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CHEBI:66022 - hookerianamide J

ChEBI IDCHEBI:66022
ChEBI Namehookerianamide J
Stars
DefinitionA 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.
Last Modified7 March 2018
DownloadsMolfile
FormulaC28H46N2O2
Net Charge0
Average Mass442.688
Monoisotopic Mass442.35593
SMILES[H][C@@]12CC[C@@]3([H])[C@@H](O)[C@@H](NC(=O)C=C(C)C)CC[C@]3(C)[C@@]1([H])CC[C@]1(C)C([C@H](C)N(C)C)=CC[C@@]21[H]
InChIInChI=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
InChIKeyUBWMSSICUOCSHT-BJHCZKLTSA-N
Species of MetaboliteComponentSourceComments
Sarcococca hookeriana (ncbitaxon:153579) whole plant (BTO:0001461) PubMed (18681480)
Roles Classification
Biological Roles:
antileishmanial agent  An antiprotozoal drug used to treat or prevent infections caused by protozoan parasites that belong to the genus Leishmania.
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
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.
Application:
antileishmanial agent  An antiprotozoal drug used to treat or prevent infections caused by protozoan parasites that belong to the genus Leishmania.
ChEBI Ontology
Outgoing Relation(s)
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-olChEBI
Registry NumbersSources
Reaxys:18885924Reaxys
Citations