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CHEBI:65720 - cytotrienin A

Default Structure
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:
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.
antibacterial agent  A substance (or active part thereof) that kills or slows the growth of bacteria.
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