Chaulmoogric acid

• CAS: 29106-32-9
• Catalog Number: ACM29106329
• Category: Main Products
• Molecular Weight: 280.45
• Molecular Formula: C₁₈H₃₂O₂
• Synonyms: Chaulmoogrinsaeure; hydnocarpylacetic acid; (-)-(S)-13-(cyclopent-2-en-1-yl)tridecanoic acid; 2-Cyclopentene-1-tridecanoic acid; 13-(Cyclopent-2-enyl)tridecanoic acid; chaulmoogric acid; 13-cyclopent-2-en-1-yltridecanoic acid; 2-Cyclopentene-1-tridecanoic acid,(S); (S)-2-Cyclopentene-1-tridecanoic acid
• IUPAC Name: (S)-chaulmoogric acid
• Boiling Point: 408.2ºC at 760mmHg
• Melting Point: 68.5ºC
• Flash Point: 305ºC
• Density: 0.948g/cm³
• Exact Mass: 280.24000

Case Study

Chaulmoogric Acid Activates Protein Phosphatase 5 via a Novel TPR Domain Unfolding Pathway Distinct from Endogenous Lipid Activators

Cher, Charmian, et al. Applied biochemistry and biotechnology 160.5 (2010): 1450-1459.

Protein phosphatase 5 (PP5) is a serine/threonine phosphatase implicated in tau dephosphorylation, and its activity is reduced by approximately 20% in Alzheimer's disease neocortex. Discovering small molecule PP5 activators could therefore represent a therapeutic strategy for tauopathies. This study identified chaulmoogric acid, a cyclopentenyl fatty acid, as a structurally distinct PP5 activator through high-throughput biochemical screening.
Experimental Protocol: A library of approximately 1,120 compounds was screened at 25 micromolar using a robotic pNPP phosphatase assay with recombinant full-length PP5 (residues 16-499). Hit validation employed concentration-response curves (3.9 micromolar to 1 millimolar) to determine EC₅₀ values. Structural effects on the N-terminal TPR domain were probed by far-UV circular dichroism spectroscopy and limited proteolysis with proteinase K. Synergy between chaulmoogric acid and the known endogenous activator arachidonic acid was evaluated by co-administration experiments across combinatorial concentration ranges.
Performance Evaluation: Chaulmoogric acid activated PP5 with an EC₅₀ of 134.5 micromolar, achieving a maximal 16-17 fold activation comparable to arachidonic acid (EC₅₀ = 77.6 micromolar). Circular dichroism revealed that chaulmoogric acid disrupted TPR domain alpha-helical content in a fundamentally different manner from arachidonic acid, producing a beta-sheet-like spectral signature indicating distinct conformational changes. Limited proteolysis confirmed divergent binding modes: arachidonic acid nearly abolished proteinase K-resistant TPR fragments, while approximately 40% resistance persisted with chaulmoogric acid. Remarkably, the two activators displayed strong synergism; chaulmoogric acid at 31.25 micromolar, which alone produced no activation, elicited 2-20 fold PP5 activity when combined with 10-200 micromolar arachidonic acid. This synergism at physiologically relevant concentrations suggests chaulmoogric acid derivatives could potentiate endogenous PP5 activation for therapeutic benefit.

Custom Q&A

What is the molecular formula of chaulmoogric acid?

The molecular formula of chaulmoogric acid is C18H32O2.

What are some synonyms of chaulmoogric acid?

Some synonyms of chaulmoogric acid are 13-cyclopent-2-en-1-yltridecanoic acid, CHEMBL1649743, CHEBI:27939, and NSC14979.

What is the molecular weight of chaulmoogric acid?

The molecular weight of chaulmoogric acid is 280.4 g/mol.

What is the role of chaulmoogric acid?

Chaulmoogric acid has a role as a plant metabolite.

What is the IUPAC name of chaulmoogric acid?

The IUPAC name of chaulmoogric acid is 13-cyclopent-2-en-1-yltridecanoic acid.

What is the InChI of chaulmoogric acid?

The InChI of chaulmoogric acid is InChI=1S/C18H32O2/c19-18(20)16-10-8-6-4-2-1-3-5-7-9-13-17-14-11-12-15-17/h11,14,17H,1-10,12-13,15-16H2,(H,19,20).

What is the InChIKey of chaulmoogric acid?

The InChIKey of chaulmoogric acid is XMVQWNRDPAAMJB-UHFFFAOYSA-N.

What is the canonical SMILES of chaulmoogric acid?

The canonical SMILES of chaulmoogric acid is C1CC(C=C1)CCCCCCCCCCCCC(=O)O.

What is the CAS number of chaulmoogric acid?

The CAS number of chaulmoogric acid is 29106-32-9.

What is the European Community (EC) number of chaulmoogric acid?

The European Community (EC) number of chaulmoogric acid is 249-440-7.