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CHEBI:72750 - neosartoricin

ChEBI IDCHEBI:72750
ChEBI Nameneosartoricin
Stars
DefinitionA 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 μM, suggesting a possible physiological role as an immunosuppressive agent.
Last Modified5 August 2014
SubmitterGareth Owen
DownloadsMolfile
FormulaC26H28O9
Net Charge0
Average Mass484.501
Monoisotopic Mass484.17333
SMILESCC(=O)O[C@@H]1C(=O)c2c(c(CC=C(C)C)c3cc(O)cc(O)c3c2O)C[C@@]1(O)CC(=O)/C=C(/C)O
InChIInChI=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
InChIKeyYDWVJROLLAILGE-VAAQKJRKSA-N
Roles Classification
Biological Roles:
fungal metabolite  Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
immunosuppressive agent  An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.
Application:
immunosuppressive agent  An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.
ChEBI Ontology
Outgoing Relation(s)
neosartoricin (CHEBI:72750) has part prenyl group (CHEBI:26248)
neosartoricin (CHEBI:72750) has role fungal metabolite (CHEBI:76946)
neosartoricin (CHEBI:72750) has role immunosuppressive agent (CHEBI:35705)
neosartoricin (CHEBI:72750) is a acetate ester (CHEBI:47622)
neosartoricin (CHEBI:72750) is a anthracenes (CHEBI:46955)
neosartoricin (CHEBI:72750) is a carbotricyclic compound (CHEBI:38032)
neosartoricin (CHEBI:72750) is a cyclic ketone (CHEBI:3992)
neosartoricin (CHEBI:72750) is a phenols (CHEBI:33853)
neosartoricin (CHEBI:72750) is a polyketide (CHEBI:26188)
neosartoricin (CHEBI:72750) is a tertiary alcohol (CHEBI:26878)
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
Synonyms  Source
(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 acetateIUPAC
(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 acetateIUPAC
Citations