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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:45 UTC

HMDB ID

HMDB0014812

Secondary Accession Numbers

HMDB14812

Metabolite Identification

Common Name

Galantamine

Description

Galantamine, also known as reminyl or nivalin, belongs to the class of organic compounds known as galanthamine-type amaryllidaceae alkaloids. These are amaryllidaceae alkaloids with a structure characterized a tetracyclic skeleton with two ortho aromatic protons in ring A. Galantamine is a drug which is used for the treatment of mild to moderate dementia of the alzheimer's type. has also been investigated in patients with mild cognitive impairment who did not meet the diagnostic criteria for alzheimer's disease. Galantamine is a very strong basic compound (based on its pKa). Galantamine is a potentially toxic compound. A benzazepine alkaloid isolated from certain species of daffodils.

Structure

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

HMDB0014812
     RDKit          3D
Galantamine
 42 45  0  0  0  0  0  0  0  0999 V2000
   -3.6295   -3.8079    0.2942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2083   -2.4627    0.1230 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8869   -2.0907    0.2594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -3.0511    0.5724 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3759   -2.6859    0.7085 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7503   -1.3492    0.5318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1845   -0.4136    0.2257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5096   -0.7610    0.0844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2506    0.3769   -0.2276 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3821    1.4392   -0.6155 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9261    2.7141   -0.0605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7382    3.6695    0.1517 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1543    4.9358    0.4746 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0333    3.0563    1.3435 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2743    1.7733    1.2299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0779    1.0479   -0.0138 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0673    1.3066   -1.0136 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8076    0.0245   -1.3045 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7450   -0.3378   -0.2963 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9843   -0.8123   -0.8266 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2359   -1.1874    0.7298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7304   -3.9036    0.2293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0863   -4.5104   -0.3594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3573   -4.0699    1.3546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2725   -4.0932    0.7033 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1353   -3.4019    0.9495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3214    1.5010   -1.7283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6806    3.1854   -0.7249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3512    2.5406    0.9457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1259    3.6029   -0.7626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3823    5.4428   -0.3442 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2007    3.6373    2.2286 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7924    1.2523    2.0656 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7368    2.0965   -0.6799 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5824    1.6289   -1.9541 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3530    0.1669   -2.2620 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0498   -0.7843   -1.5099 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5610    0.0132   -1.3067 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6223   -1.1684    0.0259 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8749   -1.6685   -1.5323 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7238   -2.1709    0.8087 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3516   -0.6815    1.7103 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
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 16 15  1  1
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
  8  3  1  0
 16 10  1  0
 21  6  1  0
 16  7  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
 10 27  1  6
 11 28  1  0
 11 29  1  0
 12 30  1  6
 13 31  1  0
 14 32  1  0
 15 33  1  0
 17 34  1  0
 17 35  1  0
 18 36  1  0
 18 37  1  0
 20 38  1  0
 20 39  1  0
 20 40  1  0
 21 41  1  0
 21 42  1  0
M  END

674
  Mrv0541 02231214552D          

 22 25  0  0  1  0            999 V2000
    4.2096   -1.4415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3588   -1.5573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4433   -1.0636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5414    1.3240    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1288   -0.4833    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8105   -0.0186    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3855   -0.1254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8722   -0.1254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5538   -0.3765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1905   -1.3061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8202   -0.7197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0558    0.6790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2019    0.6790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6155   -1.1993    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7163    1.3240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9338   -1.6640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0365   -0.4902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4101    0.8794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8335    0.3010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8993    2.0674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6501   -0.8367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7612    0.6396    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  1 11  1  0  0  0  0
 14  2  1  1  0  0  0
  3 17  1  0  0  0  0
  3 21  1  0  0  0  0
  4 12  1  0  0  0  0
  4 15  1  0  0  0  0
  4 20  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  6  0  0  0
  5 10  1  0  0  0  0
  6  9  1  0  0  0  0
  6 22  1  1  0  0  0
  7 11  1  0  0  0  0
  7 13  2  0  0  0  0
  8 12  1  0  0  0  0
  9 14  1  0  0  0  0
 10 16  2  0  0  0  0
 11 17  2  0  0  0  0
 13 15  1  0  0  0  0
 13 18  1  0  0  0  0
 14 16  1  0  0  0  0
 17 19  1  0  0  0  0
 18 19  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014812

