Benzoylecgonine (CED0006440)

Record Information
Version1.0
Creation Date2016-05-22 05:56:10 UTC
Update Date2026-08-19 16:25:41 UTC
SynCED IDCED0006440
Secondary Accession Numbers
  • CHEM019232
Identification
Common NameBenzoylecgonine
ClassSmall Molecule
Description
Benzoylecgonine is an organic compound with the formula C16H19NO4 and an average molecular weight of 289.33 g/mol. Benzoylecgonine belongs to the benzoic acids and derivatives, a subclass of benzene and substituted derivatives within the organic compounds. Biologically, this substance functions as a metabolite (PMC11982668 , PMC9754092 ). It has been identified in five recorded sources, including drinking water and water supply (drinking water), household cleaning and consumer products (tobacco product moisture control), and electrical and electronic equipment such as antennas, auxiliary devices, and radio transmission systems. The recorded exposure route for this compound is oral.
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
(-)-BenzoylecgonineChEBI
(1R,2R,3S,5S)-8-Methyl-3-[(phenylcarbonyl)oxy]-8-azabicyclo[3.2.1]octane-2-carboxylic acidChEBI
3-(Benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acidChEBI
BCGChEBI
BEGChEBI
O-Benzoyl-(-)-ecgonineChEBI
O-BenzoylecgonineChEBI
(1R,2R,3S,5S)-8-Methyl-3-[(phenylcarbonyl)oxy]-8-azabicyclo[3.2.1]octane-2-carboxylateGenerator
3-(Benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylateGenerator
Benzoylecgonine, (1R-(2-endo,3-exo))-isomerMeSH
Benzoyl ecgonineMeSH
BenzoylecgonineChEBI
Ecgonine benzoic acidGenerator
Chemical FormulaC16H19NO4
Average Molecular Mass289.326 g/mol
Monoisotopic Mass289.131 g/mol
CAS Registry Number519-09-5
IUPAC Name(1R,2R,3S,5S)-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid
Traditional Namebenzoylecgonine
SMILES[H][C@]12CC[C@]([H])([C@H]([C@H](C1)OC(=O)C1=CC=CC=C1)C(O)=O)N2C
InChI IdentifierInChI=1S/C16H19NO4/c1-17-11-7-8-12(17)14(15(18)19)13(9-11)21-16(20)10-5-3-2-4-6-10/h2-6,11-14H,7-9H2,1H3,(H,18,19)/t11-,12+,13-,14+/m0/s1
InChI KeyGVGYEFKIHJTNQZ-RFQIPJPRSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentBenzoic acid esters
Alternative Parents
Substituents
  • Benzoate ester
  • Piperidinecarboxylic acid
  • Tropane alkaloid
  • Benzoyl
  • Dicarboxylic acid or derivatives
  • Piperidine
  • N-alkylpyrrolidine
  • Pyrrolidine
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Amino acid
  • Tertiary aliphatic amine
  • Tertiary amine
  • Carboxylic acid derivative
  • Carboxylic acid
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic oxide
  • Amine
  • Carbonyl group
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.82 g/LALOGPS
logP1.71ALOGPS
logP-0.59ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)3.15ChemAxon
pKa (Strongest Basic)9.54ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area66.84 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity76.39 m³·mol⁻¹ChemAxon
Polarizability29.93 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0590000000-63cd666addb0ec431ed9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ab9-1940000000-7bbbc9c1090789aebcc9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-6900000000-380a14d86c89a1ac7706Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0190000000-3bdddf883ffa7af32815Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-006x-1690000000-7832e304ed3fe450a24eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0fi9-3910000000-9ad134e82515eb476d60Not AvailableView Spectrum
Toxicity Profile
Toxicity Values
Toxicity ValueOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalToxicity RatingReference
864.0 Log mg/kg [490:1500]RatLD50oralpredictedNot AvailableNot Available
Toxicity / Toxin ClassNot Available
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Health Effects
Health EffectRelationshipDirectionDescriptionReference
lung cancerAssociated With?Not AvailableA respiratory system cancer that is located in the lung. (DO)PMC10727122
kidney failureAssociated With?increaseNot AvailablePMC9914985
