(3S,4R)-3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-4-carboxylic acid
PubChem CID
442997
Structure
Molecular Formula
Synonyms
- benzoyl ecgonine
- SCHEMBL328884
- CHEMBL608547
- CHEBI:181959
- (3S,4R)-3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-4-carboxylic acid
Molecular Weight
289.33 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
- Create:2005-06-24
- Modify:2025-01-18
Description
(3S,4R)-3-Benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-4-carboxylic acid is a benzoate ester.
See also: Benzoylecgonine (annotation moved to).
Chemical Structure Depiction
(2R,3S)-3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)
InChI=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
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
GVGYEFKIHJTNQZ-CLRIEMFWSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
CN1C2CCC1[C@H]([C@H](C2)OC(=O)C3=CC=CC=C3)C(=O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)
C16H19NO4
Computed by PubChem 2.2 (PubChem release 2021.10.14)
- benzoyl ecgonine
- benzoylecgonine
- benzoylecgonine, (1R-(2-endo,3-exo))-isomer
Property Name
Property Value
Reference
Property Name
Molecular Weight
Property Value
289.33 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
-0.3
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
289.13140809 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
289.13140809 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
66.8 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
21
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
419
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
2
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
2
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)
Accession ID
Authors
Nikiforos Alygizakis, Nikolaos Thomaidis, University of Athens
Instrument
Bruker maXis Impact
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
10 eV
Fragmentation Mode
CID
Column Name
Acclaim RSLC C18 2.2um, 2.1x100mm, Thermo
Retention Time
4.5 min
Precursor m/z
290.1387
Precursor Adduct
[M+H]+
Top 5 Peaks
290.1394 999
291.1422 154
168.1012 42
292.1444 16
272.1276 3
License
CC BY-SA
Accession ID
Authors
Nikiforos Alygizakis, Nikolaos Thomaidis, University of Athens
Instrument
Bruker maXis Impact
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
20 eV
Fragmentation Mode
CID
Column Name
Acclaim RSLC C18 2.2um, 2.1x100mm, Thermo
Retention Time
4.5 min
Precursor m/z
290.1387
Precursor Adduct
[M+H]+
Top 5 Peaks
168.1011 999
290.1394 767
291.1422 85
272.1279 46
150.0903 28
License
CC BY-SA
Follow these links to do a live 2D search or do a live 3D search for this compound, sorted by annotation score. This section is deprecated (see here for details), but these live search links provide equivalent functionality to the table that was previously shown here.
Same Connectivity Count
Same Stereo Count
Same Isotope Count
Same Parent, Connectivity Count
Same Parent, Stereo Count
Same Parent, Isotope Count
Similar Compounds (2D)
Similar Conformers (3D)
Same Count
Benzoylecgonine (annotation moved to)
Benzoylecgonine is a known transformation product of Cocaine.
S66 | EAWAGTPS | Parent-Transformation Product Pairs from Eawag | DOI:10.5281/zenodo.3754448
Pharmaceuticals -> Anaesthetics -> Transformation products
S66 | EAWAGTPS | Parent-Transformation Product Pairs from Eawag | DOI:10.5281/zenodo.3754448
Patents are available for this chemical structure:
https://patentscope.wipo.int/search/en/result.jsf?inchikey=GVGYEFKIHJTNQZ-CLRIEMFWSA-N
- ChEBI(3S,4R)-3-Benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-4-carboxylic acidhttps://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:181959
- ChEMBLLICENSEAccess to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).http://www.ebi.ac.uk/Information/termsofuse.html
- KEGGLICENSEAcademic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial licensehttps://www.kegg.jp/kegg/legal.htmlPhytochemical compoundshttp://www.genome.jp/kegg-bin/get_htext?br08003.keg
- MassBank Europe
- MassBank of North America (MoNA)LICENSEThe content of the MoNA database is licensed under CC BY 4.0.https://mona.fiehnlab.ucdavis.edu/documentation/license
- Metabolomics Workbench
- NORMAN Suspect List ExchangeLICENSEData: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0https://creativecommons.org/licenses/by/4.0/BenzoylecgonineNORMAN Suspect List Exchange Classificationhttps://www.norman-network.com/nds/SLE/
- PubChem
- Medical Subject Headings (MeSH)LICENSEWorks produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.https://www.nlm.nih.gov/copyright.htmlbenzoylecgoninehttps://www.ncbi.nlm.nih.gov/mesh/67005618
- MolGenieMolGenie Organic Chemistry Ontologyhttps://github.com/MolGenie/ontology/
- PATENTSCOPE (WIPO)SID 389142468https://pubchem.ncbi.nlm.nih.gov/substance/389142468
- NCBI
CONTENTS