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CHEBI:156294 - steffimycin D

ChEBI IDCHEBI:156294
ChEBI Namesteffimycin D
Stars
DefinitionAn anthracycline antibiotic that is steffimycin in which the carbonyl group that is adjacent to the carbon bearing both a hydroxy group and a methyl group has been reduced to the corresponding methylene group. An antitumour anthracycline first isolated from Streptomyces steffisburgensis.
Last Modified18 August 2020
SubmitterMartin Larralde
DownloadsMolfile
FormulaC28H32O12
Net Charge0
Average Mass560.552
Monoisotopic Mass560.18938
SMILESCOc1cc(O)c2c(c1)C(=O)c1cc3c(c(O)c1C2=O)C(O[C@@H]1O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1OC)[C@H](OC)[C@](C)(O)C3
InChIInChI=1S/C28H32O12/c1-10-19(30)23(34)25(37-4)27(39-10)40-24-16-11(9-28(2,35)26(24)38-5)6-13-18(21(16)32)22(33)17-14(20(13)31)7-12(36-3)8-15(17)29/h6-8,10,19,23-27,29-30,32,34-35H,9H2,1-5H3/t10-,19-,23+,24?,25+,26-,27-,28+/m0/s1
InChIKeyFAXXYXLNSNAHOO-MICZPBMFSA-N
Species of MetaboliteComponentSourceComments
Streptomyces steffisburgensis (ncbitaxon:68271) - PubMed (16751529) Strain: NRRL 3193
Roles Classification
Biological Roles:
bacterial metabolite  Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
intercalator  A role played by a chemical agent which exhibits the capability of occupying space between DNA base pairs due to particular properties in size, shape and charge. Intercalation of chemical compounds in DNA helix can result in replication errors (shift, mutation) or DNA damages.
EC 3.4.24.3 (microbial collagenase) inhibitor  An EC 3.4.24.* (metalloendopeptidase) inhibitor which interferes with the action of microbial collagenase (EC 3.4.24.3, also formerly EC 3.4.4.19 and EC 3.4.99.5).
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)
steffimycin D (CHEBI:156294) has functional parent 2-O-methyl-α-L-rhamnose (CHEBI:139586)
steffimycin D (CHEBI:156294) has role antineoplastic agent (CHEBI:35610)
steffimycin D (CHEBI:156294) has role bacterial metabolite (CHEBI:76969)
steffimycin D (CHEBI:156294) has role EC 3.4.24.3 (microbial collagenase) inhibitor (CHEBI:67189)
steffimycin D (CHEBI:156294) has role intercalator (CHEBI:24853)
steffimycin D (CHEBI:156294) is a anthracycline antibiotic (CHEBI:49322)
IUPAC Name 
(2S,3R)-3,10,12-trihydroxy-2,8-dimethoxy-3-methyl-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 6-deoxy-2-O-methyl-α-L-mannopyranoside
Synonyms  Source
7-deoxosteffimycinChEBI
7-deoxo-steffimycinChEBI
Registry NumbersSources
CAS:132354-06-4ChEBI
Citations