Didesmethylrocaglamide, a derivative of Rocaglamide, is a potent eukaryotic initiation factor 4A (eIF4A) inhibitor. Didesmethylrocaglamide has potent growth-inhibitory activity with an IC 50 of 5 nM. Didesmethylrocaglamide suppresses multiple growth-promoting signaling pathways and induces apoptosis in tumor cells. Antitumor activity
In Vitro
Didesmethylrocaglamide (5 nM, and 10 nM; 72 hours; MPNST cells) treatment arrests MPNST cells at G2-M, increases the sub-G1 population, induces cleavage of caspases and PARP, and elevates the levels of the DNA-damage response marker γH2A.X, while decreasing the expression of AKT and ERK1/2. Didesmethylrocaglamide inhibits MPNST cell proliferation by inducing cell cycle arrest at G2/M and subsequently, cell death. Didesmethylrocaglamide-treated 697-R cells exhibits IC 50 values is very similar to those of parental 697 cells (4 vs 3nM of IC 50 , respectively). Didesmethylrocaglamide induces apoptosis in both neurofibromatosis type 1 (NF1)-expressing and NF1-deficient MPNST cells, possibly subsequent to the activation of the DNA damage response. Didesmethylrocaglamide-treated sarcoma cells show decreased levels of multiple oncogenic kinases, including insulin-like growth factor-1 receptor. MCE has not independently confirmed the accuracy of these methods. They are for reference only. Western Blot AnalysisCell Line: Malignant peripheral nerve sheath tumors (MPNST) cells Concentration: 5 nM, and 10 nM Incubation Time: 72 hours Result: Induced cleavage of caspases and PARP, and elevated the levels of the DNA-damage response marker γH2A.X.
Form:Solid
IC50& Target:Eukaryotic initiation factor 4A (eIF4A)
| Canonical Smiles | COC1=CC=C(C=C1)C23C(C(C(C2(C4=C(O3)C=C(C=C4OC)OC)O)O)C(=O)N)C5=CC=CC=C5 |
|---|---|
| IUPAC Name | (1R,2R,3S,3aR,8bS)-1,8b-dihydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-2-carboxamide |
| InChIKey | RMNPQEWLGQURNX-PXIJUOARSA-N |
| INCHI | 1S/C27H27NO7/c1-32-17-11-9-16(10-12-17)27-22(15-7-5-4-6-8-15)21(25(28)30)24(29)26(27,31)23-19(34-3)13-18(33-2)14-20(23)35-27/h4-14,21-22,24,29,31H,1-3H3,(H2,28,30)/t21-,22-,24-,26+,27+/m1/s1 |
| Isomeric SMILES | COC1=CC=C(C=C1)[C@]23[C@@H]([C@H]([C@H]([C@]2(C4=C(O3)C=C(C=C4OC)OC)O)O)C(=O)N)C5=CC=CC=C5 |
| PubChem CID | 397614 |
| NSC Number | 705956 |
| Molecular Weight | 477.51 |
Comprehensive hazard, handling, storage, and regulatory compliance document.
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View spec sheet →Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Organoheterocyclic compounds |
| Class | Benzofurans |
| Subclass | Flavaglines |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Flavaglines |
| Alternative Parents | Stilbenes Coumarans Anisoles Methoxybenzenes Phenoxy compounds Alkyl aryl ethers Tertiary alcohols Cyclic alcohols and derivatives 1,2-diols Primary carboxylic acid amides Secondary alcohols Oxacyclic compounds Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Flavagline skeleton - Stilbene - Coumaran - Phenoxy compound - Anisole - Phenol ether - Methoxybenzene - Alkyl aryl ether - Monocyclic benzene moiety - Benzenoid - Cyclic alcohol - Tertiary alcohol - 1,2-diol - Carboxamide group - Primary carboxylic acid amide - Secondary alcohol - Ether - Carboxylic acid derivative - Oxacycle - Organonitrogen compound - Hydrocarbon derivative - Organic oxide - Alcohol - Carbonyl group - Organopnictogen compound - Organooxygen compound - Organic nitrogen compound - Organic oxygen compound - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as flavaglines. These are heterocyclic compounds with a structure characterized by a cyclopenta[b]benzofuran skeleton. |
| External Descriptors | Not available |
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| Solubility | DMSO : 100 mg/mL (209.42 mM; Need ultrasonic) |
|---|---|
| Molecular Weight | 477.500 g/mol |
| XLogP3 | 2.200 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 7 |
| Rotatable Bond Count | 6 |
| Exact Mass | 477.179 Da |
| Monoisotopic Mass | 477.179 Da |
| Topological Polar Surface Area | 120.000 Ų |
| Heavy Atom Count | 35 |
| Formal Charge | 0 |
| Complexity | 767.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 5 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 0 |
| Covalently-Bonded Unit Count | 1 |
