEBI:7986 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0014944)
Membrane (HMDB: HMDB0014944)

Source

Exogenous

Exogenous (HMDB: HMDB0014944)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	105 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	5.17 g/L	Not Available
LogP	0	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	5.17 g/L	ALOGPS
logP	0.08	ALOGPS
logP	0.23	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	19.64	ChemAxon
pKa (Strongest Basic)	-0.93	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	75.51 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	73.52 m³·mol⁻¹	ChemAxon
Polarizability	29.27 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	166.211	31661259
DarkChem	[M-H]-	161.335	31661259
DeepCCS	[M+H]+	159.584	30932474
DeepCCS	[M-H]-	157.226	30932474
DeepCCS	[M-2H]-	191.48	30932474
DeepCCS	[M+Na]+	166.492	30932474
AllCCS	[M+H]+	162.9	32859911
AllCCS	[M+H-H2O]+	159.5	32859911
AllCCS	[M+NH4]+	166.0	32859911
AllCCS	[M+Na]+	166.9	32859911
AllCCS	[M-H]-	167.7	32859911
AllCCS	[M+Na-2H]-	167.9	32859911
AllCCS	[M+HCOO]-	168.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.76 minutes	32390414
Predicted by Siyang on May 30, 2022	10.6873 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.51 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1920.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	243.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	141.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	159.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	93.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	322.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	396.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	71.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	878.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	411.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1138.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	249.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	299.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	384.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	201.2 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	14.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Pentoxifylline	CN1C=NC2=C1C(=O)N(CCCCC(C)=O)C(=O)N2C	2976.4	Standard polar	33892256
Pentoxifylline	CN1C=NC2=C1C(=O)N(CCCCC(C)=O)C(=O)N2C	2348.0	Standard non polar	33892256
Pentoxifylline	CN1C=NC2=C1C(=O)N(CCCCC(C)=O)C(=O)N2C	2390.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Pentoxifylline,1TMS,isomer #1	CC(=CCCCN1C(=O)C2=C(N=CN2C)N(C)C1=O)O[Si](C)(C)C	2442.5	Semi standard non polar	33892256
Pentoxifylline,1TMS,isomer #1	CC(=CCCCN1C(=O)C2=C(N=CN2C)N(C)C1=O)O[Si](C)(C)C	2442.5	Standard non polar	33892256
Pentoxifylline,1TMS,isomer #1	CC(=CCCCN1C(=O)C2=C(N=CN2C)N(C)C1=O)O[Si](C)(C)C	3384.4	Standard polar	33892256
Pentoxifylline,1TMS,isomer #2	C=C(CCCCN1C(=O)C2=C(N=CN2C)N(C)C1=O)O[Si](C)(C)C	2396.6	Semi standard non polar	33892256
Pentoxifylline,1TMS,isomer #2	C=C(CCCCN1C(=O)C2=C(N=CN2C)N(C)C1=O)O[Si](C)(C)C	2377.3	Standard non polar	33892256
Pentoxifylline,1TMS,isomer #2	C=C(CCCCN1C(=O)C2=C(N=CN2C)N(C)C1=O)O[Si](C)(C)C	3437.2	Standard polar	33892256
Pentoxifylline,1TBDMS,isomer #1	CC(=CCCCN1C(=O)C2=C(N=CN2C)N(C)C1=O)O[Si](C)(C)C(C)(C)C	2661.7	Semi standard non polar	33892256
Pentoxifylline,1TBDMS,isomer #1	CC(=CCCCN1C(=O)C2=C(N=CN2C)N(C)C1=O)O[Si](C)(C)C(C)(C)C	2655.2	Standard non polar	33892256
Pentoxifylline,1TBDMS,isomer #1	CC(=CCCCN1C(=O)C2=C(N=CN2C)N(C)C1=O)O[Si](C)(C)C(C)(C)C	3392.5	Standard polar	33892256
Pentoxifylline,1TBDMS,isomer #2	C=C(CCCCN1C(=O)C2=C(N=CN2C)N(C)C1=O)O[Si](C)(C)C(C)(C)C	2637.0	Semi standard non polar	33892256
Pentoxifylline,1TBDMS,isomer #2	C=C(CCCCN1C(=O)C2=C(N=CN2C)N(C)C1=O)O[Si](C)(C)C(C)(C)C	2578.7	Standard non polar	33892256
Pentoxifylline,1TBDMS,isomer #2	C=C(CCCCN1C(=O)C2=C(N=CN2C)N(C)C1=O)O[Si](C)(C)C(C)(C)C	3433.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Pentoxifylline GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9480000000-5858a0a94add96d62994	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pentoxifylline GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pentoxifylline GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pentoxifylline LC-ESI-qTof , Positive-QTOF	splash10-001r-2900000000-d54457aaede5317cef72	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pentoxifylline , positive-QTOF	splash10-0059-1890000000-c9be2fe26b2862cba4f5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pentoxifylline , positive-QTOF	splash10-001r-2900000000-d54457aaede5317cef72	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pentoxifylline LC-ESI-QFT , positive-QTOF	splash10-0059-2970000000-95d1edcd63b61b13b22e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pentoxifylline 35V, Positive-QTOF	splash10-0059-2970000000-0c35991320854cec88dd	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pentoxifylline 50V, Positive-QTOF	splash10-0019-0900000000-dd015a4509f33caa03c0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pentoxifylline 40V, Positive-QTOF	splash10-001r-0900000000-65fb6e1754eabaf86ab4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pentoxifylline 35V, Positive-QTOF	splash10-001r-3910000000-848959253dccbbc260a7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pentoxifylline 10V, Positive-QTOF	splash10-004i-0090000000-4f61bb0b4f8342199149	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pentoxifylline 30V, Positive-QTOF	splash10-001i-0900000000-79465a5f4259ad7a5fd7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pentoxifylline 20V, Positive-QTOF	splash10-001i-0940000000-a097189c3d45a68b6674	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pentoxifylline 10V, Positive-QTOF	splash10-01t9-0090000000-e92064736a2f3e194af7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pentoxifylline 20V, Positive-QTOF	splash10-03fr-1590000000-3aa22ac7d56a3f0cb967	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pentoxifylline 40V, Positive-QTOF	splash10-001i-9300000000-9e889c5028746f141557	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pentoxifylline 10V, Negative-QTOF	splash10-004i-0390000000-a66c81c066b3055aee27	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pentoxifylline 20V, Negative-QTOF	splash10-004i-2790000000-10e4eef90ade382bc5f4	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pentoxifylline 40V, Negative-QTOF	splash10-052f-9500000000-23bd0511497da2b1fc18	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pentoxifylline 10V, Positive-QTOF	splash10-004i-0390000000-3e633d64da435129d91b	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pentoxifylline 20V, Positive-QTOF	splash10-001i-0910000000-285222c9846c41ea2ed2	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pentoxifylline 40V, Positive-QTOF	splash10-03di-3900000000-3902c6584393e2a548ed	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pentoxifylline 10V, Negative-QTOF	splash10-004i-0290000000-2d198d549fd71c261d88	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pentoxifylline 20V, Negative-QTOF	splash10-004i-1930000000-cbb2368f24d9797f040a	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pentoxifylline 40V, Negative-QTOF	splash10-056r-5950000000-89a80796e36b81a0c4a3	2021-10-11	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00806	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00806	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00806

