Lansamide 4 (CHEBI:141771)

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ChEBI Name	Lansamide 4

ChEBI ID	CHEBI:141771

Definition	A 3-hydroxy-6-methoxy-1-methyl-4,5-diphenyl-2-piperidinone in which positions 3,4,5 and 6 have S,S,R,R stereochemistry, respectively.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information

Download	Molfile XML SDF

Formula

C19H21NO3

Net Charge

Average Mass

311.376

Monoisotopic Mass

311.15214

InChI

InChI=1S/C19H21NO3/c1-20-18(22)17(21)15(13-9-5-3-6-10-13)16(19(20)23-2)14-11-7-4-8-12-14/h3-12,15-17,19,21H,1-2H3/t15-,16+,17+,19-/m1/s1

InChIKey

HGOXSQCBJLZRJO-VUHPKUFZSA-N

SMILES

O([C@H]1N(C(=O)[C@@H](O)[C@@H]([C@@H]1C2=CC=CC=C2)C3=CC=CC=C3)C)C

Metabolite of Species	Details
Clausena lansium (NCBI:txid159037)	Found in leaf (BTO:0000713). See: PubMed

Roles Classification
Biological Role(s):	plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. (via 3-hydroxy-6-methoxy-1-methyl-4,5-diphenyl-2-piperidinone )

ChEBI Ontology
Outgoing	Lansamide 4 (CHEBI:141771) has role plant metabolite (CHEBI:76924) Lansamide 4 (CHEBI:141771) is a 3-hydroxy-6-methoxy-1-methyl-4,5-diphenyl-2-piperidinone (CHEBI:141548)

IUPAC Name

(3S,4S,5R,6R)-3-hydroxy-6-methoxy-1-methyl-4,5-diphenylpiperidin-2-one

Citation	Type	Source
26523463	PubMed citation	Europe PMC

Last Modified

24 August 2018

General Comment
2018-08-24	This compound was reported as a racemate in a previous study but without relative stereochemistry shown (Lakshmi, V. Raj, K. Kapil, RS. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1998, 37B, 422-424). However, it is now confirmed as a pure enantiomer with specific stereochemistry.