Showing metabocard for Atropine (BMDB0109651)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2020-05-05 15:49:10 UTC
Update Date2020-05-05 18:40:46 UTC
BMDB IDBMDB0109651
Secondary Accession NumbersNone
Metabolite Identification
Common NameAtropine
DescriptionAtropine, also known as (+-)-atropine or DL-hyoscyamine, 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. Atropine is a drug which is used for the treatment of poisoning by susceptible organophosphorous nerve agents having anti-cholinesterase activity (cholinesterase inhibitors) as well as organophosphorous or carbamate insecticides. Atropine is a very strong basic compound (based on its pKa). Atropine is a potentially toxic compound. It is obtained from deadly nightshade (Atropa belladonna) and other plants of the family Solanaceae.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(+-)-AtropineChEBI
(+-)-HyoscyamineChEBI
(+,-)-Tropyl tropateChEBI
(3-endo)-8-Methyl-8-azabicyclo[3.2.1]oct-3-yl tropateChEBI
8-Methyl-8-azabicyclo[3.2.1]oct-3-yl 3-hydroxy-2-phenylpropanoateChEBI
8-Methyl-8-azabicyclo[3.2.1]oct-3-yl tropateChEBI
[(1S,5R)-8-Methyl-8-azabicyclo[3.2.1]oct-3-yl] 3-hydroxy-2-phenyl-propanoateChEBI
AtropinChEBI
AtropinaChEBI
DL-HyoscyamineChEBI
DL-TropyltropateChEBI
Tropine tropateChEBI
AtropenKegg
(+,-)-Tropyl tropic acidGenerator
(3-endo)-8-Methyl-8-azabicyclo[3.2.1]oct-3-yl tropic acidGenerator
8-Methyl-8-azabicyclo[3.2.1]oct-3-yl 3-hydroxy-2-phenylpropanoic acidGenerator
8-Methyl-8-azabicyclo[3.2.1]oct-3-yl tropic acidGenerator
[(1S,5R)-8-Methyl-8-azabicyclo[3.2.1]oct-3-yl] 3-hydroxy-2-phenyl-propanoic acidGenerator
DL-Tropyltropic acidGenerator
Tropine tropic acidGenerator
Atropine sulfateHMDB
DL-Tropyl tropateHMDB
Chemical FormulaC17H23NO3
Average Molecular Weight289.3694
Monoisotopic Molecular Weight289.167793607
IUPAC Name(1R,3S,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 3-hydroxy-2-phenylpropanoate
Traditional Name(1R,3S,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 3-hydroxy-2-phenylpropanoate
CAS Registry NumberNot Available
SMILES
CN1[C@H]2CC[C@@H]1C[C@@H](C2)OC(=O)C(CO)C1=CC=CC=C1
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?
InChI KeyRKUNBYITZUJHSG-SPUOUPEWSA-N
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
Ontology
StatusDetected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.19ALOGPS
logP1.57ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)15.15ChemAxon
pKa (Strongest Basic)9.39ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area49.77 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity80.82 m³·mol⁻¹ChemAxon
Polarizability31.28 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-5900000000-f705f96b0219dcd47d66View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0006-4900000000-d0c3228da9df55297f7bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-006x-6951100000-dad9042cce0338579e31View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0006-0090000000-b8bc13dbb3c507a0f6b6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0006-0190000000-c8603eb138fb8f0e3404View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00dl-3940000000-da1a38da6babdc138c49View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-006x-9700000000-2f9f7ce546a61df93bfaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0006-9300000000-6a976c404c7b299bbdd6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0006-9200000000-0eb0ff987d891c85a047View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-0090000000-59d025c22f64675dc295View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-0090000000-661bc87f4d92ae6353d7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00dl-1960000000-dafd68e61cc5909f5decView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00dl-7900000000-48d355c9eef2af0979ccView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9300000000-659231292b6eba371158View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-00di-2900000000-3d5f34ceb343969b3c91View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF , positivesplash10-00fr-0900000000-a216bda74712aba9b341View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-006x-6951100000-dad9042cce0338579e31View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dl-0790000000-b3809a4d9f3d53472626View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-1920000000-5cf6a284aa0360bfa6f5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0g02-2900000000-03a359b67b71a8d41b5aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0490000000-42268e6db552a2d85a66View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05g3-1960000000-db1243e11ae5ea609f09View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00bc-5900000000-3453e9ae42b1ccba243cView in MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Liver
  • Mammary Gland
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0014712
DrugBank IDDB00572
Phenol Explorer Compound IDNot Available
FooDB IDFDB004090
KNApSAcK IDC00002277
Chemspider ID10194105
KEGG Compound IDC01479
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAtropine
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID16684
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available