NP-MRD: Showing NP-Card for Galantamine (NP0001554)

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Record Information

Version

1.0

Created at

2020-09-20 17:22:19 UTC

Updated at

2020-11-24 22:24:28 UTC

NP-MRD ID

NP0001554

Secondary Accession Numbers

None

Natural Product 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 primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Galantamine is found in Brunsvigia comptonii, Crinum amabile, Crinum asiaticum, Crinum jagus, Crinum moorei, Cyanella alba, Eucharis amazonica, Galanthus elwesii, Hippeastrum papilio, Hippeastrum puniceum, Hymenocallis littoralis, Hymenocallis rotata, Lycoris aurea, Lycoris incarnata, Lycoris radiata, Lycoris squamigera, Lycoris traubii, Narcissus jonquilla, Narcissus obesus, Narcissus tazetta L. , Narcissus tortifolius, Nerine bowdenii, Pancratium maritimum, Pancratium trianthum and Phaedranassa dubia. It was first documented in 1999 (PMID: 10606746). Based on a literature review a significant number of articles have been published on Galantamine (PMID: 11129124) (PMID: 11172080) (PMID: 12137632) (PMID: 16437532).

Structure

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

NP0001554
     RDKit          3D

 42 45  0  0  0  0  0  0  0  0999 V2000
    1.5323    5.1070   -0.0851 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6878    3.7101   -0.1427 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6083    2.8293   -0.0335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6823    3.2893    0.1387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7460    2.4005    0.2457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4685    1.0510    0.1744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1722    0.5942    0.0018 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8763    1.4690   -0.1040 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0931    0.7913   -0.2737 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7312   -0.5271   -0.7091 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8149   -1.4614   -0.2504 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2303   -2.7752    0.2600 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2825   -3.5817    0.6336 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3748   -2.3819    1.4304 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5027   -1.4235    1.2216 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3813   -0.7779   -0.0984 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4763   -1.6707   -0.9689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7392   -1.0131   -1.4364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7624   -0.9109   -0.4462 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0193   -2.0916    0.2958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7485    0.3037    0.3110 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8313    5.3838   -0.9076 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5400    5.5505   -0.2134 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1357    5.4587    0.8874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8684    4.3536    0.1909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7499    2.7808    0.3802 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6471   -0.5505   -1.8222 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3377   -0.9916    0.6055 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4927   -1.6354   -1.1131 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6616   -3.2837   -0.5286 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3618   -3.6998    1.6210 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5329   -2.9103    2.3600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1360   -1.1013    2.0257 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1274   -1.8948   -1.8828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6518   -2.6516   -0.4867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5001   -0.0079   -1.8069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1371   -1.5875   -2.2980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8219   -1.8759    1.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1692   -2.4933    0.8674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4376   -2.8644   -0.4127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9169    0.1529    1.3999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5802    0.9373   -0.0608 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>
NP0001554

