CHEBI:171673 - dutomycin

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ChEBI Name dutomycin
ChEBI ID CHEBI:171673
Definition An anthracycline antibiotic of formula C44H54O17 isolated from Streptomyces species. It directly binds to the human serine protease inhibitor B6 (SERPINB6), inducing autophagy and apoptosis.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Martin Larralde
Supplier Information
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Formula C44H54O17
Net Charge 0
Average Mass 854.899
Monoisotopic Mass 854.33610
InChI InChI=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
InChIKey XLXKPBAXLAAHEN-WNMWLNICSA-N
SMILES CCCC(C)\C=C(\C)C(=O)OC1C(C)OC(CC1(C)O)OC1CCC(OC2C(O)=C(C(C)=O)C(=O)C3(O)C(=O)C4=C(O)C5=C(C(C)=C4CC23O)C(=O)C(OC)=CC5=O)OC1C
Metabolite of Species Details
Streptomyces sp. (NCBI:txid1931) of strain 1725 See: PubMed
Streptomyces minoensis (NCBI:txid67329) GenBank: KP710956.1 of strain NRRL B-5482 See: PubMed
Roles Classification
Biological Role(s): bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
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).
apoptosis inducer
Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
(via anthracycline antibiotic )
(via carbohydrate-containing antibiotic )
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via anthracycline )
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Number Type Source
146663-67-4 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
1490891 PubMed citation SUBMITTER
27195476 PubMed citation SUBMITTER
32474644 PubMed citation Europe PMC
33517652 PubMed citation SUBMITTER
Last Modified
30 June 2021