metabolic acidosisIs Biomarker OfNot AvailableNot AvailablePMC12237636
pneumonitisAssociated With?Not AvailableNot AvailablePMC10727122
allergic diseaseAssociated With?Not AvailableAllergic diseases, also known as allergies, are a number of conditions caused by hypersensitivity of the immune system to typically harmless substances in the environment. These diseases include hay fever, food allergies, atopic dermatitis, allergic asthma, and anaphylaxis. Symptoms may include red eyes, an itchy rash, sneezing, a runny nose, shortness of breath, or swelling. Common allergens include pollen and certain foods. Metals and other substances may also cause allergies. Food, insect stings, and medications are common causes of severe allergic reactions. Allergies can be due to both genetic and environmental factors. The underlying mechanism involves immunoglobulin E antibodies (IgE) binding to an allergen and then to a receptor on mast cells or basophils where it triggers the release of inflammatory chemicals such as histamine. Allergies are among the most common conditions in the world. In the developed world, about 20% of people are affected by allergic rhinitis, about 6% of people have at least one food allergy, and about 20% have atopic dermatitis at some point in time.PMC8348050
brain diseaseAssociated With?Not AvailableNot AvailablePMC12237636 , PMC12237636
nephritisAssociated With?increaseA kidney disease that is characterized by an inflammation of the kidneys. (DO)PMC9914985
kidney disorderAssociated With?Not AvailableNot AvailablePMC9914985
VasoconstrictionAssociated With?Not AvailableNot AvailablePMC2780362
FerroptosisHas Therapeutic Effect OnNot AvailableNot AvailablePMC13223821
chronic beryllium diseaseAssociated With?Not AvailableNot AvailablePMC9914985 , PMC10727122
nephrosclerosisAssociated With?increaseNot AvailablePMC9914985
berylliosisAssociated With?Not AvailableNot AvailablePMC10727122
Exposure Sources
Source IDSourceSectorReference
CEDs000010Insecticides?Insecticides are synthetic chemicals designed to control or eliminate insect pests that threaten crops and other agricultural products.Agriculture & land managementPubChem
CEDs000013Soil?Soil serves as a critical medium for plant growth and sustains various ecological functions; however, it can become a reservoir for synthetic chemical contamination.Agriculture & land managementPMC10264418 , PMC10264418
CEDs000050Groundwater?Groundwater serves as a vital resource for drinking water and agricultural irrigation but is increasingly susceptible to contamination from synthetic chemicals.Aquatic systems & sedimentsPMC13452764
CEDs000115Drinking water?Drinking water can be a medium for synthetic chemical contamination, often originating from various industrial processes and agricultural practices.Drinking water & water supplyNot Available
CEDs000506Antennas?Antennas, commonly used in communication technologies, can be a source of synthetic chemical contamination through the materials and coatings used in their construction.Electrical & Electronic EquipmentPubChem
CEDs000507Auxiliary Devices?Auxiliary devices, such as capacitors, transformers, and circuit breakers, are integral components in various electronic systems.Electrical & Electronic EquipmentPubChem
CEDs000511Conductors Or Conductive Bodies Characterised By The Conductive Materials?Conductors, or conductive bodies, are materials that allow the flow of electrical current, typically made from metals such as copper, aluminum, or silver.Electrical & Electronic EquipmentPubChem
CEDs000518Electrically Stimulated Smoking Devices?Electrically stimulated smoking devices, commonly known as e-cigarettes or vape pens, utilize electrical components to heat a liquid solution, often containing nicotine, flavorings, and other additives, to produce an aerosol for inhalation.Electrical & Electronic EquipmentPubChem
CEDs000530Radio Transmission Systems?Radio transmission systems utilize a variety of synthetic chemicals in their manufacturing and maintenance processes.Electrical & Electronic EquipmentPubChem
CEDs000555Bleaching Agents?Bleaching agents are chemical substances used to whiten or lighten materials, often employed in various cleaning products for their stain removal and disinfecting properties.Household cleaning & consumer productsPubChem
CEDs000556Cigar Cigarettes?Cigar cigarettes are a source of synthetic chemical contamination due to the combustion of various tobacco blends and additives.Household cleaning & consumer productsPubChem
CEDs000568Tobacco Product Moisture Control?Tobacco product moisture control involves the use of synthetic chemicals to manage the humidity levels in tobacco products, aiming to preserve flavor and extend shelf life.Household cleaning & consumer productsPubChem
CEDs000580Manufacture Preparation Of Tobacco Products?The manufacture and preparation of tobacco products involve various processes that can result in the introduction of synthetic chemicals into the environment.Industrial manufacturing & chemical processingPubChem
CEDs000605Pest Repellants?Pest repellents, often formulated from synthetic chemicals, are widely used to protect crops from insect infestations and other pests.Agriculture & land managementPubChem
CEDs000611Anti Perspirants Or Body Deoderants?Antiperspirants and body deodorants commonly contain synthetic chemicals such as aluminum compounds, parabens, and synthetic fragrances.Personal care & cosmeticsPubChem
CEDs000642Footwear?Footwear production often involves the use of various synthetic chemicals, such as adhesives, dyes, and treatments, which can contribute to environmental contamination.Textiles, leather & furnishingsPubChem
CEDs000650Purses Luggage Hand Bags?Purses, luggage, and handbags are often manufactured using synthetic materials such as polyvinyl chloride (PVC), polyurethane, and various types of nylon.Textiles, leather & furnishingsPubChem
CEDs000671Airplanes And Helicopters?Airplanes and helicopters are significant sources of synthetic chemical contamination primarily through the use of aviation fuels, lubricants, and de-icing agents.Aviation & AerospacePubChem
CEDs000696Nanotechnology?Nanotechnology involves the manipulation of materials at the molecular or atomic level, typically within the range of 1 to 100 nanometers.Industrial manufacturing & chemical processingPubChem
CEDs000739Inks?Inks are complex mixtures composed of pigments or dyes, solvents, resins, and additives used primarily for printing and writing applications.Paper, pulp & fiber productsPubChem
CEDs000740Paper?Paper production involves the processing of wood fibers and the use of various chemicals, which can lead to synthetic chemical contamination.Paper, pulp & fiber productsPubChem
CEDs000744Water, Wastewater, & Sewage Treatment?Water, wastewater, and sewage treatment processes are critical for managing and mitigating pollutants in water systems.Wastewater, sanitation & biosolidsPubChem
CEDs00753Agricultural SoilAgriculture & land managementPMC11173707
CEDs00764Surface SoilAgriculture & land managementPMC7398612 , PMC7908638
CEDs01012Outdoor SoilAgriculture & land managementPMC3622451
CEDs01143DietFood, food processing & cookwarePMC3603549
CEDs01199Honey SamplesFood, food processing & cookwarePMC11275487
CEDs01244BeefFood, food processing & cookwarePMC13359659
CEDs02111E-wasteWaste management, landfill & incinerationPMC13325153
CEDs02255WaterAquatic systems & sedimentsPMC12309966 , PMC11801561
CEDs02264SedimentAquatic systems & sedimentsPMC7084565 , PMC10559780
CEDs02268Water SamplesAquatic systems & sedimentsPMC4946308
CEDs02291Sediment SamplesAquatic systems & sedimentsPMC4127282
CEDs02346Bottom SedimentsAquatic systems & sedimentsPMC7794470 , PMC6783557
CEDs02353Aquatic SystemAquatic systems & sedimentsPMC4127282
CEDs02361Stream SedimentAquatic systems & sedimentsPMC9492602
CEDs02387Sediment CoresAquatic systems & sedimentsPMC9492602 , PMC9492602
CEDs02439Bottom SedimentAquatic systems & sedimentsPMC7794470
CEDs02589AirAir, dust & atmospheric transportPMC4131935 , PMC8759033
