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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (5) Show 5 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:00:36 UTC

Update Date

2021-09-16 15:29:20 UTC

HMDB ID

HMDB0013958

Secondary Accession Numbers

HMDB13958

Metabolite Identification

Common Name

5-O-Desmethyldonepezil

Description

5-O-Desmethyldonepezil 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. 5-O-Desmethyldonepezil is a very strong basic compound (based on its pKa).

Structure

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


  Mrv0541 06191310342D          

 27 30  0  0  0  0            999 V2000
    7.7207   -1.4134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5402   -3.6866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5402   -2.0366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0084   -5.0051    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1834   -3.5760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7708   -2.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9458   -2.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0084   -3.5760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7708   -4.2905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4209   -4.2905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1834   -5.0051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4643   -3.5255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4643   -2.1977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6837   -3.2740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6837   -2.4490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4209   -5.7195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9693   -3.6866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9693   -2.0366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2459   -5.7195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2547   -3.2740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2547   -2.4490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6584   -5.0051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6584   -6.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4834   -5.0051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4834   -6.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8959   -5.7195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5402   -1.2115    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
  3 21  1  0  0  0  0
  3 27  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

HMDB0013958
     RDKit          3D
5-O-Desmethyldonepezil
 54 57  0  0  0  0  0  0  0  0999 V2000
   -7.4200    1.9995    0.0094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4641    0.5845    0.1529 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2853   -0.1605    0.0784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0544    0.4372   -0.1334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8959   -0.3014   -0.2059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9497   -1.6682   -0.0662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1633   -2.2691    0.1438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3424   -1.5249    0.2185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5651   -2.1476    0.4319 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5932   -2.1914   -0.1892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6676   -1.0014    0.1951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3708   -1.2971   -0.4446 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7619   -0.3887   -0.2619 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1897   -0.1944    1.1817 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6295    0.2714    1.1268 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8792    1.3223    0.2393 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0775    2.0505    0.3982 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2442    1.1242    0.2457 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7890    0.4904    1.3323 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8740   -0.3755    1.2130 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4026   -0.5930   -0.0214 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8916    0.0192   -1.1418 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8121    0.8740   -0.9852 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2153    1.3756   -0.9958 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7476    0.9459   -0.9054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4713    0.0866   -0.4162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1984    1.1389   -1.0030 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6132    2.4205    0.6681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2438    2.2236   -1.0486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3686    2.4435    0.3739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0245    1.5221   -0.2429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2838   -3.3365    0.2629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6783   -3.1282    0.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3802   -2.3711   -1.2713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3693   -3.0650    0.4276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6278   -0.9226    1.2972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5505   -1.4102   -1.5410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0232   -2.3286   -0.1190 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6659   -0.9315   -0.7192 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1214   -1.1200    1.7705 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5706    0.6308    1.5867 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9913    0.5469    2.1431 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2280   -0.6285    0.8036 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1509    2.4567    1.4494 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2350    2.8553   -0.3417 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3802    0.6539    2.3165 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2903   -0.8647    2.0715 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2497   -1.2632   -0.1471 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3188   -0.1607   -2.1158 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3660    1.3862   -1.8357 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2244    2.4236   -1.3764 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6661    0.7211   -1.7774 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3399    0.9049   -1.9078 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2922    1.7346   -0.2374 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
  6 10  1  0
 10 11  1  0
 11 12  1  0
 12 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  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 16 24  1  0
 24 25  1  0
 11 26  1  0
 26 27  2  0
  8  3  1  0
 25 13  1  0
 26  5  1  0
 23 18  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  4 31  1  0
  7 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  0
 14 40  1  0
 14 41  1  0
 15 42  1  0
 15 43  1  0
 17 44  1  0
 17 45  1  0
 19 46  1  0
 20 47  1  0
 21 48  1  0
 22 49  1  0
 23 50  1  0
 24 51  1  0
 24 52  1  0
 25 53  1  0
 25 54  1  0
M  END


