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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2017-12-07 02:48:26 UTC
HMDB IDHMDB0014962
Secondary Accession Numbers
  • HMDB14962
Metabolite Identification
Common NameEnprofylline
DescriptionEnprofylline is a derivative of theophylline which shares bronchodilator properties. Enprofylline is used in asthma, chronic obstructive pulmonary disease, and in the management of cerebrovascular insufficiency, sickle cell disease, and diabetic neuropathy. Long-term enprofylline administration may be associated with elevation in liver enzyme levels and unpredictable blood levels.
Structure
Thumb
Synonyms
ValueSource
3,7-dihydro-3-Propyl-1H-purine-2,6-dioneChEBI
3-N-PropylxanthineChEBI
3-Propyl-3,7-dihydro-purine-2,6-dioneChEBI
3-PropylxanthineChEBI
EnprofilinaChEBI
EnprofyllinumChEBI
Chemical FormulaC8H10N4O2
Average Molecular Weight194.1906
Monoisotopic Molecular Weight194.080375584
IUPAC Name3-propyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
Traditional Nameenprofylline
CAS Registry Number41078-02-8
SMILES
CCCN1C2=C(NC=N2)C(=O)NC1=O
InChI Identifier
InChI=1S/C8H10N4O2/c1-2-3-12-6-5(9-4-10-6)7(13)11-8(12)14/h4H,2-3H2,1H3,(H,9,10)(H,11,13,14)
InChI KeySIQPXVQCUCHWDI-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassImidazopyrimidines
Direct ParentXanthines
Alternative Parents
Substituents
  • Xanthine
  • 6-oxopurine
  • Purinone
  • Alkaloid or derivatives
  • Pyrimidone
  • Pyrimidine
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Vinylogous amide
  • Lactam
  • Urea
  • Azacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Role

Industrial application:

  Pharmaceutical industry:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point287 - 289 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility5.68 g/LNot Available
LogP-0.2Not Available
Predicted Properties
PropertyValueSource
Water Solubility5.68 g/LALOGPS
logP0.35ALOGPS
logP-0.11ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)7.83ChemAxon
pKa (Strongest Basic)-0.77ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area78.09 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity49.31 m³·mol⁻¹ChemAxon
Polarizability18.72 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-016r-2900000000-c23c015100b016aff55fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-d25d51b1acc26b8dc862View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udj-0900000000-9fd84535ea9d9ea87af3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gwu-6900000000-335bd4f20033a9cbbc8fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-20221857ee2dedfb76c1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udl-0900000000-5ddf6a6c791e76339082View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9600000000-645991400e045b55658aView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00824 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00824 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00824
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID1613
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound1676
PDB IDNot Available
ChEBI ID126237
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

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
  1. 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 ]
  2. 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 ]
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
  1. Featherstone RL, Chambers DJ: Long-term hypothermic lung preservation: does adenosine A1 receptor antagonism have a role in ischemic preconditioning protection? Interact Cardiovasc Thorac Surg. 2004 Mar;3(1):182-7. [PubMed:17670210 ]
  2. Dulloo AG, Seydoux J, Girardier L: Peripheral mechanisms of thermogenesis induced by ephedrine and caffeine in brown adipose tissue. Int J Obes. 1991 May;15(5):317-26. [PubMed:1885257 ]
  3. Dar MS: Central adenosinergic system involvement in ethanol-induced motor incoordination in mice. J Pharmacol Exp Ther. 1990 Dec;255(3):1202-9. [PubMed:2262902 ]
  4. Ukena D, Schirren CG, Schwabe U: Effects of enprofylline on A1 and A2 adenosine receptors. Eur J Pharmacol. 1985 Oct 29;117(1):25-33. [PubMed:3002801 ]
  5. Berg G, Andersson RG, Ryden G: Effects of different phosphodiesterase-inhibiting drugs on human pregnant myometrium: an in vitro study. Arch Int Pharmacodyn Ther. 1987 Dec;290(2):288-92. [PubMed:3446047 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
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:
ADORA2B
Uniprot ID:
P29275
Molecular weight:
36332.7
References
  1. Holgate ST: The Quintiles Prize Lecture 2004. The identification of the adenosine A2B receptor as a novel therapeutic target in asthma. Br J Pharmacol. 2005 Aug;145(8):1009-15. [PubMed:15980878 ]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]