CHEBI:156294 - steffimycin D

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name steffimycin D
ChEBI ID CHEBI:156294
Definition An 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.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Martin Larralde
Supplier Information
Download Molfile XML SDF
Formula C28H32O12
Net Charge 0
Average Mass 560.552
Monoisotopic Mass 560.18938
InChI InChI=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
InChIKey FAXXYXLNSNAHOO-MICZPBMFSA-N
SMILES CO[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1OC1[C@H](OC)[C@](C)(O)CC2=C1C(O)=C1C(=O)C3=C(O)C=C(OC)C=C3C(=O)C1=C2
Metabolite of Species Details
Streptomyces steffisburgensis (NCBI:txid68271) of strain NRRL 3193 See: PubMed
Roles Classification
Biological Role(s): 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).
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.
bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
(via anthracycline 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 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 Sources
7-deoxo-steffimycin ChEBI
7-deoxosteffimycin ChEBI
Registry Number Type Source
132354-06-4 CAS Registry Number ChEBI
Citations Waiting for Citations Types Sources
16751529 PubMed citation SUBMITTER
1741962 PubMed citation SUBMITTER
Last Modified
18 August 2020