Irofulven
PubChem CID
148189
Structure
Molecular Formula
Synonyms
- Irofulven
- 158440-71-2
- HMAF
- MGI 114
- (-)-Irofulven
Molecular Weight
246.30 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
- Create:2005-03-26
- Modify:2025-01-11
Description
Irofulven is a member of cyclohexenones.
A novel anti-cancer compound synthesized by scientists at the University of California, San Diego more than a decade ago from toxins of the poisonous jack-o-lantern mushroom, has been granted “fast track” status by the U.S. Food and Drug Administration (FDA) after demonstrating promise against one of the most deadly cancers. MGI-114 (Irofulven) is currently being developed by MGI PHARMA, Inc., an emerging oncology-focused pharmaceutical company based in Minneapolis. Phase III clinical trials involving the drug have been underway since early 2001 at sites in the U.S. and Europe.
Irofulven is a semisynthetic sesquiterpene derivative of illudin S, a natural toxin isolated from the fungus Omphalotus illudens. Irofulven alkylates DNA and protein macromolecules, forms adducts, and arrests cells in the S-phase of the cell cycle. This agent requires NADPH-dependent metabolism by alkenal/one oxidoreductase for activity. Irofulven is more active in vitro against tumor cells of epithelial origin and is more resistant to deactivation by p53 loss and MDR1 than other alkylating agents. (NCI04)
Chemical Structure Depiction
(5'R)-5'-hydroxy-1'-(hydroxymethyl)-2',5',7'-trimethylspiro[cyclopropane-1,6'-indene]-4'-one
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)
InChI=1S/C15H18O3/c1-8-6-10-12(11(8)7-16)9(2)15(4-5-15)14(3,18)13(10)17/h6,16,18H,4-5,7H2,1-3H3/t14-/m0/s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
NICJCIQSJJKZAH-AWEZNQCLSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
CC1=C(C2=C(C3(CC3)[C@@](C(=O)C2=C1)(C)O)C)CO
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)
C15H18O3
Computed by PubChem 2.2 (PubChem release 2021.10.14)
- 6-(hydroxymethyl)acylfulvene
- 6-hydroxymethylacylfulvene
- HMAF cpd
- irofulven
- MGI 114
- MGI-114
- MGI.114
- Irofulven
- 158440-71-2
- HMAF
- MGI 114
- (-)-Irofulven
- 6-Hydroxymethylacylfulvene
- MGI-114
- (R)-Irofulven
- NSC 683863
- (hydroxymethyl)acylfulvene
- (5'R)-5'-hydroxy-1'-(hydroxymethyl)-2',5',7'-trimethylspiro[cyclopropane-1,6'-indene]-4'-one
- NSC-683863
- MGI114
- 6B799IH05A
- LP-100
- (R)-6'-Hydroxy-3'-(hydroxymethyl)-2',4',6'-trimethylspiro(cyclopropane-1,5'-(5H)inden)-7'(6'H)-one
- Spiro[cyclopropane-1,5'-[5H]inden]-7'(6'H)-one, 6'-hydroxy-3'-(hydroxymethyl)-2',4',6'-trimethyl-, (6'R)-
- 6-(Hydroxymethyl)acylfulvene
- Acylfulvene, 6-(hydroxymethyl)-
- Irofulven [USAN:INN]
- UNII-6B799IH05A
- MGI.114
- IROFULVEN [INN]
- IROFULVEN [MI]
- Irofulven (USAN/INN)
- IROFULVEN [USAN]
- IROFULVEN [WHO-DD]
- SCHEMBL8800
- CHEMBL118218
- DTXSID50166423
- CHEBI:135002
- NICJCIQSJJKZAH-AWEZNQCLSA-N
- BDBM50410835
- NSC683863
- AKOS027256650
- DB05786
- HY-14429
- MS-23493
- NCI60_030149
- Spiro(cyclopropane-1,5'(5H)-inden)-7'(6'H)-one, 6'-hydroxy-3'-(hydroxymethyl)-2',4',6'-trimethyl-, (R)-
- CS-0003353
- NS00069566
- D04614
- G12892
- Q6072197
Property Name
Property Value
Reference
Property Name
Molecular Weight
Property Value
246.30 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
-0.2
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
246.125594432 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
246.125594432 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
57.5 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
18
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
558
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
1
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)
Pharmaceuticals -> Listed in ZINC15
S55 | ZINC15PHARMA | Pharmaceuticals from ZINC15 | DOI:10.5281/zenodo.3247749
Follow these links to do a live 2D search or do a live 3D search for this compound, sorted by annotation score. This section is deprecated (see here for details), but these live search links provide equivalent functionality to the table that was previously shown here.
Same Connectivity Count
Same Stereo Count
Same Isotope Count
Same Parent, Connectivity Count
Same Parent, Stereo Count
Same Parent, Isotope Count
Similar Compounds (2D)
Similar Conformers (3D)
Same Count
Investigated for use/treatment in brain cancer, breast cancer, endometrial cancer, liver cancer, lung cancer, ovarian cancer, pancreatic cancer, pediatric indications, prostate cancer, and sarcoma.
Antineoplastic Agents, Alkylating
A class of drugs that differs from other alkylating agents used clinically in that they are monofunctional and thus unable to cross-link cellular macromolecules. Among their common properties are a requirement for metabolic activation to intermediates with antitumor efficacy and the presence in their chemical structures of N-methyl groups, that after metabolism, can covalently modify cellular DNA. The precise mechanisms by which each of these drugs acts to kill tumor cells are not completely understood. (From AMA, Drug Evaluations Annual, 1994, p2026) (See all compounds classified as Antineoplastic Agents, Alkylating.)
Radiation-Sensitizing Agents
Drugs used to potentiate the effectiveness of radiation therapy in destroying unwanted cells. (See all compounds classified as Radiation-Sensitizing Agents.)
MGI-114(Irofulven) has unique mechanism of action as an anti-tumor agent is due to its ability to be rapidly absorbed by tumor cells. Once inside the cells, the compound binds to DNA and protein targets. This binding interferes with DNA replication and cell division of tumor cells, leading to tumor-specific apoptotic cell death, or “cell suicide.” During this process, tumor cells tend to automatically shut themselves down when they sense their function is compromised.
Patents are available for this chemical structure:
https://patentscope.wipo.int/search/en/result.jsf?inchikey=NICJCIQSJJKZAH-AWEZNQCLSA-N
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- ChemIDplusIrofulven [USAN:INN]https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0158440712ChemIDplus Chemical Information Classificationhttps://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
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- Therapeutic Target Database (TTD)
- DTP/NCILICENSEUnless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.https://www.cancer.gov/policies/copyright-reuse
- EU Clinical Trials Register
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- Metabolomics Workbench
- NORMAN Suspect List ExchangeLICENSEData: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0https://creativecommons.org/licenses/by/4.0/IrofulvenNORMAN Suspect List Exchange Classificationhttps://www.norman-network.com/nds/SLE/
- SpectraBase
- Springer Nature
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- Wikipedia
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- Medical Subject Headings (MeSH)LICENSEWorks produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.https://www.nlm.nih.gov/copyright.htmlAntineoplastic Agents, Alkylatinghttps://www.ncbi.nlm.nih.gov/mesh/68018906Radiation-Sensitizing Agentshttps://www.ncbi.nlm.nih.gov/mesh/68011838
- MolGenieMolGenie Organic Chemistry Ontologyhttps://github.com/MolGenie/ontology/
- PATENTSCOPE (WIPO)SID 388784638https://pubchem.ncbi.nlm.nih.gov/substance/388784638
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