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neosartoricin

Go to external page http://purl.obolibrary.org/obo/CHEBI_72750

A carbotricyclic compound obtained from the pathogenic fungi Aspergillus fumigatus and Neosartorya fischeri following activation of their polycyclic polyketide prenyltransferase (pcPTase)-containing silent clusters. It exhibits T-cell antiproliferative activity with an IC50 of 3 muM, suggesting a possible physiological role as an immunosuppressive agent.

Term info

Label

neosartoricin

Synonyms
  • (2S,3R)-3,6,8,9-tetrahydroxy-3-[(3Z)-4-hydroxy-2-oxopent-3-en-1-yl]-10-(3-methylbut-2-en-1-yl)-1-oxo-1,2,3,4-tetrahydroanthracen-2-yl acetate
database cross reference
Subsets

3_STAR

IUPAC NAME
(2S,3R)-3,6,8,9-tetrahydroxy-3-[(3Z)-4-hydroxy-2-oxopent-3-en-1-yl]-10-(3-methylbut-2-en-1-yl)-1-oxo-1,2,3,4-tetrahydroanthracen-2-yl acetate [ IUPAC ]

charge

0

formula

C26H28O9

has obo namespace

chebi_ontology

has related synonym

(2S,3R)-3-(2,4-dioxopentyl)-3,6,8,9-tetrahydroxy-10-(3-methylbut-2-en-1-yl)-1-oxo-1,2,3,4-tetrahydroanthracen-2-yl acetate, (2S,3R)-3,6,8,9-tetrahydroxy-3-[(2Z)-2-hydroxy-4-oxopent-2-en-1-yl]-10-(3-methylbut-2-en-1-yl)-1-oxo-1,2,3,4-tetrahydroanthracen-2-yl acetate

id

CHEBI:72750

inchi

InChI=1S/C26H28O9/c1-12(2)5-6-17-18-8-15(29)9-20(31)21(18)23(32)22-19(17)11-26(34,10-16(30)7-13(3)27)25(24(22)33)35-14(4)28/h5,7-9,25,27,29,31-32,34H,6,10-11H2,1-4H3/b13-7-/t25-,26+/m1/s1

inchikey

YDWVJROLLAILGE-VAAQKJRKSA-N

mass

484.49510

monoisotopicmass

484.17333

smiles

CC(=O)O[C@@H]1C(=O)c2c(O)c3c(O)cc(O)cc3c(CC=C(C)C)c2C[C@@]1(O)CC(=O)\C=C(\C)O