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enzymes (5) Show 5 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-10-17 11:44:46 UTC

Update Date

2022-03-07 02:49:25 UTC

HMDB ID

HMDB0005041

Secondary Accession Numbers

HMDB05041

Metabolite Identification

Common Name

Donepezil

Description

Donepezil, marketed under the trade name Aricept (Eisai), is a centrally acting reversible acetyl cholinesterase inhibitor. Its main therapeutic use is in the treatment of Alzheimer's disease where it is used to increase cortical acetylcholine. It has an oral bioavailability of 100% and easily crosses the blood-brain barrier. Because it has a half life of about 70 hours, it can be taken once a day. Initial dose is 5 mg per day, which can be increased to 10 mg per day after an adjustment period of at least 4 weeks. Donepezil is a centrally acting reversible acetyl cholinesterase inhibitor. Its main therapeutic use is in the treatment of Alzheimer's disease where it is used to increase cortical acetylcholine. It is well absorbed in the gut with an oral bioavailability of 100% and easily crosses the blood-brain barrier. Because it has a half life of about 70 hours, it can be taken once a day. Currently, there is no definitive proof that use of donepezil or other similar agents alters the course or progression of Alzheimer's disease. However, 6-12 month controlled studies have shown modest benefits in cognition and/or behavior. Pilot studies have reported that donepezil therapy may potentially have effects on markers of disease progression, such as hippocampal volume. Therefore, many neurologists, psychiatrists, and primary care physicians use donepezil in patients with Alzheimer's disease. In 2005, the UK National Institute for Clinical Excellence (NICE) withdrew its recommendation for use of the drug for mild-to-moderate AD, on the basis that there is no significant improvement in functional outcome; Currently, there is no definitive proof that use of donepezil or other similar agents alters the course or progression of Alzheimer's disease. However, 6-12 month controlled studies have shown modest benefits in cognition and/or behavior. Pilot studies have reported that donepezil therapy may potentially have effects on markers of disease progression, such as hippocampal volume. Therefore, many neurologists, psychiatrists, and primary care physicians use donepezil in patients with Alzheimer's disease. In 2005, the UK National Institute for Clinical Excellence (NICE) withdrew its recommendation for use of the drug for mild-to-moderate AD, on the basis that there is no significant improvement in functional outcome; of quality of life or of behavioral symptoms. However, NICE revised its guidelines to suggest that donepezil be used in moderate stage patients for whom the evidence is strongest. While the drug is currently indicated for mild to moderate Alzheimer's, there is also evidence from 2 trials that it may be effective for moderate to severe disease. An example of this is a Karolinska Institute paper published in The Lancet in early 2006, which states that donepezil improves cognitive function even in patients with severe Alzheimer's disease symptoms. of quality of life or of behavioral symptoms. However, NICE revised its guidelines to suggest that donepezil be used in moderate stage patients for whom the evidence is strongest. While the drug is currently indicated for mild to moderate Alzheimer's, there is also evidence from 2 trials that it may be effective for moderate to severe disease. An example of this is a Karolinska Institute paper published in The Lancet in early 2006, which states that donepezil improves cognitive function even in patients with severe Alzheimer's disease symptoms.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

