CHEBI:63227 - hapten GNL

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ChEBI Name hapten GNL
ChEBI ID CHEBI:63227
Definition An azabicycloalkane that consists of ecgonine having phenylphosphonyl and alkyl groups attached to the hydroxy and carboxy groups respectively. Used as a transition state analogue of cocaine.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C24H35N2O8P
Net Charge 0
Average Mass 510.51710
Monoisotopic Mass 510.21310
InChI InChI=1S/C24H35N2O8P/c1-26-17-11-12-19(26)23(20(16-17)34-35(31,32)18-8-4-2-5-9-18)24(30)33-15-7-3-6-10-21(27)25-14-13-22(28)29/h2,4-5,8-9,17,19-20,23H,3,6-7,10-16H2,1H3,(H,25,27)(H,28,29)(H,31,32)/t17-,19+,20-,23+/m0/s1
InChIKey XCVMZQUXSKASCG-JBYGMCGMSA-N
SMILES [H][C@]12CC[C@]([H])([C@H]([C@H](C1)OP(O)(=O)c1ccccc1)C(=O)OCCCCCC(=O)NCCC(O)=O)N2C
Roles Classification
Biological Role(s): 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing hapten GNL (CHEBI:63227) has functional parent ecgonine (CHEBI:4743)
hapten GNL (CHEBI:63227) has role hapten (CHEBI:59174)
hapten GNL (CHEBI:63227) is a β-alanine derivative (CHEBI:22823)
hapten GNL (CHEBI:63227) is a azabicycloalkane (CHEBI:38295)
hapten GNL (CHEBI:63227) is a organic phosphonate (CHEBI:37592)
IUPAC Name
N-[6-({[(1R,2R,3S,5S)-3-{[hydroxy(phenyl)phosphoryl]oxy}-8-methyl-8-azabicyclo[3.2.1]oct-2-yl]carbonyl}oxy)hexanoyl]-β-alanine
Synonyms Sources
GNL ChEBI
GNL hapten ChEBI
Registry Number Type Source
8812525 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
11206477 PubMed citation Europe PMC
16472740 PubMed citation Europe PMC
17084858 PubMed citation Europe PMC
Last Modified
21 November 2011