Ergolide - Moligand™, ≥98% , CAS No.54999-07-4

CAS: 54999-07-4 Cat. No.: E648474 Formula: C₁₇H₂₂O₅ Molecular Weight: 306.35

GRADE & PURITY Moligand™, ≥98%

Synonyms

(3ar,4s,4ar,7as,8r,9as)-4a,8-dimethyl-3-methylidene-2,5-dioxododecahydroazuleno[6,5-b]furan-4-yl acetate | Q27137681 | Dihydrobigelovin | HY-N6893 | Ergolide | 4a,8-Dimethyl-3-methylidene-2,5-dioxododecahydroazuleno[6,5-b]furan-4-yl acetate | MS-24435 | D

Storage

Protected from light,Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Ergolide is a dual inhibitor targeting NF-κB/p65 and NLRP3. Ergolide blocks the NF-κB signaling pathway and the nuclear translocation of p65, and irreversibly binds to the NACHT domain of NLRP3 to inhibit inflammasome assembly. Ergolide significantly reduces the production of inflammatory mediators (e.g., NO, PGE2) and cytokines, induces cancer cell apoptosis (apoptosis), autophagy (autophagy) and ROS generation. Ergolide also enhances the anti-tumor effect of vincristine. Ergolide alleviates acute lung injury via an NLRP3-dependent mechanism, and effectively improves the survival rate and behavioral function of septic mice and inflammatory zebrafish models. Ergolide is used in the research of metastatic uveal melanoma, neurodegenerative diseases (such as Alzheimer's disease, Parkinson's disease), sepsis and acute lymphoblastic leukemia .

Specifications

Synonyms

(3ar,4s,4ar,7as,8r,9as)-4a,8-dimethyl-3-methylidene-2,5-dioxododecahydroazuleno[6,5-b]furan-4-yl acetate | Q27137681 | Dihydrobigelovin | HY-N6893 | Ergolide | 4a,8-Dimethyl-3-methylidene-2,5-dioxododecahydroazuleno[6,5-b]furan-4-yl acetate | MS-24435 | D

Specifications & Purity

Moligand™, ≥98%

Biochemical and Physiological Mechanisms

Ergolide is a sesquiterpene lactone isolated from the dried flowers of Inula Britannica . Ergolide inhibits inducible nitric oxide synthase and cyclo-oxygenase-2 expression in RAW 264.7 macrophages through the inactivation of NF-κB.

Storage

Protected from light,Store at -20°C

Shipped In

Ice chest + Ice pads

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

Grade

Moligand™

Action Type

INHIBITOR

Purity

≥98%

Names and Identifiers

Canonical Smiles

CC1CC2C(C(C3(C1CCC3=O)C)OC(=O)C)C(=C)C(=O)O2

IUPAC Name

[(3aS,5R,5aS,8aR,9S,9aR)-5,8a-dimethyl-1-methylidene-2,8-dioxo-3a,4,5,5a,6,7,9,9a-octahydroazuleno[6,5-b]furan-9-yl] acetate

InChIKey

JCDZXDWMCKMXFF-MMLVVLEOSA-N

INCHI

1S/C17H22O5/c1-8-7-12-14(9(2)16(20)22-12)15(21-10(3)18)17(4)11(8)5-6-13(17)19/h8,11-12,14-15H,2,5-7H2,1,3-4H3/t8-,11+,12+,14-,15+,17+/m1/s1

Isomeric SMILES

C[C@@H]1C[C@H]2[C@H]([C@@H]([C@]3([C@H]1CCC3=O)C)OC(=O)C)C(=C)C(=O)O2

Alternate CAS

54999-07-4

MeSH Entry Terms

ergolide

Molecular Weight

306.35

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Prenol lipids
      • Subclass Terpene lactones

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Prenol lipids
• Subclass: Terpene lactones
• Intermediate Tree Nodes: Not available
• Direct Parent: Sesquiterpene lactones
• Alternative Parents: Ambrosanolides and secoambrosanolides Pseudoguaianes Gamma butyrolactones Dicarboxylic acids and derivatives Tetrahydrofurans Enoate esters Ketones Oxacyclic compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Helenalin-skeleton - Ambrosanolide - Pseudoguaiane sesquiterpenoid - Sesquiterpenoid - Dicarboxylic acid or derivatives - Gamma butyrolactone - Enoate ester - Tetrahydrofuran - Alpha,beta-unsaturated carboxylic ester - Lactone - Ketone - Carboxylic acid ester - Oxacycle - Carboxylic acid derivative - Organoheterocyclic compound - Hydrocarbon derivative - Organic oxide - Organooxygen compound - Organic oxygen compound - Carbonyl group - Aliphatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as sesquiterpene lactones. These are sesquiterpenoids containing a lactone ring.
• External Descriptors: cyclic ketone - organic heterotricyclic compound - acetate ester - gamma-lactone - sesquiterpene lactone

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

Associated Targets(Human)

PTGS2 Tclin Cyclooxygenase-2 (13999 Activities)

Discover Target: PTGS2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Solubility: DMSO : 50 mg/mL (163.21 mM; Need ultrasonic)
• Sensitivity: light & Moisture sensitive
• Molecular Weight: 306.400 g/mol
• XLogP3: 1.700
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 306.147 Da
• Monoisotopic Mass: 306.147 Da
• Topological Polar Surface Area: 69.700 Ų
• Heavy Atom Count: 22
• Formal Charge: 0
• Complexity: 565.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 6
• 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