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

HMDB0005041
     RDKit          3D
Donepezil
 57 60  0  0  0  0  0  0  0  0999 V2000
   -6.1932   -3.2754    0.2286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6442   -1.9168    0.1605 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6609   -0.9390    0.1709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3053   -1.2182    0.2423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3525   -0.2262    0.2509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7464    1.0927    0.1865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1072    1.3740    0.1150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0648    0.3776    0.1065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4257    0.6737    0.0344 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8097    2.0322   -0.0306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5680    1.9359    0.2044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4654    3.1041    0.5866 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4769    1.0361   -0.3636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1470    1.6191   -0.0759 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9808    0.8155   -0.6335 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3038    1.5325   -0.3043 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3783    0.8560   -1.1414 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3122   -0.5657   -1.0132 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5271   -1.2796   -1.2100 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5548   -0.8634   -0.2307 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5741   -1.3758    1.0470 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5480   -0.9770    1.9451 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5134   -0.0649    1.5836 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4763    0.4352    0.3014 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5098    0.0489   -0.6126 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4941   -1.0154    0.0652 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0344   -0.5979   -0.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8367   -0.2365    0.3280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0212   -3.9841    0.2598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4709   -3.4442   -0.5945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5909   -3.3322    1.1780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0064   -2.2508    0.2921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4057    2.4255    0.0651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2638    2.4661   -0.9109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8874    2.1400   -0.2579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5268    2.5807    0.9026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6489    0.8900   -1.4446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1049    2.6875   -0.4082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0355    1.6249    1.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9520    0.8035   -1.7543 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2068    2.5606   -0.6390 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5821    1.4000    0.7532 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3058    1.2149   -2.1949 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3618    1.1968   -0.7648 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3418   -2.3753   -1.1557 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9523   -1.1199   -2.2354 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8470   -2.0937    1.3944 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5845   -1.3669    2.9591 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2781    0.2382    2.3130 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2330    1.1583   -0.0015 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5490    0.4840   -1.5913 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8376   -0.6775    1.0702 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5017   -2.1235    0.0897 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6492   -1.3231   -0.8906 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5537   -0.7748    0.8250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6432   -0.2231    1.4301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5340   -1.1636   -0.1763 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  6 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 18 26  1  0
 26 27  1  0
 13 28  1  0
  8  3  1  0
 27 15  1  0
 28  5  1  0
 25 20  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  4 32  1  0
  7 33  1  0
 10 34  1  0
 10 35  1  0
 10 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
 17 43  1  0
 17 44  1  0
 19 45  1  0
 19 46  1  0
 21 47  1  0
 22 48  1  0
 23 49  1  0
 24 50  1  0
 25 51  1  0
 26 52  1  0
 26 53  1  0
 27 54  1  0
 27 55  1  0
 28 56  1  0
 28 57  1  0
M  END

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>
HMDB0005041

> <DATABASE_NAME>
hmdb

> <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

$$$$

HMDB0005041
     RDKit          3D
Donepezil
 57 60  0  0  0  0  0  0  0  0999 V2000
   -6.1932   -3.2754    0.2286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6442   -1.9168    0.1605 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6609   -0.9390    0.1709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3053   -1.2182    0.2423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3525   -0.2262    0.2509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7464    1.0927    0.1865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1072    1.3740    0.1150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0648    0.3776    0.1065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4257    0.6737    0.0344 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8097    2.0322   -0.0306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5680    1.9359    0.2044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4654    3.1041    0.5866 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4769    1.0361   -0.3636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1470    1.6191   -0.0759 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9808    0.8155   -0.6335 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3038    1.5325   -0.3043 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3783    0.8560   -1.1414 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3122   -0.5657   -1.0132 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5271   -1.2796   -1.2100 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5548   -0.8634   -0.2307 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5741   -1.3758    1.0470 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5480   -0.9770    1.9451 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5134   -0.0649    1.5836 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4763    0.4352    0.3014 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5098    0.0489   -0.6126 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4941   -1.0154    0.0652 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0344   -0.5979   -0.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8367   -0.2365    0.3280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0212   -3.9841    0.2598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4709   -3.4442   -0.5945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5909   -3.3322    1.1780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0064   -2.2508    0.2921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4057    2.4255    0.0651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2638    2.4661   -0.9109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8874    2.1400   -0.2579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5268    2.5807    0.9026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6489    0.8900   -1.4446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1049    2.6875   -0.4082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0355    1.6249    1.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9520    0.8035   -1.7543 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2068    2.5606   -0.6390 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5821    1.4000    0.7532 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3058    1.2149   -2.1949 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3618    1.1968   -0.7648 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3418   -2.3753   -1.1557 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9523   -1.1199   -2.2354 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8470   -2.0937    1.3944 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5845   -1.3669    2.9591 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2781    0.2382    2.3130 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2330    1.1583   -0.0015 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5490    0.4840   -1.5913 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8376   -0.6775    1.0702 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5017   -2.1235    0.0897 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6492   -1.3231   -0.8906 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5537   -0.7748    0.8250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6432   -0.2231    1.4301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5340   -1.1636   -0.1763 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  6 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 18 26  1  0
 26 27  1  0
 13 28  1  0
  8  3  1  0
 27 15  1  0
 28  5  1  0
 25 20  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  4 32  1  0
  7 33  1  0
 10 34  1  0
 10 35  1  0
 10 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
 17 43  1  0
 17 44  1  0
 19 45  1  0
 19 46  1  0
 21 47  1  0
 22 48  1  0
 23 49  1  0
 24 50  1  0
 25 51  1  0
 26 52  1  0
 26 53  1  0
 27 54  1  0
 27 55  1  0
 28 56  1  0
 28 57  1  0
M  END

