NP-MRD: Showing NP-Card for Scopolamine (NP0000601)

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Record Information

Version

1.0

Created at

2006-08-13 00:44:39 UTC

Updated at

2021-10-07 20:42:18 UTC

NP-MRD ID

NP0000601

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Scopolamine

Description

Scopolamine, also known as hyoscine, is a tropane alkaloid drug obtained from plants of the family Solanaceae (nightshades), such as henbane or jimson weed (Datura species). It is part of the secondary metabolites of plants. Scopolamine is used criminally as a date rape drug and as an aid to robbery, the most common act being the clandestine drugging of a victim's drink. It is preferred because it induces retrograde amnesia, or an inability to recall events prior to its administration. Victims of this crime are often admitted to a hospital in police custody, under the assumption that the patient is experiencing a psychotic episode. A telltale sign is a fever accompanied by a lack of sweat. An alkaloid from Solanaceae, especially Datura metel L. And Scopola carniolica. Scopolamine and its quaternary derivatives act as antimuscarinics like atropine, but may have more central nervous system effects. Among the many uses are as an anesthetic premedication, in urinary incontinence, in motion sickness, as an antispasmodic, and as a mydriatic and cycloplegic.

Structure

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

HMDB0003573
     RDKit          3D
Scopolamine
 43 46  0  0  0  0  0  0  0  0999 V2000
   -5.3127   -1.2445    0.1200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8987   -1.0008    0.1066 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4582   -0.2596    1.2759 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9848   -0.3957    1.4100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2329   -0.5640    0.1372 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0999    0.3064    0.1957 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1977   -0.1575    0.1581 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3719   -1.4039    0.0681 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3147    0.8156    0.2243 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1740    1.8663   -0.8746 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1853    1.2966   -2.1361 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6325    0.1496    0.1710 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5165    0.2726    1.2262 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7457   -0.3294    1.2130 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1298   -1.0825    0.1269 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2480   -1.2046   -0.9244 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9969   -0.6001   -0.9268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9815   -0.2356   -1.0997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4589   -0.1486   -0.9637 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8017    1.2742   -0.5320 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9079    1.5013    0.2466 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7779    1.1969    0.9810 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.9050   -0.4997   -0.4456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6271   -1.3181    1.1860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4843   -2.2605   -0.3197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0125   -0.6219    2.1570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6170    0.4747    2.0158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7895   -1.2873    2.0711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8208   -1.5964    0.0620 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2139    1.3668    1.1814 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2647    2.4613   -0.6676 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0330    2.5410   -0.7918 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3921    0.7240   -2.2806 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2062    0.8604    2.0638 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4061   -0.2147    2.0452 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0995   -1.5820    0.0693 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5188   -1.7890   -1.7925 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3604   -0.7381   -1.7812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6335    0.7308   -1.5697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7662   -1.0053   -1.8948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9791   -0.3777   -1.9222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2817    2.0908   -1.0454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1757    1.9881    1.4563 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
  5 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 19  2  1  0
 22 20  1  0
 22  3  1  0
 17 12  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  1
  4 27  1  0
  4 28  1  0
  5 29  1  6
  9 30  1  1
 10 31  1  0
 10 32  1  0
 11 33  1  0
 13 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
 19 41  1  6
 20 42  1  6
 22 43  1  1
M  END


  Mrv1652309272007482D          

 22 25  0  0  1  0            999 V2000
   16.9220  -13.7298    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.9219  -15.5836    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.7261  -15.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7262  -13.9133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2768  -14.2441    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.2768  -15.0691    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.5624  -14.6567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7714  -14.6364    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.4735  -14.6364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0841  -14.6567    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.9092  -14.6567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6237  -15.8941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6237  -15.0691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3381  -13.8317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0526  -13.4191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3381  -14.6567    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   21.0526  -15.0691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7671  -14.6567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0526  -15.8941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7671  -16.3067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4815  -15.8941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4815  -15.0691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  4  1  1  0  0  0  0
  5  6  1  0  0  0  0
  6  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3 10  1  0  0  0  0
 10  4  1  0  0  0  0
  5  7  1  1  0  0  0
  6  7  1  1  0  0  0
  1  8  1  1  0  0  0
  2  8  1  1  0  0  0
  8  9  1  0  0  0  0
 10 11  1  6  0  0  0
 11 13  1  0  0  0  0
 13 12  2  0  0  0  0
 13 16  1  0  0  0  0
 16 14  1  6  0  0  0
 14 15  1  0  0  0  0
 16 17  1  0  0  0  0
 18 17  2  0  0  0  0
 17 19  1  0  0  0  0
 18 22  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0000601