  Mrv0541 06191310342D          

 27 30  0  0  0  0            999 V2000
    7.7207   -1.4134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5402   -3.6866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5402   -2.0366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0084   -5.0051    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1834   -3.5760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7708   -2.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9458   -2.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0084   -3.5760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7708   -4.2905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4209   -4.2905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1834   -5.0051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4643   -3.5255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4643   -2.1977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6837   -3.2740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6837   -2.4490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4209   -5.7195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9693   -3.6866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9693   -2.0366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2459   -5.7195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2547   -3.2740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2547   -2.4490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6584   -5.0051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6584   -6.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4834   -5.0051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4834   -6.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8959   -5.7195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5402   -1.2115    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
  3 21  1  0  0  0  0
  3 27  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>
HMDB0013958

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=C2CC(CC3CCN(CC4=CC=CC=C4)CC3)C(=O)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C23H27NO3/c1-27-22-14-20-18(13-21(22)25)12-19(23(20)26)11-16-7-9-24(10-8-16)15-17-5-3-2-4-6-17/h2-6,13-14,16,19,25H,7-12,15H2,1H3

> <INCHI_KEY>
DSMISVLYMKJMLP-UHFFFAOYSA-N

> <FORMULA>
C23H27NO3

> <MOLECULAR_WEIGHT>
365.4654

> <EXACT_MASS>
365.199093735

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
42.28522373561475

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
4.14

> <JCHEM_LOGP>
3.184093150089699

> <ALOGPS_LOGS>
-4.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
17.649363180293708

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.055849037503243

> <JCHEM_PKA_STRONGEST_BASIC>
8.76131599693818

> <JCHEM_POLAR_SURFACE_AREA>
49.77

> <JCHEM_REFRACTIVITY>
107.63240000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.11e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(1-benzylpiperidin-4-yl)methyl]-5-hydroxy-6-methoxy-2,3-dihydroinden-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013958
     RDKit          3D
5-O-Desmethyldonepezil
 54 57  0  0  0  0  0  0  0  0999 V2000
   -7.4200    1.9995    0.0094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4641    0.5845    0.1529 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2853   -0.1605    0.0784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0544    0.4372   -0.1334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8959   -0.3014   -0.2059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9497   -1.6682   -0.0662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1633   -2.2691    0.1438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3424   -1.5249    0.2185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5651   -2.1476    0.4319 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5932   -2.1914   -0.1892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6676   -1.0014    0.1951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3708   -1.2971   -0.4446 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7619   -0.3887   -0.2619 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1897   -0.1944    1.1817 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6295    0.2714    1.1268 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8792    1.3223    0.2393 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0775    2.0505    0.3982 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2442    1.1242    0.2457 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7890    0.4904    1.3323 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8740   -0.3755    1.2130 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4026   -0.5930   -0.0214 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8916    0.0192   -1.1418 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8121    0.8740   -0.9852 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2153    1.3756   -0.9958 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7476    0.9459   -0.9054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4713    0.0866   -0.4162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1984    1.1389   -1.0030 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6132    2.4205    0.6681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2438    2.2236   -1.0486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3686    2.4435    0.3739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0245    1.5221   -0.2429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2838   -3.3365    0.2629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6783   -3.1282    0.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3802   -2.3711   -1.2713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3693   -3.0650    0.4276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6278   -0.9226    1.2972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5505   -1.4102   -1.5410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0232   -2.3286   -0.1190 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6659   -0.9315   -0.7192 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1214   -1.1200    1.7705 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5706    0.6308    1.5867 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9913    0.5469    2.1431 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2280   -0.6285    0.8036 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1509    2.4567    1.4494 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2350    2.8553   -0.3417 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3802    0.6539    2.3165 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2903   -0.8647    2.0715 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2497   -1.2632   -0.1471 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3188   -0.1607   -2.1158 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3660    1.3862   -1.8357 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2244    2.4236   -1.3764 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6661    0.7211   -1.7774 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3399    0.9049   -1.9078 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2922    1.7346   -0.2374 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
  6 10  1  0
 10 11  1  0
 11 12  1  0
 12 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  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 16 24  1  0
 24 25  1  0
 11 26  1  0
 26 27  2  0
  8  3  1  0
 25 13  1  0
 26  5  1  0
 23 18  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  4 31  1  0
  7 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  0
 14 40  1  0
 14 41  1  0
 15 42  1  0
 15 43  1  0
 17 44  1  0
 17 45  1  0
 19 46  1  0
 20 47  1  0
 21 48  1  0
 22 49  1  0
 23 50  1  0
 24 51  1  0
 24 52  1  0
 25 53  1  0
 25 54  1  0
M  END

