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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2022-03-07 02:51:54 UTC
HMDB IDHMDB0015222
Secondary Accession Numbers
  • HMDB15222
Metabolite Identification
Common NamePentolinium
DescriptionPentolinium is only found in individuals that have used or taken this drug. It is a nicotinic antagonist that has been used as a ganglionic blocking agent in hypertension. [PubChem]Pentolinium binds to the nicotinic (ganglion) acetylcholine receptor. This receptor/channel is permeable to a range of divalent cations including calcium, the influx of which may activate a potassium current which hyperpolarizes the cell membrane. Blockage of the receptor leads to smooth muscle relaxation and vasodilaton.
Structure
Data?1582753272
Synonyms
ValueSource
PentolineumChEBI
PentoloniumChEBI
PentolonumChEBI
Pentolinium tartrateHMDB
Tartrate, pentoliniumHMDB
Tartrate, pentoloniumHMDB
Pentolonium tartrateHMDB
PentoliniumMeSH
Chemical FormulaC15H32N2
Average Molecular Weight240.428
Monoisotopic Molecular Weight240.256549034
IUPAC Name1-methyl-1-[5-(1-methylpyrrolidin-1-ium-1-yl)pentyl]pyrrolidin-1-ium
Traditional Namepentolinium
CAS Registry Number52-62-0
SMILES
C[N+]1(CCCCC[N+]2(C)CCCC2)CCCC1
InChI Identifier
InChI=1S/C15H32N2/c1-16(12-6-7-13-16)10-4-3-5-11-17(2)14-8-9-15-17/h3-15H2,1-2H3/q+2
InChI KeyXSBSKEQEUFOSDD-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as n-alkylpyrrolidines. N-alkylpyrrolidines are compounds containing a pyrrolidine moiety that is substituted at the N1-position with an alkyl group. Pyrrolidine is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrrolidines
Sub ClassN-alkylpyrrolidines
Direct ParentN-alkylpyrrolidines
Alternative Parents
Substituents
  • N-alkylpyrrolidine
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic salt
  • Organonitrogen compound
  • Amine
  • Organic cation
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point213 °C (tartrate salt)Not Available
Boiling PointNot AvailableNot Available
Water Solubility1.2e-05 g/LNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.2e-05 g/LALOGPS
logP-2.3ALOGPS
logP-6.3ChemAxon
logS-7.4ALOGPS
Physiological Charge2ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity99.03 m³·mol⁻¹ChemAxon
Polarizability31.36 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+159.74430932474
DeepCCS[M-H]-157.38630932474
DeepCCS[M-2H]-191.08830932474
DeepCCS[M+Na]+165.8830932474
AllCCS[M+H]+162.132859911
AllCCS[M+H-H2O]+158.832859911
AllCCS[M+NH4]+165.232859911
AllCCS[M+Na]+166.132859911
AllCCS[M-H]-198.832859911
AllCCS[M+Na-2H]-199.332859911
AllCCS[M+HCOO]-199.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PentoliniumC[N+]1(CCCCC[N+]2(C)CCCC2)CCCC12084.0Standard polar33892256
PentoliniumC[N+]1(CCCCC[N+]2(C)CCCC2)CCCC11531.5Standard non polar33892256
PentoliniumC[N+]1(CCCCC[N+]2(C)CCCC2)CCCC11824.0Semi standard non polar33892256
Spectra

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 DB01090 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01090 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01090
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5641
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPentolinium
METLIN IDNot Available
PubChem Compound5850
PDB IDNot Available
ChEBI ID347401
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 extracellular ligand-gated ion channel activity
Specific function:
Ionotropic receptor with a probable role in the modulation of auditory stimuli. Agonist binding may induce an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane. The channel is permeable to a range of divalent cations including calcium, the influx of which may activate a potassium current which hyperpolarizes the cell membrane. In the ear, this may lead to a reduction in basilar membrane motion, altering the activity of auditory nerve fibers and reducing the range of dynamic hearing. This may protect against acoustic trauma
Gene Name:
CHRNA10
Uniprot ID:
Q9GZZ6
Molecular weight:
49704.3
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. McKay DB, Burkman AM: Nicotinic and nonnicotinic receptor-mediated actions of vinblastine. Proc Soc Exp Biol Med. 1993 Jul;203(3):372-6. [PubMed:8516349 ]
  4. Cachelin AB, Rust G: Beta-subunits co-determine the sensitivity of rat neuronal nicotinic receptors to antagonists. Pflugers Arch. 1995 Jan;429(3):449-51. [PubMed:7761270 ]