cinchonidine (CHEBI:3703)

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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

Download	Molfile XML SDF

Formula

C19H22N2O

Net Charge

Average Mass

294.39080

Monoisotopic Mass

294.17321

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 )

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

Last Modified

25 February 2016