Showing metabocard for Scopolamine (BMDB0003573)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:05:24 UTC
Update Date2020-05-11 20:30:57 UTC
BMDB IDBMDB0003573
Secondary Accession Numbers
  • BMDB03573
Metabolite Identification
Common NameScopolamine
DescriptionScopolamine, also known as hyoscine or transderm-scop, 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. Based on a literature review a significant number of articles have been published on Scopolamine.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(-)-HyoscineChEBI
(-)-ScopolamineChEBI
(1S,3S,5R,6R,7S)-6,7-Epoxytropan-3-yl (2S)-3-hydroxy-2-phenylpropanoateChEBI
6,7-Epoxytropine tropateChEBI
6-beta,7-beta-Epoxy-3-alpha-tropanyl S-(-)-tropateChEBI
alpha-(Hydroxymethyl)benzeneacetic acid 9-methyl-3-oxa-9-azatricyclo(3.3.1.0(2.4))non-7-yl esterChEBI
HyoscineChEBI
Scopine (-)-tropateChEBI
Transderm-scopChEBI
(1S,3S,5R,6R,7S)-6,7-Epoxytropan-3-yl (2S)-3-hydroxy-2-phenylpropanoic acidGenerator
6,7-Epoxytropine tropic acidGenerator
6-b,7-b-Epoxy-3-a-tropanyl S-(-)-tropateGenerator
6-b,7-b-Epoxy-3-a-tropanyl S-(-)-tropic acidGenerator
6-beta,7-beta-Epoxy-3-alpha-tropanyl S-(-)-tropic acidGenerator
6-Β,7-β-epoxy-3-α-tropanyl S-(-)-tropateGenerator
6-Β,7-β-epoxy-3-α-tropanyl S-(-)-tropic acidGenerator
a-(Hydroxymethyl)benzeneacetate 9-methyl-3-oxa-9-azatricyclo(3.3.1.0(2.4))non-7-yl esterGenerator
a-(Hydroxymethyl)benzeneacetic acid 9-methyl-3-oxa-9-azatricyclo(3.3.1.0(2.4))non-7-yl esterGenerator
alpha-(Hydroxymethyl)benzeneacetate 9-methyl-3-oxa-9-azatricyclo(3.3.1.0(2.4))non-7-yl esterGenerator
Α-(hydroxymethyl)benzeneacetate 9-methyl-3-oxa-9-azatricyclo(3.3.1.0(2.4))non-7-yl esterGenerator
Α-(hydroxymethyl)benzeneacetic acid 9-methyl-3-oxa-9-azatricyclo(3.3.1.0(2.4))non-7-yl esterGenerator
Scopine (-)-tropic acidGenerator
(+)-HyoscineHMDB
(+)-ScopolamineHMDB
(-)-Hyoscine hydrobromideHMDB
(-)-Scopolamine bromideHMDB
(-)-Scopolamine hydrobromideHMDB
AtrochinHMDB
AtroquinHMDB
BeldavrinHMDB
BuscopanHMDB
Epoxytropine tropateHMDB
EuscopolHMDB
Hydroscine hydrobromideHMDB
HyosceineHMDB
Hyoscine bromideHMDB
Hyoscine hydrobromideHMDB
Hyoscyine hydrobromideHMDB
HyosolHMDB
HyscoHMDB
Isopto hyoscineHMDB
IsoscopilHMDB
KwellsHMDB
L-Hyoscine hydrobromideHMDB
L-Scopolamine-hydrobromideHMDB
Methscopolamine bromideHMDB
OscineHMDB
PamineHMDB
S-(-)-TropateHMDB
ScopHMDB
ScopaminHMDB
Scopine tropateHMDB
Scopolamine bromideHMDB
Scopolamine hydrobromideHMDB
Scopolaminium bromideHMDB
Scopolammonium bromideHMDB
SEEHMDB
TranaxineHMDB
NorhyoscineHMDB
6beta,7beta-Epoxy-3alpha-tropanyl S-(-)-tropatePhytoBank
6β,7β-Epoxy-3α-tropanyl S-(-)-tropatePhytoBank
9-Methyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-7-ol (-)-tropatePhytoBank
l-ScopolaminePhytoBank
(-)-AtropinePhytoBank
(-)-HyoscyaminePhytoBank
(S)-(-)-HyoscyaminePhytoBank
(S)-AtropinePhytoBank
1alphaH,5alphaH-Tropan-3alpha-yl (-)-tropatePhytoBank
1αH,5αH-Tropan-3α-yl (-)-tropatePhytoBank
CystospazPhytoBank
DaturinePhytoBank
DuboisinePhytoBank
HyoscyaminePhytoBank
L-HyoscyaminPhytoBank
l-HyoscyaminePhytoBank
l-AtropinePhytoBank
l-Tropine tropatePhytoBank
(±)-AtropinePhytoBank
(±)-HyoscyaminePhytoBank
AtropinPhytoBank
AtropinePhytoBank
Atropinum sulfuricumPhytoBank
Atropinum sulphuricumPhytoBank
dl-HyoscyaminePhytoBank
Tropine (±)-tropatePhytoBank
Tropine tropatePhytoBank
dl-Tropyl tropatePhytoBank
Chemical FormulaC17H21NO4
Average Molecular Weight303.3529
Monoisotopic Molecular Weight303.147058165
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 Number51-34-3
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 KeySTECJAGHUSJQJN-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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassBeta hydroxy acids and derivatives
