Ecgonine (CHEM036139)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 07:15:46 UTC
Update Date2016-11-09 01:21:26 UTC
Accession NumberCHEM036139
Identification
Common NameEcgonine
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical 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 Mass185.220 g/mol
Monoisotopic Mass185.105 g/mol
CAS Registry Number481-37-8
IUPAC Name(2R,3S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid
Traditional Nameecgonine
SMILESCN1C2CCC1[C@H]([C@@H](O)C2)C(O)=O
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility1050 g/LALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001j-9200000000-48c3b8ee572b2dc52292Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-006t-9132000000-9a8887ca9dce4b08af81Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0900000000-84cf8248e17a8b226247Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gb9-0900000000-ada9e3b58a4a68bf34feSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fk9-3900000000-4fe8aa09d75ccea8cb33Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-007o-0900000000-c8352412d369827945bcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dl-0900000000-143c9c6dc9126fa654dcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dl-1900000000-cb49be4d17eb1921ff3eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-4a6fc2f9a39f6a7a3d44Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kv-5900000000-a2ec3ebcb3ee1f393d9bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dj-9700000000-ac3cdeb9ee66f2c193dbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0159-0900000000-dc9636670e82e30cec7cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-007o-1900000000-5cbac175885e0c570c49Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0089-6900000000-987da97e182a8b3e0ba9Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0006548
FooDB IDFDB023968
Phenol Explorer IDNot Available
KNApSAcK IDC00002291
BiGG ID2273742
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkEcgonine
Chemspider ID391305
ChEBI ID708641
PubChem Compound ID443003
Kegg Compound IDC10858
YMDB IDNot Available
ECMDB IDM2MDB004880
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Valente MJ, Henrique R, Vilas-Boas V, Silva R, Bastos Mde L, Carvalho F, Guedes de Pinho P, Carvalho M: Cocaine-induced kidney toxicity: an in vitro study using primary cultured human proximal tubular epithelial cells. Arch Toxicol. 2012 Feb;86(2):249-61. doi: 10.1007/s00204-011-0749-3. Epub 2011 Oct 8.
2. Yao D, Shi X, Wang L, Gosnell BA, Chen C: Characterization of differential cocaine metabolism in mouse and rat through metabolomics-guided metabolite profiling. Drug Metab Dispos. 2013 Jan;41(1):79-88. doi: 10.1124/dmd.112.048678. Epub 2012 Oct 3.
3. Hezinova V, Aturki Z, Kleparnik K, D'Orazio G, Foret F, Fanali S: Simultaneous analysis of cocaine and its metabolites in urine by capillary electrophoresis-electrospray mass spectrometry using a pressurized liquid junction nanoflow interface. Electrophoresis. 2012 Feb;33(4):653-60. doi: 10.1002/elps.201100410.
4. Brim RL, Noon KR, Collins GT, Nichols J, Narasimhan D, Sunahara RK, Woods JH: The ability of bacterial cocaine esterase to hydrolyze cocaine metabolites and their simultaneous quantification using high-performance liquid chromatography-tandem mass spectrometry. Mol Pharmacol. 2011 Dec;80(6):1119-27. doi: 10.1124/mol.111.074534. Epub 2011 Sep 1.
5. van Nuijs AL, Abdellati K, Bervoets L, Blust R, Jorens PG, Neels H, Covaci A: The stability of illicit drugs and metabolites in wastewater, an important issue for sewage epidemiology? J Hazard Mater. 2012 Nov 15;239-240:19-23. doi: 10.1016/j.jhazmat.2012.04.030. Epub 2012 Apr 21.
6. Gonzalez-Marino I, Quintana JB, Rodriguez I, Sanchez-Mendez N, Cela R: Transformation of cocaine during water chlorination. Anal Bioanal Chem. 2012 Dec;404(10):3135-44. doi: 10.1007/s00216-012-6428-2. Epub 2012 Sep 30.
7. Hantson P, Capron A, Wallemacq P: Toxicokinetics of cocaine and metabolites in a body-packer becoming symptomatic. J Forensic Leg Med. 2011 Nov;18(8):385-7. doi: 10.1016/j.jflm.2011.07.004. Epub 2011 Aug 9.
8. Saussereau E, Lacroix C, Gaulier JM, Goulle JP: On-line liquid chromatography/tandem mass spectrometry simultaneous determination of opiates, cocainics and amphetamines in dried blood spots. J Chromatogr B Analyt Technol Biomed Life Sci. 2012 Feb 15;885-886:1-7. doi: 10.1016/j.jchromb.2011.11.035. Epub 2011 Dec 2.