CHEBI:27509 - cinchonine

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name cinchonine
ChEBI ID CHEBI:27509
Definition Cinchonan in which a hydrogen at position 9 is substituted by hydroxy (S configuration). 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.
Secondary ChEBI IDs CHEBI:3704, CHEBI:622763, CHEBI:23241
Supplier Information
Download Molfile XML SDF
Formula C19H22N2O
Net Charge 0
Average Mass 294.39080
Monoisotopic Mass 294.173
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-QAMTZSDWSA-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 cinchonine (CHEBI:27509) has parent hydride cinchonan (CHEBI:35933)
cinchonine (CHEBI:27509) has role metabolite (CHEBI:25212)
cinchonine (CHEBI:27509) is a (8ξ)-cinchonan-9-ol (CHEBI:115155)
cinchonine (CHEBI:27509) is a cinchona alkaloid (CHEBI:51323)
IUPAC Name
(9S)-cinchonan-9-ol
Synonyms Sources
(+)-cinchonine ChEBI
(8R,9S)-cinchonine ChemIDplus
(9S)-Cinchonan-9-ol KEGG COMPOUND
(S)-quinolin-4-yl-(5-vinyl-1-aza-bicyclo[2.2.2]oct-2-yl)-methanol ChEBI
cinchonine ChEMBL
Cinchonine KEGG COMPOUND
D-cinchonine ChemIDplus
Manual Xrefs Databases
C06528 KEGG COMPOUND
D07153 KEGG DRUG
View more database links
Registry Numbers Types Sources
118-10-5 CAS Registry Number KEGG COMPOUND
118-10-5 CAS Registry Number NIST Chemistry WebBook
118-10-5 CAS Registry Number ChemIDplus
89689 Beilstein Registry Number Beilstein
Last Modified
04 August 2014