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@]12C[C@@H](O)C=C[C@]11CCN(C)CC3=C1C(O2)=C(OC)C=C3

> <INCHI_IDENTIFIER>
InChI=1S/C17H21NO3/c1-18-8-7-17-6-5-12(19)9-14(17)21-16-13(20-2)4-3-11(10-18)15(16)17/h3-6,12,14,19H,7-10H2,1-2H3/t12-,14-,17-/m0/s1

> <INCHI_KEY>
ASUTZQLVASHGKV-JDFRZJQESA-N

> <FORMULA>
C17H21NO3

> <MOLECULAR_WEIGHT>
287.3535

> <EXACT_MASS>
287.152143543

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
31.402295977028217

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,12S,14R)-9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.0¹,¹².0⁶,¹⁷]heptadeca-6(17),7,9,15-tetraen-14-ol

> <ALOGPS_LOGP>
1.39

> <JCHEM_LOGP>
1.163042803666667

> <ALOGPS_LOGS>
-2.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.810376678600381

> <JCHEM_PKA_STRONGEST_BASIC>
8.90951741506554

> <JCHEM_POLAR_SURFACE_AREA>
41.93

> <JCHEM_REFRACTIVITY>
82.3049

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.70e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
galantamine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014812
     RDKit          3D
Galantamine
 42 45  0  0  0  0  0  0  0  0999 V2000
   -3.6295   -3.8079    0.2942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2083   -2.4627    0.1230 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8869   -2.0907    0.2594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -3.0511    0.5724 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3759   -2.6859    0.7085 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7503   -1.3492    0.5318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1845   -0.4136    0.2257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5096   -0.7610    0.0844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2506    0.3769   -0.2276 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3821    1.4392   -0.6155 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9261    2.7141   -0.0605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7382    3.6695    0.1517 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1543    4.9358    0.4746 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0333    3.0563    1.3435 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2743    1.7733    1.2299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0779    1.0479   -0.0138 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0673    1.3066   -1.0136 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8076    0.0245   -1.3045 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7450   -0.3378   -0.2963 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9843   -0.8123   -0.8266 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2359   -1.1874    0.7298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7304   -3.9036    0.2293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0863   -4.5104   -0.3594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3573   -4.0699    1.3546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2725   -4.0932    0.7033 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1353   -3.4019    0.9495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3214    1.5010   -1.7283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6806    3.1854   -0.7249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3512    2.5406    0.9457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1259    3.6029   -0.7626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3823    5.4428   -0.3442 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2007    3.6373    2.2286 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7924    1.2523    2.0656 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7368    2.0965   -0.6799 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5824    1.6289   -1.9541 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3530    0.1669   -2.2620 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0498   -0.7843   -1.5099 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5610    0.0132   -1.3067 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6223   -1.1684    0.0259 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8749   -1.6685   -1.5323 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7238   -2.1709    0.8087 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3516   -0.6815    1.7103 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
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 16 15  1  1
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
  8  3  1  0
 16 10  1  0
 21  6  1  0
 16  7  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
 10 27  1  6
 11 28  1  0
 11 29  1  0
 12 30  1  6
 13 31  1  0
 14 32  1  0
 15 33  1  0
 17 34  1  0
 17 35  1  0
 18 36  1  0
 18 37  1  0
 20 38  1  0
 20 39  1  0
 20 40  1  0
 21 41  1  0
 21 42  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 674                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       7.858  -2.691   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      13.736  -2.907   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       4.561  -1.985   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0      10.344   2.471   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       9.574  -0.902   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.846  -0.035   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.186  -0.234   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.961  -0.234   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.234  -0.703   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.689  -2.438   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.131  -1.343   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.304   1.267   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.844   1.267   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.349  -2.239   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.804   2.471   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.076  -3.106   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.668  -0.915   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.366   1.642   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.289   0.562   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.012   3.859   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.080  -1.562   0.000  0.00  0.00           C+0
HETATM   22  H   UNK     0      10.754   1.194   0.000  0.00  0.00           H+0
CONECT    1    6   11                                                       
CONECT    2   14                                                            
CONECT    3   17   21                                                       
CONECT    4   12   15   20                                                  
CONECT    5    6    7    8   10                                             
CONECT    6    1    5    9   22                                             
CONECT    7    5   11   13                                                  
CONECT    8    5   12                                                       
CONECT    9    6   14                                                       
CONECT   10    5   16                                                       
CONECT   11    1    7   17                                                  
CONECT   12    4    8                                                       
CONECT   13    7   15   18                                                  
CONECT   14    2    9   16                                                  
CONECT   15    4   13                                                       
CONECT   16   10   14                                                       
CONECT   17    3   11   19                                                  
CONECT   18   13   19                                                       
CONECT   19   17   18                                                       
CONECT   20    4                                                            
CONECT   21    3                                                            
CONECT   22    6                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

