Harringtonolide - ≥98% , CAS No.64761-48-4

CAS: 64761-48-4 Cat. No.: H651650 Formula: C₁₉H₁₈O₄ Molecular Weight: 310.34 PubChem CID: 188356

GRADE & PURITY ≥98%

Synonyms

Harringtonolide|5,11-Dimethyl-2a,4a,9,10,10b,10c-hexahydro-1H-3,10a-methano-2,4-dioxacyclohepta[bc]cyclopenta[jk]acenaphthylene-1,7(3H)-dione|(11s,12r,13s,19r)-8,19-dimethyl-14,17-dioxahexacyclo[13.3.1.01,11.04,10.09,13.012,16]nonadeca-4,7,9-triene-6,18-dione

Storage

Protected from light,Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

Harringtonolide is a potent RACK1 inhibitor ( IC 50 =39.66 μM in A375 cells). Harringtonolide inhibits the epithelial-mesenchymal transition (EMT) process and cell proliferation by affecting the interaction between FAK and RACK1 . Harringtonolide has plant growth inhibitory, antiviral, anti-inflammatory, and antiproliferation activities

In Vitro

Harringtonolide (0-50 μM; 24 hours) exhibits good antiproliferation activity in A375 cells with IC 50 of 39.66 μM. Harringtonolide (0-20 μM; 1 hour) restrains the proteolysis of RACK1 by Pronase, and protects temperature-dependent degradation of RACK1. Harringtonolide (0-4 μM; 24 hours) suppresses the phosphorylation of FAK dose-dependently and inhibits Src and STAT3, the downstream proteins of FAK. Harringtonolide (0-4 μM; 24 hours) dose-dependently inhibits the RACK1–FAK interaction in A375 cells. MCE has not independently confirmed the accuracy of these methods. They are for reference only. Cell Proliferation Assay Cell Line: A375 melanoma cellsConcentration: 0-50 μM Incubation Time: 24 hours Result: Showed good antiproliferation activity with IC 50 of 39.66 μM. Western Blot Analysis Cell Line: A375 melanoma cellsConcentration: 0, 0.5, 1, 2, 4 μM Incubation Time: 24 hours Result: Suppressed the phosphorylation of FAK dose-dependently and inhibited Src and STAT3, the downstream proteins of FAK.

Form:Solid

IC50& Target:IC 50 : 39.66 μM (RACK1) in A375 cells

Specifications

Synonyms

Harringtonolide | 5,11-Dimethyl-2a,4a,9,10,10b,10c-hexahydro-1H-3,10a-methano-2,4-dioxacyclohepta[bc]cyclopenta[jk]acenaphthylene-1,7(3H)-dione | (11s,12r,13s,19r)-8,19-dimethyl-14,17-dioxahexacyclo[13.3.1.01,11.04,10.09,13.012,16]nonadeca-4,7,9-triene-6,18-dione

Specifications & Purity

≥98%

Biochemical and Physiological Mechanisms

Harringtonolide is a potent RACK1 inhibitor ( IC 50 =39.66 μM in A375 cells). Harringtonolide inhibits the epithelial-mesenchymal transition (EMT) process and cell proliferation by affecting the interaction between FAK and RACK1 . Harringtonolide has plan

Storage

Protected from light,Store at -80°C

Shipped In

Dry ice packs + Cold packs

This product requires cold chain shipping. Ground and other economy services are not available.

Action Type

INHIBITOR

Purity

≥98%

Names and Identifiers

Canonical Smiles

CC1C2C3C4C5C1(CCC6=CC(=O)C=C(C(=C56)C4O2)C)C(=O)O3

IUPAC Name

(11S,12R,13S,19R)-8,19-dimethyl-14,17-dioxahexacyclo[13.3.1.01,11.04,10.09,13.012,16]nonadeca-4,7,9-triene-6,18-dione

InChIKey

QNJIIOHVULPMRL-OFSDVKARSA-N

INCHI

1S/C19H18O4/c1-7-5-10(20)6-9-3-4-19-8(2)15-17(23-18(19)21)13-14(19)12(9)11(7)16(13)22-15/h5-6,8,13-17H,3-4H2,1-2H3/t8-,13+,14+,15?,16+,17?,19?/m0/s1

Isomeric SMILES

C[C@H]1C2C3[C@@H]4[C@@H]5C1(CCC6=CC(=O)C=C(C(=C56)[C@H]4O2)C)C(=O)O3

Alternate CAS

64761-48-4

PubChem CID

188356

MeSH Entry Terms

hainanolide;harringtonolide

Molecular Weight

310.34

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Furopyrans

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Furopyrans
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Furopyrans
• Alternative Parents: Tropones Oxepanes Delta valerolactones Pyrans Oxanes Tetrahydrofurans Furans Cyclic ketones Carboxylic acid esters Oxacyclic compounds Monocarboxylic acids and derivatives Dialkyl ethers Organic oxides
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Furopyran - Tropone - Oxepane - Delta_valerolactone - Delta valerolactone - Pyran - Oxane - Tetrahydrofuran - Furan - Cyclic ketone - Lactone - Carboxylic acid ester - Oxacycle - Monocarboxylic acid or derivatives - Ether - Dialkyl ether - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as furopyrans. These are organic polycyclic compounds containing a furan ring fused to a pyran ring. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y