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1[C@H]2C[C@@H](C[C@@H]1[C@H]1O[C@@H]21)OC(=O)[C@H](CO)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H21NO4/c1-18-13-7-11(8-14(18)16-15(13)22-16)21-17(20)12(9-19)10-5-3-2-4-6-10/h2-6,11-16,19H,7-9H2,1H3/t11-,12-,13-,14+,15-,16+/m1/s1

> <INCHI_KEY>
STECJAGHUSJQJN-FWXGHANASA-N

> <FORMULA>
C17H21NO4

> <MOLECULAR_WEIGHT>
303.3529

> <EXACT_MASS>
303.147058165

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
31.24346801979366

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,4S,5S,7S)-9-methyl-3-oxa-9-azatricyclo[3.3.1.0^{2,4}]nonan-7-yl (2S)-3-hydroxy-2-phenylpropanoate

> <ALOGPS_LOGP>
1.40

> <JCHEM_LOGP>
0.8949522950000002

> <ALOGPS_LOGS>
-1.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.145739865848086

> <JCHEM_PKA_STRONGEST_BASIC>
6.953523808607151

> <JCHEM_POLAR_SURFACE_AREA>
62.3

> <JCHEM_REFRACTIVITY>
79.72130000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.61e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,4S,5S,7S)-9-methyl-3-oxa-9-azatricyclo[3.3.1.0^{2,4}]nonan-7-yl (2S)-3-hydroxy-2-phenylpropanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0003573
     RDKit          3D
Scopolamine
 43 46  0  0  0  0  0  0  0  0999 V2000
   -5.3127   -1.2445    0.1200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8987   -1.0008    0.1066 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4582   -0.2596    1.2759 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9848   -0.3957    1.4100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2329   -0.5640    0.1372 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0999    0.3064    0.1957 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1977   -0.1575    0.1581 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3719   -1.4039    0.0681 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3147    0.8156    0.2243 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1740    1.8663   -0.8746 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1853    1.2966   -2.1361 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6325    0.1496    0.1710 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5165    0.2726    1.2262 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7457   -0.3294    1.2130 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1298   -1.0825    0.1269 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2480   -1.2046   -0.9244 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9969   -0.6001   -0.9268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9815   -0.2356   -1.0997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4589   -0.1486   -0.9637 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8017    1.2742   -0.5320 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9079    1.5013    0.2466 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7779    1.1969    0.9810 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.9050   -0.4997   -0.4456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6271   -1.3181    1.1860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4843   -2.2605   -0.3197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0125   -0.6219    2.1570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6170    0.4747    2.0158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7895   -1.2873    2.0711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8208   -1.5964    0.0620 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2139    1.3668    1.1814 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2647    2.4613   -0.6676 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0330    2.5410   -0.7918 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3921    0.7240   -2.2806 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2062    0.8604    2.0638 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4061   -0.2147    2.0452 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0995   -1.5820    0.0693 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5188   -1.7890   -1.7925 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3604   -0.7381   -1.7812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6335    0.7308   -1.5697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7662   -1.0053   -1.8948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9791   -0.3777   -1.9222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2817    2.0908   -1.0454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1757    1.9881    1.4563 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
  5 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 19  2  1  0
 22 20  1  0
 22  3  1  0
 17 12  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  1
  4 27  1  0
  4 28  1  0
  5 29  1  6
  9 30  1  1
 10 31  1  0
 10 32  1  0
 11 33  1  0
 13 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
 19 41  1  6
 20 42  1  6
 22 43  1  1
M  END

