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CHEBI:65720 - cytotrienin A

ChEBI IDCHEBI:65720
ChEBI Namecytotrienin A
Stars
DefinitionA 21-membered macrocyclic lactam which contains three conjugated double bonds as part of the ring system. It acts as an apoptosis inducer in human leukemia HL-60 cells and is isolated from Streptomyces sp.
Last Modified10 May 2024
DownloadsMolfile
FormulaC37H48N2O8
Net Charge0
Average Mass648.797
Monoisotopic Mass648.34107
SMILESCO[C@H]1/C=C/C=C/C=C/C[C@H](OC(=O)C2(NC(=O)C3=CCCCC3)CC2)[C@H](C)[C@@H](O)/C(C)=C\CCc2cc(O)cc(c2O)NC(=O)C1
InChIInChI=1S/C37H48N2O8/c1-24-13-12-16-27-21-28(40)22-30(34(27)43)38-32(41)23-29(46-3)17-10-5-4-6-11-18-31(25(2)33(24)42)47-36(45)37(19-20-37)39-35(44)26-14-8-7-9-15-26/h4-6,10-11,13-14,17,21-22,25,29,31,33,40,42-43H,7-9,12,15-16,18-20,23H2,1-3H3,(H,38,41)(H,39,44)/b5-4+,11-6+,17-10+,24-13-/t25-,29-,31-,33-/m0/s1
InChIKeyHNVKTRONBDHSPT-QETCNUOWSA-N
Species of MetaboliteComponentSourceComments
Streptomyces sp. (ncbitaxon:1931) - PubMed (9186568) Strain: RK95 74
Roles Classification
Biological Roles:
antibacterial agent  A substance (or active part thereof) that kills or slows the growth of bacteria.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
apoptosis inducer  Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
cytotrienin A (CHEBI:65720) has role antibacterial agent (CHEBI:33282)
cytotrienin A (CHEBI:65720) has role antimicrobial agent (CHEBI:33281)
cytotrienin A (CHEBI:65720) has role antineoplastic agent (CHEBI:35610)
cytotrienin A (CHEBI:65720) has role apoptosis inducer (CHEBI:68495)
cytotrienin A (CHEBI:65720) has role metabolite (CHEBI:25212)
cytotrienin A (CHEBI:65720) is a cyclopropanecarboxylate ester (CHEBI:50351)
cytotrienin A (CHEBI:65720) is a ether (CHEBI:25698)
cytotrienin A (CHEBI:65720) is a hydroquinones (CHEBI:24646)
cytotrienin A (CHEBI:65720) is a lactam (CHEBI:24995)
cytotrienin A (CHEBI:65720) is a macrocycle (CHEBI:51026)
cytotrienin A (CHEBI:65720) is a secondary alcohol (CHEBI:35681)
IUPAC Name 
(5R,6E,8E,10E,13S,14R,15R,16Z)-15,22,24-trihydroxy-5-methoxy-14,16-dimethyl-3-oxo-2-azabicyclo[18.3.1]tetracosa-1(24),6,8,10,16,20,22-heptaen-13-yl 1-[(cyclohex-1-en-1-ylcarbonyl)amino]cyclopropanecarboxylate
Registry NumbersSources
Reaxys:18866746Reaxys
Citations