Showing metabocard for Ecgonine (BMDB0006548)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:23:14 UTC
Update Date2020-04-22 15:17:48 UTC
BMDB IDBMDB0006548
Secondary Accession Numbers
  • BMDB06548
Metabolite Identification
Common NameEcgonine
DescriptionEcgonine, also known as ekgonin, 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. Ecgonine is a very strong basic compound (based on its pKa). Ecgonine exists in all living organisms, ranging from bacteria to humans.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2R,3S)-3-Hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acidHMDB
3-b-Hydroxy-2-b-tropanecarboxylic acidHMDB
3-beta-Hydroxy-2-beta-tropanecarboxylic acidHMDB
EkgoninHMDB
L-EcgonineHMDB
Ecgonine acetate, (1R-(exo,exo))-isomerHMDB
Ecgonine hydrochlorideHMDB
Ecgonine, (1R-(2-endo,3-exo))-isomerHMDB
Chemical FormulaC9H15NO3
Average Molecular Weight185.2203
Monoisotopic Molecular Weight185.105193351
IUPAC Name(2R,3S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid
Traditional Nameecgonine
CAS Registry Number481-37-8
SMILES
CN1C2CCC1[C@H]([C@@H](O)C2)C(O)=O
InChI Identifier
InChI=1S/C9H15NO3/c1-10-5-2-3-6(10)8(9(12)13)7(11)4-5/h5-8,11H,2-4H2,1H3,(H,12,13)/t5?,6?,7-,8+/m0/s1
InChI KeyPHMBVCPLDPDESM-RLXKETGRSA-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
  • Piperidinecarboxylic acid
  • Tropane alkaloid
  • Beta-hydroxy acid
  • Hydroxy acid
  • Piperidine
  • N-alkylpyrrolidine
  • Cyclic alcohol
  • Pyrrolidine
  • Amino acid or derivatives
  • Amino acid
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Organoheterocyclic compound
  • Amine
  • Organic oxide
  • Organopnictogen compound
  • Alcohol
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Endoplasmic reticulum
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point205 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility178 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.69ALOGPS
logP-3.1ChemAxon
logS0.75ALOGPS
pKa (Strongest Acidic)3.48ChemAxon
pKa (Strongest Basic)9.69ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area60.77 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity46.57 m³·mol⁻¹ChemAxon
Polarizability18.83 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Endoplasmic reticulum
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0006548
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023968
KNApSAcK IDC00002291
Chemspider ID391305
KEGG Compound IDC10858
BioCyc IDNot Available
BiGG ID2273742
Wikipedia LinkEcgonine
METLIN IDNot Available
PubChem Compound443003
PDB IDNot Available
ChEBI ID708641
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available