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0      31.588 -25.629   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      31.587 -29.089   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      33.089 -28.747   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      33.089 -25.971   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      30.383 -26.589   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      30.383 -28.129   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      29.050 -27.359   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0      31.307 -27.321   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      32.617 -27.321   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      33.757 -27.359   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      35.297 -27.359   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      36.631 -29.669   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      36.631 -28.129   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      37.964 -25.819   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      39.298 -25.049   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      37.964 -27.359   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      39.298 -28.129   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      40.632 -27.359   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      39.298 -29.669   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      40.632 -30.439   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      41.966 -29.669   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      41.966 -28.129   0.000  0.00  0.00           C+0
CONECT    1    5    4    8                                                  
CONECT    2    6    3    8                                                  
CONECT    3    2   10                                                       
CONECT    4    1   10                                                       
CONECT    5    1    6    7                                                  
CONECT    6    5    2    7                                                  
CONECT    7    5    6                                                       
CONECT    8    1    2    9                                                  
CONECT    9    8                                                            
CONECT   10    3    4   11                                                  
CONECT   11   10   13                                                       
CONECT   12   13                                                            
CONECT   13   11   12   16                                                  
CONECT   14   16   15                                                       
CONECT   15   14                                                            
CONECT   16   13   14   17                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17   22                                                       
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   18   21                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

COMPND    HMDB0003573
HETATM    1  C1  UNL     1      -5.313  -1.244   0.120  1.00  0.00           C  
HETATM    2  N1  UNL     1      -3.899  -1.001   0.107  1.00  0.00           N  
HETATM    3  C2  UNL     1      -3.458  -0.260   1.276  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.985  -0.396   1.410  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.233  -0.564   0.137  1.00  0.00           C  
HETATM    6  O1  UNL     1      -0.100   0.306   0.196  1.00  0.00           O  
HETATM    7  C5  UNL     1       1.198  -0.158   0.158  1.00  0.00           C  
HETATM    8  O2  UNL     1       1.372  -1.404   0.068  1.00  0.00           O  
HETATM    9  C6  UNL     1       2.315   0.816   0.224  1.00  0.00           C  
HETATM   10  C7  UNL     1       2.174   1.866  -0.875  1.00  0.00           C  
HETATM   11  O3  UNL     1       2.185   1.297  -2.136  1.00  0.00           O  
HETATM   12  C8  UNL     1       3.633   0.150   0.171  1.00  0.00           C  
HETATM   13  C9  UNL     1       4.517   0.273   1.226  1.00  0.00           C  
HETATM   14  C10 UNL     1       5.746  -0.329   1.213  1.00  0.00           C  
HETATM   15  C11 UNL     1       6.130  -1.083   0.127  1.00  0.00           C  
HETATM   16  C12 UNL     1       5.248  -1.205  -0.924  1.00  0.00           C  
HETATM   17  C13 UNL     1       3.997  -0.600  -0.927  1.00  0.00           C  
HETATM   18  C14 UNL     1      -1.981  -0.236  -1.100  1.00  0.00           C  
HETATM   19  C15 UNL     1      -3.459  -0.149  -0.964  1.00  0.00           C  
HETATM   20  C16 UNL     1      -3.802   1.274  -0.532  1.00  0.00           C  
HETATM   21  O4  UNL     1      -4.908   1.501   0.247  1.00  0.00           O  
HETATM   22  C17 UNL     1      -3.778   1.197   0.981  1.00  0.00           C  
HETATM   23  H1  UNL     1      -5.905  -0.500  -0.446  1.00  0.00           H  
HETATM   24  H2  UNL     1      -5.627  -1.318   1.186  1.00  0.00           H  
HETATM   25  H3  UNL     1      -5.484  -2.261  -0.320  1.00  0.00           H  
HETATM   26  H4  UNL     1      -4.013  -0.622   2.157  1.00  0.00           H  
HETATM   27  H5  UNL     1      -1.617   0.475   2.016  1.00  0.00           H  
HETATM   28  H6  UNL     1      -1.790  -1.287   2.071  1.00  0.00           H  
HETATM   29  H7  UNL     1      -0.821  -1.596   0.062  1.00  0.00           H  
HETATM   30  H8  UNL     1       2.214   1.367   1.181  1.00  0.00           H  
HETATM   31  H9  UNL     1       1.265   2.461  -0.668  1.00  0.00           H  
HETATM   32  H10 UNL     1       3.033   2.541  -0.792  1.00  0.00           H  
HETATM   33  H11 UNL     1       1.392   0.724  -2.281  1.00  0.00           H  
HETATM   34  H12 UNL     1       4.206   0.860   2.064  1.00  0.00           H  
HETATM   35  H13 UNL     1       6.406  -0.215   2.045  1.00  0.00           H  
HETATM   36  H14 UNL     1       7.099  -1.582   0.069  1.00  0.00           H  
HETATM   37  H15 UNL     1       5.519  -1.789  -1.792  1.00  0.00           H  
HETATM   38  H16 UNL     1       3.360  -0.738  -1.781  1.00  0.00           H  
HETATM   39  H17 UNL     1      -1.634   0.731  -1.570  1.00  0.00           H  
HETATM   40  H18 UNL     1      -1.766  -1.005  -1.895  1.00  0.00           H  
HETATM   41  H19 UNL     1      -3.979  -0.378  -1.922  1.00  0.00           H  
HETATM   42  H20 UNL     1      -3.282   2.091  -1.045  1.00  0.00           H  
HETATM   43  H21 UNL     1      -3.176   1.988   1.456  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   19
CONECT    3    4   22   26
CONECT    4    5   27   28
CONECT    5    6   18   29
CONECT    6    7
CONECT    7    8    8    9
CONECT    9   10   12   30
CONECT   10   11   31   32
CONECT   11   33
CONECT   12   13   13   17
CONECT   13   14   34
CONECT   14   15   15   35
CONECT   15   16   36
CONECT   16   17   17   37
CONECT   17   38
CONECT   18   19   39   40
CONECT   19   20   41
CONECT   20   21   22   42
CONECT   21   22
CONECT   22   43
END