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4578

KEGG Compound ID

C07424

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Pentoxifylline

METLIN ID

Not Available

PubChem Compound

4740

PDB ID

PNX

ChEBI ID

127029

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Authors unspecified: European Pentoxifylline Multi-Infarct Dementia Study. Eur Neurol. 1996;36(5):315-21. [PubMed:8864715 ]

Enzymes

Enzyme Details

1. 5'-nucleotidase

General function:: Involved in hydrolase activity
Specific function:: Hydrolyzes extracellular nucleotides into membrane permeable nucleosides.
Gene Name:: NT5E
Uniprot ID:: P21589
Molecular weight:: 57948.125

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Ustunsoy H, Sivrikoz MC, Tarakcioglu M, Bakir K, Guldur E, Celkan MA: The effects of pentoxifylline on the myocardial inflammation and ischemia-reperfusion injury during cardiopulmonary bypass. J Card Surg. 2006 Jan-Feb;21(1):57-61. [PubMed:16426349 ]

Enzyme Details

2. cAMP-specific 3',5'-cyclic phosphodiesterase 4B

General function:: Involved in catalytic activity
Specific function:: Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes. May be involved in mediating central nervous system effects of therapeutic agents ranging from antidepressants to antiasthmatic and anti-inflammatory agents.
Gene Name:: PDE4B
Uniprot ID:: Q07343
Molecular weight:: 64351.765

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]

Enzyme Details

3. cAMP-specific 3',5'-cyclic phosphodiesterase 4A

General function:: Involved in 3',5'-cyclic-nucleotide phosphodiesterase activity
Specific function:: Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes.
Gene Name:: PDE4A
Uniprot ID:: P27815
Molecular weight:: 98142.155

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

4. cGMP-specific 3',5'-cyclic phosphodiesterase

General function:: Involved in catalytic activity
Specific function:: Plays a role in signal transduction by regulating the intracellular concentration of cyclic nucleotides. This phosphodiesterase catalyzes the specific hydrolysis of cGMP to 5'-GMP.
Gene Name:: PDE5A
Uniprot ID:: O76074
Molecular weight:: 99984.14

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

5. Cytochrome P450 1A2

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

6. Adenosine receptor A1

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Receptor for adenosine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase
Gene Name:: ADORA1
Uniprot ID:: P30542
Molecular weight:: 36511.3

References

Daly JW, Jacobson KA, Ukena D: Adenosine receptors: development of selective agonists and antagonists. Prog Clin Biol Res. 1987;230:41-63. [PubMed:3588607 ]

Enzyme Details

7. Adenosine receptor A2a

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Receptor for adenosine. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase
Gene Name:: ADORA2A
Uniprot ID:: P29274
Molecular weight:: 44706.9

References

Kreth S, Ledderose C, Luchting B, Weis F, Thiel M: Immunomodulatory properties of pentoxifylline are mediated via adenosine-dependent pathways. Shock. 2010 Jul;34(1):10-6. doi: 10.1097/SHK.0b013e3181cdc3e2. [PubMed:19997047 ]

Showing metabocard for Pentoxifylline (HMDB0014944)

MOL for HMDB0014944 (Pentoxifylline)

3D MOL for HMDB0014944 (Pentoxifylline)

3D SDF for HMDB0014944 (Pentoxifylline)

3D-SDF for HMDB0014944 (Pentoxifylline)

PDB for HMDB0014944 (Pentoxifylline)

3D PDB for HMDB0014944 (Pentoxifylline)

SMILES for HMDB0014944 (Pentoxifylline)

INCHI for HMDB0014944 (Pentoxifylline)

Structure for HMDB0014944 (Pentoxifylline)

3D Structure for HMDB0014944 (Pentoxifylline)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References

References

References

References

References

References

References