CHEBI:3703 - cinchonidine

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ChEBI Name cinchonidine
ChEBI ID CHEBI:3703
Definition 8-epi-Cinchonan in which a hydrogen at position 9 is substituted by hydroxy (R configuration). A diasteroisomer of cinchonine, it occurs in the bark of most varieties of Cinchona shrubs, and is frequently used for directing chirality in asymmetric synthesis.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C19H22N2O
Net Charge 0
Average Mass 294.39080
InChI InChI=1S/C19H22N2O/c1-2-13-12-21-10-8-14(13)11-18(21)19(22)16-7-9-20-17-6-4-3-5-15(16)17/h2-7,9,13-14,18-19,22H,1,8,10-12H2/t13-,14-,18-,19+/m0/s1
InChIKey KMPWYEUPVWOPIM-KODHJQJWSA-N
SMILES [H][C@]1(C[C@@H]2CC[N@]1C[C@@H]2C=C)[C@H](O)c1ccnc2ccccc12
Roles Classification
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing cinchonidine (CHEBI:3703) has parent hydride (8S)-cinchonan (CHEBI:59138)
cinchonidine (CHEBI:3703) has role metabolite (CHEBI:25212)
cinchonidine (CHEBI:3703) is a (8ξ)-cinchonan-9-ol (CHEBI:115155)
cinchonidine (CHEBI:3703) is a cinchona alkaloid (CHEBI:51323)
IUPAC Name
(8α,9R)-cinchonan-9-ol
Synonyms Sources
(-)-cinchonidine ChemIDplus
(8alpha,9R)-Cinchonan-9-ol KEGG COMPOUND
(8S,9R)-cinchonan-9-ol ChEBI
(8S,9R)-cinchonidine ChemIDplus
(R)-[(4S,5S,7S)-5-ethenyl-1-azabicyclo[2.2.2]octan-7-yl]-quinolin-4-ylmethanol ChEBI
α-quinidine ChemIDplus
Cinchonidine KEGG COMPOUND
cinchovatine NIST Chemistry WebBook
L-cinchonidine NIST Chemistry WebBook
Database Links Databases
C00002147 KNApSAcK
C11379 KEGG COMPOUND
D07153 KEGG DRUG
View more database links
Registry Numbers Types Sources
485-71-2 CAS Registry Number ChemIDplus
485-71-2 CAS Registry Number NIST Chemistry WebBook
89690 Beilstein Registry Number Beilstein
Last Modified
04 August 2014