| Identification | Back Directory | [Name]
illudin M | [CAS]
1146-04-9 | [Synonyms]
illudin M
(3S)-2,3-Dihydro-3α,6β-dihydroxy-2,2,4,6-tetramethylspiro[5H-indene-5,1'-cyclopropan]-7(6H)-one
(3'S,6'R)-2',3'-Dihydro-3',6'-dihydroxy-2',2',4',6'-tetramethylspiro[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',2',4',6'-tetramethyl-, (3'S,6'R)- | [Molecular Formula]
C15H20O3 | [MDL Number]
MFCD01683965 | [MOL File]
1146-04-9.mol | [Molecular Weight]
248.32 |
| Chemical Properties | Back Directory | [Melting point ]
120-122.5° (Matsumoto); mp 128-130° (McMorris) | [Boiling point ]
452.4±45.0 °C(Predicted) | [density ]
1.24±0.1 g/cm3(Predicted) | [storage temp. ]
Store at -20°C | [solubility ]
DMF: Soluble; DMSO: Soluble; Ethanol: Soluble; Methanol: Soluble | [form ]
A solid | [pka]
12.57±0.70(Predicted) | [color ]
Off-white to light yellow | [InChI]
InChI=1S/C15H20O3/c1-8-10-9(7-13(2,3)12(10)17)11(16)14(4,18)15(8)5-6-15/h7,12,17-18H,5-6H2,1-4H3/t12-,14+/m1/s1 | [InChIKey]
QVMDIQLUNODCTG-OCCSQVGLSA-N | [SMILES]
C12([C@](O)(C)C(=O)C3C(=C1C)[C@@H](O)C(C)(C)C=3)CC2 |
| Hazard Information | Back Directory | [Description]
Illudin M is a cytotoxic sesquiterpene from the fungus O. illudens that alkylates DNA.1 It is cytotoxic to HL-60 human leukemia cells at 6-100 nM.2 Illudin M was used as a base structure for the development of potential anticancer agents with less toxicity and improved efficacy.3,1 It is closely related to illudin S (Item No. 17451), which has been the focus of additional studies. | [Uses]
Illudin M is a cytotoxic sesquiterpene from Omphalotus illudens and Granulobasidium vellereum. It acts as an alkylating agent that can cause inhibition of cell growth or replication. | [Definition]
ChEBI: Illudin M is a sesquiterpenoid. | [storage]
Store at -20°C | [References]
[1] J. JACOBSON. Pharmacokinetics, Safety, and Antiviral Effects of Hypericin, a Derivative of St. John’s Wort Plant, in Patients with Chronic Hepatitis C Virus Infection[J]. Antimicrobial Agents and Chemotherapy, 2001, 45 1: 517-524. DOI: 10.1128/aac.45.2.517-524.2001
[2] M J KELNER. Preclinical evaluation of illudins as anticancer agents.[J]. Cancer research, 1987, 47 12: 3186-3189.
[3] R SCHOBERT. Anticancer active illudins: recent developments of a potent alkylating compound class.[J]. Current medicinal chemistry, 2011, 18 6: 790-807. DOI: 10.2174/092986711794927766 |
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