HMDB0003573
     RDKit          3D
Scopolamine
 43 46  0  0  0  0  0  0  0  0999 V2000
   -5.3127   -1.2445    0.1200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8987   -1.0008    0.1066 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4582   -0.2596    1.2759 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9848   -0.3957    1.4100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2329   -0.5640    0.1372 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0999    0.3064    0.1957 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1977   -0.1575    0.1581 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3719   -1.4039    0.0681 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3147    0.8156    0.2243 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1740    1.8663   -0.8746 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1853    1.2966   -2.1361 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6325    0.1496    0.1710 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5165    0.2726    1.2262 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7457   -0.3294    1.2130 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1298   -1.0825    0.1269 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2480   -1.2046   -0.9244 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9969   -0.6001   -0.9268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9815   -0.2356   -1.0997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4589   -0.1486   -0.9637 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8017    1.2742   -0.5320 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9079    1.5013    0.2466 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7779    1.1969    0.9810 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.9050   -0.4997   -0.4456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6271   -1.3181    1.1860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4843   -2.2605   -0.3197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0125   -0.6219    2.1570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6170    0.4747    2.0158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7895   -1.2873    2.0711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8208   -1.5964    0.0620 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2139    1.3668    1.1814 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2647    2.4613   -0.6676 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0330    2.5410   -0.7918 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3921    0.7240   -2.2806 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2062    0.8604    2.0638 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4061   -0.2147    2.0452 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0995   -1.5820    0.0693 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5188   -1.7890   -1.7925 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3604   -0.7381   -1.7812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6335    0.7308   -1.5697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7662   -1.0053   -1.8948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9791   -0.3777   -1.9222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2817    2.0908   -1.0454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1757    1.9881    1.4563 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
