fostriecin (CHEBI:167004)

CHEBI:167004 - fostriecin

ChEBI ID	CHEBI:167004
ChEBI Name	fostriecin
Stars
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.
Last Modified	9 August 2021
Submitter	Martin Larralde
Downloads	Molfile

Formula	C19H27O9P
Net Charge	0
Average Mass	430.390
Monoisotopic Mass	430.13927
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
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

Wikipedia

Species of Metabolite	Component	Source	Comments
Streptomyces pulveraceus (ncbitaxon:68258)	-	PubMed (23352138)

Roles Classification

topoisomerase II inhibitor A topoisomerase inhibitor that inhibits DNA topoisomerase II.

bacterial metabolite Any prokaryotic metabolite produced during a metabolic reaction in bacteria.

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).

apoptosis inhibitor Any substance that inhibits the process of apoptosis (programmed cell death) in multi-celled organisms.

antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms.

ChEBI Ontology

Outgoing Relation(s)
	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

Synonyms	Source
(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

Registry Numbers	Sources
CAS:87810-56-8	ChemIDplus

Citations