Direct ParentBeta 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 FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.4ALOGPS
logP0.89ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)15.15ChemAxon
pKa (Strongest Basic)6.95ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area62.3 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity79.72 m³·mol⁻¹ChemAxon
Polarizability31.24 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0f7c-7900000000-28f924e821203772c1adView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-4910000000-24c90e50ab88ad57e82cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0006-4900000000-596180a39c76ec0fe1aeView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udi-0009000000-9733effdc3262b114ed6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udi-0809000000-a686e4c768aedb57cf8eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-1901000000-f66f538c7db471e86fd5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-3900000000-5eedeba4bedea55de9adView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udr-7900000000-1309364bbca3810a6afaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-000i-0900000000-1c1d2f52fb7a5d745e1eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-0udi-9700000000-80887cb9e3f0d05c8bf5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-0udi-9800000000-80887cb9e3f0d05c8bf5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-0udi-6900000000-010e6e0ca9f0d9f3618bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-0f79-4900000000-a0695c5add6db92de8b2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-000i-2900000000-887570e409db5eca481cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-0f79-4900000000-5e1feadfe643a530d956View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-000i-2900000000-9556767e32b410cf8d73View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-0udi-0309000000-fda2d2422fa0a3b4172eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0k9i-0903000000-cc938997b1c67e020c14View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-0955000000-64498c50c4e2afb15c32View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1930000000-5d768d7bc9f10614fd97View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0lxt-4900000000-f39cfd7374383b7b1aafView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0549000000-2102ba2525a572e05e74View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uk9-1952000000-23caf7102d633b0031b2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0hr0-4900000000-854ad2f78678cc2d4db3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f6t-0904000000-0366209ad3f767f88736View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f79-1900000000-bd791764fd2502fdc39dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gb9-2910000000-c7c4ffc22c1425ab3dbdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0019000000-cc4ab81a673ee149c93eView in MoNA
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Membrane
Biospecimen Locations
  • Adipose Tissue
  • Brain
  • Epidermis
  • Neuron
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Adipose TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
BrainExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
EpidermisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
NeuronExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0003573
DrugBank IDDB00747
Phenol Explorer Compound IDNot Available
FooDB IDFDB023199
KNApSAcK IDC00002292
Chemspider ID10194106
KEGG Compound IDC01851
BioCyc IDSCOPOLAMINE
BiGG IDNot Available
Wikipedia LinkScopolamine
METLIN ID3433
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID16794
References
Synthesis ReferenceChemnitius, F. Method for the technical preparation of scopolamine. Journal fuer Praktische Chemie (Leipzig) (1928), 120 221-4.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available