| Identification | Back Directory | [Name]
illudin S | [CAS]
1149-99-1 | [Synonyms]
Illudin
CS-1385
Lunamycin
illudin S
Illusin S
Lampterol
NSC-626369
Illudine S
NSC 400979
(1R,2S,5R)-1,5-dihydroxy-2-(hydroxymethyl)-2,5,7-trimethylspiro[1H-indene-6,1'-cyclopropane]-4-one
(2'S,3'R,6'R)-2',3'-Dihydro-3',6'-dihydroxy-2'-hydroxymethyl-2',4',6'-trimethylspiro[cyclopropane-1,5'-[5H]inden]-7'(6'H)-one
Spiro[cyclopropane-1,5'-[5H]inden]-7'(6'H)-one, 2',3'-dihydro-3',6'-dihydroxy-2'-(hydroxymethyl)-2',4',6'-trimethyl-, (2'S,3'R,6'R)- | [Molecular Formula]
C15H20O4 | [MDL Number]
MFCD00870487 | [MOL File]
1149-99-1.mol | [Molecular Weight]
264.32 |
| Chemical Properties | Back Directory | [Melting point ]
124-126℃ | [Boiling point ]
327.55°C (rough estimate) | [density ]
1.0583 (rough estimate) | [refractive index ]
1.4300 (estimate) | [storage temp. ]
-20°C, Inert atmosphere | [solubility ]
DMSO (Slightly), Methanol (Slightly) | [form ]
A light yellow solid | [pka]
12.50±0.70(Predicted) | [color ]
Off-white to yellow | [InChI]
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 | [InChIKey]
DDLLIYKVDWPHJI-RDBSUJKOSA-N | [SMILES]
C12([C@](O)(C)C(=O)C3C(=C1C)[C@@H](O)[C@@](CO)(C)C=3)CC2 |
| Hazard Information | Back Directory | [Description]
Illudins are fungal sesquiterpenes that, through their unique DNA alkylating actions, have anticancer potential.1,2 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 (Item No. 15007), 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 | [Uses]
Illudin S is potent antitumor sesquiterpene, first isolated from the fungus, Clitocybe illudens, in 1963. Illudin S is metabolically activated to reactive intermediates that bind DNA. The DNA damage appears to differ from that of other reactive metabolites. Importantly, illudin S exhibits in vitro and in vivo potency against multi-drug resistant tumours. | [Definition]
ChEBI: Illudin S is a sesquiterpenoid. | [References]
[1] De Souza, F.I., Zumiotti, A.V., and Da Silva, C.F. Neuregulins 1-α and 1-β on the regeneration the peripheral nerves[J]. Acta Ortop Bras.
[2] NICOLAAS G.J JASPERS . Anti-tumour compounds illudin S and Irofulven induce DNA lesions ignored by global repair and exclusively processed by transcription- and replication-coupled repair pathways[J]. DNA Repair, 2002, 1 12: Pages 1027-1038. DOI: 10.1016/s1568-7864(02)00166-0 |
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