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CHEBI:233670 - GND

ChEBI IDCHEBI:233670
ChEBI NameGND
Stars
DefinitionAn azabicycloalkane that is cocaine in which the methoxycarbonyl group at position 2R is replaced by a 6-aminocarbonylhexanoic acid group and the benzoyloxy group at position 3S is replaced by a benzoylamino 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
FormulaC22H31N3O4
Net Charge0
Average Mass401.507
Monoisotopic Mass401.23146
SMILES[H][C@]12CC[C@]([H])([C@@H](C(=O)NCCCCCC(=O)O)[C@@H](NC(=O)c3ccccc3)C1)N2C
InChIInChI=1S/C22H31N3O4/c1-25-16-11-12-18(25)20(22(29)23-13-7-3-6-10-19(26)27)17(14-16)24-21(28)15-8-4-2-5-9-15/h2,4-5,8-9,16-18,20H,3,6-7,10-14H2,1H3,(H,23,29)(H,24,28)(H,26,27)/t16-,17-,18+,20-/m0/s1
InChIKeyYDSMKSOXBLPMIQ-GNBUJSLZSA-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)
GND (CHEBI:233670) has role hapten (CHEBI:59174)
GND (CHEBI:233670) is a azabicycloalkane (CHEBI:38295)
GND (CHEBI:233670) is a benzamides (CHEBI:22702)
GND (CHEBI:233670) is a monocarboxylic acid (CHEBI:25384)
GND (CHEBI:233670) is a secondary carboxamide (CHEBI:140325)
GND (CHEBI:233670) is a tertiary amino compound (CHEBI:50996)
IUPAC Name 
6-({[(1R,2S,3S,5S)-3-benzamido-8-methyl-8-azabicyclo[3.2.1]octan-2-yl]carbonyl}amino)hexanoic acid
Synonyms  Source
cocaine analog GNDChEBI
hapten GNDChEBI
cocaine hapten GNDChEBI
6-((1R,2S,3S,5S)-3-benzamido-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxamido)hexanoic acidChEBI
GND haptenChEBI
Citations