Structure Database (LMSD)

Common Name
(-)-Illudin S
Systematic Name
(-)-1α,7β,12-trihydroxy-2,9-illudadien-8-one
Synonyms
LM ID
LMPR0103590002
Formula
C15H20O4
Exact Mass
Calculate m/z
264.13616
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View NP-MRD ID(NMR) spectrum

Classification

Category
Main Class
Sub Class
Level 4 Class
Prenol Lipids [PR]
Isoprenoids [PR01]
C15 isoprenoids (sesquiterpenes) [PR0103]
Illudane and protoilludane sesquiterpenoids [PR010359]

Biological Context

Illudin S is a cytotoxic illudin that is converted, intracellularly, to metabolites that cause a complete block of cell cycling at the G1-S phase interface, particularly in myeloid and T-lymphocyte leukemia cells (IC50 = 6-11 nM).1 T-lymphocyte leukemia CEM cells that are resistant to doxorubicin , epipodophyllotoxins, and 1-β-D-arabinofuranosylcytosine display only 2-fold increased resistance to illudin S.1 Illudin S metabolites induce DNA damage that is not repaired by the processes that counter conventional DNA alkylating agents.2,3,4

This information has been provided by Cayman Chemical

References

1. Schobert, R., Knauer, S., Seibt, S., et al. Anticancer active illudins: Recent developments of a potent alkylating compound class. Curr. Med. Chem. 18, 790-807 (2011).
2. Kelner, M.J., McMorris, T.C., Estes, L., et al. Characterization of illudin S sensitivity in DNA repair-deficient Chinese hamster cells. Unusually high sensitivity of ERCC2 and ERCC3 DNA helicase-deficient mutants in comparison to other chemotherapeutic agents. Biochem. Pharmacol. 48, 403-409 (1994).
3. Kelner, M.J., McMorris, T.C., Beck, W.T., et al. Preclinical evaluation of illudins as anticancer agents. Cancer Res. 47(12), 3186-3189 (1987).
4. Jaspers, N.G.J., Raams, A., Kelner, M.J., et al. Anti-tumour compounds illudin S and Irofulven induce DNA lesions ignored by global repair and exclusively processed by transcription- and replication-coupled repair pathways. DNA Repair (Amst) 1(12), 1027-1038 (2002).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Omphalotus nidiformis (#71963)
Agaricomycetes (#155619)
Identification of illudins in Omphalotus nidiformis and Omphalotus olivascens var. indigo by column liquid chromatography-atmospheric pressure chemical ionization tandem mass spectrometry.,
J Chromatogr A, 1999
Pubmed ID: 10070774

String Representations

InChiKey (Click to copy)
DDLLIYKVDWPHJI-RDBSUJKOSA-N
InChi (Click to copy)
InChI=1S/C15H20O4/c1-8-10-9(6-13(2,7-16)12(10)18)11(17)14(3,19)15(8)4-5-15/h6,12,16,18-19H,4-5,7H2,1-3H3/t12-,13+,14+/m1/s1
SMILES (Click to copy)
[C@@]1(C)(O)C(=O)C2=C[C@](CO)(C)[C@H](O)C2=C(C)C21CC2

Other Databases

Wikipedia
Illudin_S
KEGG ID
C09688
CHEBI ID
5867
PubChem CID
344200
Cayman ID
17451

Calculated Physicochemical Properties

Heavy Atoms 19
Rings 3
Aromatic Rings 0
Rotatable Bonds 1
Van der Waals Molecular Volume 258.22
Topological Polar Surface Area 77.76
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 4
logP 1.57
Molar Refractivity 70.79

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Created at
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Updated at
14th Nov 2024