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(-)-Scopolamine

PubChem CID: 5184

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Compound Synonyms scopolamine, (-)-Scopolamine, 51-34-3, Atroscine, CHEMBL13030, Scopoderm-TTS, 138-12-5, 475199-31-6, 9-methyl-3-oxa-9-azatricyclo[3.3.1.0~2,4~]non-7-yl tropate, Atroscin, Plexonal, Scopolamine?, 9-methyl-3-oxa-9-azatricyclo[3.3.1.0~2,4~]non-7-yl 3-hydroxy-2-phenylpropanoate, NSC61806, SCHEMBL16227, 6-.beta.,7-.beta.-Epoxy-3-.alpha.-tropanyl S-(-)-tropate, ChEMBL_11434, MLS006012038, 3-Oxa-9-azatricyclo(3.3.1.O(2,4))nonan-7-ol, 9-methyl-, tropate, 9-Methyl-3-oxa-9-azatricyclo[3.3.1.0(2,4)]nonan-7-ol (-)-tropate, Tropic acid, 9-methyl-3-oxa-9-azatricyclo(3.3.1.O(2,4))non-7-yl ester, CHEBI:91541, DTXSID60858963, 1.alpha.H,5.alpha.H-Tropan-3.alpha.-ol, 6.beta.,7.beta.-epoxy-, (-)-tropate (ester), STECJAGHUSJQJN-UHFFFAOYSA-N, AAA13812, Benzeneacetic acid, .alpha.-(hydroxymethyl)-, 9-methyl-3-oxa-9-azatricyclo[3.3.1.0(2,4)]non-7-yl ester, [7(S)-(1.alpha.,2.beta.,4.beta.,5.alpha.,7.beta.)]-, BBL033894, BDBM50015720, STL377948, AKOS001581155, AKOS016038549, NCGC00015932-03, NCGC00162334-01, Benzeneacetic acid, .alpha.-(hydroxymethyl)-, (1.alpha.,2.beta.,4.beta.,5.alpha.,7.beta.)-9-methyl-3-oxa-9-azatricyclo[3.3.1.02,4]non-7-yl ester, (.alpha.S)-, SMR001307730, VS-12336, DB-050193, DB-055774, DB-088470, AB00826823-11, L001096, BRD-A14566392-004-03-5, 81D34684-E0B2-4B3A-A36C-FB916BBC90F7, 9-Methyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-7-yl tropate, (9-methyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-7-yl) 3-hydroxy-2-phenylpropanoate, 9-methyl-3-oxa-9-azatricyclo[3.3.1.0(2),?]nonan-7-yl 3-hydroxy-2-phenylpropanoate, 9-methyl-3-oxa-9-azatricyclo[3.3.1.02,4]non-7-yl 3-hydroxy-2-phenylpropanoate, (hyoscine)3-Hydroxy-2-phenyl-propionic acid 9-methyl-3-oxa-9-aza-tricyclo[3.3.1.0*2,4*]non-7-yl ester, [(1S,2S,4R,5S)-9-Methyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-7-yl] (2S)-3-hydroxy-2-phenylpropanoate, 911467-97-5, Benzotropine3-Hydroxy-2-phenyl-propionic acid 9-methyl-3-oxa-9-aza-tricyclo[3.3.1.0*2,4*]non-7-yl ester
Topological Polar Surface Area 62.3
Hydrogen Bond Donor Count 1.0
Heavy Atom Count 22.0
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. [HMDB]
Isotope Atom Count 0.0
Molecular Complexity 418.0
Database Name cmaup_ingredients;fooddb_chem_all;hmdb_chem_all;npass_chem_all;pubchem
Defined Atom Stereocenter Count 0.0
Uniprot Id P51450, O94782, n.a.
Iupac Name (9-methyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-7-yl) 3-hydroxy-2-phenylpropanoate
Prediction Hob 1.0
Class Benzene and substituted derivatives
Xlogp 0.9
Superclass Benzenoids
Subclass Phenylacetic acid derivatives
Molecular Formula C17H21NO4
Prediction Swissadme 1.0
Inchi Key STECJAGHUSJQJN-UHFFFAOYSA-N
Fcsp3 0.5882352941176471
Logs -2.596
Rotatable Bond Count 5.0
State Solid
Logd 1.168
