You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2020-02-26 21:41:28 UTC
HMDB IDHMDB0015359
Secondary Accession Numbers
  • HMDB15359
Metabolite Identification
Common NameEncainide
DescriptionEncainide, also known as encainidum or enkaid, belongs to the class of organic compounds known as benzanilides. These are aromatic compounds containing an anilide group in which the carboxamide group is substituted with a benzene ring. They have the general structure RNC(=O)R', where R,R'= benzene. Encainide is a drug. Encainide is a very strong basic compound (based on its pKa). Encainide is a potentially toxic compound.
Structure
Data?1582753288
Synonyms
ValueSource
(+-)-2'-[2-(1-Methyl-2-piperidyl)ethyl]-p-anisanilideChEBI
(+-)-4-Methoxy-N-(2-(2-(1-methyl-2-piperidinyl)ethyl)phenyl)benzamideChEBI
4-Methoxy-2'-[2-(1-methyl-2-piperidyl)ethyl]benzanilideChEBI
4-Methoxy-N-{2-[2-(1-methyl-piperidin-2-yl)-ethyl]-phenyl}-benzamideChEBI
EncainidaChEBI
EncainidumChEBI
Encainide, (+)-isomerHMDB
EnkaidHMDB
Encainide hydrochlorideHMDB
Encainide hydrochloride, (+-)-isomerHMDB
Bristol myers squibb brand OF encainide hydrochlorideHMDB
Bristol-myers squibb brand OF encainide hydrochlorideHMDB
Encainide, (-)-isomerHMDB
Chemical FormulaC22H28N2O2
Average Molecular Weight352.4699
Monoisotopic Molecular Weight352.21507815
IUPAC Name4-methoxy-N-{2-[2-(1-methylpiperidin-2-yl)ethyl]phenyl}benzamide
Traditional Nameencainide
CAS Registry Number66778-36-7
SMILES
COC1=CC=C(C=C1)C(=O)NC1=CC=CC=C1CCC1CCCCN1C
InChI Identifier
InChI=1S/C22H28N2O2/c1-24-16-6-5-8-19(24)13-10-17-7-3-4-9-21(17)23-22(25)18-11-14-20(26-2)15-12-18/h3-4,7,9,11-12,14-15,19H,5-6,8,10,13,16H2,1-2H3,(H,23,25)
InChI KeyPJWPNDMDCLXCOM-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzanilides. These are aromatic compounds containing an anilide group in which the carboxamide group is substituted with a benzene ring. They have the general structure RNC(=O)R', where R,R'= benzene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassAnilides
Direct ParentBenzanilides
Alternative Parents
Substituents
  • Benzanilide
  • Benzamide
  • Benzoic acid or derivatives
  • Alkaloid or derivatives
  • Anisole
  • Phenoxy compound
  • Benzoyl
  • Phenol ether
  • Methoxybenzene
  • Aralkylamine
  • Alkyl aryl ether
  • Piperidine
  • Amino acid or derivatives
  • Carboxamide group
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Ether
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Amine
  • Organic nitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.004 g/LNot Available
LogP4Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.004 g/LALOGPS
logP4.29ALOGPS
logP4.49ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)12.37ChemAxon
pKa (Strongest Basic)9.48ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area41.57 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity107.77 m³·mol⁻¹ChemAxon
Polarizability41.04 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052n-9311000000-985044a85c7ca1fc4601Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0019000000-c3aba8c66a81550a1bc5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-4489000000-fb4fa7dd76074a147422Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pbc-9741000000-30c243030c2a40b68b44Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-ace9a97974ab75eb724bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1219000000-8488789ae9ebc4c00e17Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9511000000-c16ae5ec1e6ea9df3fb7Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01228 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01228 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01228
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID43697
KEGG Compound IDC06978
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEncainide
METLIN IDNot Available
PubChem Compound48041
PDB IDNot Available
ChEBI ID4788
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
References
  1. 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 ]
General function:
Involved in ion channel activity
Specific function:
This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient. It is a tetrodotoxin-resistant Na(+) channel isoform. This channel is responsible for the initial upstroke of the action potential in the electrocardiogram
Gene Name:
SCN5A
Uniprot ID:
Q14524
Molecular weight:
226937.5
References
  1. 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 ]
  2. Starmer CF, Lastra AA, Nesterenko VV, Grant AO: Proarrhythmic response to sodium channel blockade. Theoretical model and numerical experiments. Circulation. 1991 Sep;84(3):1364-77. [PubMed:1653123 ]
  3. Guo J, Zhan S, Somers J, Westenbroek RE, Catterall WA, Roach DE, Sheldon RS, Lees-Miller JP, Li P, Shimoni Y, Duff HJ: Decrease in density of INa is in the common final pathway to heart block in murine hearts overexpressing calcineurin. Am J Physiol Heart Circ Physiol. 2006 Dec;291(6):H2669-79. Epub 2006 Jun 2. [PubMed:16751287 ]
  4. Krishnan SC, Josephson ME: ST segment elevation induced by class IC antiarrhythmic agents: underlying electrophysiologic mechanisms and insights into drug-induced proarrhythmia. J Cardiovasc Electrophysiol. 1998 Nov;9(11):1167-72. [PubMed:9835260 ]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]