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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2022-03-07 02:51:35 UTC
HMDB IDHMDB0014364
Secondary Accession Numbers
  • HMDB14364
Metabolite Identification
Common NameOxyphenonium
DescriptionOxyphenonium, also known as DCF or methocidin, belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. Oxyphenonium is a drug which is used for the treatment of visceral spasms. Oxyphenonium bromide is an antimuscarinic drug. Oxyphenonium is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1582753169
Synonyms
ValueSource
DCFHMDB
HydroxymethylgramicidinHMDB
MethocidinHMDB
OxiphenonumHMDB
Oxyphenonium bromideHMDB
Chloride, oxyphenoniumHMDB
Oxyphenonium, (R)-isomerHMDB
Oxyphenonium, (S)-isomerHMDB
Bromide, oxyphenoniumHMDB
MethacinHMDB
OxyphenonHMDB
Oxyphenonium bromide, (-)-isomerHMDB
Oxyphenonium chlorideHMDB
Oxyphenonium iodide, (S)-isomerHMDB
Oxyphenonium, (+-)-isomerHMDB
SpastrexHMDB
2-((Cyclohexylhydroxyphenylacetyl)oxy)-N,N-diethyl-N-methylethanaminiumHMDB
MetacinHMDB
Oxyphenonium bromide, (+)-isomerHMDB
Oxyphenonium iodide, (R)-isomerHMDB
AtrenylHMDB
Iodide, oxyphenoniumHMDB
Oxyphenonium bromide, (+-)-isomerHMDB
Oxyphenonium iodideHMDB
OxyphenoniumMeSH
Chemical FormulaC21H34NO3
Average Molecular Weight348.4996
Monoisotopic Molecular Weight348.253868959
IUPAC Name{2-[(2-cyclohexyl-2-hydroxy-2-phenylacetyl)oxy]ethyl}diethylmethylazanium
Traditional Namemethacin
CAS Registry Number50-10-2
SMILES
CC[N+](C)(CC)CCOC(=O)C(O)(C1CCCCC1)C1=CC=CC=C1
InChI Identifier
InChI=1S/C21H34NO3/c1-4-22(3,5-2)16-17-25-20(23)21(24,18-12-8-6-9-13-18)19-14-10-7-11-15-19/h6,8-9,12-13,19,24H,4-5,7,10-11,14-17H2,1-3H3/q+1
InChI KeyGFRUPHOKLBPHTQ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNot Available
Direct ParentBenzene and substituted derivatives
Alternative Parents
Substituents
  • Monocyclic benzene moiety
  • Quaternary ammonium salt
  • Tertiary alcohol
  • Tetraalkylammonium salt
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Aromatic alcohol
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • Organic nitrogen compound
  • Organic salt
  • Hydrocarbon derivative
  • Organic cation
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point191.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.00014 g/LNot Available
LogP0.17Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00014 g/LALOGPS
logP0.2ALOGPS
logP-0.2ChemAxon
logS-6.4ALOGPS
pKa (Strongest Acidic)11.53ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity112.61 m³·mol⁻¹ChemAxon
Polarizability40.65 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+185.75430932474
DeepCCS[M-H]-183.39630932474
DeepCCS[M-2H]-217.52830932474
DeepCCS[M+Na]+192.75530932474
AllCCS[M+H]+184.632859911
AllCCS[M+H-H2O]+181.932859911
AllCCS[M+NH4]+187.132859911
AllCCS[M+Na]+187.832859911
AllCCS[M-H]-190.832859911
AllCCS[M+Na-2H]-191.832859911
AllCCS[M+HCOO]-193.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
OxyphenoniumCC[N+](C)(CC)CCOC(=O)C(O)(C1CCCCC1)C1=CC=CC=C12718.1Standard polar33892256
OxyphenoniumCC[N+](C)(CC)CCOC(=O)C(O)(C1CCCCC1)C1=CC=CC=C12201.6Standard non polar33892256
OxyphenoniumCC[N+](C)(CC)CCOC(=O)C(O)(C1CCCCC1)C1=CC=CC=C12430.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Oxyphenonium,1TMS,isomer #1CC[N+](C)(CC)CCOC(=O)C(O[Si](C)(C)C)(C1=CC=CC=C1)C1CCCCC12499.6Semi standard non polar33892256
Oxyphenonium,1TBDMS,isomer #1CC[N+](C)(CC)CCOC(=O)C(O[Si](C)(C)C(C)(C)C)(C1=CC=CC=C1)C1CCCCC12718.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Oxyphenonium GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-4900000000-e03c3b59b900deeaac2f2017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Oxyphenonium GC-MS (1 TMS) - 70eV, Positivesplash10-0h90-9680000000-26ce147dacfb433b31752017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Oxyphenonium 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 - Oxyphenonium 10V, Positive-QTOFsplash10-00kb-2937000000-78dd494fe0c49e68a9302017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxyphenonium 20V, Positive-QTOFsplash10-015i-8935000000-70e753490553c3c250992017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxyphenonium 40V, Positive-QTOFsplash10-0f79-9300000000-3ac649475662748995ec2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxyphenonium 10V, Positive-QTOFsplash10-0002-0039000000-df1ae6ec9429a514f4ce2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxyphenonium 20V, Positive-QTOFsplash10-01p9-5593000000-991f6309e4b6d774dca52021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxyphenonium 40V, Positive-QTOFsplash10-001i-9100000000-64875a59718dc9b34e7e2021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
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 DB00219 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00219 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00219
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5547
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkOxyphenonium bromide
METLIN IDNot Available
PubChem Compound5749
PDB IDNot Available
ChEBI ID775237
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 G-protein coupled receptor protein signaling pathway
Specific function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover
Gene Name:
CHRM1
Uniprot ID:
P11229
Molecular weight:
51420.4
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. Eglen RM, Whiting RL: Competitive and non-competitive antagonism exhibited by 'selective' antagonists at atrial and ileal muscarinic receptor subtypes. Br J Pharmacol. 1987 Apr;90(4):701-7. [PubMed:3580704 ]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]