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

COMPND    HMDB0243726
HETATM    1  C1  UNL     1      -7.089  -0.129   1.229  1.00  0.00           C  
HETATM    2  O1  UNL     1      -6.447  -0.347  -0.009  1.00  0.00           O  
HETATM    3  C2  UNL     1      -5.237   0.309  -0.242  1.00  0.00           C  
HETATM    4  C3  UNL     1      -4.671   1.147   0.697  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.473   1.777   0.427  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.881   1.531  -0.801  1.00  0.00           C  
HETATM    7  C6  UNL     1      -3.449   0.688  -1.745  1.00  0.00           C  
HETATM    8  C7  UNL     1      -4.645   0.060  -1.477  1.00  0.00           C  
HETATM    9  O2  UNL     1      -5.233  -0.787  -2.402  1.00  0.00           O  
HETATM   10  C8  UNL     1      -4.572  -0.991  -3.635  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.613   2.305  -0.876  1.00  0.00           C  
HETATM   12  O3  UNL     1      -1.109   2.636  -1.970  1.00  0.00           O  
HETATM   13  C10 UNL     1      -1.233   2.510   0.521  1.00  0.00           C  
HETATM   14  C11 UNL     1      -0.525   1.403   1.212  1.00  0.00           C  
HETATM   15  C12 UNL     1       0.772   1.012   0.599  1.00  0.00           C  
HETATM   16  C13 UNL     1       0.743   0.509  -0.796  1.00  0.00           C  
HETATM   17  C14 UNL     1       1.538  -0.782  -0.965  1.00  0.00           C  
HETATM   18  N1  UNL     1       2.870  -0.655  -0.415  1.00  0.00           N  
HETATM   19  C15 UNL     1       3.547  -1.916  -0.613  1.00  0.00           C  
HETATM   20  C16 UNL     1       4.922  -1.815  -0.079  1.00  0.00           C  
HETATM   21  C17 UNL     1       5.261  -2.406   1.121  1.00  0.00           C  
HETATM   22  C18 UNL     1       6.534  -2.330   1.645  1.00  0.00           C  
HETATM   23  C19 UNL     1       7.507  -1.644   0.956  1.00  0.00           C  
HETATM   24  C20 UNL     1       7.205  -1.032  -0.262  1.00  0.00           C  
HETATM   25  C21 UNL     1       5.916  -1.138  -0.742  1.00  0.00           C  
HETATM   26  C22 UNL     1       2.899  -0.143   0.908  1.00  0.00           C  
HETATM   27  C23 UNL     1       1.498  -0.005   1.462  1.00  0.00           C  
HETATM   28  C24 UNL     1      -2.613   2.712   1.184  1.00  0.00           C  
HETATM   29  H1  UNL     1      -6.440  -0.428   2.093  1.00  0.00           H  
HETATM   30  H2  UNL     1      -8.057  -0.659   1.266  1.00  0.00           H  
HETATM   31  H3  UNL     1      -7.311   0.952   1.402  1.00  0.00           H  
HETATM   32  H4  UNL     1      -5.148   1.325   1.647  1.00  0.00           H  
HETATM   33  H5  UNL     1      -2.978   0.497  -2.716  1.00  0.00           H  
HETATM   34  H6  UNL     1      -5.127  -1.735  -4.257  1.00  0.00           H  
HETATM   35  H7  UNL     1      -4.436  -0.044  -4.184  1.00  0.00           H  
HETATM   36  H8  UNL     1      -3.545  -1.357  -3.386  1.00  0.00           H  
HETATM   37  H9  UNL     1      -0.722   3.483   0.635  1.00  0.00           H  
HETATM   38  H10 UNL     1      -1.158   0.485   1.319  1.00  0.00           H  
HETATM   39  H11 UNL     1      -0.294   1.698   2.284  1.00  0.00           H  
HETATM   40  H12 UNL     1       1.401   1.959   0.587  1.00  0.00           H  
HETATM   41  H13 UNL     1       1.129   1.235  -1.528  1.00  0.00           H  
HETATM   42  H14 UNL     1      -0.292   0.236  -1.066  1.00  0.00           H  
HETATM   43  H15 UNL     1       1.655  -0.923  -2.063  1.00  0.00           H  
HETATM   44  H16 UNL     1       0.976  -1.600  -0.511  1.00  0.00           H  
HETATM   45  H17 UNL     1       3.657  -2.158  -1.700  1.00  0.00           H  
HETATM   46  H18 UNL     1       2.965  -2.730  -0.123  1.00  0.00           H  
HETATM   47  H19 UNL     1       4.495  -2.954   1.677  1.00  0.00           H  
HETATM   48  H20 UNL     1       6.797  -2.791   2.581  1.00  0.00           H  
HETATM   49  H21 UNL     1       8.521  -1.571   1.351  1.00  0.00           H  
HETATM   50  H22 UNL     1       7.992  -0.500  -0.778  1.00  0.00           H  
HETATM   51  H23 UNL     1       5.666  -0.675  -1.673  1.00  0.00           H  
HETATM   52  H24 UNL     1       3.529  -0.760   1.563  1.00  0.00           H  
HETATM   53  H25 UNL     1       3.304   0.912   0.867  1.00  0.00           H  
HETATM   54  H26 UNL     1       0.955  -0.951   1.414  1.00  0.00           H  
HETATM   55  H27 UNL     1       1.519   0.341   2.515  1.00  0.00           H  
HETATM   56  H28 UNL     1      -2.558   2.484   2.257  1.00  0.00           H  
HETATM   57  H29 UNL     1      -2.921   3.753   1.057  1.00  0.00           H  
CONECT    1    2   29   30   31
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   32
CONECT    5    6    6   28
CONECT    6    7   11
CONECT    7    8    8   33
CONECT    8    9
CONECT    9   10
CONECT   10   34   35   36
CONECT   11   12   12   13
CONECT   13   14   28   37
CONECT   14   15   38   39
CONECT   15   16   27   40
CONECT   16   17   41   42
CONECT   17   18   43   44
CONECT   18   19   26
CONECT   19   20   45   46
CONECT   20   21   21   25
CONECT   21   22   47
CONECT   22   23   23   48
CONECT   23   24   49
CONECT   24   25   25   50
CONECT   25   51
CONECT   26   27   52   53
CONECT   27   54   55
CONECT   28   56   57
END