  5 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 19  2  1  0
 22 20  1  0
 22  3  1  0
 17 12  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  1
  4 27  1  0
  4 28  1  0
  5 29  1  6
  9 30  1  1
 10 31  1  0
 10 32  1  0
 11 33  1  0
 13 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
 19 41  1  6
 20 42  1  6
 22 43  1  1
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(-)-Hyoscine	ChEBI
(-)-Scopolamine	ChEBI
(1S,3S,5R,6R,7S)-6,7-Epoxytropan-3-yl (2S)-3-hydroxy-2-phenylpropanoate	ChEBI
6,7-Epoxytropine tropate	ChEBI
6-beta,7-beta-Epoxy-3-alpha-tropanyl S-(-)-tropate	ChEBI
alpha-(Hydroxymethyl)benzeneacetic acid 9-methyl-3-oxa-9-azatricyclo(3.3.1.0(2.4))non-7-yl ester	ChEBI
Hyoscine	ChEBI
Scopine (-)-tropate	ChEBI
Transderm-scop	ChEBI
(1S,3S,5R,6R,7S)-6,7-Epoxytropan-3-yl (2S)-3-hydroxy-2-phenylpropanoic acid	Generator
6,7-Epoxytropine tropic acid	Generator
6-b,7-b-Epoxy-3-a-tropanyl S-(-)-tropate	Generator
6-b,7-b-Epoxy-3-a-tropanyl S-(-)-tropic acid	Generator
6-beta,7-beta-Epoxy-3-alpha-tropanyl S-(-)-tropic acid	Generator
6-Β,7-β-epoxy-3-α-tropanyl S-(-)-tropate	Generator
6-Β,7-β-epoxy-3-α-tropanyl S-(-)-tropic acid	Generator
a-(Hydroxymethyl)benzeneacetate 9-methyl-3-oxa-9-azatricyclo(3.3.1.0(2.4))non-7-yl ester	Generator
a-(Hydroxymethyl)benzeneacetic acid 9-methyl-3-oxa-9-azatricyclo(3.3.1.0(2.4))non-7-yl ester	Generator
alpha-(Hydroxymethyl)benzeneacetate 9-methyl-3-oxa-9-azatricyclo(3.3.1.0(2.4))non-7-yl ester	Generator
Α-(hydroxymethyl)benzeneacetate 9-methyl-3-oxa-9-azatricyclo(3.3.1.0(2.4))non-7-yl ester	Generator
Α-(hydroxymethyl)benzeneacetic acid 9-methyl-3-oxa-9-azatricyclo(3.3.1.0(2.4))non-7-yl ester	Generator
Scopine (-)-tropic acid	Generator
(+)-Hyoscine	HMDB
(+)-Scopolamine	HMDB
(-)-Hyoscine hydrobromide	HMDB
(-)-Scopolamine bromide	HMDB
(-)-Scopolamine hydrobromide	HMDB
Atrochin	HMDB
Atroquin	HMDB
Beldavrin	HMDB
Buscopan	HMDB
Epoxytropine tropate	HMDB
Euscopol	HMDB
Hydroscine hydrobromide	HMDB
Hyosceine	HMDB
Hyoscine bromide	HMDB
Hyoscine hydrobromide	HMDB
Hyoscyine hydrobromide	HMDB
Hyosol	HMDB
Hysco	HMDB
Isopto hyoscine	HMDB
Isoscopil	HMDB
Kwells	HMDB
L-Hyoscine hydrobromide	HMDB
L-Scopolamine-hydrobromide	HMDB
Methscopolamine bromide	HMDB
Oscine	HMDB
Pamine	HMDB
S-(-)-Tropate	HMDB
Scop	HMDB
Scopamin	HMDB
Scopine tropate	HMDB
Scopolamine bromide	HMDB
Scopolamine hydrobromide	HMDB
Scopolaminium bromide	HMDB
Scopolammonium bromide	HMDB
SEE	HMDB
Tranaxine	HMDB
Norhyoscine	HMDB
6beta,7beta-Epoxy-3alpha-tropanyl S-(-)-tropate	HMDB
6Β,7β-epoxy-3α-tropanyl S-(-)-tropate	HMDB
9-Methyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-7-ol (-)-tropate	HMDB
L-Scopolamine	HMDB
(-)-Atropine	HMDB
(-)-Hyoscyamine	HMDB
(S)-(-)-Hyoscyamine	HMDB
(S)-Atropine	HMDB
1AlphaH,5alphah-tropan-3alpha-yl (-)-tropate	HMDB
1ΑH,5αh-tropan-3α-yl (-)-tropate	HMDB
Cystospaz	HMDB
Daturine	HMDB
Duboisine	HMDB
Hyoscyamine	HMDB
L-Hyoscyamin	HMDB
L-Hyoscyamine	HMDB
L-Atropine	HMDB
L-Tropine tropate	HMDB
(±)-atropine	HMDB
(±)-hyoscyamine	HMDB
Atropin	HMDB
Atropine	HMDB
Atropinum sulfuricum	HMDB
Atropinum sulphuricum	HMDB
DL-Hyoscyamine	HMDB
Tropine (±)-tropate	HMDB
Tropine tropate	HMDB
DL-Tropyl tropate	HMDB

