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Rocaglamide

CAT: 0804-HY-19356-02Size: 1 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-19356-02Size:1 mg
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Description
Rocaglamide (Roc-A) is isolated from the genus Aglaia and can be used for coughs, injuries, asthma and inflammatory skin diseases. Rocaglamide is a potent inhibitor of NF-κB activation in T-cells. Rocaglamide is a potent and selective heat shock factor 1 (HSF1) activation inhibitor with an IC50 of ~50 nM. Rocaglamide inhibits the function of the translation initiation factor eIF4A. Rocaglamide also has anticancer properties in leukemia[1][2][3].
CAS Number
84573-16-0
Product Name Alternative
Roc-A
UNSPSC
12352005
Hazard Statement
H302, H315, H319, H335
Target
Eukaryotic Initiation Factor (eIF) ; HSP; NF-κB
Type
Natural Products
Related Pathways
Cell Cycle/DNA Damage; Metabolic Enzyme/Protease; NF-κB
Applications
Cancer-programmed cell death
Field of Research
Cancer; Inflammation/Immunology
Assay Protocol
https://www.medchemexpress.com/Rocaglamide.html
Purity
99.34
Solubility
DMSO : 100 mg/mL (ultrasonic)
Smiles
O[C@]12[C@](OC3=CC(OC)=CC(OC)=C32)(C4=CC=C(C=C4)OC)[C@H](C5=CC=CC=C5)[C@H]([C@H]1O)C(N(C)C)=O
Molecular Formula
C29H31NO7
Molecular Weight
505.56
Precautions
H302, H315, H319, H335
References & Citations
[1]Santagata S, et al. Tight coordination of protein translation and heat shock factor 1 activation supports the anabolic malignant state. Science. 2013 Jul 19; 341 (6143) : 1238303.|[2]Luan Z, et al. Rocaglamide overcomes tumor necrosis factor-related apoptosis-inducing ligand resistance in hepatocellular carcinoma cells by attenuating the inhibition of caspase-8 through cellular FLICE-like-inhibitory protein downregulation. Mol Med Rep|[3]Baumann B, et al. Rocaglamide derivatives are potent inhibitors of NF-kappa B activation in T-cells. J Biol Chem. 2002 Nov 22;277 (47) :44791-800.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Natural Products
Clinical Information
No Development Reported
Isoform
EIF4; HSF1

Chemical Information

Rocaglamide

Rocaglamide is an organic heterotricyclic compound that is 2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan substituted by hydroxy groups at positions 1 and 8b, methoxy groups at positions 6 and 8, a 4-methoxyphenyl group at position 3a, a phenyl group at position 3 and a N,N-dimethylcarbamoyl group at position 1. Isolated from Aglaia odorata and Aglaia duperreana, it exhibits antineoplastic activity. It has a role as a metabolite, an antineoplastic agent and an antileishmanial agent. It is a monomethoxybenzene, an organic heterotricyclic compound and a monocarboxylic acid amide.

CAS Number84573-16-0
PubChem CID331783
IUPAC Name(1R,2R,3S,3aR,8bS)-1,8b-dihydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-2-carboxamide
Molecular FormulaC29H31NO7
Molecular Weight505.6
XLogP2.8
Topological Polar Surface Area97.7
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count7
Rotatable Bond Count6
Heavy Atom Count37
Formal Charge0
Complexity810
SMILES
CN(C)C(=O)[C@@H]1[C@H]([C@]2([C@@]([C@@H]1O)(C3=C(O2)C=C(C=C3OC)OC)O)C4=CC=C(C=C4)OC)C5=CC=CC=C5
InChI
InChI=1S/C29H31NO7/c1-30(2)27(32)23-24(17-9-7-6-8-10-17)29(18-11-13-19(34-3)14-12-18)28(33,26(23)31)25-21(36-5)15-20(35-4)16-22(25)37-29/h6-16,23-24,26,31,33H,1-5H3/t23-,24-,26-,28+,29+/m1/s1
InChIKey
DAPAQENNNINUPW-IDAMAFBJSA-N
Chemical Structure
2D Structure
2D structure of Rocaglamide
CAS: 84573-16-0
CID: 331783
Formula: C29H31NO7
MW: 505.6
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight505.6
XLogP32.8
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count7
Rotatable Bond Count6
Exact Mass505.21005233
Monoisotopic Mass505.21005233
Topological Polar Surface Area97.7 Ų
Heavy Atom Count37
Formal Charge0
Complexity810
Isotope Atom Count0
Defined Atom Stereocenter Count5
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

Alternative Products

CatalogName
MBS6062694-01Rocaglamide (Rocaglamide A)
CS-BT-00549Rocaglamide
TQ0131L-01(+) -Rocaglamide

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