Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C7H6O4 |
Molecular Weight | 154.1201 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1=C(O)C(=O)[C@@H]2O[C@@H]2C1=O
InChI
InChIKey=ATFNSNUJZOYXFC-RQJHMYQMSA-N
InChI=1S/C7H6O4/c1-2-3(8)5(10)7-6(11-7)4(2)9/h6-8H,1H3/t6-,7+/m1/s1
Molecular Formula | C7H6O4 |
Molecular Weight | 154.1201 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Terreic acid is a metabolite with antibiotic properties produced by the fungus Aspergillus terreus. It was found, that terreic acid inactivated UDP-N-acetylglucosamine 1-carboxyvinyltransferase (MurA), a bacterial cell wall biosynthetic enzyme, by covalently attaching to Cys115. This compound also inhibits the catalytic activity of BTK (Bruton's tyrosine kinase) and the interaction of Btk with protein kinase C beta type (PKCβII) without affecting the activity of PKC.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: P33038 Gene ID: 9127042.0 Gene Symbol: murA Target Organism: Enterobacter cloacae subsp. cloacae (strain ATCC 13047 / DSM 30054 /|||NBRC 13535 / NCDC 279-56) Sources: https://www.ncbi.nlm.nih.gov/pubmed/20392080 |
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Target ID: Q06187 Gene ID: 695.0 Gene Symbol: BTK Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/10051623 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
Gas chromatographic analysis of the mycotoxins kojic acid, terreic acid, and terrein. | 1970 May |
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In vivo and in vitro studies on the binding nature of terreic acid with macromolecules such as protein and nucleic acids. | 1982 Feb |
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Terreic acid, a quinone epoxide inhibitor of Bruton's tyrosine kinase. | 1999 Mar 2 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10051623
in mice: the effects of terreic acid (TA) (0.15; 1.5; 15 mg/kg) on IgE/antigen-mediated cutaneous reactions in BALB/c were examined. Mice received i.v. injection of antidinitrophenyl IgE antibody followed by epicutaneous administration of 0.15% dinitrofluorobenzene 24 hr later. TA was injected i.p. 1 hr before antigen challenge. The increased ear thickness resulting from an edematous allergic reaction occurs from 2 hr after antigen challenge and continues for at least 48 hr. The early response, as examined 1 hr after antigen challenge, was not affected by TA.
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10051623
In vitro binding assays were perfomed using GST-BtkPH beads and HMC-1 cell lysates. GST-BtkPH beads were incubated with HMC-1 cell lysates in the absence or presence of various concentrations of terreic acid (0, 50, 100, 300 uM). PKC in HMC-1 lysates, which bound to the Btk PH domain beads, was detected by immunoblotting with anti-PKC (MC5). It was shown, that terreic acid inhibited the binding of GST-BtkPH to PKC in lysates of HMC-1 human mast cells with an IC50 of ≈100 μM
Substance Class |
Chemical
Created
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Edited
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Record UNII |
XM2Y0DRJ7D
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Record Status |
Validated (UNII)
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Record Version |
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