Chemical Formula

C₁₇H₂₁NO₄

Average Mass

303.3529 Da

Monoisotopic Mass

303.14706 Da

IUPAC Name

(1R,2R,4S,5S,7S)-9-methyl-3-oxa-9-azatricyclo[3.3.1.0^{2,4}]nonan-7-yl (2S)-3-hydroxy-2-phenylpropanoate

Traditional Name

(1R,2R,4S,5S,7S)-9-methyl-3-oxa-9-azatricyclo[3.3.1.0^{2,4}]nonan-7-yl (2S)-3-hydroxy-2-phenylpropanoate

CAS Registry Number

51-34-3

SMILES

CN1[C@H]2C[C@@H](C[C@@H]1[C@H]1O[C@@H]21)OC(=O)[C@H](CO)C1=CC=CC=C1

InChI Identifier

InChI=1S/C17H21NO4/c1-18-13-7-11(8-14(18)16-15(13)22-16)21-17(20)12(9-19)10-5-3-2-4-6-10/h2-6,11-16,19H,7-9H2,1H3/t11-,12-,13-,14+,15-,16+/m1/s1

InChI Key

STECJAGHUSJQJN-FWXGHANASA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anisodus acutangulus	KNApSAcK Database	22123792
Anisodus belladonna	KNApSAcK Database	22123792
Anisodus tanguticus	KNApSAcK Database	22123792
Anthocercis fasciculata	KNApSAcK Database	22123792
Anthocercis myoporoides	KNApSAcK Database	22123792
Anthocercis pannosa	KNApSAcK Database	22123792
Anthocercis viscosa	KNApSAcK Database	22123792
Anthocercis walcottii	KNApSAcK Database	22123792
Anthotroche myoporoides	KNApSAcK Database	22123792
Anthotroche pannosa	KNApSAcK Database	22123792
Anthotroche walcottii	KNApSAcK Database	22123792
Atropa baetica	Plant	KNApSAcK
Atropa bella-donna	KNApSAcK Database	22123792
Atropa belladona	KNApSAcK Database	22123792
Atropa belladonna	KNApSAcK Database	22123792
Atropanthe sinensis	LOTUS Database	35616633
Brugmansia arborea	KNApSAcK Database	22123792
Brugmansia x candida	LOTUS Database	35616633
Corydalis yanhusuo	KNApSAcK Database	22123792
Crenidium spinescens	-	KNApSAcK
Cyphanthera anthocercidea	KNApSAcK Database	22123792
Datura arborea L.	KNApSAcK Database	22123792
Datura candida	KNApSAcK Database	22123792
Datura ceratocaula	Plant	KNApSAcK
Datura clorantha	KNApSAcK Database	22123792
Datura ferox	KNApSAcK Database	22123792
Datura fustuosa	KNApSAcK Database	22123792
Datura innoxia	KNApSAcK Database	22123792
Datura inoxia	Plant	KNApSAcK
Datura kymatocarpa	KNApSAcK Database	22123792
Datura lanosa	KNApSAcK Database	22123792
Datura leichardtii	KNApSAcK Database	22123792
Datura leichhardtii	LOTUS Database	35616633
Datura metel	KNApSAcK Database	22123792
Datura meteloides	KNApSAcK Database	22123792
Datura myoporoides	KNApSAcK Database	22123792
Datura pruinosa	KNApSAcK Database	22123792
Datura quercifolia	KNApSAcK Database	22123792
Datura rosei	KNApSAcK Database	22123792
Datura sanguinea	KNApSAcK Database	22123792
Datura stramonium	KNApSAcK Database	22123792
Datura tatula	KNApSAcK Database	22123792
Duboisia arenitensis	KNApSAcK Database	22123792
Duboisia hopwoodii	KNApSAcK Database	22123792
Duboisia leichhardtii	KNApSAcK Database	22123792
Duboisia myoporoides	KNApSAcK Database	22123792
Hyoscamus albus	-	KNApSAcK
Hyoscamus aurea	-	KNApSAcK
Hyoscamus muticus	-	KNApSAcK
Hyoscamus niger	-	KNApSAcK
Hyoscamus reticulatus	-	KNApSAcK
Hyosciamus niger	-	KNApSAcK
Hyoscyamus albus	KNApSAcK Database	22123792
Hyoscyamus aureus	KNApSAcK Database	22123792
Hyoscyamus bohemicus	KNApSAcK Database	22123792
Hyoscyamus boveanus	Plant	KNApSAcK
Hyoscyamus canariensis	KNApSAcK Database	22123792
Hyoscyamus desertorum	Plant	KNApSAcK
Hyoscyamus gyorffi	KNApSAcK Database	22123792
Hyoscyamus muticus	KNApSAcK Database	22123792
Hyoscyamus niger	KNApSAcK Database	22123792
Hyoscyamus pusillus	KNApSAcK Database	22123792
Hyoscyamus reticulatus	LOTUS Database	35616633
Latua pubiflora	LOTUS Database	35616633
Mandragora autumnalis	KNApSAcK Database	22123792
Mandragora autunnale	KNApSAcK Database	22123792
Mandragora officinarum	LOTUS Database	35616633
Mandragora officinarum L.	KNApSAcK Database	22123792
Mandragora turcomanica	LOTUS Database	35616633
Mandragora turcomanica Mizger	KNApSAcK Database	22123792
Mandragora vernalis	KNApSAcK Database	22123792
Physochlaina alaica	KNApSAcK Database	22123792
Physochlaina orientalis	KNApSAcK Database	22123792
Scopolia carniolica	KNApSAcK Database	22123792
Scopolia japonica	KNApSAcK Database	22123792
Scopolia parviflora	KNApSAcK Database	22123792
Solandra grandiflora	LOTUS Database	35616633
Symonanthus aromaticus	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Hydroxy acids and derivatives

