Hmdb loader
Show more...Show more...Show more...
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2023-02-21 17:18:20 UTC
HMDB IDHMDB0014962
Secondary Accession Numbers
  • HMDB14962
Metabolite Identification
Common NameEnprofylline
DescriptionEnprofylline, also known as 3-propylxanthine or enprofilina, 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. Enprofylline is a drug which is used in the management of symptoms of asthma. also used in the treatment of peripheral vascular diseases and in the management of cerebrovascular insufficiency, sickle cell disease, and diabetic neuropathy. Enprofylline is an extremely weak basic (essentially neutral) compound (based on its pKa). Xanthine bearing a propyl substituent at position 3.
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
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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point287 - 289 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility5.68 g/LNot Available
LogP-0.2Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00824 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00824 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00824
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID1613
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEnprofylline
METLIN IDNot Available
PubChem Compound1676
PDB IDNot Available
ChEBI ID126237
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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 ]