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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-08-13 00:44:39 UTC

Update Date

2022-03-07 02:49:19 UTC

HMDB ID

HMDB0003573

Secondary Accession Numbers

HMDB0014885
HMDB03573
HMDB14885

Metabolite 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>
HMDB0003573

> <DATABASE_NAME>
hmdb

> <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 View Stereo Labels

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	PhytoBank
6β,7β-Epoxy-3α-tropanyl S-(-)-tropate	PhytoBank
9-Methyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-7-ol (-)-tropate	PhytoBank
l-Scopolamine	PhytoBank
(-)-Atropine	PhytoBank
(-)-Hyoscyamine	PhytoBank
(S)-(-)-Hyoscyamine	PhytoBank
(S)-Atropine	PhytoBank
1alphaH,5alphaH-Tropan-3alpha-yl (-)-tropate	PhytoBank
1αH,5αH-Tropan-3α-yl (-)-tropate	PhytoBank
Cystospaz	PhytoBank
Daturine	PhytoBank
Duboisine	PhytoBank
Hyoscyamine	PhytoBank
L-Hyoscyamin	PhytoBank
l-Hyoscyamine	PhytoBank
l-Atropine	PhytoBank
l-Tropine tropate	PhytoBank
(±)-Atropine	PhytoBank
(±)-Hyoscyamine	PhytoBank
Atropin	PhytoBank
Atropine	PhytoBank
Atropinum sulfuricum	PhytoBank
Atropinum sulphuricum	PhytoBank
dl-Hyoscyamine	PhytoBank
Tropine (±)-tropate	PhytoBank
Tropine tropate	PhytoBank
dl-Tropyl tropate	PhytoBank

Chemical Formula

C₁₇H₂₁NO₄

Average Molecular Weight

303.3529

Monoisotopic Molecular Weight

303.147058165

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

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 )

Ontology

Not Available

Adipose Tissue (HMDB: HMDB0003573)

Epithelium

Epidermis (HMDB: HMDB0003573)

Organ

Brain (HMDB: HMDB0003573)

Cell

Neuron (HMDB: HMDB0003573)
Nerve cell (HMDB: HMDB0003573)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 11204211)

Cellular substructure

Brain (HMDB: HMDB0003573)
Stratum Corneum (HMDB: HMDB0003573)

Process

Not Available

Role

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

antidepressant (HMDB: HMDB0003573)
muscarinic antagonist (HMDB: HMDB0003573)
antiemetic (HMDB: HMDB0003573)
anaesthesia adjuvant (HMDB: HMDB0003573)
adjuvant (HMDB: HMDB0003573)
mydriatic agent (HMDB: HMDB0003573)

Pharmaceutical industry

antispasmodic drug (HMDB: HMDB0003573)

Biological role

muscarinic antagonist (HMDB: HMDB0003573)
metabolite (HMDB: HMDB0003573)

Physical Properties

State

Solid

Experimental Molecular 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 (1994)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	171.1	30932474