HEADER    PROTEIN                                 19-JUN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-13         0                                  
HETATM    1  O   UNK     0      14.412  -2.638   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       8.475  -6.882   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       8.475  -3.802   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0      18.682  -9.343   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      17.142  -6.675   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.372  -5.342   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.832  -5.342   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      18.682  -6.675   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      16.372  -8.009   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      19.452  -8.009   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      17.142  -9.343   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.933  -6.581   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.933  -4.102   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.476  -6.112   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.476  -4.572   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      19.452 -10.676   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.143  -6.882   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.143  -3.802   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      20.992 -10.676   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.809  -6.112   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.809  -4.572   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      21.762  -9.343   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      21.762 -12.010   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      23.302  -9.343   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      23.302 -12.010   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      24.072 -10.676   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.475  -2.261   0.000  0.00  0.00           C+0
CONECT    1   13                                                            
CONECT    2   20                                                            
CONECT    3   21   27                                                       
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    3                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

COMPND    HMDB0013958
HETATM    1  C1  UNL     1      -7.420   1.999   0.009  1.00  0.00           C  
HETATM    2  O1  UNL     1      -7.464   0.585   0.153  1.00  0.00           O  
HETATM    3  C2  UNL     1      -6.285  -0.161   0.078  1.00  0.00           C  
HETATM    4  C3  UNL     1      -5.054   0.437  -0.133  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.896  -0.301  -0.206  1.00  0.00           C  
HETATM    6  C5  UNL     1      -3.950  -1.668  -0.066  1.00  0.00           C  
HETATM    7  C6  UNL     1      -5.163  -2.269   0.144  1.00  0.00           C  
HETATM    8  C7  UNL     1      -6.342  -1.525   0.219  1.00  0.00           C  
HETATM    9  O2  UNL     1      -7.565  -2.148   0.432  1.00  0.00           O  
HETATM   10  C8  UNL     1      -2.593  -2.191  -0.189  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.668  -1.001   0.195  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.371  -1.297  -0.445  1.00  0.00           C  
HETATM   13  C11 UNL     1       0.762  -0.389  -0.262  1.00  0.00           C  
HETATM   14  C12 UNL     1       1.190  -0.194   1.182  1.00  0.00           C  
HETATM   15  C13 UNL     1       2.629   0.271   1.127  1.00  0.00           C  
HETATM   16  N1  UNL     1       2.879   1.322   0.239  1.00  0.00           N  
