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Showing NP-Card for Donepezil (NP0334582)

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Record Information
Version2.0
Created at2024-09-10 19:00:33 UTC
Updated at2024-09-10 19:00:33 UTC
NP-MRD IDNP0334582
Secondary Accession NumbersNone
Natural Product Identification
Common NameDonepezil
DescriptionDonepezil, also known as donaz or aricept, 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. Donepezil is a very strong basic compound (based on its pKa). Donepezil is a potentially toxic compound. Donepezil was first documented in 2001 (PMID: 11585854). A centrally acting reversible acetylcholinesterase inhibitor, its main therapeutic use is in the treatment of Alzheimer's disease where it is used to increase cortical acetylcholine (PMID: 16045972) (PMID: 15631830) (PMID: 12139369) (PMID: 15132713).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0334582 (Donepezil)

843
  Mrv0541 02231215022D          

 28 31  0  0  1  0            999 V2000
    4.8305    2.4093    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.1362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.7862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1182   -1.1823    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2932    0.2467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8806    0.9612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0556    0.9612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1182    0.2467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8806   -0.4678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5307   -0.4678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2932   -1.1823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5741    0.2973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5741    1.6251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.5487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.3737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5307   -1.8967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.1362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.7862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3557   -1.8967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.5487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.3737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7682   -1.1823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7682   -2.6113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5932   -1.1823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5932   -2.6113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0057   -1.8967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.6888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    2.6113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 13  2  0  0  0  0
  2 20  1  0  0  0  0
  2 27  1  0  0  0  0
  3 21  1  0  0  0  0
  3 28  1  0  0  0  0
  4 10  1  0  0  0  0
  4 11  1  0  0  0  0
  4 16  1  0  0  0  0
  5  6  1  0  0  0  0
  5  8  1  0  0  0  0
  5  9  1  0  0  0  0
  6  7  1  0  0  0  0
  7 12  1  0  0  0  0
  7 13  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  1  0  0  0  0
 14 15  1  0  0  0  0
 14 17  2  0  0  0  0
 15 18  2  0  0  0  0
 16 19  1  0  0  0  0
 17 20  1  0  0  0  0
 18 21  1  0  0  0  0
 19 22  2  0  0  0  0
 19 23  1  0  0  0  0
 20 21  2  0  0  0  0
 22 24  1  0  0  0  0
 23 25  2  0  0  0  0
 24 26  2  0  0  0  0
 25 26  1  0  0  0  0
M  END
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3D MOL for NP0334582 (Donepezil)

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3D SDF for NP0334582 (Donepezil)
843
  Mrv0541 02231215022D          

 28 31  0  0  1  0            999 V2000
    4.8305    2.4093    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.1362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.7862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1182   -1.1823    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2932    0.2467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8806    0.9612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0556    0.9612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1182    0.2467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8806   -0.4678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5307   -0.4678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2932   -1.1823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5741    0.2973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5741    1.6251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.5487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.3737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5307   -1.8967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.1362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.7862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3557   -1.8967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.5487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.3737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7682   -1.1823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7682   -2.6113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5932   -1.1823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5932   -2.6113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0057   -1.8967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.6888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    2.6113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 13  2  0  0  0  0
  2 20  1  0  0  0  0
  2 27  1  0  0  0  0
  3 21  1  0  0  0  0
  3 28  1  0  0  0  0
  4 10  1  0  0  0  0
  4 11  1  0  0  0  0
  4 16  1  0  0  0  0
  5  6  1  0  0  0  0
  5  8  1  0  0  0  0
  5  9  1  0  0  0  0
  6  7  1  0  0  0  0
  7 12  1  0  0  0  0
  7 13  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  1  0  0  0  0
 14 15  1  0  0  0  0
 14 17  2  0  0  0  0
 15 18  2  0  0  0  0
 16 19  1  0  0  0  0
 17 20  1  0  0  0  0
 18 21  1  0  0  0  0
 19 22  2  0  0  0  0
 19 23  1  0  0  0  0
 20 21  2  0  0  0  0
 22 24  1  0  0  0  0
 23 25  2  0  0  0  0
 24 26  2  0  0  0  0
 25 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0334582

> <DATABASE_NAME>
NP-MRD

> <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

> <FORMULA>
C24H29NO3

> <MOLECULAR_WEIGHT>
379.492

> <EXACT_MASS>
379.214743799

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
44.33556165455788

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
4.14

> <JCHEM_LOGP>
4.207932993666668

> <ALOGPS_LOGS>
-4.93

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.021937144753494

> <JCHEM_PKA_STRONGEST_BASIC>
8.62472894729726

> <JCHEM_POLAR_SURFACE_AREA>
38.77

> <JCHEM_REFRACTIVITY>
112.1147

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.50e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
donepezil

