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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:52:02 UTC
HMDB IDHMDB0015591
Secondary Accession Numbers
  • HMDB15591
Metabolite Identification
Common NameMepenzolate
DescriptionMepenzolate is a post-ganglionic parasympathetic inhibitor. It decreases gastric acid and pepsin secretion and suppresses spontaneous contractions of the colon. Mepenzolate diminishes gastric acid and pepsin secretion. Mepenzolate also suppresses spontaneous contractions of the colon. Pharmacologically, it is a post-ganglionic parasympathetic inhibitor. It has not been shown to be effective in contributing to the healing of peptic ulcer, decreasing the rate of recurrence, or preventing complications.
Structure
Data?1582753313
Synonyms
ValueSource
Mepenzolic acidGenerator
1-Methyl-3-piperidyl benzilate methyl bromideHMDB
Mepenzolate bromideHMDB
N-Methyl-3-piperidyl benzilate methyl bromideHMDB
N-Methyl-3-piperidyldiphenylglycolate methobromideHMDB
Mepenzolic acid, bromine saltHMDB
CantilHMDB
Mepenzolate bromide, (+-)-isomerHMDB
Aventis behring brand OF mepenzolate bromideHMDB
N-Methyl-3-piperidylbenzilate methyl bromideHMDB
Mepenzolate iodideHMDB
Mepenzolic acid, bromine salt, 1-(methyl-(14)C)-labeledHMDB
Chemical FormulaC21H26NO3
Average Molecular Weight340.436
Monoisotopic Molecular Weight340.191268703
IUPAC Name3-[(2-hydroxy-2,2-diphenylacetyl)oxy]-1,1-dimethylpiperidin-1-ium
Traditional Namemepenzolate
CAS Registry Number25990-43-6
SMILES
C[N+]1(C)CCCC(C1)OC(=O)C(O)(C1=CC=CC=C1)C1=CC=CC=C1
InChI Identifier
InChI=1S/C21H26NO3/c1-22(2)15-9-14-19(16-22)25-20(23)21(24,17-10-5-3-6-11-17)18-12-7-4-8-13-18/h3-8,10-13,19,24H,9,14-16H2,1-2H3/q+1
InChI KeyGKNPSSNBBWDAGH-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassDiphenylmethanes
Direct ParentDiphenylmethanes
Alternative Parents
Substituents
  • Diphenylmethane
  • Piperidine
  • Quaternary ammonium salt
  • Tertiary alcohol
  • Tetraalkylammonium salt
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Organopnictogen compound
  • Organic oxide
  • Aromatic alcohol
  • Amine
  • Alcohol
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organic salt
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic cation
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.00063 g/LNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available180.728http://allccs.zhulab.cn/database/detail?ID=AllCCS00000820
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00063 g/LALOGPS
logP-1.1ALOGPS
logP-0.97ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)11.05ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity109.4 m³·mol⁻¹ChemAxon
Polarizability37.76 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+180.88930932474
DeepCCS[M-H]-178.53130932474
DeepCCS[M-2H]-211.70530932474
DeepCCS[M+Na]+187.15530932474
AllCCS[M+H]+181.832859911
AllCCS[M+H-H2O]+178.832859911
AllCCS[M+NH4]+184.632859911
AllCCS[M+Na]+185.432859911
AllCCS[M-H]-188.832859911
AllCCS[M+Na-2H]-189.432859911
AllCCS[M+HCOO]-190.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MepenzolateC[N+]1(C)CCCC(C1)OC(=O)C(O)(C1=CC=CC=C1)C1=CC=CC=C13035.5Standard polar33892256
MepenzolateC[N+]1(C)CCCC(C1)OC(=O)C(O)(C1=CC=CC=C1)C1=CC=CC=C12256.8Standard non polar33892256
MepenzolateC[N+]1(C)CCCC(C1)OC(=O)C(O)(C1=CC=CC=C1)C1=CC=CC=C12456.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Mepenzolate,1TMS,isomer #1C[N+]1(C)CCCC(OC(=O)C(O[Si](C)(C)C)(C2=CC=CC=C2)C2=CC=CC=C2)C12530.8Semi standard non polar33892256
Mepenzolate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(C(=O)OC1CCC[N+](C)(C)C1)(C1=CC=CC=C1)C1=CC=CC=C12762.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Mepenzolate GC-MS (Non-derivatized) - 70eV, Positivesplash10-053r-4900000000-bba2c7e06054ee5b98892017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Mepenzolate GC-MS (1 TMS) - 70eV, Positivesplash10-0zfr-3090000000-75247afb1f7cc37997432017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Mepenzolate 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 - Mepenzolate 10V, Positive-QTOFsplash10-03ec-0915000000-279c2f267ec9c60be8e52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mepenzolate 20V, Positive-QTOFsplash10-03di-1932000000-3cc3ed2add9a9bcdc3452017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mepenzolate 40V, Positive-QTOFsplash10-01px-9500000000-8076c276b72604a21f0a2017-09-01Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C 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 DB04843 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB04843 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB04843
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3917
KEGG Compound IDC07818
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMepenzolate
METLIN IDNot Available
PubChem Compound4057
PDB IDNot Available
ChEBI ID569580
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:
CHRM3
Uniprot ID:
P20309
Molecular weight:
66127.4
References
  1. Tsai CS, Guede-Guina F, Smith MO, Vangah-Manda M, Ochillo RF: Isolation of cholinergic active ingredients in aqueous extracts of Mareya micrantha using the longitudinal muscle of isolated guinea-pig ileum as a pharmacological activity marker. J Ethnopharmacol. 1995 Mar;45(3):215-22. [PubMed:7623487 ]
  2. Tsai CS, Ochillo RF: Low temperature and muscarinic receptor activities. Cryobiology. 1989 Oct;26(5):485-95. [PubMed:2791613 ]
  3. Ochillo RF, Pugh DA: Atropine and mepenzolate mydriasis in rabbits: a comparative pupillographic analysis of two antimuscarinic agents. Res Commun Chem Pathol Pharmacol. 1982 Jun;36(3):503-6. [PubMed:7122991 ]
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. Tsai CS, Guede-Guina F, Smith MO, Vangah-Manda M, Ochillo RF: Isolation of cholinergic active ingredients in aqueous extracts of Mareya micrantha using the longitudinal muscle of isolated guinea-pig ileum as a pharmacological activity marker. J Ethnopharmacol. 1995 Mar;45(3):215-22. [PubMed:7623487 ]
  2. Tsai CS, Ochillo RF: Low temperature and muscarinic receptor activities. Cryobiology. 1989 Oct;26(5):485-95. [PubMed:2791613 ]
  3. Ochillo RF, Pugh DA: Atropine and mepenzolate mydriasis in rabbits: a comparative pupillographic analysis of two antimuscarinic agents. Res Commun Chem Pathol Pharmacol. 1982 Jun;36(3):503-6. [PubMed:7122991 ]