Sub Class

Beta hydroxy acids and derivatives

Direct Parent

Beta hydroxy acids and derivatives

Alternative Parents

Substituents

Beta-hydroxy acid
Monocyclic benzene moiety
Morpholine
Oxazinane
Piperidine
N-alkylpyrrolidine
Benzenoid
Pyrrolidine
Amino acid or derivatives
Carboxylic acid ester
Tertiary amine
Tertiary aliphatic amine
Oxacycle
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Monocarboxylic acid or derivatives
Primary alcohol
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Amine
Organic oxide
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Alcohol
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tertiary amino compound (CHEBI:16794 )
epoxide (CHEBI:16794 )
propanoate ester (CHEBI:16794 )
tropane alkaloid (CHEBI:16794 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	59 °C	Not Available
Boiling Point	188.10 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	100 mg/mL	Not Available
LogP	0.98	Sangster, J. (1993). LOGKOW- a Databank of Evaluated Octanol-Water Partition Coefficients. Sangster Research Laboratories, Montreal.

Predicted Properties

Property	Value	Source
Water Solubility	6.61 g/L	ALOGPS
logP	1.4	ALOGPS
logP	0.89	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	15.15	ChemAxon
pKa (Strongest Basic)	6.95	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	62.3 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	79.72 m³·mol⁻¹	ChemAxon
Polarizability	31.24 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