> <DATABASE_NAME>
NP-MRD

> <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

$$$$

NP0001554
     RDKit          3D

 42 45  0  0  0  0  0  0  0  0999 V2000
    1.5323    5.1070   -0.0851 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6878    3.7101   -0.1427 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6083    2.8293   -0.0335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6823    3.2893    0.1387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7460    2.4005    0.2457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4685    1.0510    0.1744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1722    0.5942    0.0018 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8763    1.4690   -0.1040 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0931    0.7913   -0.2737 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7312   -0.5271   -0.7091 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8149   -1.4614   -0.2504 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2303   -2.7752    0.2600 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2825   -3.5817    0.6336 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3748   -2.3819    1.4304 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5027   -1.4235    1.2216 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3813   -0.7779   -0.0984 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4763   -1.6707   -0.9689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7392   -1.0131   -1.4364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7624   -0.9109   -0.4462 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0193   -2.0916    0.2958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7485    0.3037    0.3110 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8313    5.3838   -0.9076 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5400    5.5505   -0.2134 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1357    5.4587    0.8874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8684    4.3536    0.1909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7499    2.7808    0.3802 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6471   -0.5505   -1.8222 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3377   -0.9916    0.6055 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4927   -1.6354   -1.1131 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6616   -3.2837   -0.5286 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3618   -3.6998    1.6210 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5329   -2.9103    2.3600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1360   -1.1013    2.0257 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1274   -1.8948   -1.8828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6518   -2.6516   -0.4867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5001   -0.0079   -1.8069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1371   -1.5875   -2.2980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8219   -1.8759    1.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1692   -2.4933    0.8674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4376   -2.8644   -0.4127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9169    0.1529    1.3999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5802    0.9373   -0.0608 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    NP0001554
HETATM    1  C1  UNL     1       1.532   5.107  -0.085  1.00  0.00           C  
HETATM    2  O1  UNL     1       1.688   3.710  -0.143  1.00  0.00           O  
HETATM    3  C2  UNL     1       0.608   2.829  -0.033  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.682   3.289   0.139  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.746   2.401   0.246  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.468   1.051   0.174  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.172   0.594   0.002  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.876   1.469  -0.104  1.00  0.00           C  
HETATM    9  O2  UNL     1       2.093   0.791  -0.274  1.00  0.00           O  
HETATM   10  C8  UNL     1       1.731  -0.527  -0.709  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.815  -1.461  -0.250  1.00  0.00           C  
HETATM   12  C10 UNL     1       2.230  -2.775   0.260  1.00  0.00           C  
HETATM   13  O3  UNL     1       3.282  -3.582   0.634  1.00  0.00           O  
HETATM   14  C11 UNL     1       1.375  -2.382   1.430  1.00  0.00           C  
HETATM   15  C12 UNL     1       0.503  -1.423   1.222  1.00  0.00           C  
HETATM   16  C13 UNL     1       0.381  -0.778  -0.098  1.00  0.00           C  
HETATM   17  C14 UNL     1      -0.476  -1.671  -0.969  1.00  0.00           C  
HETATM   18  C15 UNL     1      -1.739  -1.013  -1.436  1.00  0.00           C  
HETATM   19  N1  UNL     1      -2.762  -0.911  -0.446  1.00  0.00           N  
HETATM   20  C16 UNL     1      -3.019  -2.092   0.296  1.00  0.00           C  
HETATM   21  C17 UNL     1      -2.748   0.304   0.311  1.00  0.00           C  
HETATM   22  H1  UNL     1       0.831   5.384  -0.908  1.00  0.00           H  
HETATM   23  H2  UNL     1       2.540   5.550  -0.213  1.00  0.00           H  
HETATM   24  H3  UNL     1       1.136   5.459   0.887  1.00  0.00           H  
HETATM   25  H4  UNL     1      -0.868   4.354   0.191  1.00  0.00           H  
HETATM   26  H5  UNL     1      -2.750   2.781   0.380  1.00  0.00           H  
HETATM   27  H6  UNL     1       1.647  -0.551  -1.822  1.00  0.00           H  
HETATM   28  H7  UNL     1       3.338  -0.992   0.606  1.00  0.00           H  
HETATM   29  H8  UNL     1       3.493  -1.635  -1.113  1.00  0.00           H  
HETATM   30  H9  UNL     1       1.662  -3.284  -0.529  1.00  0.00           H  
HETATM   31  H10 UNL     1       3.362  -3.700   1.621  1.00  0.00           H  
HETATM   32  H11 UNL     1       1.533  -2.910   2.360  1.00  0.00           H  
HETATM   33  H12 UNL     1      -0.136  -1.101   2.026  1.00  0.00           H  
HETATM   34  H13 UNL     1       0.127  -1.895  -1.883  1.00  0.00           H  
HETATM   35  H14 UNL     1      -0.652  -2.652  -0.487  1.00  0.00           H  
HETATM   36  H15 UNL     1      -1.500  -0.008  -1.807  1.00  0.00           H  
HETATM   37  H16 UNL     1      -2.137  -1.588  -2.298  1.00  0.00           H  
HETATM   38  H17 UNL     1      -3.822  -1.876   1.030  1.00  0.00           H  
HETATM   39  H18 UNL     1      -2.169  -2.493   0.867  1.00  0.00           H  
HETATM   40  H19 UNL     1      -3.438  -2.864  -0.413  1.00  0.00           H  
HETATM   41  H20 UNL     1      -2.917   0.153   1.400  1.00  0.00           H  
HETATM   42  H21 UNL     1      -3.580   0.937  -0.061  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

NP0001554
     RDKit          3D

42 45  0  0  0  0  0  0  0  0999 V2000
    1.5323    5.1070   -0.0851 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6878    3.7101   -0.1427 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6083    2.8293   -0.0335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6823    3.2893    0.1387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7460    2.4005    0.2457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4685    1.0510    0.1744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1722    0.5942    0.0018 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8763    1.4690   -0.1040 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0931    0.7913   -0.2737 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7312   -0.5271   -0.7091 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8149   -1.4614   -0.2504 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2303   -2.7752    0.2600 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2825   -3.5817    0.6336 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3748   -2.3819    1.4304 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5027   -1.4235    1.2216 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3813   -0.7779   -0.0984 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4763   -1.6707   -0.9689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7392   -1.0131   -1.4364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7624   -0.9109   -0.4462 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0193   -2.0916    0.2958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7485    0.3037    0.3110 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8313    5.3838   -0.9076 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5400    5.5505   -0.2134 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1357    5.4587    0.8874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8684    4.3536    0.1909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7499    2.7808    0.3802 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6471   -0.5505   -1.8222 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3377   -0.9916    0.6055 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4927   -1.6354   -1.1131 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6616   -3.2837   -0.5286 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3618   -3.6998    1.6210 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5329   -2.9103    2.3600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1360   -1.1013    2.0257 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1274   -1.8948   -1.8828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6518   -2.6516   -0.4867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5001   -0.0079   -1.8069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1371   -1.5875   -2.2980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8219   -1.8759    1.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1692   -2.4933    0.8674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4376   -2.8644   -0.4127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9169    0.1529    1.3999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5802    0.9373   -0.0608 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

Synonyms

Value	Source
(-)-Galantamine	ChEBI
(-)-Galanthamine	ChEBI
(4AS,6R,8as)-3-methoxy-11-methyl-5,6,9,10,11,12-hexahydro-4ah-[1]benzofuro[3a,3,2-ef][2]benzazepin-6-ol	ChEBI
Galantamina	ChEBI
Galanthaminum	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 Mass

287.3535 Da

Monoisotopic Mass

287.15214 Da

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

Not Available

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

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
2D NMR	[¹H, ¹³C] NMR Spectrum (2D, 600Mz, CDCL3, simulated)	John.cort			2020-09-20	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Brunsvigia comptonii	LOTUS Database	35616633
Crinum amabile	LOTUS Database	35616633
Crinum asiaticum	LOTUS Database	35616633
Crinum jagus	LOTUS Database	35616633
Crinum moorei	LOTUS Database	35616633
Crinum spp.	KNApSAcK Database	22123792
Cyanella alba	LOTUS Database	35616633
Cyrtanthus elatus	KNApSAcK Database	22123792
Eucharis amazonica	LOTUS Database	35616633
Galanthus caucasicus	KNApSAcK Database	22123792
Galanthus elewesii	KNApSAcK Database	22123792
Galanthus elwesii	LOTUS Database	35616633
Galanthus elwesii Hook.	KNApSAcK Database	22123792
Galanthus nivalis	KNApSAcK Database	22123792
Galanthus spp.	KNApSAcK Database	22123792
Galanthus woronowii Losinsk.	KNApSAcK Database	22123792
Hippeastrum papilio	LOTUS Database	35616633
Hippeastrum puniceum	LOTUS Database	35616633
Hippeastrum spp.	KNApSAcK Database	22123792
Hymenocallis littoralis	LOTUS Database	35616633
Hymenocallis rotata	LOTUS Database	35616633
Hymenocallis spp.	KNApSAcK Database	22123792
Leucojum aestivum	KNApSAcK Database	22123792
Leucojum spp.	KNApSAcK Database	22123792
Leucojum vernum	KNApSAcK Database	22123792
Lycoris aurea	LOTUS Database	35616633
Lycoris incarnata	LOTUS Database	35616633
Lycoris radiata	LOTUS Database	35616633
Lycoris radiata Herb.	KNApSAcK Database	22123792
Lycoris sanguinea	KNApSAcK Database	22123792
Lycoris spp.	KNApSAcK Database	22123792
Lycoris squamigera	LOTUS Database	35616633
Lycoris traubii	LOTUS Database	35616633
Narcissus confusus	KNApSAcK Database	22123792
Narcissus jonquilla	LOTUS Database	35616633
Narcissus obesus	LOTUS Database	35616633
Narcissus pseudonarcissus subsp.pseudonarcissus	KNApSAcK Database	22123792
Narcissus spp.	KNApSAcK Database	22123792
Narcissus tazetta	Plant	KNApSAcK
Narcissus tortifolius	LOTUS Database	35616633
Nerine bowdenii	LOTUS Database	35616633
Pancratium maritimum	LOTUS Database	35616633
Pancratium spp.	KNApSAcK Database	22123792
Pancratium trianthum	LOTUS Database	35616633
Phaedranassa dubia	LOTUS Database	35616633
Ungernia spp.	KNApSAcK Database	22123792

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 )

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
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

External Links

HMDB ID

HMDB0014812

DrugBank ID

DB00674

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Galantamine

METLIN ID

Not Available

PubChem Compound

9651

PDB ID

Not Available

ChEBI ID

42944

Good Scents ID

Not Available

References

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. doi: 10.1016/s0014-5793(99)01637-3. [PubMed:10606746 ]
Scott LJ, Goa KL: Galantamine: a review of its use in Alzheimer's disease. Drugs. 2000 Nov;60(5):1095-122. doi: 10.2165/00003495-200060050-00008. [PubMed:11129124 ]
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. doi: 10.1073/pnas.031584398. Epub 2001 Feb 6. [PubMed:11172080 ]
Olin J, Schneider L: Galantamine for Alzheimer's disease. Cochrane Database Syst Rev. 2002;(3):CD001747. doi: 10.1002/14651858.CD001747. [PubMed:12137632 ]
Birks J: Cholinesterase inhibitors for Alzheimer's disease. Cochrane Database Syst Rev. 2006 Jan 25;(1):CD005593. doi: 10.1002/14651858.CD005593. [PubMed:16437532 ]

Showing NP-Card for Galantamine (NP0001554)

MOL for NP0001554 (Galantamine)

3D MOL for NP0001554 (Galantamine)

3D SDF for NP0001554 (Galantamine)

3D-SDF for NP0001554 (Galantamine)

PDB for NP0001554 (Galantamine)

3D PDB for NP0001554 (Galantamine)

SMILES for NP0001554 (Galantamine)

INCHI for NP0001554 (Galantamine)

Structure for NP0001554 (Galantamine)

3D Structure for NP0001554 (Galantamine)