HMDB0005041
     RDKit          3D
Donepezil
 57 60  0  0  0  0  0  0  0  0999 V2000
   -6.1932   -3.2754    0.2286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6442   -1.9168    0.1605 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6609   -0.9390    0.1709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3053   -1.2182    0.2423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3525   -0.2262    0.2509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7464    1.0927    0.1865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1072    1.3740    0.1150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0648    0.3776    0.1065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4257    0.6737    0.0344 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8097    2.0322   -0.0306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5680    1.9359    0.2044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4654    3.1041    0.5866 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4769    1.0361   -0.3636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1470    1.6191   -0.0759 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9808    0.8155   -0.6335 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3038    1.5325   -0.3043 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3783    0.8560   -1.1414 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3122   -0.5657   -1.0132 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5271   -1.2796   -1.2100 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5548   -0.8634   -0.2307 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5741   -1.3758    1.0470 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5480   -0.9770    1.9451 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5134   -0.0649    1.5836 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4763    0.4352    0.3014 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5098    0.0489   -0.6126 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4941   -1.0154    0.0652 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0344   -0.5979   -0.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8367   -0.2365    0.3280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0212   -3.9841    0.2598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4709   -3.4442   -0.5945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5909   -3.3322    1.1780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0064   -2.2508    0.2921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4057    2.4255    0.0651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2638    2.4661   -0.9109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8874    2.1400   -0.2579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5268    2.5807    0.9026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6489    0.8900   -1.4446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1049    2.6875   -0.4082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0355    1.6249    1.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9520    0.8035   -1.7543 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2068    2.5606   -0.6390 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5821    1.4000    0.7532 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3058    1.2149   -2.1949 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3618    1.1968   -0.7648 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3418   -2.3753   -1.1557 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9523   -1.1199   -2.2354 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8470   -2.0937    1.3944 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5845   -1.3669    2.9591 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2781    0.2382    2.3130 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2330    1.1583   -0.0015 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5490    0.4840   -1.5913 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8376   -0.6775    1.0702 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5017   -2.1235    0.0897 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6492   -1.3231   -0.8906 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5537   -0.7748    0.8250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6432   -0.2231    1.4301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5340   -1.1636   -0.1763 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  6 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 18 26  1  0
 26 27  1  0
 13 28  1  0
  8  3  1  0
 27 15  1  0
 28  5  1  0
 25 20  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  4 32  1  0
  7 33  1  0
 10 34  1  0
 10 35  1  0
 10 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
 17 43  1  0
 17 44  1  0
 19 45  1  0
 19 46  1  0
 21 47  1  0
 22 48  1  0
 23 49  1  0
 24 50  1  0
 25 51  1  0
 26 52  1  0
 26 53  1  0
 27 54  1  0
 27 55  1  0
 28 56  1  0
 28 57  1  0
M  END

View in JSmol View Stereo Labels

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

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular 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

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	198.1	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0045 g/L	ALOGPS
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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	190.295	31661259
DarkChem	[M-H]-	190.118	31661259
DeepCCS	[M+H]+	195.883	30932474
DeepCCS	[M-H]-	193.525	30932474
DeepCCS	[M-2H]-	227.501	30932474
DeepCCS	[M+Na]+	202.729	30932474
AllCCS	[M+H]+	195.0	32859911
AllCCS	[M+H-H2O]+	192.3	32859911
AllCCS	[M+NH4]+	197.4	32859911
AllCCS	[M+Na]+	198.1	32859911
AllCCS	[M-H]-	196.1	32859911
AllCCS	[M+Na-2H]-	196.5	32859911
AllCCS	[M+HCOO]-	197.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Donepezil	COC1=C(OC)C=C2C(=O)C(CC3CCN(CC4=CC=CC=C4)CC3)CC2=C1	3911.9	Standard polar	33892256
Donepezil	COC1=C(OC)C=C2C(=O)C(CC3CCN(CC4=CC=CC=C4)CC3)CC2=C1	3193.7	Standard non polar	33892256
Donepezil	COC1=C(OC)C=C2C(=O)C(CC3CCN(CC4=CC=CC=C4)CC3)CC2=C1	3279.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Donepezil GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fdo-6948000000-6c7dc19cab1af35fbb59	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Donepezil GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Donepezil GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Donepezil 35V, Negative-QTOF	splash10-004i-0079000000-97441986dda64eeb2ed0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Donepezil 35V, Positive-QTOF	splash10-000x-4279000000-8057308579d31f5bbb76	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Donepezil 10V, Positive-QTOF	splash10-001l-3109000000-7610503c88b3d172ef5d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Donepezil 20V, Positive-QTOF	splash10-0006-9322000000-f0d3e8edeecc7f261b94	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Donepezil 40V, Positive-QTOF	splash10-0006-9000000000-9934c235983cbddb269c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Donepezil 10V, Negative-QTOF	splash10-004i-0019000000-efb0e051a3400937c1e3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Donepezil 20V, Negative-QTOF	splash10-004i-0239000000-f766ac8eda8a1a30facc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Donepezil 40V, Negative-QTOF	splash10-00ai-4693000000-8d87007bbd84d8b72159	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Donepezil 10V, Negative-QTOF	splash10-004i-0009000000-4b6aa6423da10b561e2e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Donepezil 20V, Negative-QTOF	splash10-004i-1009000000-4727eca26ceeec565366	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Donepezil 40V, Negative-QTOF	splash10-01di-0059000000-3fb1cd564ce0fcc93f62	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Donepezil 10V, Positive-QTOF	splash10-001i-0009000000-bcd66f7c41688cf26726	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Donepezil 20V, Positive-QTOF	splash10-001i-1009000000-7b9769e47f72dc71726a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Donepezil 40V, Positive-QTOF	splash10-0006-9123000000-bace768387e44aecb5ba	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Brain

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

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

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

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

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 ]
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 ]
Emre M: Switching cholinesterase inhibitors in patients with Alzheimer's disease. Int J Clin Pract Suppl. 2002 Jun;(127):64-72. [PubMed:12139369 ]
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 ]
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. [PubMed:15132713 ]

Enzymes

Enzyme Details

1. Acetylcholinesterase

General function:: Involved in carboxylesterase activity
Specific function:: Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
Gene Name:: ACHE
Uniprot ID:: P22303
Molecular weight:: 67795.525

Enzyme Details

2. Cholinesterase

General function:: Involved in carboxylesterase activity
Specific function:: Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name:: BCHE
Uniprot ID:: P06276
Molecular weight:: 68417.575

Enzyme Details

3. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

Enzyme Details

4. Cytochrome P450 2D6

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

Enzyme Details

5. 5-hydroxytryptamine receptor 2A

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. This receptor is involved in tracheal smooth muscle contraction, bronchoconstriction, and control of aldosterone production
Gene Name:: HTR2A
Uniprot ID:: P28223
Molecular weight:: 52602.6

Showing metabocard for Donepezil (HMDB0005041)

MOL for HMDB0005041 (Donepezil)

3D MOL for HMDB0005041 (Donepezil)

3D SDF for HMDB0005041 (Donepezil)

3D-SDF for HMDB0005041 (Donepezil)

PDB for HMDB0005041 (Donepezil)

3D PDB for HMDB0005041 (Donepezil)

SMILES for HMDB0005041 (Donepezil)

INCHI for HMDB0005041 (Donepezil)

Structure for HMDB0005041 (Donepezil)

3D Structure for HMDB0005041 (Donepezil)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes