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CHEBI:65433 - arenamide A

ChEBI IDCHEBI:65433
ChEBI Namearenamide A
Stars
DefinitionA 19-membered cyclodepsipeptide consisting of a 3-hydroxy-4-methyldecanoyl moiety linked to the peptide sequence of 5 amino acids. Isolated from the fermentation broth of marine actinomycete Salinispora arenicola, it has been found to block tumour necrosis factor (TNF)-induced activation of NFκB-Luc human embryonic kidney cells.
Last Modified12 November 2012
DownloadsMolfile
FormulaC36H57N5O7
Net Charge0
Average Mass671.880
Monoisotopic Mass671.42580
SMILESCCCCCC[C@H](C)[C@@H]1CC(=O)NCC(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C)C(=O)N[C@@H](Cc2ccccc2)C(=O)O1
InChIInChI=1S/C36H57N5O7/c1-8-9-10-12-15-24(6)29-20-30(42)37-21-31(43)41-32(23(4)5)35(46)39-27(18-22(2)3)34(45)38-25(7)33(44)40-28(36(47)48-29)19-26-16-13-11-14-17-26/h11,13-14,16-17,22-25,27-29,32H,8-10,12,15,18-21H2,1-7H3,(H,37,42)(H,38,45)(H,39,46)(H,40,44)(H,41,43)/t24-,25-,27-,28-,29-,32-/m0/s1
InChIKeyHQEBGENSMXBRMP-GZMZQGJJSA-N
Species of MetaboliteComponentSourceComments
Salinispora arenicola (ncbitaxon:168697) - PubMed (19117399)
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Role:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
arenamide A (CHEBI:65433) has functional parent (3S,4S)-3-hydroxy-4-methyldecanoic acid (CHEBI:71005)
arenamide A (CHEBI:65433) has role antineoplastic agent (CHEBI:35610)
arenamide A (CHEBI:65433) has role metabolite (CHEBI:25212)
arenamide A (CHEBI:65433) is a cyclodepsipeptide (CHEBI:35213)
arenamide A (CHEBI:65433) is a macrocycle (CHEBI:51026)
IUPAC Name 
(3S,6S,9S,12S,19S)-3-benzyl-6-methyl-9-(2-methylpropyl)-19-[(2S)-octan-2-yl]-12-(propan-2-yl)-1-oxa-4,7,10,13,16-pentaazacyclononadecane-2,5,8,11,14,17-hexone
Registry NumbersSources
Reaxys:19756158Reaxys
Citations