CHEBI:167004 - fostriecin

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ChEBI Name fostriecin
ChEBI ID CHEBI:167004
Definition A structurally unique, naturally-occurring phosphate monoester isolated from the soil bacterium Streptomyces pulveraceus. It inhibits DNA topoisomerase II as well as several protein phosphatase including PP2A and PPA4, and exhibits potent antitumor activity against several cancer cell lines.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Martin Larralde
Supplier Information
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Formula C19H27O9P
Net Charge 0
Average Mass 430.390
Monoisotopic Mass 430.13927
InChI InChI=1S/C19H27O9P/c1-19(23,12-11-16-9-7-10-18(22)27-16)17(28-29(24,25)26)14-15(21)8-5-3-2-4-6-13-20/h2-8,10-12,15-17,20-21,23H,9,13-14H2,1H3,(H2,24,25,26)/b3-2-,6-4+,8-5-,12-11+/t15-,16+,17+,19+/m0/s1
InChIKey ZMQRJWIYMXZORG-DSWNLJKISA-N
SMILES C[C@@](O)(\C=C\[C@H]1CC=CC(=O)O1)[C@@H](C[C@@H](O)\C=C/C=C\C=C\CO)OP(O)(O)=O
Metabolite of Species Details
Streptomyces pulveraceus (NCBI:txid68258) See: PubMed
Roles Classification
Biological Role(s): EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor
Any EC 3.1.3.* (phosphoric monoester hydrolase) inhibitor that interferes with the action of phosphoprotein phosphatase (EC 3.1.3.16).
bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
topoisomerase II inhibitor
A topoisomerase inhibitor that inhibits DNA topoisomerase II.
apoptosis inhibitor
Any substance that inhibits the process of apoptosis (programmed cell death) in multi-celled organisms.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
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ChEBI Ontology
Outgoing fostriecin (CHEBI:167004) has role antineoplastic agent (CHEBI:35610)
fostriecin (CHEBI:167004) has role apoptosis inhibitor (CHEBI:68494)
fostriecin (CHEBI:167004) has role bacterial metabolite (CHEBI:76969)
fostriecin (CHEBI:167004) has role EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor (CHEBI:37153)
fostriecin (CHEBI:167004) has role topoisomerase II inhibitor (CHEBI:156203)
fostriecin (CHEBI:167004) is a 2-pyranones (CHEBI:75885)
fostriecin (CHEBI:167004) is a olefinic compound (CHEBI:78840)
fostriecin (CHEBI:167004) is a phosphate monoester (CHEBI:7794)
fostriecin (CHEBI:167004) is a polyketide (CHEBI:26188)
fostriecin (CHEBI:167004) is a primary allylic alcohol (CHEBI:134394)
fostriecin (CHEBI:167004) is a secondary allylic alcohol (CHEBI:134396)
fostriecin (CHEBI:167004) is a triol (CHEBI:27136)
IUPAC Name
(1E,3R,4R,6R,7Z,9Z,11E)-3,6,13-trihydroxy-3-methyl-1-[(2R)-6-oxo-3,6-dihydro-2H-pyran-2-yl]trideca-1,7,9,11-tetraen-4-yl dihydrogen phosphate
INNs Sources
fostriecin WHO MedNet
fostriecina WHO MedNet
fostriécine WHO MedNet
fostriecinum WHO MedNet
Synonyms Sources
(+)-fostriecin KNApSAcK
(6R)-5,6-dihydro-6-[(1E,3R,4R,6R,7Z,9Z,11E)-3,6,13-trihydroxy-3-methyl-4-(phosphonooxy)-1,7,9,11-tridecatetraenyl]-2H-pyran-2-one ChEBI
antibiotic CI 920 ChemIDplus
antibiotic CL 1565A ChemIDplus
CI 920 ChemIDplus
CI-920 ChemIDplus
CL 1565A ChemIDplus
CL-1565A ChEBI
PD 110,161 ChemIDplus
PD 110161 ChEBI
PD-110,161 ChEBI
phosphotrienin ChemIDplus
Manual Xrefs Databases
4510160 ChemSpider
C00018551 KNApSAcK
Fostriecin Wikipedia
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Registry Number Type Source
87810-56-8 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
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Last Modified
09 August 2021