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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:00:36 UTC
Update Date2021-09-14 14:57:58 UTC
HMDB IDHMDB0013960
Secondary Accession Numbers
  • HMDB13960
Metabolite Identification
Common NameDonepezil metabolite M4
DescriptionDonepezil metabolite M4 is a metabolite of Donepezil. Donepezil, marketed under the trade name Aricept by its developer Eisai and partner Pfizer, and also marketed under the brand name DONEP by Alkem Pentacare, is a centrally acting reversible acetylcholinesterase inhibitor. Its main therapeutic use is in the palliative treatment of Alzheimer's disease. Common side effects include gastrointestinal upset. It has an oral bioavailability of 100% and easily crosses the blood–brain barrier. Because it has a biological half-life of about 70 hours, it can be taken once a day. (Wikipedia)
Structure
Data?1582753158
Synonyms
ValueSource
(2S,3R,4E)-2-Alkanamido-3-hydroxyoctadec-4-en-1-yl 3-O-(5-acetamido-3,5-dideoxy-D-glycero-alpha-D-galacto-non-2-ulopyranonosyl)-beta-D-galactopyranosideHMDB
(2S,3R,4E)-2-Alkanamido-3-hydroxyoctadec-4-en-1-yl 5-acetamido-3,5-dideoxy-D-glycero-alpha-D-galacto-non-2-ulopyranonosyl-(2Right3)-beta-D-galactopyranosideHMDB
(Acetyloxy)(tributyl)stannane (acd/name 4.0)HMDB
(Acetyloxy)tributyl-stannaneHMDB
(Gal)1 (neu5ac)1 (cer)1HMDB
Acetoxytributyl-stannaneHMDB
Acetoxytributyl-tinHMDB
AcetoxytributylstannaneHMDB
AcetoxytributyltinHMDB
alpha-Neu5ac-(2Right3)-beta-D-gal-(1leftright1')-cerHMDB
alpha-Neup5ac-(2Right3)-beta-D-galp-(1leftright1')-cerHMDB
Ganglioside GM4HMDB
GM4HMDB
N-Acetyl-alpha-neuraminosyl-(2Right3)-beta-D-galactosylceramidesHMDB
N-Acetylneuraminyl-galactosylceramideHMDB
Neu5ac-alpha2->3gal-beta1->1'cerHMDB
Neu5ac-gal-beta1->1'cerHMDB
NeuAcalpha2-3galbeta-cerHMDB
TBTAHMDB
Tin, tributyl-, acetateHMDB
Tri-N-butyltin acetateHMDB
TributylacetoxystannaneHMDB
Tributylstannyl acetateHMDB
Tributyltin acetateHMDB
Tribuyltin acetateHMDB
Chemical FormulaC17H23NO3
Average Molecular Weight289.3694
Monoisotopic Molecular Weight289.167793607
IUPAC Name5,6-dimethoxy-2-(piperidin-4-ylmethyl)-2,3-dihydro-1H-inden-1-one
Traditional Name5,6-dimethoxy-2-(piperidin-4-ylmethyl)-2,3-dihydroinden-1-one
CAS Registry Number56-36-0
SMILES
COC1=C(OC)C=C2C(=O)C(CC3CCNCC3)CC2=C1
InChI Identifier
InChI=1S/C17H23NO3/c1-20-15-9-12-8-13(7-11-3-5-18-6-4-11)17(19)14(12)10-16(15)21-2/h9-11,13,18H,3-8H2,1-2H3
InChI KeyPGBZORAISITZTF-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as indanones. Indanones are compounds containing an indane ring bearing a ketone group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassIndanes
Sub ClassIndanones
Direct ParentIndanones
Alternative Parents
Substituents
  • Indanone
  • Anisole
  • Aryl ketone
  • Aryl alkyl ketone
  • Alkyl aryl ether
  • Aralkylamine
  • Piperidine
  • Ketone
  • Secondary aliphatic amine
  • Ether
  • Secondary amine
  • Azacycle
  • Organoheterocyclic compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point84.7 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.065 mg/mLNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.033 g/LALOGPS
logP2.49ALOGPS
logP2.1ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)17.02ChemAxon
pKa (Strongest Basic)10.26ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area47.56 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity82.21 m³·mol⁻¹ChemAxon
Polarizability33.04 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+167.59631661259
DarkChem[M-H]-169.35531661259
DeepCCS[M+H]+170.16730932474
DeepCCS[M-H]-167.80930932474