HMDB0003573

DrugBank ID

DB00747

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Scopolamine

METLIN ID

3433

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

16794

Good Scents ID

rw1510091

References

General References

Lee HW, Park WS, Kim YW, Cho SH, Kim SS, Seo JH, Lee KT: A rapid and sensitive liquid chromatography/positive ion tandem mass spectrometry method for the determination of cimetropium in human plasma by liquid-liquid extraction. J Mass Spectrom. 2006 Jul;41(7):855-60. [PubMed:16810649 ]
Blin J, Piercey MF, Giuffra ME, Mouradian MM, Chase TN: Metabolic effects of scopolamine and physostigmine in human brain measured by positron emission tomography. J Neurol Sci. 1994 May;123(1-2):44-51. [PubMed:8064320 ]
Frey KA, Koeppe RA, Mulholland GK, Jewett D, Hichwa R, Ehrenkaufer RL, Carey JE, Wieland DM, Kuhl DE, Agranoff BW: In vivo muscarinic cholinergic receptor imaging in human brain with [11C]scopolamine and positron emission tomography. J Cereb Blood Flow Metab. 1992 Jan;12(1):147-54. [PubMed:1727135 ]
Kranke P, Morin AM, Roewer N, Wulf H, Eberhart LH: The efficacy and safety of transdermal scopolamine for the prevention of postoperative nausea and vomiting: a quantitative systematic review. Anesth Analg. 2002 Jul;95(1):133-43, table of contents. [PubMed:12088957 ]
Hagemann K, Piek K, Stockigt J, Weiler EW: Monoclonal antibody-based enzyme immunoassay for the quantitative determination of the tropane alkaloid, scopolamine. Planta Med. 1992 Feb;58(1):68-72. [PubMed:1620747 ]
Boumba VA, Mitselou A, Vougiouklakis T: Fatal poisoning from ingestion of Datura stramonium seeds. Vet Hum Toxicol. 2004 Apr;46(2):81-2. [PubMed:15080209 ]
Rosier A, Cornette L, Orban GA: Scopolamine-induced impairment of delayed recognition of abstract visual shapes. Neuropsychobiology. 1998;37(2):98-103. [PubMed:9566275 ]
Smith AM, Cadoret G, St-Amour D: Scopolamine increases prehensile force during object manipulation by reducing palmar sweating and decreasing skin friction. Exp Brain Res. 1997 May;114(3):578-83. [PubMed:9187293 ]
Ebert U, Grossmann M, Oertel R, Gramatte T, Kirch W: Pharmacokinetic-pharmacodynamic modeling of the electroencephalogram effects of scopolamine in healthy volunteers. J Clin Pharmacol. 2001 Jan;41(1):51-60. [PubMed:11144994 ]
Renner UD, Oertel R, Kirch W: Pharmacokinetics and pharmacodynamics in clinical use of scopolamine. Ther Drug Monit. 2005 Oct;27(5):655-65. [PubMed:16175141 ]
Gordon C, Ben-Aryeh H, Attias J, Szargel R, Gutman D: Effect of transdermal scopolamine on salivation. J Clin Pharmacol. 1985 Sep;25(6):407-12. [PubMed:4056076 ]
Fan Y, Hu J, Li J, Yang Z, Xin X, Wang J, Ding J, Geng M: Effect of acidic oligosaccharide sugar chain on scopolamine-induced memory impairment in rats and its related mechanisms. Neurosci Lett. 2005 Feb 21;374(3):222-6. Epub 2004 Dec 10. [PubMed:15663967 ]
Stetina PM, Madai B, Kulemann V, Kirch W, Joukhadar C: Pharmacokinetics of scopolamine in serum and subcutaneous adipose tissue in healthy volunteers. Int J Clin Pharmacol Ther. 2005 Mar;43(3):134-9. [PubMed:15792397 ]
Schwarz RD, Callahan MJ, Coughenour LL, Dickerson MR, Kinsora JJ, Lipinski WJ, Raby CA, Spencer CJ, Tecle H: Milameline (CI-979/RU35926): a muscarinic receptor agonist with cognition-activating properties: biochemical and in vivo characterization. J Pharmacol Exp Ther. 1999 Nov;291(2):812-22. [PubMed:10525104 ]
Suojaranta-Ylinen R, Hendolin H, Tuomisto L: The effects of morphine, morphine plus scopolamine, midazolam and promethazine on cerebrospinal fluid histamine concentration and postoperative analgesic consumption. Agents Actions. 1991 May;33(1-2):212-4. [PubMed:1897441 ]
Dreyfuss P, Vogel D, Walsh N: The use of transdermal scopolamine to control drooling. A case report. Am J Phys Med Rehabil. 1991 Aug;70(4):220-2. [PubMed:1878183 ]
Putcha L, Cintron NM, Tsui J, Vanderploeg JM, Kramer WG: Pharmacokinetics and oral bioavailability of scopolamine in normal subjects. Pharm Res. 1989 Jun;6(6):481-5. [PubMed:2762223 ]

Showing NP-Card for Scopolamine (NP0000601)

MOL for NP0000601 (Scopolamine)

3D MOL for NP0000601 (Scopolamine)

3D SDF for NP0000601 (Scopolamine)

3D-SDF for NP0000601 (Scopolamine)

PDB for NP0000601 (Scopolamine)

3D PDB for NP0000601 (Scopolamine)

SMILES for NP0000601 (Scopolamine)

INCHI for NP0000601 (Scopolamine)

Structure for NP0000601 (Scopolamine)

3D Structure for NP0000601 (Scopolamine)