pipercallosine (CHEBI:69685)

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ChEBI Name	pipercallosine

ChEBI ID	CHEBI:69685

Definition	An alkaloid enamide that is (2E,4E)-N-(2-methylpropyl)nona-2,4-dienamide substituted at position 9 by a 1,3-benzodioxol-5-yl group. Isolated from Piper sarmentosum, it has been found to induce apoptosis in HT-29 cells.

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

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Formula

C20H27NO3

Net Charge

Average Mass

329.434

Monoisotopic Mass

329.19909

InChI

InChI=1S/C20H27NO3/c1-16(2)14-21-20(22)10-8-6-4-3-5-7-9-17-11-12-18-19(13-17)24-15-23-18/h4,6,8,10-13,16H,3,5,7,9,14-15H2,1-2H3,(H,21,22)/b6-4+,10-8+

InChIKey

KXYVTCVLCVPQKR-ONNLMXTPSA-N

SMILES

C(/C=C/C=C/CCCCC1=CC=C2C(=C1)OCO2)(=O)NCC(C)C

Metabolite of Species	Details
Piper boehmeriaefolium (NCBI:txid130389)	Found in whole plant (BTO:0001461). Methanolic extract of air-dried, powdered whole plant See: PubMed
Piper sarmentosum (NCBI:txid405319)	Found in stem (BTO:0001300). Chloroform soluble extract of aerial parts(leaves, twigs, stems, inflorescence) See: PubMed
Piper sarmentosum (NCBI:txid405319)	Found in twig (BTO:0001411). Chloroform soluble extract of aerial parts(leaves, twigs, stems, inflorescence) See: PubMed
Piper sarmentosum (NCBI:txid405319)	Found in leaf (BTO:0000713). Chloroform soluble extract of aerial parts(leaves, twigs, stems, inflorescence) See: PubMed
Piper sarmentosum (NCBI:txid405319)	Found in inflorescence (BTO:0000628). Chloroform soluble extract of aerial parts(leaves, twigs, stems, inflorescence) See: PubMed

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 ) apoptosis inducer Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms. plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.

ChEBI Ontology
Outgoing	pipercallosine (CHEBI:69685) has functional parent 2-methylpropanamine (CHEBI:15997) pipercallosine (CHEBI:69685) has role apoptosis inducer (CHEBI:68495) pipercallosine (CHEBI:69685) has role metabolite (CHEBI:25212) pipercallosine (CHEBI:69685) has role plant metabolite (CHEBI:76924) pipercallosine (CHEBI:69685) is a alkaloid (CHEBI:22315) pipercallosine (CHEBI:69685) is a benzodioxoles (CHEBI:38298) pipercallosine (CHEBI:69685) is a enamide (CHEBI:51751) pipercallosine (CHEBI:69685) is a secondary carboxamide (CHEBI:140325)

IUPAC Name

(2E,4E)-9-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)nona-2,4-dienamide

Registry Number	Type	Source
5596775	Reaxys Registry Number	Reaxys

Last Modified

07 March 2018