≥98% for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
Store at -20°C Ships Ice chest + Ice pads Check lot-specific COA for exact specifications.
SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.
Cited in 0 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
CR-1-31-B is a synthetic rocaglate and a potent eIF4A inhibitor. CR-1-31-B exhibits powerful inhibitory effects over eIF4A by perturbing the interaction between eIF4A and RNA, sequentially impeding initiation during protein synthesis. CR-1-31-B perturbs association of Plasmodium falciparum eIF4A (PfeIF4A) with RNA. CR-1-31-B induces apoptosis of neuroblastoma and gallbladder cancer cells
In Vitro
CR-1-31-B (100 nM; 24 hours) inhibits MUC1-C translation in MCF-10A cells (EGF-stimulated). ?\nCR-1-31-B (10 and 100 nM) decreases MUC1-C abundance in MDA-MB-468 breast cancer cells. ?\nCR-1-31B sensitizes gallbladder cancer cells to TRAIL-mediated apoptosis through the translational downregulation of c-FLIP. ?\nNeuroblastoma (NB) cell lines exhibit decreased viability, increased apoptosis rates as well as changes in cell cycle distribution when treated with the synthetic rocaglate CR-1-31-B (24-72 hours), which clamps eIF4A and eIF4F onto mRNA, resulting in a translational block . ?\nCR-1-31-B (100 nM; 5 hours) treatment increases reverse glutamine metabolism in pancreatic cancer cells . MCE has not independently confirmed the accuracy of these methods. They are for reference only. Western Blot AnalysisCell Line: MCF-10A cells (EGF-stimulated) Concentration: 100 nM Incubation Time: 24 hours Result: Blocked increases in MUC1-C abundance. Cell Viability Assay Cell Line: SH-SY5Y cells and Kelly cells Concentration: 0.1-100 nM Incubation Time: 24-72 hours Result: A significant decrease in SH-SY5Y viability was observed at 10 nM for all time points. Significantly decreased the viability of Kelly cells at 5 nM. The calculated IC 50 at 48 h was 20 nM for SH-SY5Y and 4 nM for Kelly cells. Apoptosis Analysis Cell Line: SH-SY5Y and Kelly cells Concentration: SH-SY5Y cells were treated with 10, 20, and 50 nM and Kelly cells with 1, 5, and 10 nM Incubation Time: 24-72 hours Result: Triggered apoptosis.
In Vivo
CR-1-31-B (2 mg/kg in 60 μL olive oil; IP; once every 2 days for 28 days) reduces the growth and initiates TRAIL-induced apoptosis in a BALB/c nude mice model of gallbladder cancer cells (GBC). ?\nCR-1-31-B (0.2?mg/kg;? IP; daily for 7 days; murine orthotopic transplant model of pancreatic ductal adenocarcinoma) effectively inhibits protein synthesis and growth of pancreatic tumours. MCE has not independently confirmed the accuracy of these methods. They are for reference only.
Form:Solid
IC50& Target:eIF4
| Canonical Smiles | COC1=CC=C(C=C1)C23C(C(C(C2(C4=C(O3)C=C(C=C4OC)OC)O)O)C(=O)NOC)C5=CC=CC=C5 |
|---|---|
| IUPAC Name | (1R,2R,3S,3aR,8bS)-1,8b-dihydroxy-N,6,8-trimethoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-2-carboxamide |
| InChIKey | KLSIFOJPWJBRFH-GWNOIRNCSA-N |
| INCHI | 1S/C28H29NO8/c1-33-18-12-10-17(11-13-18)28-23(16-8-6-5-7-9-16)22(26(31)29-36-4)25(30)27(28,32)24-20(35-3)14-19(34-2)15-21(24)37-28/h5-15,22-23,25,30,32H,1-4H3,(H,29,31)/t22-,23-,25-,27+,28+/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)NOC)C5=CC=CC=C5 |
| PubChem CID | 56946209 |
| Molecular Weight | 507.53 |
Comprehensive hazard, handling, storage, and regulatory compliance document.
Download SDS →Lot-specific quality data. Enter your lot number to retrieve the exact COA.
Look up COA →Full quality attributes and acceptance criteria for this grade.
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 Phenoxy compounds Anisoles Methoxybenzenes Alkyl aryl ethers Tertiary alcohols Secondary alcohols 1,2-diols Cyclic alcohols and derivatives Oxacyclic compounds Carboxylic acids and derivatives Organopnictogen compounds Carbonyl compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Flavagline skeleton - Stilbene - Coumaran - Phenoxy compound - Anisole - Methoxybenzene - Phenol ether - Alkyl aryl ether - Monocyclic benzene moiety - Benzenoid - Cyclic alcohol - Tertiary alcohol - 1,2-diol - Secondary alcohol - Carboxylic acid derivative - Ether - Oxacycle - Alcohol - Hydrocarbon derivative - Organic nitrogen compound - Carbonyl group - Organic oxide - Organopnictogen compound - Organic oxygen compound - Organonitrogen compound - Organooxygen 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 |
| Activity Type | Activity Value -log(M) | Mechanism of Action | Activity Reference | Publications (PubMed IDs) |
|---|
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
| Solubility | DMSO : 230 mg/mL (453.18 mM; Need ultrasonic) |
|---|