Synonyms (-)-Hyoscine, (-)-Hyoscine hydrobromide, (-)-Scopolamine, (-)-Scopolamine bromide, (-)-Scopolamine hydrobromide, (+)-Hyoscine, (+)-Scopolamine, (1S,3S,5R,6R,7S)-6,7-Epoxytropan-3-yl (2S)-3-hydroxy-2-phenylpropanoate, (1S,3S,5R,6R,7S)-6,7-Epoxytropan-3-yl (2S)-3-hydroxy-2-phenylpropanoic acid, 6-b,7-b-Epoxy-3-a-tropanyl S-(-)-tropate, 6-b,7-b-Epoxy-3-a-tropanyl S-(-)-tropic acid, 6-beta,7-beta-Epoxy-3-alpha-tropanyl S-(-)-tropate, 6-beta,7-beta-Epoxy-3-alpha-tropanyl S-(-)-tropic acid, 6-β,7-β-epoxy-3-α-tropanyl S-(-)-tropate, 6-β,7-β-epoxy-3-α-tropanyl S-(-)-tropic acid, 6,7-Epoxytropine Tropate, 6,7-Epoxytropine tropic acid, a-(Hydroxymethyl)benzeneacetate 9-methyl-3-oxa-9-azatricyclo(3.3.1.0(2.4))non-7-yl ester, a-(Hydroxymethyl)benzeneacetic acid 9-methyl-3-oxa-9-azatricyclo(3.3.1.0(2.4))non-7-yl ester, alpha-(Hydroxymethyl)benzeneacetate 9-methyl-3-oxa-9-azatricyclo(3.3.1.0(2.4))non-7-yl ester, alpha-(Hydroxymethyl)benzeneacetic acid 9-methyl-3-oxa-9-azatricyclo(3.3.1.0(2.4))non-7-yl ester, Atrochin, Atroquin, Beldavrin, Buscopan, Epoxytropine tropate, Euscopol, Hydroscine hydrobromide, Hyosceine, Hyoscine, Hyoscine bromide, Hyoscine hydrobromide, Hyoscyine hydrobromide, Hyosol, Hysco, Isopto Hyoscine, Isoscopil, Kwells, L-Hyoscine hydrobromide, l-Scopolamine-hydrobromide, Methscopolamine Bromide, Oscine, Pamine, S-(-)-Tropate, Scop, Scopamin, Scopine (-)-tropate, Scopine (-)-tropic acid, Scopine tropate, Scopolamine bromide, Scopolamine hydrobromide, Scopolaminium bromide, Scopolammonium bromide, SEE, Tranaxine, Transderm-scop, α-(hydroxymethyl)benzeneacetate 9-methyl-3-oxa-9-azatricyclo(3.3.1.0(2.4))non-7-yl ester, α-(hydroxymethyl)benzeneacetic acid 9-methyl-3-oxa-9-azatricyclo(3.3.1.0(2.4))non-7-yl ester, Boro scopol, BoroScopol, Scoburen, Winzer brand OF scopolamine borate, Bull brand OF scopolamine hydrobromide, Hamilton brand OF scopolamine hydrobromide, Hope brand OF scopolamine, Hydrobromide, scopolamine, Novartis brand OF scopolamine, Novartis consumer health brand OF scopolamine, Scopolamine cooper, Cooper brand OF scopolamine hydrobromide, Inibisa brand OF scopolamine hydrobromide, Renaudin brand OF scopolamine hydrobromide, Scopoderm TTS, Travacalm ho, Vorigeno, Alcon brand OF scopolamine hydrobromide, Boro-scopol, Isopto hyoscine, Roche brand OF scopolamine hydrobromide, Scopace, Transderm scop, Transderm V, Transderm-V, [(1S,2S,4R,5S)-9-Methyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-7-yl] (2S)-3-hydroxy-2-phenylpropanoic acid
Substituent Name Phenylacetate, Beta-hydroxy acid, N-alkylpyrrolidine, Piperidine, Oxazinane, Morpholine, Hydroxy acid, Pyrrolidine, Tertiary aliphatic amine, Tertiary amine, Carboxylic acid ester, Oxacycle, Azacycle, Organoheterocyclic compound, Monocarboxylic acid or derivatives, Ether, Oxirane, Dialkyl ether, Carboxylic acid derivative, Hydrocarbon derivative, Primary alcohol, Organooxygen compound, Organonitrogen compound, Carbonyl group, Amine, Alcohol, Aromatic heteropolycyclic compound
Compound Name (-)-Scopolamine
Kingdom Organic compounds
Prediction Hob Swissadme 1.0
Exact Mass 303.147
Formal Charge 0.0
Monoisotopic Mass 303.147
Hydrogen Bond Acceptor Count 5.0
Molecular Weight 303.35
Covalent Unit Count 1.0
Total Atom Stereocenter Count 5.0
Total Bond Stereocenter Count 0.0
Molecular Framework Aromatic heteropolycyclic compounds
Esol -2.210037781818181
Inchi 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
Smiles CN1C2CC(CC1C3C2O3)OC(=O)C(CO)C4=CC=CC=C4
Nring 4.0
Defined Bond Stereocenter Count 0.0
Taxonomy Direct Parent Beta hydroxy acids and derivatives

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