HETATM   17  C14 UNL     1       4.078   2.051   0.398  1.00  0.00           C  
HETATM   18  C15 UNL     1       5.244   1.124   0.246  1.00  0.00           C  
HETATM   19  C16 UNL     1       5.789   0.490   1.332  1.00  0.00           C  
HETATM   20  C17 UNL     1       6.874  -0.375   1.213  1.00  0.00           C  
HETATM   21  C18 UNL     1       7.403  -0.593  -0.021  1.00  0.00           C  
HETATM   22  C19 UNL     1       6.892   0.019  -1.142  1.00  0.00           C  
HETATM   23  C20 UNL     1       5.812   0.874  -0.985  1.00  0.00           C  
HETATM   24  C21 UNL     1       2.215   1.376  -0.996  1.00  0.00           C  
HETATM   25  C22 UNL     1       0.748   0.946  -0.905  1.00  0.00           C  
HETATM   26  C23 UNL     1      -2.471   0.087  -0.416  1.00  0.00           C  
HETATM   27  O3  UNL     1      -2.198   1.139  -1.003  1.00  0.00           O  
HETATM   28  H1  UNL     1      -6.613   2.420   0.668  1.00  0.00           H  
HETATM   29  H2  UNL     1      -7.244   2.224  -1.049  1.00  0.00           H  
HETATM   30  H3  UNL     1      -8.369   2.444   0.374  1.00  0.00           H  
HETATM   31  H4  UNL     1      -5.024   1.522  -0.243  1.00  0.00           H  
HETATM   32  H5  UNL     1      -5.284  -3.337   0.263  1.00  0.00           H  
HETATM   33  H6  UNL     1      -7.678  -3.128   0.542  1.00  0.00           H  
HETATM   34  H7  UNL     1      -2.380  -2.371  -1.271  1.00  0.00           H  
HETATM   35  H8  UNL     1      -2.369  -3.065   0.428  1.00  0.00           H  
HETATM   36  H9  UNL     1      -1.628  -0.923   1.297  1.00  0.00           H  
HETATM   37  H10 UNL     1      -0.550  -1.410  -1.541  1.00  0.00           H  
HETATM   38  H11 UNL     1      -0.023  -2.329  -0.119  1.00  0.00           H  
HETATM   39  H12 UNL     1       1.666  -0.931  -0.719  1.00  0.00           H  
HETATM   40  H13 UNL     1       1.121  -1.120   1.771  1.00  0.00           H  
HETATM   41  H14 UNL     1       0.571   0.631   1.587  1.00  0.00           H  
HETATM   42  H15 UNL     1       2.991   0.547   2.143  1.00  0.00           H  
HETATM   43  H16 UNL     1       3.228  -0.628   0.804  1.00  0.00           H  
HETATM   44  H17 UNL     1       4.151   2.457   1.449  1.00  0.00           H  
HETATM   45  H18 UNL     1       4.235   2.855  -0.342  1.00  0.00           H  
HETATM   46  H19 UNL     1       5.380   0.654   2.316  1.00  0.00           H  
HETATM   47  H20 UNL     1       7.290  -0.865   2.071  1.00  0.00           H  
HETATM   48  H21 UNL     1       8.250  -1.263  -0.147  1.00  0.00           H  
HETATM   49  H22 UNL     1       7.319  -0.161  -2.116  1.00  0.00           H  
HETATM   50  H23 UNL     1       5.366   1.386  -1.836  1.00  0.00           H  
HETATM   51  H24 UNL     1       2.224   2.424  -1.376  1.00  0.00           H  
HETATM   52  H25 UNL     1       2.666   0.721  -1.777  1.00  0.00           H  
HETATM   53  H26 UNL     1       0.340   0.905  -1.908  1.00  0.00           H  
HETATM   54  H27 UNL     1       0.292   1.735  -0.237  1.00  0.00           H  
CONECT    1    2   28   29   30
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   31
CONECT    5    6    6   26
CONECT    6    7   10
CONECT    7    8    8   32
CONECT    8    9
CONECT    9   33
CONECT   10   11   34   35
CONECT   11   12   26   36
CONECT   12   13   37   38
CONECT   13   14   25   39
CONECT   14   15   40   41
CONECT   15   16   42   43
CONECT   16   17   24
CONECT   17   18   44   45
CONECT   18   19   19   23
CONECT   19   20   46
CONECT   20   21   21   47
CONECT   21   22   48
CONECT   22   23   23   49
CONECT   23   50
CONECT   24   25   51   52
CONECT   25   53   54
CONECT   26   27   27
END

HMDB0013958
     RDKit          3D
5-O-Desmethyldonepezil
 54 57  0  0  0  0  0  0  0  0999 V2000
   -7.4200    1.9995    0.0094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4641    0.5845    0.1529 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2853   -0.1605    0.0784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0544    0.4372   -0.1334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8959   -0.3014   -0.2059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9497   -1.6682   -0.0662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1633   -2.2691    0.1438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3424   -1.5249    0.2185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5651   -2.1476    0.4319 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5932   -2.1914   -0.1892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6676   -1.0014    0.1951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3708   -1.2971   -0.4446 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7619   -0.3887   -0.2619 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1897   -0.1944    1.1817 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6295    0.2714    1.1268 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8792    1.3223    0.2393 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0775    2.0505    0.3982 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2442    1.1242    0.2457 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7890    0.4904    1.3323 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8740   -0.3755    1.2130 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4026   -0.5930   -0.0214 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8916    0.0192   -1.1418 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8121    0.8740   -0.9852 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2153    1.3756   -0.9958 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7476    0.9459   -0.9054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4713    0.0866   -0.4162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1984    1.1389   -1.0030 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6132    2.4205    0.6681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2438    2.2236   -1.0486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3686    2.4435    0.3739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0245    1.5221   -0.2429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2838   -3.3365    0.2629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6783   -3.1282    0.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3802   -2.3711   -1.2713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3693   -3.0650    0.4276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6278   -0.9226    1.2972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5505   -1.4102   -1.5410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0232   -2.3286   -0.1190 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6659   -0.9315   -0.7192 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1214   -1.1200    1.7705 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5706    0.6308    1.5867 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9913    0.5469    2.1431 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2280   -0.6285    0.8036 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1509    2.4567    1.4494 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2350    2.8553   -0.3417 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3802    0.6539    2.3165 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2903   -0.8647    2.0715 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2497   -1.2632   -0.1471 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3188   -0.1607   -2.1158 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3660    1.3862   -1.8357 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2244    2.4236   -1.3764 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6661    0.7211   -1.7774 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3399    0.9049   -1.9078 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2922    1.7346   -0.2374 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
  6 10  1  0
 10 11  1  0
 11 12  1  0
 12 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  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 16 24  1  0
 24 25  1  0
 11 26  1  0
 26 27  2  0
  8  3  1  0
 25 13  1  0
 26  5  1  0
 23 18  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  4 31  1  0
  7 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  0
 14 40  1  0
 14 41  1  0
 15 42  1  0
 15 43  1  0
 17 44  1  0
 17 45  1  0
 19 46  1  0
 20 47  1  0
 21 48  1  0
 22 49  1  0
 23 50  1  0
 24 51  1  0
 24 52  1  0
 25 53  1  0
 25 54  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₃H₂₇NO₃

Average Molecular Weight

365.4654

Monoisotopic Molecular Weight

365.199093735

IUPAC Name

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

Traditional Name

2-[(1-benzylpiperidin-4-yl)methyl]-5-hydroxy-6-methoxy-2,3-dihydroinden-1-one

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=C2CC(CC3CCN(CC4=CC=CC=C4)CC3)C(=O)C2=C1

InChI Identifier

InChI=1S/C23H27NO3/c1-27-22-14-20-18(13-21(22)25)12-19(23(20)26)11-16-7-9-24(10-8-16)15-17-5-3-2-4-6-17/h2-6,13-14,16,19,25H,7-12,15H2,1H3

InChI Key

DSMISVLYMKJMLP-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
Anisole
Benzylamine
Phenylmethylamine
Aryl ketone
Aryl alkyl ketone
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Monocyclic benzene moiety
Benzenoid
Tertiary aliphatic amine
Tertiary amine
Ketone
Ether
Azacycle
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Amine
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Organ

Liver (HMDB: HMDB0013958)
Kidney (HMDB: HMDB0013958)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Extracellular (HMDB: HMDB0013958)

Source

Endogenous

Endogenous (HMDB: HMDB0013958)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

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

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.021 g/L	ALOGPS
logP	4.14	ALOGPS
logP	3.18	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	8.06	ChemAxon
pKa (Strongest Basic)	8.76	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.77 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	107.63 m³·mol⁻¹	ChemAxon
Polarizability	42.29 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	187.225	31661259
DarkChem	[M-H]-	184.612	31661259
DeepCCS	[M+H]+	195.394	30932474
DeepCCS	[M-H]-	193.036	30932474
DeepCCS	[M-2H]-	227.241	30932474
DeepCCS	[M+Na]+	202.511	30932474
AllCCS	[M+H]+	191.0	32859911
AllCCS	[M+H-H2O]+	188.3	32859911
AllCCS	[M+NH4]+	193.5	32859911
AllCCS	[M+Na]+	194.2	32859911
AllCCS	[M-H]-	192.3	32859911
AllCCS	[M+Na-2H]-	192.5	32859911
AllCCS	[M+HCOO]-	192.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.71 minutes	32390414
Predicted by Siyang on May 30, 2022	10.8757 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.48 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	45.7 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1602.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	192.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	184.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	169.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	104.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	417.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	404.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	408.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	883.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	368.6 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1046.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	278.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	315.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	394.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	414.3 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	97.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5-O-Desmethyldonepezil	COC1=C(O)C=C2CC(CC3CCN(CC4=CC=CC=C4)CC3)C(=O)C2=C1	3981.5	Standard polar	33892256
5-O-Desmethyldonepezil	COC1=C(O)C=C2CC(CC3CCN(CC4=CC=CC=C4)CC3)C(=O)C2=C1	3140.3	Standard non polar	33892256
5-O-Desmethyldonepezil	COC1=C(O)C=C2CC(CC3CCN(CC4=CC=CC=C4)CC3)C(=O)C2=C1	3262.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5-O-Desmethyldonepezil,1TMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C)CC(CC1CCN(CC3=CC=CC=C3)CC1)C2=O	3143.3	Semi standard non polar	33892256
5-O-Desmethyldonepezil,1TBDMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)CC(CC1CCN(CC3=CC=CC=C3)CC1)C2=O	3366.2	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 - 5-O-Desmethyldonepezil GC-MS (Non-derivatized) - 70eV, Positive	splash10-0076-7962000000-cd9808b75874a019166b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-O-Desmethyldonepezil GC-MS (1 TMS) - 70eV, Positive	splash10-00dl-9425400000-49a8ba9cbb54b0f1ecf6	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-O-Desmethyldonepezil GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-O-Desmethyldonepezil 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-O-Desmethyldonepezil 10V, Positive-QTOF	splash10-014l-3209000000-50a5e17dc83b7a7e3b3c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-O-Desmethyldonepezil 20V, Positive-QTOF	splash10-0006-9422000000-d773292e758d958f40e8	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-O-Desmethyldonepezil 40V, Positive-QTOF	splash10-0006-9000000000-b2ca1c86f200fd45024b	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-O-Desmethyldonepezil 10V, Negative-QTOF	splash10-03di-0019000000-acb0a258339ab79c2c4d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-O-Desmethyldonepezil 20V, Negative-QTOF	splash10-03di-0239000000-74fddf8c4efdfa5d49b6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-O-Desmethyldonepezil 40V, Negative-QTOF	splash10-056r-6792000000-9eb8cbce74a27d2636c0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-O-Desmethyldonepezil 10V, Positive-QTOF	splash10-014i-0009000000-a1d0f5f0342c7143f665	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-O-Desmethyldonepezil 20V, Positive-QTOF	splash10-014i-3109000000-44569b0ed40c21fef6bd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-O-Desmethyldonepezil 40V, Positive-QTOF	splash10-0006-9143000000-d23d5abcad6fd43b06d7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-O-Desmethyldonepezil 10V, Negative-QTOF	splash10-03di-0009000000-ffffb190b205b7f90e41	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-O-Desmethyldonepezil 20V, Negative-QTOF	splash10-03di-1009000000-868002d9b616da08db7f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-O-Desmethyldonepezil 40V, Negative-QTOF	splash10-03di-1149000000-7e629881ae7e0217d450	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry	21059682	details

Abnormal Concentrations

Not Available

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

9678036

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11503234

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

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

References

Davis KL: Alzheimer's disease: seeking new ways to preserve brain function. Interview by Alice V. Luddington. Geriatrics. 1999 Feb;54(2):42-7; quiz 48. [PubMed:10024872 ]
Kryger G, Silman I, Sussman JL: Structure of acetylcholinesterase complexed with E2020 (Aricept): implications for the design of new anti-Alzheimer drugs. Structure. 1999 Mar 15;7(3):297-307. [PubMed:10368299 ]
Shepherd G, Klein-Schwartz W, Edwards R: Donepezil overdose: a tenfold dosing error. Ann Pharmacother. 1999 Jul-Aug;33(7-8):812-5. [PubMed:10466911 ]
Kosasa T, Kuriya Y, Matsui K, Yamanishi Y: Effect of donepezil hydrochloride (E2020) on basal concentration of extracellular acetylcholine in the hippocampus of rats. Eur J Pharmacol. 1999 Sep 10;380(2-3):101-7. [PubMed:10513568 ]
Jann MW: Rivastigmine, a new-generation cholinesterase inhibitor for the treatment of Alzheimer's disease. Pharmacotherapy. 2000 Jan;20(1):1-12. [PubMed:10641971 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Sugimoto H: Donepezil hydrochloride: a treatment drug for Alzheimer's disease. Chem Rec. 2001;1(1):63-73. [PubMed:11893059 ]
Ki YS, Park EY, Lee HW, Oh MS, Cho YW, Kwon YK, Moon JH, Lee KT: Donepezil, a potent acetylcholinesterase inhibitor, induces caspase-dependent apoptosis in human promyelocytic leukemia HL-60 cells. Biol Pharm Bull. 2010;33(6):1054-9. [PubMed:20522977 ]
Repantis D, Laisney O, Heuser I: Acetylcholinesterase inhibitors and memantine for neuroenhancement in healthy individuals: a systematic review. Pharmacol Res. 2010 Jun;61(6):473-81. doi: 10.1016/j.phrs.2010.02.009. Epub 2010 Mar 1. [PubMed:20193764 ]

Enzyme Details

2. 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

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
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 ]

Enzyme Details

3. Cytochrome P450 2C9

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 oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]

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

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
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 ]

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

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 ]
Hayslett RL, Tizabi Y: Effects of donepezil on DOI-induced head twitch response in mice: implications for Tourette syndrome. Pharmacol Biochem Behav. 2003 Dec;76(3-4):409-15. [PubMed:14643839 ]

Showing metabocard for 5-O-Desmethyldonepezil (HMDB0013958)

MOL for HMDB0013958 (5-O-Desmethyldonepezil)

3D MOL for HMDB0013958 (5-O-Desmethyldonepezil)

3D SDF for HMDB0013958 (5-O-Desmethyldonepezil)

3D-SDF for HMDB0013958 (5-O-Desmethyldonepezil)

PDB for HMDB0013958 (5-O-Desmethyldonepezil)

3D PDB for HMDB0013958 (5-O-Desmethyldonepezil)

SMILES for HMDB0013958 (5-O-Desmethyldonepezil)

INCHI for HMDB0013958 (5-O-Desmethyldonepezil)

Structure for HMDB0013958 (5-O-Desmethyldonepezil)

3D Structure for HMDB0013958 (5-O-Desmethyldonepezil)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References