COMPND    HMDB0014812
HETATM    1  C1  UNL     1      -3.629  -3.808   0.294  1.00  0.00           C  
HETATM    2  O1  UNL     1      -3.208  -2.463   0.123  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.887  -2.091   0.259  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.936  -3.051   0.572  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.376  -2.686   0.709  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.750  -1.349   0.532  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.184  -0.414   0.226  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.510  -0.761   0.084  1.00  0.00           C  
HETATM    9  O2  UNL     1      -2.251   0.377  -0.228  1.00  0.00           O  
HETATM   10  C8  UNL     1      -1.382   1.439  -0.616  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.926   2.714  -0.061  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.738   3.669   0.152  1.00  0.00           C  
HETATM   13  O3  UNL     1      -1.154   4.936   0.475  1.00  0.00           O  
HETATM   14  C11 UNL     1      -0.033   3.056   1.343  1.00  0.00           C  
HETATM   15  C12 UNL     1       0.274   1.773   1.230  1.00  0.00           C  
HETATM   16  C13 UNL     1      -0.078   1.048  -0.014  1.00  0.00           C  
HETATM   17  C14 UNL     1       1.067   1.307  -1.014  1.00  0.00           C  
HETATM   18  C15 UNL     1       1.808   0.025  -1.304  1.00  0.00           C  
HETATM   19  N1  UNL     1       2.745  -0.338  -0.296  1.00  0.00           N  
HETATM   20  C16 UNL     1       3.984  -0.812  -0.827  1.00  0.00           C  
HETATM   21  C17 UNL     1       2.236  -1.187   0.730  1.00  0.00           C  
HETATM   22  H1  UNL     1      -4.730  -3.904   0.229  1.00  0.00           H  
HETATM   23  H2  UNL     1      -3.086  -4.510  -0.359  1.00  0.00           H  
HETATM   24  H3  UNL     1      -3.357  -4.070   1.355  1.00  0.00           H  
HETATM   25  H4  UNL     1      -1.272  -4.093   0.703  1.00  0.00           H  
HETATM   26  H5  UNL     1       1.135  -3.402   0.950  1.00  0.00           H  
HETATM   27  H6  UNL     1      -1.321   1.501  -1.728  1.00  0.00           H  
HETATM   28  H7  UNL     1      -2.681   3.185  -0.725  1.00  0.00           H  
HETATM   29  H8  UNL     1      -2.351   2.541   0.946  1.00  0.00           H  
HETATM   30  H9  UNL     1      -0.126   3.603  -0.763  1.00  0.00           H  
HETATM   31  H10 UNL     1      -1.382   5.443  -0.344  1.00  0.00           H  
HETATM   32  H11 UNL     1       0.201   3.637   2.229  1.00  0.00           H  
HETATM   33  H12 UNL     1       0.792   1.252   2.066  1.00  0.00           H  
HETATM   34  H13 UNL     1       1.737   2.096  -0.680  1.00  0.00           H  
HETATM   35  H14 UNL     1       0.582   1.629  -1.954  1.00  0.00           H  
HETATM   36  H15 UNL     1       2.353   0.167  -2.262  1.00  0.00           H  
HETATM   37  H16 UNL     1       1.050  -0.784  -1.510  1.00  0.00           H  
HETATM   38  H17 UNL     1       4.561   0.013  -1.307  1.00  0.00           H  
HETATM   39  H18 UNL     1       4.622  -1.168   0.026  1.00  0.00           H  
HETATM   40  H19 UNL     1       3.875  -1.668  -1.532  1.00  0.00           H  
HETATM   41  H20 UNL     1       2.724  -2.171   0.809  1.00  0.00           H  
HETATM   42  H21 UNL     1       2.352  -0.681   1.710  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   25
CONECT    5    6    6   26
CONECT    6    7   21
CONECT    7    8    8   16
CONECT    8    9
CONECT    9   10
CONECT   10   11   16   27
CONECT   11   12   28   29
CONECT   12   13   14   30
CONECT   13   31
CONECT   14   15   15   32
CONECT   15   16   33
CONECT   16   17
CONECT   17   18   34   35
CONECT   18   19   36   37
CONECT   19   20   21
CONECT   20   38   39   40
CONECT   21   41   42
END

HMDB0014812
     RDKit          3D
Galantamine
 42 45  0  0  0  0  0  0  0  0999 V2000
   -3.6295   -3.8079    0.2942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2083   -2.4627    0.1230 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8869   -2.0907    0.2594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -3.0511    0.5724 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3759   -2.6859    0.7085 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7503   -1.3492    0.5318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1845   -0.4136    0.2257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5096   -0.7610    0.0844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2506    0.3769   -0.2276 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3821    1.4392   -0.6155 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9261    2.7141   -0.0605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7382    3.6695    0.1517 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1543    4.9358    0.4746 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0333    3.0563    1.3435 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2743    1.7733    1.2299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0779    1.0479   -0.0138 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0673    1.3066   -1.0136 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8076    0.0245   -1.3045 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7450   -0.3378   -0.2963 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9843   -0.8123   -0.8266 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2359   -1.1874    0.7298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7304   -3.9036    0.2293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0863   -4.5104   -0.3594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3573   -4.0699    1.3546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2725   -4.0932    0.7033 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1353   -3.4019    0.9495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3214    1.5010   -1.7283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6806    3.1854   -0.7249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3512    2.5406    0.9457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1259    3.6029   -0.7626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3823    5.4428   -0.3442 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2007    3.6373    2.2286 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7924    1.2523    2.0656 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7368    2.0965   -0.6799 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5824    1.6289   -1.9541 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3530    0.1669   -2.2620 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0498   -0.7843   -1.5099 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5610    0.0132   -1.3067 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6223   -1.1684    0.0259 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8749   -1.6685   -1.5323 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7238   -2.1709    0.8087 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3516   -0.6815    1.7103 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
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 16 15  1  1
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
  8  3  1  0
 16 10  1  0
 21  6  1  0
 16  7  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
 10 27  1  6
 11 28  1  0
 11 29  1  0
 12 30  1  6
 13 31  1  0
 14 32  1  0
 15 33  1  0
 17 34  1  0
 17 35  1  0
 18 36  1  0
 18 37  1  0
 20 38  1  0
 20 39  1  0
 20 40  1  0
 21 41  1  0
 21 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-GALANTHAMINE	ChEBI
Reminyl	Kegg
Galanthamine	HMDB
Galanthamine hydrobromide	HMDB
Lycoremine	HMDB
Galantamin	HMDB
Razadyne	HMDB
Nivalin	HMDB
Nivaline	HMDB
Ortho mcneil neurologics brand OF galantamine	HMDB
Ortho-mcneil neurologics brand OF galantamine	HMDB
Galantamine	ChEBI

Chemical Formula

C₁₇H₂₁NO₃

Average Molecular Weight

287.3535

Monoisotopic Molecular Weight

287.152143543

IUPAC Name

(1S,12S,14R)-9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.0¹,¹².0⁶,¹⁷]heptadeca-6(17),7,9,15-tetraen-14-ol

Traditional Name

galantamine

CAS Registry Number

357-70-0

SMILES

[H][C@]12C[C@@H](O)C=C[C@]11CCN(C)CC3=C1C(O2)=C(OC)C=C3

InChI Identifier

InChI=1S/C17H21NO3/c1-18-8-7-17-6-5-12(19)9-14(17)21-16-13(20-2)4-3-11(10-18)15(16)17/h3-6,12,14,19H,7-10H2,1-2H3/t12-,14-,17-/m0/s1

InChI Key

ASUTZQLVASHGKV-JDFRZJQESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as galanthamine-type amaryllidaceae alkaloids. These are amaryllidaceae alkaloids with a structure characterized a tetracyclic skeleton with two ortho aromatic protons in ring A.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Amaryllidaceae alkaloids

Sub Class

Galanthamine-type amaryllidaceae alkaloids

Direct Parent

Galanthamine-type amaryllidaceae alkaloids

Alternative Parents

Substituents

Galanthamine-type amaryllidaceae alkaloid
Benzazepine
Coumaran
Anisole
Alkyl aryl ether
Azepine
Aralkylamine
Benzenoid
Secondary alcohol
Tertiary amine
Tertiary aliphatic amine
Ether
Oxacycle
Organoheterocyclic compound
Azacycle
Amine
Organic nitrogen compound
Alcohol
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tertiary amino compound (CHEBI:42944 )
organic heterotetracyclic compound (CHEBI:42944 )
benzazepine alkaloid (CHEBI:42944 )
benzazepine alkaloid fundamental parent (CHEBI:42944 )
Isoquinoline alkaloids (C08526 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0014812)

Not Available

EC 3.1.1.8 (cholinesterase) inhibitor (HMDB: HMDB0014812)
EC 3.1.1.7 (acetylcholinesterase) inhibitor (HMDB: HMDB0014812)

Plant metabolite (HMDB: HMDB0014812)

Industrial application

Antidote to curare poisoning (HMDB: HMDB0014812)

Pharmaceutical industry

Cholinergic drug (HMDB: HMDB0014812)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	269 - 270 °C (hydrogen bromide salt)	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1.7 g/L	Not Available
LogP	1.8	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	166.9	30932474
[M+H]+	Not Available	166.68	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001355

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.7 g/L	ALOGPS
logP	1.39	ALOGPS
logP	1.16	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	14.81	ChemAxon
pKa (Strongest Basic)	8.91	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	41.93 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	82.3 m³·mol⁻¹	ChemAxon
Polarizability	31.4 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]+	169.327	31661259
DarkChem	[M-H]-	165.7	31661259
DeepCCS	[M-2H]-	202.593	30932474
DeepCCS	[M+Na]+	177.447	30932474
AllCCS	[M+H]+	168.3	32859911
AllCCS	[M+H-H2O]+	164.9	32859911
AllCCS	[M+NH4]+	171.5	32859911
AllCCS	[M+Na]+	172.4	32859911
AllCCS	[M-H]-	174.3	32859911
AllCCS	[M+Na-2H]-	174.0	32859911
AllCCS	[M+HCOO]-	173.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Galantamine	[H][C@]12C[C@@H](O)C=C[C@]11CCN(C)CC3=C1C(O2)=C(OC)C=C3	3416.5	Standard polar	33892256
Galantamine	[H][C@]12C[C@@H](O)C=C[C@]11CCN(C)CC3=C1C(O2)=C(OC)C=C3	2262.5	Standard non polar	33892256
Galantamine	[H][C@]12C[C@@H](O)C=C[C@]11CCN(C)CC3=C1C(O2)=C(OC)C=C3	2405.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Galantamine,1TMS,isomer #1	COC1=CC=C2CN(C)CC[C@@]34C=C[C@H](O[Si](C)(C)C)C[C@@H]3OC1=C24	2367.5	Semi standard non polar	33892256
Galantamine,1TBDMS,isomer #1	COC1=CC=C2CN(C)CC[C@@]34C=C[C@H](O[Si](C)(C)C(C)(C)C)C[C@@H]3OC1=C24	2608.9	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 - Galantamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-010u-2090000000-ce0fee33e6fee456fb64	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Galantamine GC-MS (1 TMS) - 70eV, Positive	splash10-00fu-9137000000-e759a1bc34f489765011	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Galantamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-000l-5980000000-928ad889466b6a2b3827	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Galantamine , positive-QTOF	splash10-000i-0390000000-f4f443a7f842d92dec39	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Galantamine 35V, Positive-QTOF	splash10-03ei-0390000000-5f20c8cd1421554a2365	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Galantamine 10V, Positive-QTOF	splash10-00dr-0090000000-c09fea1137eb040ccff3	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Galantamine 20V, Positive-QTOF	splash10-00dr-1090000000-e8fc73122c750f4a8b29	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Galantamine 40V, Positive-QTOF	splash10-1000-4190000000-4e6f34da3d49bbf029b4	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Galantamine 10V, Negative-QTOF	splash10-000i-0090000000-d57ff615302227895e9b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Galantamine 20V, Negative-QTOF	splash10-000i-0090000000-084d311da94f251627eb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Galantamine 40V, Negative-QTOF	splash10-0w2c-1490000000-3ee999f09979ab3820f1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Galantamine 10V, Positive-QTOF	splash10-000i-0090000000-8e23f9bfe8905382513a	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Galantamine 20V, Positive-QTOF	splash10-0079-0090000000-a9adf4464f8392bb18ad	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Galantamine 40V, Positive-QTOF	splash10-000l-1090000000-cd82eceaf8d38fd37298	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Galantamine 10V, Negative-QTOF	splash10-000i-0090000000-32affc6af32f5da1d257	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Galantamine 20V, Negative-QTOF	splash10-000i-0090000000-6b6acbca4d5713d4973f	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Galantamine 40V, Negative-QTOF	splash10-02u3-0090000000-5c86743e445ac6cabb6a	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

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 DB00674	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00674	21059682	details

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

DB00674

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00001570

Chemspider ID

9272

KEGG Compound ID

C08526

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Galantamine

METLIN ID

Not Available

PubChem Compound

9651

PDB ID

Not Available

ChEBI ID

42944

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

Greenblatt HM, Kryger G, Lewis T, Silman I, Sussman JL: Structure of acetylcholinesterase complexed with (-)-galanthamine at 2.3 A resolution. FEBS Lett. 1999 Dec 17;463(3):321-6. [PubMed:10606746 ]
Olin J, Schneider L: Galantamine for Alzheimer's disease. Cochrane Database Syst Rev. 2002;(3):CD001747. [PubMed:12137632 ]
Scott LJ, Goa KL: Galantamine: a review of its use in Alzheimer's disease. Drugs. 2000 Nov;60(5):1095-122. [PubMed:11129124 ]
Birks J: Cholinesterase inhibitors for Alzheimer's disease. Cochrane Database Syst Rev. 2006 Jan 25;(1):CD005593. [PubMed:16437532 ]
Woodruff-Pak DS, Vogel RW 3rd, Wenk GL: Galantamine: effect on nicotinic receptor binding, acetylcholinesterase inhibition, and learning. Proc Natl Acad Sci U S A. 2001 Feb 13;98(4):2089-94. Epub 2001 Feb 6. [PubMed:11172080 ]

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

Tonkopii VD, Prozorovskii VB, Suslova IM: [Interaction of reversible inhibitors with the catalytic centers and allosteric sites of cholinesterases]. Biull Eksp Biol Med. 1976 Aug;82(8):947-50. [PubMed:1026294 ]
Greenblatt HM, Kryger G, Lewis T, Silman I, Sussman JL: Structure of acetylcholinesterase complexed with (-)-galanthamine at 2.3 A resolution. FEBS Lett. 1999 Dec 17;463(3):321-6. [PubMed:10606746 ]
Guillou C, Mary A, Renko DZ, Gras E, Thal C: Potent acetylcholinesterase inhibitors: design, synthesis and structure-activity relationships of alkylene linked bis-galanthamine and galanthamine-galanthaminium salts. Bioorg Med Chem Lett. 2000 Apr 3;10(7):637-9. [PubMed:10762042 ]
Blesa R: Galantamine: therapeutic effects beyond cognition. Dement Geriatr Cogn Disord. 2000 Sep;11 Suppl 1:28-34. [PubMed:10971049 ]
Stahl SM: The new cholinesterase inhibitors for Alzheimer's disease, Part 1: their similarities are different. J Clin Psychiatry. 2000 Oct;61(10):710-1. [PubMed:11078030 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Lilienfeld S: Galantamine--a novel cholinergic drug with a unique dual mode of action for the treatment of patients with Alzheimer's disease. CNS Drug Rev. 2002 Summer;8(2):159-76. [PubMed:12177686 ]
Olin J, Schneider L: Galantamine for Alzheimer's disease. Cochrane Database Syst Rev. 2002;(3):CD001747. [PubMed:12137632 ]
Scott LJ, Goa KL: Galantamine: a review of its use in Alzheimer's disease. Drugs. 2000 Nov;60(5):1095-122. [PubMed:11129124 ]
Lilienfeld S, Parys W: Galantamine: additional benefits to patients with Alzheimer's disease. Dement Geriatr Cogn Disord. 2000 Sep;11 Suppl 1:19-27. [PubMed:10971048 ]
Woodruff-Pak DS, Lander C, Geerts H: Nicotinic cholinergic modulation: galantamine as a prototype. CNS Drug Rev. 2002 Winter;8(4):405-26. [PubMed:12481195 ]
Hansen RA, Gartlehner G, Kaufer DJ, Lohr KN, Carey T: [PubMed:20480924 ]
Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]

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

References

Svoboda Z, Kvetina J, Kunesova G, Herink J, Bajgar J, Bartosova L, Zivny P, Palicka V: Effect of galantamine on acetylcholinesterase and butyrylcholinesterase activities in the presence of L-carnitine in rat selected brain and peripheral tissues. Neuro Endocrinol Lett. 2006 Dec;27 Suppl 2:183-6. [PubMed:17159811 ]
Giacobini E: Selective inhibitors of butyrylcholinesterase: a valid alternative for therapy of Alzheimer's disease? Drugs Aging. 2001;18(12):891-8. [PubMed:11888344 ]
Wilkinson DG: Galantamine: a new treatment for Alzheimer's disease. Expert Rev Neurother. 2001 Nov;1(2):153-9. doi: 10.1586/14737175.1.2.153. [PubMed:19811027 ]

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

References

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

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

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. Neuronal acetylcholine receptor subunit alpha-10

General function:: Involved in extracellular ligand-gated ion channel activity
Specific function:: Ionotropic receptor with a probable role in the modulation of auditory stimuli. Agonist binding may induce an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane. The channel is permeable to a range of divalent cations including calcium, the influx of which may activate a potassium current which hyperpolarizes the cell membrane. In the ear, this may lead to a reduction in basilar membrane motion, altering the activity of auditory nerve fibers and reducing the range of dynamic hearing. This may protect against acoustic trauma
Gene Name:: CHRNA10
Uniprot ID:: Q9GZZ6
Molecular weight:: 49704.3

References

Scott LJ, Goa KL: Galantamine: a review of its use in Alzheimer's disease. Drugs. 2000 Nov;60(5):1095-122. [PubMed:11129124 ]
Lilienfeld S: Galantamine--a novel cholinergic drug with a unique dual mode of action for the treatment of patients with Alzheimer's disease. CNS Drug Rev. 2002 Summer;8(2):159-76. [PubMed:12177686 ]
Olin J, Schneider L: Galantamine for Alzheimer's disease. Cochrane Database Syst Rev. 2002;(3):CD001747. [PubMed:12137632 ]
Lilienfeld S, Parys W: Galantamine: additional benefits to patients with Alzheimer's disease. Dement Geriatr Cogn Disord. 2000 Sep;11 Suppl 1:19-27. [PubMed:10971048 ]
Woodruff-Pak DS, Lander C, Geerts H: Nicotinic cholinergic modulation: galantamine as a prototype. CNS Drug Rev. 2002 Winter;8(4):405-26. [PubMed:12481195 ]
Hansen RA, Gartlehner G, Kaufer DJ, Lohr KN, Carey T: [PubMed:20480924 ]

Enzyme Details

6. Neuronal acetylcholine receptor subunit alpha-9

General function:: Involved in extracellular ligand-gated ion channel activity
Specific function:: Ionotropic receptor with a probable role in the modulation of auditory stimuli. Agonist binding may induce an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane. The channel is permeable to a range of divalent cations including calcium, the influx of which may activate a potassium current which hyperpolarizes the cell membrane. In the ear, this may lead to a reduction in basilar membrane motion, altering the activity of auditory nerve fibers and reducing the range of dynamic hearing. This may protect against acoustic trauma. May also regulate keratinocyte adhesion
Gene Name:: CHRNA9
Uniprot ID:: Q9UGM1
Molecular weight:: 54806.6

References

Scott LJ, Goa KL: Galantamine: a review of its use in Alzheimer's disease. Drugs. 2000 Nov;60(5):1095-122. [PubMed:11129124 ]
Lilienfeld S: Galantamine--a novel cholinergic drug with a unique dual mode of action for the treatment of patients with Alzheimer's disease. CNS Drug Rev. 2002 Summer;8(2):159-76. [PubMed:12177686 ]
Olin J, Schneider L: Galantamine for Alzheimer's disease. Cochrane Database Syst Rev. 2002;(3):CD001747. [PubMed:12137632 ]
Lilienfeld S, Parys W: Galantamine: additional benefits to patients with Alzheimer's disease. Dement Geriatr Cogn Disord. 2000 Sep;11 Suppl 1:19-27. [PubMed:10971048 ]
Woodruff-Pak DS, Lander C, Geerts H: Nicotinic cholinergic modulation: galantamine as a prototype. CNS Drug Rev. 2002 Winter;8(4):405-26. [PubMed:12481195 ]
Hansen RA, Gartlehner G, Kaufer DJ, Lohr KN, Carey T: [PubMed:20480924 ]

Enzyme Details

7. Neuronal acetylcholine receptor subunit alpha-2

General function:: Involved in extracellular ligand-gated ion channel activity
Specific function:: After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane
Gene Name:: CHRNA2
Uniprot ID:: Q15822
Molecular weight:: 59764.8

References

Scott LJ, Goa KL: Galantamine: a review of its use in Alzheimer's disease. Drugs. 2000 Nov;60(5):1095-122. [PubMed:11129124 ]
Lilienfeld S: Galantamine--a novel cholinergic drug with a unique dual mode of action for the treatment of patients with Alzheimer's disease. CNS Drug Rev. 2002 Summer;8(2):159-76. [PubMed:12177686 ]
Olin J, Schneider L: Galantamine for Alzheimer's disease. Cochrane Database Syst Rev. 2002;(3):CD001747. [PubMed:12137632 ]
Lilienfeld S, Parys W: Galantamine: additional benefits to patients with Alzheimer's disease. Dement Geriatr Cogn Disord. 2000 Sep;11 Suppl 1:19-27. [PubMed:10971048 ]
Woodruff-Pak DS, Lander C, Geerts H: Nicotinic cholinergic modulation: galantamine as a prototype. CNS Drug Rev. 2002 Winter;8(4):405-26. [PubMed:12481195 ]
Hansen RA, Gartlehner G, Kaufer DJ, Lohr KN, Carey T: [PubMed:20480924 ]

Showing metabocard for Galantamine (HMDB0014812)

MOL for HMDB0014812 (Galantamine)

3D MOL for HMDB0014812 (Galantamine)

3D SDF for HMDB0014812 (Galantamine)

3D-SDF for HMDB0014812 (Galantamine)

PDB for HMDB0014812 (Galantamine)

3D PDB for HMDB0014812 (Galantamine)

SMILES for HMDB0014812 (Galantamine)

INCHI for HMDB0014812 (Galantamine)

Structure for HMDB0014812 (Galantamine)

3D Structure for HMDB0014812 (Galantamine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

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