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	171.294	31661259
DarkChem	[M-H]-	170.129	31661259
DeepCCS	[M-2H]-	200.253	30932474
DeepCCS	[M+Na]+	175.418	30932474
AllCCS	[M+H]+	174.5	32859911
AllCCS	[M+H-H2O]+	171.4	32859911
AllCCS	[M+NH4]+	177.4	32859911
AllCCS	[M+Na]+	178.3	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
Scopolamine	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	3324.0	Standard polar	33892256
Scopolamine	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	2260.4	Standard non polar	33892256
Scopolamine	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	2279.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Scopolamine,1TMS,isomer #1	CN1[C@H]2C[C@H](OC(=O)[C@H](CO[Si](C)(C)C)C3=CC=CC=C3)C[C@@H]1[C@H]1O[C@@H]21	2371.4	Semi standard non polar	33892256
Scopolamine,1TBDMS,isomer #1	CN1[C@H]2C[C@H](OC(=O)[C@H](CO[Si](C)(C)C(C)(C)C)C3=CC=CC=C3)C[C@@H]1[C@H]1O[C@@H]21	2612.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Scopolamine GC-MS (1 TMS)	splash10-0f7c-7900000000-28f924e821203772c1ad	2018-05-25	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Scopolamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-4910000000-24c90e50ab88ad57e82c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Scopolamine GC-MS (1 TMS) - 70eV, Positive	splash10-0006-4900000000-596180a39c76ec0fe1ae	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Scopolamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Scopolamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Scopolamine LC-ESI-QQ , positive-QTOF	splash10-0udi-0009000000-9733effdc3262b114ed6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Scopolamine LC-ESI-QQ , positive-QTOF	splash10-0udi-0809000000-a686e4c768aedb57cf8e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Scopolamine LC-ESI-QQ , positive-QTOF	splash10-000i-1901000000-f66f538c7db471e86fd5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Scopolamine LC-ESI-QQ , positive-QTOF	splash10-000i-3900000000-5eedeba4bedea55de9ad	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Scopolamine LC-ESI-QQ , positive-QTOF	splash10-0udr-7900000000-1309364bbca3810a6afa	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Scopolamine LC-ESI-IT , positive-QTOF	splash10-000i-0900000000-1c1d2f52fb7a5d745e1e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Scopolamine 90V, Positive-QTOF	splash10-0udi-9700000000-80887cb9e3f0d05c8bf5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Scopolamine 90V, Positive-QTOF	splash10-0udi-9800000000-80887cb9e3f0d05c8bf5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Scopolamine 75V, Positive-QTOF	splash10-0udi-6900000000-010e6e0ca9f0d9f3618b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Scopolamine 60V, Positive-QTOF	splash10-0f79-4900000000-a0695c5add6db92de8b2	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Scopolamine 45V, Positive-QTOF	splash10-000i-2900000000-887570e409db5eca481c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Scopolamine 60V, Positive-QTOF	splash10-0f79-4900000000-5e1feadfe643a530d956	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Scopolamine 45V, Positive-QTOF	splash10-000i-2900000000-9556767e32b410cf8d73	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Scopolamine 15V, Positive-QTOF	splash10-0udi-0309000000-fda2d2422fa0a3b4172e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Scopolamine 30V, Positive-QTOF	splash10-0k9i-0903000000-cc938997b1c67e020c14	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Scopolamine 10V, Negative-QTOF	splash10-0udi-0549000000-2102ba2525a572e05e74	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Scopolamine 20V, Negative-QTOF	splash10-0uk9-1952000000-23caf7102d633b0031b2	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Scopolamine 40V, Negative-QTOF	splash10-0hr0-4900000000-854ad2f78678cc2d4db3	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Scopolamine 10V, Negative-QTOF	splash10-0f6t-0904000000-0366209ad3f767f88736	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Scopolamine 20V, Negative-QTOF	splash10-0f79-1900000000-bd791764fd2502fdc39d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Scopolamine 40V, Negative-QTOF	splash10-0gb9-2910000000-c7c4ffc22c1425ab3dbd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Scopolamine 10V, Positive-QTOF	splash10-0f79-0955000000-64498c50c4e2afb15c32	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Scopolamine 20V, Positive-QTOF	splash10-000i-1930000000-5d768d7bc9f10614fd97	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Scopolamine 40V, Positive-QTOF	splash10-0lxt-4900000000-f39cfd7374383b7b1aaf	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Scopolamine 10V, Positive-QTOF	splash10-0udi-0019000000-cc4ab81a673ee149c93e	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	2018-05-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood

Tissue Locations

Adipose Tissue
Brain
Epidermis
Neuron

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.021 (0.00021-0.043) uM	Adult (>18 years old)	Both	Normal	11204211	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
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

DB00747

Phenol Explorer Compound ID

Not Available

FooDB 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

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1510091

References

Synthesis Reference

Chemnitius, F. Method for the technical preparation of scopolamine. Journal fuer Praktische Chemie (Leipzig) (1928), 120 221-4.

Material Safety Data Sheet (MSDS)

Download (PDF)

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 ]

Enzymes

Enzyme Details

1. Muscarinic acetylcholine receptor M1

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover
Gene Name:: CHRM1
Uniprot ID:: P11229
Molecular weight:: 51420.4

Showing metabocard for Scopolamine (HMDB0003573)

MOL for HMDB0003573 (Scopolamine)

3D MOL for HMDB0003573 (Scopolamine)

3D SDF for HMDB0003573 (Scopolamine)

3D-SDF for HMDB0003573 (Scopolamine)

PDB for HMDB0003573 (Scopolamine)

3D PDB for HMDB0003573 (Scopolamine)

SMILES for HMDB0003573 (Scopolamine)

INCHI for HMDB0003573 (Scopolamine)

Structure for HMDB0003573 (Scopolamine)

3D Structure for HMDB0003573 (Scopolamine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes