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CHEBI:233655 - GNE

ChEBI IDCHEBI:233655
ChEBI NameGNE
Stars
DefinitionAn azabicycloalkane that is cocaine in which the methoxycarbonyl group at position 2R is replaced by a 6-aminocarbonylhexanoic acid group. It is a cocaine analog that is used as a hapten for the development of an anti-cocaine vaccine.
Last Modified13 March 2025
SubmitterAdnan
DownloadsMolfile
FormulaC22H30N2O5
Net Charge0
Average Mass402.491
Monoisotopic Mass402.21547
SMILES[H][C@]12CC[C@]([H])([C@@H](C(=O)NCCCCCC(=O)O)[C@@H](OC(=O)c3ccccc3)C1)N2C
InChIInChI=1S/C22H30N2O5/c1-24-16-11-12-17(24)20(21(27)23-13-7-3-6-10-19(25)26)18(14-16)29-22(28)15-8-4-2-5-9-15/h2,4-5,8-9,16-18,20H,3,6-7,10-14H2,1H3,(H,23,27)(H,25,26)/t16-,17+,18-,20+/m0/s1
InChIKeyVEDCJKKFKBXKLC-HLNWXESRSA-N
Roles Classification
Chemical Roles:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Role:
hapten  Any substance capable of eliciting an immune response only when attached to a large carrier such as a protein. Examples include dinitrophenols; oligosaccharides; peptides; and heavy metals.
ChEBI Ontology
Outgoing Relation(s)
GNE (CHEBI:233655) has role hapten (CHEBI:59174)
GNE (CHEBI:233655) is a azabicycloalkane (CHEBI:38295)
GNE (CHEBI:233655) is a benzoate ester (CHEBI:36054)
GNE (CHEBI:233655) is a monocarboxylic acid (CHEBI:25384)
GNE (CHEBI:233655) is a secondary carboxamide (CHEBI:140325)
GNE (CHEBI:233655) is a tertiary amino compound (CHEBI:50996)
IUPAC Name 
6-{[(1R,2R,3S,5S)-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carbonyl]amino}hexanoic acid
Synonyms  Source
6-(1R,2R,3S,5S)-3-(benzoyloxy)-8-methyl-8-azabicycle[3.2.1]octane-2 carboxamide-hexanoic acidChEBI
6-((1R,2R,3S,5S)-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxamido)hexanoic acidChEBI
cocaine hapten GNEChEBI
hapten GNEChEBI
cocaine analog GNEChEBI
GNE haptenChEBI
Citations