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ChemicalBook--->CAS DataBase List--->1149-99-1

1149-99-1

1149-99-1 Structure

1149-99-1 Structure
IdentificationBack 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 PropertiesBack 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
Hazard InformationBack Directory
[Description]

Illudins are fungal sesquiterpenes that, through their unique DNA alkylating actions, have anticancer potential. 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). 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. Illudin S metabolites induce DNA damage that is not repaired by the processes that counter conventional DNA alkylating agents.
[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.
Spectrum DetailBack Directory
[Spectrum Detail]

illudin S(1149-99-1)1HNMR
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