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CHEBI:72750 - neosartoricin

Default Structure
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:
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.
fungal metabolite  Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
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-(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
(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
Citations