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0334582 (Donepezil)
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PDB for NP0334582 (Donepezil)
HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 843                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       9.017   4.497   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       3.080   0.254   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       3.080   3.334   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0      13.287  -2.207   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      11.747   0.461   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.977   1.794   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.437   1.794   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.287   0.461   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.977  -0.873   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.057  -0.873   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.747  -2.207   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.538   0.555   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.538   3.034   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.081   1.024   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.081   2.564   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.057  -3.541   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.748   0.254   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.748   3.334   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      15.597  -3.541   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.414   1.024   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.414   2.564   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      16.367  -2.207   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      16.367  -4.874   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      17.907  -2.207   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      17.907  -4.874   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      18.677  -3.541   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.080  -1.286   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.080   4.874   0.000  0.00  0.00           C+0
CONECT    1   13                                                            
CONECT    2   20   27                                                       
CONECT    3   21   28                                                       
CONECT    4   10   11   16                                                  
CONECT    5    6    8    9                                                  
CONECT    6    5    7                                                       
CONECT    7    6   12   13                                                  
CONECT    8    5   10                                                       
CONECT    9    5   11                                                       
CONECT   10    4    8                                                       
CONECT   11    4    9                                                       
CONECT   12    7   14                                                       
CONECT   13    1    7   15                                                  
CONECT   14   12   15   17                                                  
CONECT   15   13   14   18                                                  
CONECT   16    4   19                                                       
CONECT   17   14   20                                                       
CONECT   18   15   21                                                       
CONECT   19   16   22   23                                                  
CONECT   20    2   17   21                                                  
CONECT   21    3   18   20                                                  
CONECT   22   19   24                                                       
CONECT   23   19   25                                                       
CONECT   24   22   26                                                       
CONECT   25   23   26                                                       
CONECT   26   24   25                                                       
CONECT   27    2                                                            
CONECT   28    3                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

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3D PDB for NP0334582 (Donepezil)
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SMILES for NP0334582 (Donepezil)
COC1=C(OC)C=C2C(=O)C(CC3CCN(CC4=CC=CC=C4)CC3)CC2=C1
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INCHI for NP0334582 (Donepezil)
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
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Synonyms
ValueSource
DonepeziloChEBI
DonepezilumChEBI
DonazKegg
AriceptHMDB
Aricept odtHMDB
Donepezil hydrochlorideHMDB
1-Benzyl-4-((5,6-dimethoxy-1-indanon)-2-yl)methylpiperidine hydrochlorideHMDB
Donepezilium oxalate trihydrateHMDB
EranzHMDB
Chemical FormulaC24H29NO3
Average Mass379.4920 Da
Monoisotopic Mass379.21474 Da
IUPAC Name2-[(1-benzylpiperidin-4-yl)methyl]-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one
Traditional Namedonepezil
CAS Registry NumberNot Available
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 KeyADEBPBSSDYVVLD-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
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.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassPiperidines  
Sub ClassBenzylpiperidines  
Direct ParentN-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 FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP4.14ALOGPS
logP4.21ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)17.02ChemAxon
pKa (Strongest Basic)8.62ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area38.77 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity112.11 m³·mol⁻¹ChemAxon
Polarizability44.34 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
HMDB IDHMDB0005041  
DrugBank IDDB00843  
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023607  
KNApSAcK IDNot Available
Chemspider ID3040  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDonepezil  
METLIN IDNot Available
PubChem Compound3152  
PDB IDNot Available
ChEBI ID53289  
Good Scents IDNot Available
References
General References
  1. Hayslett RL, Tizabi Y: Effects of donepezil, nicotine and haloperidol on the central serotonergic system in mice: implications for Tourette's syndrome. Pharmacol Biochem Behav. 2005 Aug;81(4):879-86. [PubMed:16045972  ] 
  2. Wang LN, Wang W, Zhang XH, Ma L, Yin H, Li DJ: [An interventional study on amnestic mild cognitive impairment with small dose donepezil]. Zhonghua Nei Ke Za Zhi. 2004 Oct;43(10):760-3. [PubMed:15631830  ] 
  3. Emre M: Switching cholinesterase inhibitors in patients with Alzheimer's disease. Int J Clin Pract Suppl. 2002 Jun;(127):64-72. [PubMed:12139369  ] 
  4. Nakano S, Asada T, Matsuda H, Uno M, Takasaki M: Donepezil hydrochloride preserves regional cerebral blood flow in patients with Alzheimer's disease. J Nucl Med. 2001 Oct;42(10):1441-5. [PubMed:11585854  ] 
  5. Wilkinson DG, Francis PT, Schwam E, Payne-Parrish J: Cholinesterase inhibitors used in the treatment of Alzheimer's disease: the relationship between pharmacological effects and clinical efficacy. Drugs Aging. 2004;21(7):453-78. doi: 10.2165/00002512-200421070-00004. [PubMed:15132713  ]