Bovine Metabolome Database: Showing metabocard for Donepezil (BMDB0005041)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:14:57 UTC

Update Date

2020-05-11 19:32:29 UTC

BMDB ID

BMDB0005041

Secondary Accession Numbers

BMDB05041

Metabolite Identification

Common Name

Donepezil

Description

donepezil, also known as donaz, belongs to the class of organic compounds known as n-benzylpiperidines. These are heterocyclic Compounds containing a piperidine ring conjugated to a benzyl group through one nitrogen ring atom. Based on a literature review very few articles have been published on donepezil.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Donepezilo	ChEBI
Donepezilum	ChEBI
Donaz	Kegg
Aricept	HMDB, MeSH
Aricept odt	HMDB
Donepezil hydrochloride	HMDB, MeSH
1-Benzyl-4-((5,6-dimethoxy-1-indanon)-2-yl)methylpiperidine hydrochloride	MeSH, HMDB
Donepezilium oxalate trihydrate	MeSH, HMDB
Eranz	MeSH, HMDB

Chemical Formula

C₂₄H₂₉NO₃

Average Molecular Weight

379.492

Monoisotopic Molecular Weight

379.214743799

IUPAC Name

2-[(1-benzylpiperidin-4-yl)methyl]-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one

Traditional Name

donepezil

CAS Registry Number

120014-06-4

SMILES

COC1=C(OC)C=C2C(=O)C(CC3CCN(CC4=CC=CC=C4)CC3)CC2=C1

InChI Identifier

InChI=1S/C24H29NO3/c1-27-22-14-19-13-20(24(26)21(19)15-23(22)28-2)12-17-8-10-25(11-9-17)16-18-6-4-3-5-7-18/h3-7,14-15,17,20H,8-13,16H2,1-2H3

InChI Key

ADEBPBSSDYVVLD-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as n-benzylpiperidines. These are heterocyclic Compounds containing a piperidine ring conjugated to a benzyl group through one nitrogen ring atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Piperidines

Sub Class

Benzylpiperidines

Direct Parent

N-benzylpiperidines

Alternative Parents

Substituents

N-benzylpiperidine
Indanone
Indane
Aryl alkyl ketone
Aryl ketone
Phenylmethylamine
Benzylamine
Anisole
Aralkylamine
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Tertiary aliphatic amine
Tertiary amine
Ketone
Azacycle
Ether
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

piperidines (CHEBI:53289 )
cyclic ketone (CHEBI:53289 )

Ontology

Status

Expected but not Quantified

Origin

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cell membrane
Membrane

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	4.14	ALOGPS
logP	4.21	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	17.02	ChemAxon
pKa (Strongest Basic)	8.62	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	38.77 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	112.11 m³·mol⁻¹	ChemAxon
Polarizability	44.34 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fdo-6948000000-6c7dc19cab1af35fbb59	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-004i-0079000000-97441986dda64eeb2ed0	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-000x-4279000000-8057308579d31f5bbb76	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001l-3109000000-7610503c88b3d172ef5d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9322000000-f0d3e8edeecc7f261b94	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-9934c235983cbddb269c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0019000000-efb0e051a3400937c1e3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0239000000-f766ac8eda8a1a30facc	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00ai-4693000000-8d87007bbd84d8b72159	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0009000000-4b6aa6423da10b561e2e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-1009000000-4727eca26ceeec565366	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01di-0059000000-3fb1cd564ce0fcc93f62	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0009000000-bcd66f7c41688cf26726	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-1009000000-7b9769e47f72dc71726a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9123000000-bace768387e44aecb5ba	View in MoNA

Biological Properties

Cellular Locations

Cell membrane
Membrane

Biospecimen Locations

Brain

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Brain	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3040

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Donepezil

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

53289

References

Synthesis Reference

Sugimoto, Hachiro; Tsuchiya, Yutaka; Higurashi, Kunizou; Karibe, Norio; Iimura, Yuoichi; Sasaki, Atsushi; Yamanashi, Yoshiharu; Ogura, Hiroo; Araki, Shin; et al. Preparation of 1-benzyl-4-(substituted alkyl)piperidines and analogs as acetylcholinesterase inhibitors. Eur. Pat. Appl. (1988), 103 pp. CODEN: EPXXDW EP 296560 A2 19881228 CAN 110:173102 AN 1989:173102

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Donepezil (BMDB0005041)

Structure for BMDB0005041 (Donepezil)