DeepCCS[M-2H]-200.69630932474
DeepCCS[M+Na]+176.26130932474
AllCCS[M+H]+169.532859911
AllCCS[M+H-H2O]+166.132859911
AllCCS[M+NH4]+172.732859911
AllCCS[M+Na]+173.632859911
AllCCS[M-H]-175.432859911
AllCCS[M+Na-2H]-175.532859911
AllCCS[M+HCOO]-175.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Donepezil metabolite M4COC1=C(OC)C=C2C(=O)C(CC3CCNCC3)CC2=C13082.9Standard polar33892256
Donepezil metabolite M4COC1=C(OC)C=C2C(=O)C(CC3CCNCC3)CC2=C12483.5Standard non polar33892256
Donepezil metabolite M4COC1=C(OC)C=C2C(=O)C(CC3CCNCC3)CC2=C12600.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Donepezil metabolite M4,1TMS,isomer #1COC1=CC2=C(C=C1OC)C(=O)C(CC1CCN([Si](C)(C)C)CC1)C22609.1Semi standard non polar33892256
Donepezil metabolite M4,1TMS,isomer #1COC1=CC2=C(C=C1OC)C(=O)C(CC1CCN([Si](C)(C)C)CC1)C22702.8Standard non polar33892256
Donepezil metabolite M4,1TMS,isomer #1COC1=CC2=C(C=C1OC)C(=O)C(CC1CCN([Si](C)(C)C)CC1)C23343.1Standard polar33892256
Donepezil metabolite M4,1TBDMS,isomer #1COC1=CC2=C(C=C1OC)C(=O)C(CC1CCN([Si](C)(C)C(C)(C)C)CC1)C22855.3Semi standard non polar33892256
Donepezil metabolite M4,1TBDMS,isomer #1COC1=CC2=C(C=C1OC)C(=O)C(CC1CCN([Si](C)(C)C(C)(C)C)CC1)C22924.6Standard non polar33892256
Donepezil metabolite M4,1TBDMS,isomer #1COC1=CC2=C(C=C1OC)C(=O)C(CC1CCN([Si](C)(C)C(C)(C)C)CC1)C23499.1Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Donepezil metabolite M4 GC-MS (Non-derivatized) - 70eV, Positivesplash10-008a-7390000000-30b373dbaf089a1137742017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Donepezil metabolite M4 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 - Donepezil metabolite M4 10V, Positive-QTOFsplash10-0006-0090000000-da28a41bd1b829d71a8e2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Donepezil metabolite M4 20V, Positive-QTOFsplash10-0bu3-4970000000-801d3c0b32c93fd111652016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Donepezil metabolite M4 40V, Positive-QTOFsplash10-0a59-9510000000-6d1d9c2e6a3d68e3dff02016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Donepezil metabolite M4 10V, Negative-QTOFsplash10-000i-0090000000-e07661d76997ea63c5792016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Donepezil metabolite M4 20V, Negative-QTOFsplash10-000i-1190000000-7f3cb62ab8e739b13f282016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Donepezil metabolite M4 40V, Negative-QTOFsplash10-005l-2960000000-4aff8e96600a8dcc0cd72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Donepezil metabolite M4 10V, Negative-QTOFsplash10-000i-0090000000-1f5244541851cecc34192021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Donepezil metabolite M4 20V, Negative-QTOFsplash10-000i-0090000000-ea661d63d95f0276ff502021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Donepezil metabolite M4 40V, Negative-QTOFsplash10-017i-0190000000-bbc4b50b5f9509e31d352021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Donepezil metabolite M4 10V, Positive-QTOFsplash10-0006-0090000000-33b322e33c44f750998f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Donepezil metabolite M4 20V, Positive-QTOFsplash10-0006-0090000000-a157f4737fa76857bd9f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Donepezil metabolite M4 40V, Positive-QTOFsplash10-08g4-2960000000-aa5279093d72dcc7f3742021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID8622316
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10446897
PDB IDNot Available
ChEBI ID308602
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1291941
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available