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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2022-03-07 02:51:44 UTC
HMDB IDHMDB0014783
Secondary Accession Numbers
  • HMDB14783
Metabolite Identification
Common NameDyclonine
DescriptionDyclonine is only found in individuals that have used or taken this drug. It is an oral anaesthetic found in Sucrets, an over the counter throat lozenge. It is also found in some varieties of the Cepacol sore throat spray.Dyclonine blocks both the initiation and conduction of nerve impulses by decreasing the neuronal membrane's permeability to sodium ions. This reversibly stabilizes the membrane and inhibits depolarization, resulting in the failure of a propagated action potential and subsequent conduction blockade.
Structure
Data?1582753220
Synonyms
ValueSource
1-(4-Butoxyphenyl)-3-(1-piperidinyl)-1-propanoneChEBI
2-(1-Piperidyl)ethyl p-butoxyphenyl ketoneChEBI
3-Piperidino-4'-butoxypropiophenoneChEBI
4'-Butoxy-3-piperidinopropiophenoneChEBI
4-Butoxy-beta-piperidinopropiophenoneChEBI
4-N-Butoxy-beta-(1-piperidyl)propiophenoneChEBI
DicloninaChEBI
DycloninumChEBI
4-Butoxy-b-piperidinopropiophenoneGenerator
4-Butoxy-β-piperidinopropiophenoneGenerator
4-N-Butoxy-b-(1-piperidyl)propiophenoneGenerator
4-N-Butoxy-β-(1-piperidyl)propiophenoneGenerator
SucretsHMDB
TanacHMDB
DycloneHMDB
Dyclonine hydrochlorideHMDB
Dyclonine HCLHMDB
Chemical FormulaC18H27NO2
Average Molecular Weight289.4125
Monoisotopic Molecular Weight289.204179113
IUPAC Name1-(4-butoxyphenyl)-3-(piperidin-1-yl)propan-1-one
Traditional Namedyclonine
CAS Registry Number586-60-7
SMILES
CCCCOC1=CC=C(C=C1)C(=O)CCN1CCCCC1
InChI Identifier
InChI=1S/C18H27NO2/c1-2-3-15-21-17-9-7-16(8-10-17)18(20)11-14-19-12-5-4-6-13-19/h7-10H,2-6,11-15H2,1H3
InChI KeyBZEWSEKUUPWQDQ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlkyl-phenylketones
Alternative Parents
Substituents
  • Alkyl-phenylketone
  • Phenoxy compound
  • Benzoyl
  • Phenol ether
  • Aryl alkyl ketone
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Beta-aminoketone
  • Piperidine
  • Benzenoid
  • Tertiary amine
  • Tertiary aliphatic amine
  • Organoheterocyclic compound
  • Azacycle
  • Ether
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.046 g/LNot Available
LogP3.7Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.046 g/LALOGPS
logP4.11ALOGPS
logP3.68ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)15.88ChemAxon
pKa (Strongest Basic)8.36ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area29.54 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity87.07 m³·mol⁻¹ChemAxon
Polarizability35.14 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+169.89831661259
DarkChem[M-H]-168.82431661259
DeepCCS[M+H]+175.13430932474
DeepCCS[M-H]-172.77630932474
DeepCCS[M-2H]-205.66130932474
DeepCCS[M+Na]+181.22730932474
AllCCS[M+H]+171.532859911
AllCCS[M+H-H2O]+168.332859911
AllCCS[M+NH4]+174.532859911
AllCCS[M+Na]+175.332859911
AllCCS[M-H]-174.432859911
AllCCS[M+Na-2H]-175.032859911
AllCCS[M+HCOO]-175.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DyclonineCCCCOC1=CC=C(C=C1)C(=O)CCN1CCCCC13001.8Standard polar33892256
DyclonineCCCCOC1=CC=C(C=C1)C(=O)CCN1CCCCC12361.1Standard non polar33892256
DyclonineCCCCOC1=CC=C(C=C1)C(=O)CCN1CCCCC12407.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Dyclonine GC-MS (Non-derivatized) - 70eV, Positivesplash10-006t-9440000000-a86aac6d96e16aac8d022017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dyclonine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dyclonine 10V, Positive-QTOFsplash10-0006-2190000000-c5e926d926da3f6e33872016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dyclonine 20V, Positive-QTOFsplash10-0a4j-9550000000-f1734edb24416808a4782016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dyclonine 40V, Positive-QTOFsplash10-0a4i-9100000000-ff38128b39bd16ebc42f2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dyclonine 10V, Negative-QTOFsplash10-000i-0090000000-0e2e4e5faddcfc83f1762016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dyclonine 20V, Negative-QTOFsplash10-001i-4290000000-9b6e8d8e9f7264d8fc3e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dyclonine 40V, Negative-QTOFsplash10-001i-9410000000-199b90aa399041a2e4222016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dyclonine 10V, Positive-QTOFsplash10-0006-0090000000-dab0be3d01712a81a5442021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dyclonine 20V, Positive-QTOFsplash10-0006-3190000000-98054ac06c2da05754e92021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dyclonine 40V, Positive-QTOFsplash10-0002-9200000000-6e97375e29bf89aba1e82021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dyclonine 10V, Negative-QTOFsplash10-000i-0090000000-f9f84a09fd9aec8817232021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dyclonine 20V, Negative-QTOFsplash10-000i-0290000000-c1c0c098612ca42e1f5a2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dyclonine 40V, Negative-QTOFsplash10-0081-0910000000-ebee0fba4bb1c6af25df2021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00645 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00645 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00645
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3068
KEGG Compound IDC07881
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDyclonine
METLIN IDNot Available
PubChem Compound3180
PDB IDNot Available
ChEBI ID4724
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 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 sodium ions may pass in accordance with their electrochemical gradient. It is a tetrodotoxin-resistant sodium channel isoform. Its electrophysiological properties vary depending on the type of the associated beta subunits (in vitro). Plays a role in neuropathic pain mechanisms
Gene Name:
SCN10A
Uniprot ID:
Q9Y5Y9
Molecular weight:
220623.6
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 ]
  3. Roghani S, Duperon DF, Barcohana N: Evaluating the efficacy of commonly used topical anesthetics. Pediatr Dent. 1999 May-Jun;21(3):197-200. [PubMed:10355012 ]
  4. Tella SR, Goldberg SR: Monoamine transporter and sodium channel mechanisms in the rapid pressor response to cocaine. Pharmacol Biochem Behav. 1998 Feb;59(2):305-12. [PubMed:9476974 ]