CEDs02590DustAir, dust & atmospheric transportPMC12322832
CEDs02592PM2.5Air, dust & atmospheric transportPMC10510330
CEDs02593House DustAir, dust & atmospheric transportPMC3622451 , PMC3622451
CEDs02596Ambient AirAir, dust & atmospheric transportPMC11328477
CEDs02611RainwaterAir, dust & atmospheric transportPMC9879785
CEDs02625Dust SamplesAir, dust & atmospheric transportPMC12322832
CEDs02629PM10Air, dust & atmospheric transportPMC10510330
CEDs03009Waste WaterWastewater, sanitation & biosolidsPMC11554600 , PMC13468172
CEDs03013EffluentsWastewater, sanitation & biosolidsPMC9200571
CEDs03019Raw WastewaterWastewater, sanitation & biosolidsPMC8366482
CEDs03025Industrial EffluentsWastewater, sanitation & biosolidsPMC13058720
CEDs03039Influent WastewaterWastewater, sanitation & biosolidsPMC7456777
CEDs03043WWTPsWastewater, sanitation & biosolidsPMC8366482
CEDs03158WWTP effluent channelWastewater, sanitation & biosolidsPMC13452764
CEDs03356ComputersElectrical & Electronic EquipmentPMC11328477
Pathways
0 pathwaysPathway Source: PathBank

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureSodium-dependent dopamine transporterP23977Rattus norvegicusPredicted (SEA)
Prediction Confidence Score
0.635
Applicability Domain
0.8
Statistical Significance
3.80e-04
Supporting Reference Compounds
203
E-value
2.95827
Click to view 3D structureSodium-dependent serotonin transporterP31652Rattus norvegicusPredicted (SEA)
Prediction Confidence Score
0.593
Applicability Domain
0.8
Statistical Significance
8.30e-04
Supporting Reference Compounds
297
E-value
6.46149
Click to view 3D structureNorepinephrine transporterQ9WTR4Rattus norvegicusPredicted (SEA)
Prediction Confidence Score
0.593
Applicability Domain
0.8
Statistical Significance
2.80e-04
Supporting Reference Compounds
112
E-value
2.17978
Sodium-dependent dopamine transporter structureClick to view 3D structureSodium-dependent dopamine transporterQ01959HumansPredicted (SEA)
Prediction Confidence Score
0.51
Applicability Domain
0.8
Statistical Significance
0.0012
Supporting Reference Compounds
506
E-value
9.34191
Sodium-dependent serotonin transporter structureClick to view 3D structureSodium-dependent serotonin transporterP31645HumansPredicted (SEA)
Prediction Confidence Score
0.506
Applicability Domain
0.8
Statistical Significance
0.0023
Supporting Reference Compounds
593
E-value
18.2167
Voltage-gated inwardly rectifying potassium channel KCNH2 structureClick to view 3D structureVoltage-gated inwardly rectifying potassium channel KCNH2Q12809HumansPredicted (SEA)
Prediction Confidence Score
0.491
Applicability Domain
0.8
Statistical Significance
0.007
Supporting Reference Compounds
1498
E-value
54.2609
Click to view 3D structureSodium-dependent dopamine transporterP27922Bos taurusPredicted (SEA)
Prediction Confidence Score
0.487
Applicability Domain
0.8
Statistical Significance
5.00e-05
Supporting Reference Compounds
8
E-value
0.389246
Sodium-dependent noradrenaline transporter structureClick to view 3D structureSodium-dependent noradrenaline transporterP23975HumansPredicted (SEA)
Prediction Confidence Score
0.465
Applicability Domain
0.8
Statistical Significance
0.0017
Supporting Reference Compounds
451
E-value
13.0008
Click to view 3D structureMuscarinic acetylcholine receptor M1P08482Rattus norvegicusPredicted (SEA)
Prediction Confidence Score
0.418
Applicability Domain
0.444
Statistical Significance
8.20e-04
Supporting Reference Compounds
109
E-value
6.38364
Acetylcholine-binding protein structureClick to view 3D structureAcetylcholine-binding proteinP58154Lymnaea stagnalisPredicted (SEA)
Prediction Confidence Score
0.409
Applicability Domain
0.614
Statistical Significance
2.70e-04
Supporting Reference Compounds
20
E-value
2.10193
Click to view 3D structureSodium-dependent dopamine transporterQ9GJT6Macaca fascicularisPredicted (SEA)
Prediction Confidence Score
0.405
Applicability Domain
0.8
Statistical Significance
2.20e-04
Supporting Reference Compounds
7
E-value
1.71268
Sigma non-opioid intracellular receptor 1 structureClick to view 3D structureSigma non-opioid intracellular receptor 1Q99720HumansPredicted (SEA)
Prediction Confidence Score
0.397
Applicability Domain
0.8
Statistical Significance
0.0122
Supporting Reference Compounds
562
E-value
95.3653
Click to view 3D structureMuscarinic acetylcholine receptor M2P10980Rattus norvegicusPredicted (SEA)
Prediction Confidence Score
0.392
Applicability Domain
0.417
Statistical Significance
0.0013
Supporting Reference Compounds
98
E-value
10.3539
Muscarinic acetylcholine receptor M1 structureClick to view 3D structureMuscarinic acetylcholine receptor M1P11229HumansPredicted (SEA)
Prediction Confidence Score
0.378
Applicability Domain
0.417
Statistical Significance
0.0051
Supporting Reference Compounds
385
E-value
39.5474
Muscarinic acetylcholine receptor M2 structureClick to view 3D structureMuscarinic acetylcholine receptor M2P08172HumansPredicted (SEA)
Prediction Confidence Score
0.378
Applicability Domain
0.417
Statistical Significance
0.0038
Supporting Reference Compounds
373
E-value
29.5827
Muscarinic acetylcholine receptor M3 structureClick to view 3D structureMuscarinic acetylcholine receptor M3P08483Rattus norvegicusPredicted (SEA)
Prediction Confidence Score
0.377
Applicability Domain
0.4
Statistical Significance
4.80e-04
Supporting Reference Compounds
55
E-value
3.73676
Muscarinic acetylcholine receptor M5 structureClick to view 3D structureMuscarinic acetylcholine receptor M5P08912HumansPredicted (SEA)
Prediction Confidence Score
0.371
Applicability Domain
0.4
Statistical Significance
0.003
Supporting Reference Compounds
266
E-value
23.1991
Muscarinic acetylcholine receptor M4 structureClick to view 3D structureMuscarinic acetylcholine receptor M4P08173HumansPredicted (SEA)
Prediction Confidence Score
0.354
Applicability Domain
0.417
Statistical Significance
0.0049
Supporting Reference Compounds
297
E-value
38.3797
Click to view 3D structureMuscarinic acetylcholine receptor M4P08485Rattus norvegicusPredicted (SEA)
Prediction Confidence Score
0.352
Applicability Domain
0.417
Statistical Significance
5.30e-04
Supporting Reference Compounds
38
E-value
4.12601
Muscarinic acetylcholine receptor M3 structureClick to view 3D structureMuscarinic acetylcholine receptor M3P20309HumansPredicted (SEA)
Prediction Confidence Score
0.35
Applicability Domain
0.4
Statistical Significance
0.0055
Supporting Reference Compounds
310
E-value
43.1285
Click to view 3D structureMuscarinic acetylcholine receptor M3Q8VH26Cavia porcellusPredicted (SEA)
Prediction Confidence Score
0.345
Applicability Domain
0.4
Statistical Significance
7.40e-04
Supporting Reference Compounds
52
E-value
5.76084
Neuronal acetylcholine receptor subunit alpha-7 structureClick to view 3D structureNeuronal acetylcholine receptor subunit alpha-7P36544HumansPredicted (SEA)
Prediction Confidence Score
0.325
Applicability Domain
0.386
Statistical Significance
0.0059
Supporting Reference Compounds
77
E-value
46.2424
Soluble acetylcholine receptor structureClick to view 3D structureSoluble acetylcholine receptorQ8WSF8Aplysia californicaPredicted (SEA)
Prediction Confidence Score
0.32
Applicability Domain
0.436
Statistical Significance
1.70e-04
Supporting Reference Compounds
13
E-value
1.32344
5-hydroxytryptamine receptor 2C structureClick to view 3D structure5-hydroxytryptamine receptor 2CP28335HumansPredicted (SEA)
Prediction Confidence Score
0.312
Applicability Domain
0.4
Statistical Significance
0.0512
Supporting Reference Compounds
823
E-value
398.744
Click to view 3D structureTransporterQ63380Rattus norvegicusPredicted (SEA)
Prediction Confidence Score
0.31
Applicability Domain
0.8
Statistical Significance
0.0032
Supporting Reference Compounds
54
E-value
24.9118
Concentrations
Not Available
External Links
DrugBank IDDB01515
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00002280
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkEcgonine_benzoate
Chemspider IDNot Available
ChEBI ID41001
PubChem Compound ID448223
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available