CHEBI:66022 - hookerianamide J

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ChEBI Name hookerianamide J
ChEBI ID CHEBI:66022
Definition A steroid alkaloid that is 5α-preg-16-ene substituted by a hydroxy group at position 4, a N,N-dimethylamino group at position 20 and a N-senecoylamino group at position 3 (the 3β,4β,20S stereoisomer). Isolated from Sarcococca hookeriana, it exhibits antileishmanial and antibacterial activities.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C28H46N2O2
Net Charge 0
Average Mass 442.67700
Monoisotopic Mass 442.35593
InChI InChI=1S/C28H46N2O2/c1-17(2)16-25(31)29-24-13-15-28(5)22-12-14-27(4)20(18(3)30(6)7)10-11-21(27)19(22)8-9-23(28)26(24)32/h10,16,18-19,21-24,26,32H,8-9,11-15H2,1-7H3,(H,29,31)/t18-,19-,21-,22-,23-,24-,26+,27+,28+/m0/s1
InChIKey UBWMSSICUOCSHT-BJHCZKLTSA-N
SMILES [H][C@@]12CC[C@]3([H])[C@]([H])(CC[C@]4(C)C(=CC[C@@]34[H])[C@H](C)N(C)C)[C@@]1(C)CC[C@H](NC(=O)C=C(C)C)[C@@H]2O
Metabolite of Species Details
Sarcococca hookeriana (NCBI:txid153579) Found in whole plant (BTO:0001461). 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.
antileishmanial agent
An antiprotozoal drug used to treat or prevent infections caused by protozoan parasites that belong to the genus Leishmania.
antibacterial agent
A substance (or active part thereof) that kills or slows the growth of bacteria.
EC 3.1.1.8 (cholinesterase) inhibitor
An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of cholinesterase (EC 3.1.1.8).
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
Application(s): antileishmanial agent
An antiprotozoal drug used to treat or prevent infections caused by protozoan parasites that belong to the genus Leishmania.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing hookerianamide J (CHEBI:66022) has functional parent 3-methylbut-2-enoic acid (CHEBI:37127)
hookerianamide J (CHEBI:66022) has parent hydride 5α-pregnane (CHEBI:20656)
hookerianamide J (CHEBI:66022) has role antibacterial agent (CHEBI:33282)
hookerianamide J (CHEBI:66022) has role antileishmanial agent (CHEBI:70868)
hookerianamide J (CHEBI:66022) has role EC 3.1.1.8 (cholinesterase) inhibitor (CHEBI:37733)
hookerianamide J (CHEBI:66022) has role plant metabolite (CHEBI:76924)
hookerianamide J (CHEBI:66022) is a enamide (CHEBI:51751)
hookerianamide J (CHEBI:66022) is a secondary alcohol (CHEBI:35681)
hookerianamide J (CHEBI:66022) is a secondary carboxamide (CHEBI:140325)
hookerianamide J (CHEBI:66022) is a steroid alkaloid (CHEBI:26767)
IUPAC Name
N-[(3β,4β,5α,20S)-20-(dimethylamino)-4-hydroxypregn-16-en-3-yl]-3-methylbut-2-enamide
Synonym Source
(20S)-20-(N,N-dimethylamino)-3β-(N-senecoylamino)-5α-preg-16-en-4β-ol ChEBI
Registry Number Type Source
18885924 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
18681480 PubMed citation Europe PMC
Last Modified
07 March 2018