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CHEBI:171673 - dutomycin

ChEBI IDCHEBI:171673
ChEBI Namedutomycin
Stars
DefinitionAn anthracycline antibiotic of formula C44H54O17 isolated from Streptomyces species. It directly binds to the human serine protease inhibitor B6 (SERPINB6), inducing autophagy and apoptosis.
Last Modified30 June 2021
SubmitterMartin Larralde
DownloadsMolfile
FormulaC44H54O17
Net Charge0
Average Mass854.899
Monoisotopic Mass854.33610
SMILESCCC[C@@H](C)/C=C(/C)C(=O)O[C@@H]1[C@H](C)O[C@@H](O[C@H]2CC[C@H](O[C@@H]3C(O)=C(C(C)=O)C(=O)[C@@]4(O)C(=O)c5c(O)c6c(c(C)c5C[C@@]34O)C(=O)C(OC)=CC6=O)O[C@@H]2C)C[C@@]1(C)O
InChIInChI=1S/C44H54O17/c1-10-11-18(2)14-19(3)41(52)61-39-23(7)58-29(17-42(39,8)53)59-26-12-13-28(57-22(26)6)60-40-36(49)31(21(5)45)37(50)44(55)38(51)32-24(16-43(40,44)54)20(4)30-33(35(32)48)25(46)15-27(56-9)34(30)47/h14-15,18,22-23,26,28-29,39-40,48-49,53-55H,10-13,16-17H2,1-9H3/b19-14-/t18-,22-,23+,26+,28+,29+,39-,40-,42-,43-,44-/m1/s1
InChIKeyXLXKPBAXLAAHEN-WNMWLNICSA-N
Species of MetaboliteComponentSourceComments
Streptomyces minoensis (ncbitaxon:67329) - PubMed (27195476) GenBank: KP710956.1 Strain: NRRL B-5482
Streptomyces sp. (ncbitaxon:1931) - PubMed (1490891) Strain: 1725
Roles Classification
Biological Roles:
bacterial metabolite  Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
apoptosis inducer  Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
autophagy inducer  Any compound that induces the process of autophagy (the self-digestion of one or more components of a cell through the action of enzymes originating within the same cell).
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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)
dutomycin (CHEBI:171673) has role antineoplastic agent (CHEBI:35610)
dutomycin (CHEBI:171673) has role apoptosis inducer (CHEBI:68495)
dutomycin (CHEBI:171673) has role autophagy inducer (CHEBI:138880)
dutomycin (CHEBI:171673) has role bacterial metabolite (CHEBI:76969)
dutomycin (CHEBI:171673) is a 1,4-benzoquinones (CHEBI:132124)
dutomycin (CHEBI:171673) is a anthracycline antibiotic (CHEBI:49322)
dutomycin (CHEBI:171673) is a carbohydrate-containing antibiotic (CHEBI:23007)
dutomycin (CHEBI:171673) is a carbopolycyclic compound (CHEBI:35294)
dutomycin (CHEBI:171673) is a disaccharide derivative (CHEBI:63353)
dutomycin (CHEBI:171673) is a enoate ester (CHEBI:51702)
dutomycin (CHEBI:171673) is a enol (CHEBI:33823)
dutomycin (CHEBI:171673) is a ether (CHEBI:25698)
dutomycin (CHEBI:171673) is a phenols (CHEBI:33853)
dutomycin (CHEBI:171673) is a tertiary α-hydroxy ketone (CHEBI:139592)
IUPAC Name 
(2R,3S,6S)-6-{[(1R,4aS,12aR)-3-acetyl-2,4a,6,12a-tetrahydroxy-9-methoxy-11-methyl-4,5,7,10-tetraoxo-1,4,4a,5,7,10,12,12a-octahydrotetracen-1-yl]oxy}-2-methyltetrahydro-2H-pyran-3-yl 2,6-dideoxy-4-O-[(2Z,4R)-2,4-dimethylhept-2-enoyl]-3-C-methyl-α-L-xylo-hexopyranoside
Registry NumbersSources
CAS:146663-67-4ChemIDplus
Citations