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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2007-05-23 15:30:42 UTC
Update Date2021-09-14 15:44:46 UTC
HMDB IDHMDB0006548
Secondary Accession Numbers
  • HMDB06548
Metabolite Identification
Common NameEcgonine
DescriptionEcgonine is an organic chemical and tropane alkaloid found naturally in coca leaves. It is has a close structural relation to cocaine: it is both a metabolite and a precursor, and as such, it is a controlled substance, as are all known substances which can be used as precursors to ecgonine itself. Structurally, ecgonine is a cycloheptane derivative with a nitrogen bridge. It is obtained by hydrolysis of cocaine with acids or alkalis, and crystallizes with one molecule of water, the crystals melting at 198-199oC. It is levorotary, and on warming with alkalis gives iso-ecgonine, which is dextrorotary. It is a tertiary base, and has the properties of an acid and an alcohol. It is the carboxylic acid corresponding to tropine, for it yields the same products on oxidation, and by treatment with phosphorus pentachloride is converted into anhydroecgonine, C9H13NO2, which, when heated to 280oC with hydrochloric acid, eliminates carbon dioxide and yields tropidine, C8H13N.(Wikipedia ).
Structure
Data?1582752390
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
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point205 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility178 mg/mLNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1050 g/LALOGPS
logP10(-0.69) g/LALOGPS
logP10(-3.1) g/LChemAxon
logS10(0.75) g/LALOGPS
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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+141.12931661259
DarkChem[M-H]-137.85131661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Ecgonine,1TMS,isomer #1CN1C2CCC1[C@@H](C(=O)O)[C@@H](O[Si](C)(C)C)C21668.1Semi standard non polar33892256
Ecgonine,1TMS,isomer #1CN1C2CCC1[C@@H](C(=O)O)[C@@H](O[Si](C)(C)C)C21520.4Standard non polar33892256
Ecgonine,1TMS,isomer #1CN1C2CCC1[C@@H](C(=O)O)[C@@H](O[Si](C)(C)C)C22299.7Standard polar33892256
Ecgonine,1TMS,isomer #2CN1C2CCC1[C@@H](C(=O)O[Si](C)(C)C)[C@@H](O)C21607.2Semi standard non polar33892256
Ecgonine,1TMS,isomer #2CN1C2CCC1[C@@H](C(=O)O[Si](C)(C)C)[C@@H](O)C21578.6Standard non polar33892256
Ecgonine,1TMS,isomer #2CN1C2CCC1[C@@H](C(=O)O[Si](C)(C)C)[C@@H](O)C22371.8Standard polar33892256
Ecgonine,2TMS,isomer #1CN1C2CCC1[C@@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C21686.6Semi standard non polar33892256
Ecgonine,2TMS,isomer #1CN1C2CCC1[C@@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C21653.8Standard non polar33892256
Ecgonine,2TMS,isomer #1CN1C2CCC1[C@@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C22108.2Standard polar33892256
Ecgonine,1TBDMS,isomer #1CN1C2CCC1[C@@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)C21880.3Semi standard non polar33892256
Ecgonine,1TBDMS,isomer #1CN1C2CCC1[C@@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)C21760.2Standard non polar33892256
Ecgonine,1TBDMS,isomer #1CN1C2CCC1[C@@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)C22440.8Standard polar33892256
Ecgonine,1TBDMS,isomer #2CN1C2CCC1[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)C21834.7Semi standard non polar33892256
Ecgonine,1TBDMS,isomer #2CN1C2CCC1[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)C21820.3Standard non polar33892256
Ecgonine,1TBDMS,isomer #2CN1C2CCC1[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)C22508.2Standard polar33892256
Ecgonine,2TBDMS,isomer #1CN1C2CCC1[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C22128.7Semi standard non polar33892256
Ecgonine,2TBDMS,isomer #1CN1C2CCC1[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C22125.3Standard non polar33892256
Ecgonine,2TBDMS,isomer #1CN1C2CCC1[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C22349.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Ecgonine GC-MS (Non-derivatized) - 70eV, Positivesplash10-001j-9200000000-48c3b8ee572b2dc522922017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ecgonine GC-MS (2 TMS) - 70eV, Positivesplash10-006t-9132000000-9a8887ca9dce4b08af812017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ecgonine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ecgonine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ecgonine 10V, Positive-QTOFsplash10-014r-0900000000-84cf8248e17a8b2262472017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ecgonine 20V, Positive-QTOFsplash10-0gb9-0900000000-ada9e3b58a4a68bf34fe2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ecgonine 40V, Positive-QTOFsplash10-0fk9-3900000000-4fe8aa09d75ccea8cb332017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ecgonine 10V, Negative-QTOFsplash10-007o-0900000000-c8352412d369827945bc2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ecgonine 20V, Negative-QTOFsplash10-00dl-0900000000-143c9c6dc9126fa654dc2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ecgonine 40V, Negative-QTOFsplash10-00dl-1900000000-cb49be4d17eb1921ff3e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ecgonine 10V, Positive-QTOFsplash10-000i-0900000000-4a6fc2f9a39f6a7a3d442021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ecgonine 20V, Positive-QTOFsplash10-00kv-5900000000-a2ec3ebcb3ee1f393d9b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ecgonine 40V, Positive-QTOFsplash10-00dj-9700000000-ac3cdeb9ee66f2c193db2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ecgonine 10V, Negative-QTOFsplash10-0159-0900000000-dc9636670e82e30cec7c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ecgonine 20V, Negative-QTOFsplash10-007o-1900000000-5cbac175885e0c570c492021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ecgonine 40V, Negative-QTOFsplash10-0089-6900000000-987da97e182a8b3e0ba92021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Endoplasmic reticulum
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
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
Food Biomarker OntologyNot Available
VMH IDECGON
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not 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. [PubMed:21983858 ]
  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. [PubMed:23034697 ]
  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. [PubMed:22451058 ]
  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. [PubMed:21885621 ]
  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. [PubMed:22572562 ]
  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. [PubMed:23052872 ]
  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. [PubMed:22018173 ]
  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. [PubMed:22281234 ]

Enzymes

General function:
Involved in hydrolase activity
Specific function:
Arylacetamide deacetylation is an important enzyme activity in the metabolic activation of arylamine substrates to ultimate carcinogens. Displays major serine hydrolase activity in liver microsomes. Hydrolyzes also flutamide, which is an antiandrogen drug used for the treatment of prostate cancer that occasionally causes severe hepatotoxicity. Displays cellular triglyceride lipase activity in liver. Increases intracellular fatty acids derived from hydrolysis of newly formed triglyceride stores.
Gene Name:
AADAC
Uniprot ID:
P22760
Molecular weight:
45733.28