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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2022-03-07 02:51:48 UTC
HMDB IDHMDB0014948
Secondary Accession Numbers
  • HMDB14948
Metabolite Identification
Common NameBiperiden
DescriptionBiperiden, also known as akineton or biperidine, belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group. Biperiden is a drug which is used for use as an adjunct in the therapy of all forms of parkinsonism and control of extrapyramidal disorders secondary to neuroleptic drug therapy. Biperiden is a very strong basic compound (based on its pKa). Biperiden is a potentially toxic compound.
Structure
Data?1582753240
Synonyms
ValueSource
1-Bicyclo[2.2.1]hept-5-en-2-yl-1-phenyl-3-piperidin-1-yl-propan-1-olChEBI
alpha-5-Norbornen-2-yl-alpha-phenyl-1-piperidinepropanolChEBI
alpha-Bicyclo[2.2.1]hept-5-en-2-yl-alpha-phenyl-1-piperidinepropanolChEBI
BiperideneChEBI
BiperidenoChEBI
BiperidenumChEBI
AkinetonKegg
a-5-Norbornen-2-yl-a-phenyl-1-piperidinepropanolGenerator
Α-5-norbornen-2-yl-α-phenyl-1-piperidinepropanolGenerator
a-Bicyclo[2.2.1]hept-5-en-2-yl-a-phenyl-1-piperidinepropanolGenerator
Α-bicyclo[2.2.1]hept-5-en-2-yl-α-phenyl-1-piperidinepropanolGenerator
BeperidenHMDB
BiperidineHMDB
Biperiden, 1R-(1 alpha,2 alpha(r*),4 alpha)-isomerHMDB
Biperiden hydrochlorideHMDB
Biperiden, 1S-(1 alpha,2 alpha(r*),4 alpha)-isomerHMDB
Hydrochloride, biperidenHMDB
alpha-Bicyclo(2.2.1)hept-5-en-2-yl-alpha-phenyl-1-piperidinepropanolHMDB
Chemical FormulaC21H29NO
Average Molecular Weight311.4611
Monoisotopic Molecular Weight311.224914555
IUPAC Name1-{bicyclo[2.2.1]hept-5-en-2-yl}-1-phenyl-3-(piperidin-1-yl)propan-1-ol
Traditional Namebiperiden
CAS Registry Number514-65-8
SMILES
OC(CCN1CCCCC1)(C1CC2CC1C=C2)C1=CC=CC=C1
InChI Identifier
InChI=1S/C21H29NO/c23-21(19-7-3-1-4-8-19,11-14-22-12-5-2-6-13-22)20-16-17-9-10-18(20)15-17/h1,3-4,7-10,17-18,20,23H,2,5-6,11-16H2
InChI KeyYSXKPIUOCJLQIE-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmines
Direct ParentAralkylamines
Alternative Parents
Substituents
  • Aralkylamine
  • Monocyclic benzene moiety
  • Piperidine
  • Benzenoid
  • 1,3-aminoalcohol
  • Tertiary alcohol
  • Tertiary amine
  • Tertiary aliphatic amine
  • Azacycle
  • Organoheterocyclic compound
  • Alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organopnictogen compound
  • Aromatic alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point114 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0043 g/LNot Available
LogP4.1Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM177.730932474
[M+H]+Not Available175.706http://allccs.zhulab.cn/database/detail?ID=AllCCS00000712
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0043 g/LALOGPS
logP4.28ALOGPS
logP3.54ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)13.82ChemAxon
pKa (Strongest Basic)9.3ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area23.47 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity97.02 m³·mol⁻¹ChemAxon
Polarizability36.74 ųChemAxon
Number of Rings4ChemAxon
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]+171.63931661259
DarkChem[M-H]-171.3231661259
DeepCCS[M+H]+174.9930932474
DeepCCS[M-H]-172.63230932474
DeepCCS[M-2H]-205.51830932474
DeepCCS[M+Na]+181.08330932474
AllCCS[M+H]+178.032859911
AllCCS[M+H-H2O]+174.932859911
AllCCS[M+NH4]+180.932859911
AllCCS[M+Na]+181.732859911
AllCCS[M-H]-182.232859911
AllCCS[M+Na-2H]-182.232859911
AllCCS[M+HCOO]-182.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
BiperidenOC(CCN1CCCCC1)(C1CC2CC1C=C2)C1=CC=CC=C12805.6Standard polar33892256
BiperidenOC(CCN1CCCCC1)(C1CC2CC1C=C2)C1=CC=CC=C12303.5Standard non polar33892256
BiperidenOC(CCN1CCCCC1)(C1CC2CC1C=C2)C1=CC=CC=C12398.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Biperiden,1TMS,isomer #1C[Si](C)(C)OC(CCN1CCCCC1)(C1=CC=CC=C1)C1CC2C=CC1C22469.1Semi standard non polar33892256
Biperiden,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(CCN1CCCCC1)(C1=CC=CC=C1)C1CC2C=CC1C22703.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Biperiden GC-MS (1 TMS) - 70eV, Positivesplash10-0096-9261000000-a2bf53b32ad045169c692017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Biperiden GC-MS (Non-derivatized) - 70eV, Positivesplash10-054n-9520000000-3d69a8227dbbcbaa85a22017-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Biperiden GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0002-9000000000-92eb93b999cf7f5ec5192014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Biperiden 10V, Positive-QTOFsplash10-01ox-1096000000-b99cc35f37f2763389772016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Biperiden 20V, Positive-QTOFsplash10-0002-9040000000-0e1cce5acf474b6a379f2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Biperiden 40V, Positive-QTOFsplash10-016r-9110000000-6c95e29e42a503874c092016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Biperiden 10V, Negative-QTOFsplash10-03di-0019000000-15b9d0ad97ade514831c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Biperiden 20V, Negative-QTOFsplash10-03ec-9145000000-6475a16f5449091aedb62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Biperiden 40V, Negative-QTOFsplash10-001i-9000000000-7c0cf15c2c8f5071caf72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Biperiden 10V, Positive-QTOFsplash10-03di-4009000000-5d4593f5bf86b71050632021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Biperiden 20V, Positive-QTOFsplash10-0002-9002000000-91d2484c2b5c788ee3472021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Biperiden 40V, Positive-QTOFsplash10-0002-9220000000-bd998e4698c9aaf6a99e2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Biperiden 10V, Negative-QTOFsplash10-03di-0009000000-db992041ed33362f9a422021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Biperiden 20V, Negative-QTOFsplash10-03di-1549000000-050f3e90417671bee3162021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Biperiden 40V, Negative-QTOFsplash10-0a4i-1935000000-317f7afd162e7d4dca0b2021-10-11Wishart 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 DB00810 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00810 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 IDDB00810
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2289
KEGG Compound IDC07941
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBiperiden
METLIN IDNot Available
PubChem Compound2381
PDB IDNot Available
ChEBI ID3112
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 References
  1. Nishiyama K, Mizuno T, Sakuta M, Kurisaki H: Chronic dementia in Parkinson's disease treated by anticholinergic agents. Neuropsychological and neuroradiological examination. Adv Neurol. 1993;60:479-83. [PubMed:8420174 ]

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 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. Hosoi R, Kobayashi K, Watanabe Y, Inoue O: Evaluation of in vivo binding properties of 3H-NMPB and 3H-QNB in mouse brain. J Neural Transm (Vienna). 1999;106(7-8):583-92. [PubMed:10907719 ]
  4. Pehl C, Wendl B, Kaess H, Pfeiffer A: Effects of two anticholinergic drugs, trospium chloride and biperiden, on motility and evoked potentials of the oesophagus. Aliment Pharmacol Ther. 1998 Oct;12(10):979-84. [PubMed:9798802 ]
  5. Eltze M: Multiple mechanisms of action: the pharmacological profile of budipine. J Neural Transm Suppl. 1999;56:83-105. [PubMed:10370904 ]
  6. Eltze M, Galvan M: Involvement of muscarinic M2 and M3, but not of M1 and M4 receptors in vagally stimulated contractions of rabbit bronchus/trachea. Pulm Pharmacol. 1994 Apr;7(2):109-20. [PubMed:8081071 ]
  7. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
General function:
Involved in extracellular ligand-gated ion channel activity
Specific function:
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane
Gene Name:
CHRNA2
Uniprot ID:
Q15822
Molecular weight:
59764.8
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 ]

Transporters

General function:
Involved in ATP binding
Specific function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular weight:
141477.3
References
  1. Mahar Doan KM, Humphreys JE, Webster LO, Wring SA, Shampine LJ, Serabjit-Singh CJ, Adkison KK, Polli JW: Passive permeability and P-glycoprotein-mediated efflux differentiate central nervous system (CNS) and non-CNS marketed drugs. J Pharmacol Exp Ther. 2002 Dec;303(3):1029-37. [PubMed:12438524 ]