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Showing NP-Card for Hyoscyamine (NP0001497)

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Record Information
Version1.0
Created at2012-09-06 15:16:49 UTC
Updated at2024-04-19 09:50:40 UTC
NP-MRD IDNP0001497
Secondary Accession NumbersNone
Natural Product Identification
Common NameHyoscyamine
DescriptionHyoscyamine is a chemical compound, a tropane alkaloid it is the levo-isomer to atropine. It is a secondary metabolite of some plants, particularly henbane (Hyoscamus niger.). Hyoscyamine is used to provide symptomatic relief to various gastrointestinal disorders including spasms, peptic ulcers, irritable bowel syndrome, pancreatitis, colic and cystitis. It has also been used to relieve some heart problems, control some of the symptoms of Parkinson's disease, as well as for control of respiratory secretions in end of life care.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0001497 (Hyoscyamine)

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3D MOL for NP0001497 (Hyoscyamine)

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3D SDF for NP0001497 (Hyoscyamine)

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3D-SDF for NP0001497 (Hyoscyamine)

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PDB for NP0001497 (Hyoscyamine)

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3D PDB for NP0001497 (Hyoscyamine)

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SMILES for NP0001497 (Hyoscyamine)

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INCHI for NP0001497 (Hyoscyamine)

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View in JSmol
Synonyms
ValueSource
(-)-AtropineChEBI
(-)-HyoscyamineChEBI
(S)-(-)-HyoscyamineChEBI
[3(S)-endo]-alpha-(Hydroxymethyl)benzeneacetic acid 8-methyl-8-azabicyclo[3.2.1]oct-3-yl esterChEBI
DaturineChEBI
DuboisineChEBI
L-HyoscyamineChEBI
L-Tropine tropateChEBI
Tropine, (-)-tropateChEBI
[3(S)-endo]-a-(Hydroxymethyl)benzeneacetate 8-methyl-8-azabicyclo[3.2.1]oct-3-yl esterGenerator
[3(S)-endo]-a-(Hydroxymethyl)benzeneacetic acid 8-methyl-8-azabicyclo[3.2.1]oct-3-yl esterGenerator
[3(S)-endo]-alpha-(Hydroxymethyl)benzeneacetate 8-methyl-8-azabicyclo[3.2.1]oct-3-yl esterGenerator
[3(S)-endo]-Α-(hydroxymethyl)benzeneacetate 8-methyl-8-azabicyclo[3.2.1]oct-3-yl esterGenerator
[3(S)-endo]-Α-(hydroxymethyl)benzeneacetic acid 8-methyl-8-azabicyclo[3.2.1]oct-3-yl esterGenerator
L-Tropine tropic acidGenerator
Tropine, (-)-tropic acidGenerator
(Leo)-atropineHMDB
(Leo)-hyoscyamineHMDB
(S)-(Leo)-hyoscyamineHMDB
(S)AtropineHMDB
HyocyamineHMDB
L-AtropineHMDB
L-HyopscyamineHMDB
L-HyoscamineHMDB
HyoscyamineChEBI
Chemical FormulaC17H23NO3
Average Mass289.3694 Da
Monoisotopic Mass289.16779 Da
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number101-31-5
SMILESNot Available
InChI Identifier
InChI=1S/C17H23NO3/c1-18-13-7-8-14(18)10-15(9-13)21-17(20)16(11-19)12-5-3-2-4-6-12/h2-6,13-16,19H,7-11H2,1H3/t13-,14+,15+,16-/m1/s1
InChI KeyRKUNBYITZUJHSG-FXUDXRNXSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR[1H, ] NMR Spectrum (2D, 700 MHz, CD3OD, experimental)jaewoo.choi@oregonstate.eduNot AvailableNot Available2023-08-05View Spectrum
Predicted Spectra
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Chemical Shift Submissions
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Species
Species of Origin
Species NameSourceReference
Agrobacterium rhizogenes
Anisodus acutangulusPlant
Anisodus belladonnaPlant
Anisodus luridusPlant
Anisodus luridus Link et Otto.Plant
Anisodus tanguticus
Anthocercis fasciculataPlant
Anthocercis myoporoidesPlant
Anthocercis pannosaPlant
Anthocercis viscosaPlant
Anthocercis walcottiiPlant
Anthotroche myoporoidesPlant
Anthotroche pannosaPlant
Anthotroche walcottiiPlant
Atropa acuminata
Atropa baeticaPlant
Atropa bella-donnaPlant
Atropa belladonaPlant
Atropa belladonnaPlant
Brugmansia arboreaPlant
Corydalis yanhusuoPlant
Cyphanthera anthocercideaPlant
Cyphanthera odgersii
Cyphanthera spinescensPlant
Cyphomandra betaceaePlant
Datura arborea L.Plant
Datura ceratocaulaPlant
Datura inoxiaPlant
Datura metelPlant
Datura meteloides DC.Plant
Datura quercifoliaPlant
Datura stramoniumPlant
Duboisia arenitensisPlant
Duboisia hopwoodii
Duboisia leichhardtiiPlant
Duboisia myoporoidesPlant
Erythroxylon coca-
Hyoscamus albus-
Hyoscamus aurea-
Hyoscamus muticus-
Hyoscamus niger-
Hyoscamus reticulatus-
Hyosciamus niger-
Hyoscyamus albusPlant
Hyoscyamus boveanusPlant
Hyoscyamus desertorumPlant
Hyoscyamus muticusPlant
Hyoscyamus nigerPlant
Hyoscyamus pusillus
Hyoscyamus reticulatusPlant
Latua pubiflora
Lycium barbarumPlant
Lycium chinensePlant
Mandragora autumnalePlant
Mandragora autumnalisPlant
Mandragora autunnalePlant
Mandragora officinarum
Mandragora officinarum L.Plant
Mandragora scopoliaePlant
Mandragora turcomanica
Mandragora turcomanica MizgerPlant
Mandragora vernalisPlant
Physochlaina alaicaPlant
Physochlaina orientalisPlant
Przewalkia tangutica-
Przewalskia tangutica-
Scopolia carniolicaPlant
Scopolia japonicaPlant
Scopolia parviflora
Solandra grandiflora
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tropane alkaloids. These are organic compounds containing the nitrogenous bicyclic alkaloid parent N-Methyl-8-azabicyclo[3.2.1]Octane.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassTropane alkaloids
Sub ClassNot Available
Direct ParentTropane alkaloids
Alternative Parents
Substituents
  • Tropane alkaloid
  • Beta-hydroxy acid
  • Monocyclic benzene moiety
  • Hydroxy acid
  • Piperidine
  • Benzenoid
  • N-alkylpyrrolidine
  • Pyrrolidine
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Tertiary aliphatic amine
  • Tertiary amine
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Organoheterocyclic compound
  • Organonitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Primary alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point141 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.52 g/LNot Available
LogP1.8Not Available
Predicted PropertiesNot Available
HMDB IDHMDB0014568
DrugBank IDDB00424
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00002293
Chemspider ID10246417
KEGG Compound IDC02046
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkHyoscyamine
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID17486
Good Scents IDNot Available
References
General ReferencesNot Available