A selective inhibitor of BTK
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Terreic Acid

Item No. 10010235

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(1R,6S)-3-hydroxy-4-methyl-7-oxabicyclo[4.1.0]hept-3-ene-2,5-dione
CAS Number
121-40-4
Synonyms
  • TA
  • (-)-Terreic Acid
Molecular Formula
C7H6O4
Formula Weight
154.1
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: SolubleDMSO: 10 mg/mlEthanol: SolubleMethanol: SolubleWater: 5 mg/ml
λmax
213, 316 nm
SMILES
O=C(C(O)=C1C)[C@H]2[C@H](O2)C1=O
InChi Code
InChI=1S/C7H6O4/c1-2-3(8)5(10)7-6(11-7)4(2)9/h6-8H,1H3/t6-,7+/m1/s1
InChi Key
ATFNSNUJZOYXFC-RQJHMYQMSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $75

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    5 mg

    $295

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    Product Description

    Terreic acid (TA) is a cell-permeable quinone epoxide that selectively inhibits Bruton’s tyrosine kinase (BTK) catalytic activity (IC50s = 10 and 3 µM for basal and activation levels, respectively).1,2,3 TA binds to the BTK pleckstrin homology domain (BTK-PH) and blocks the interaction between BTK-PH and PKC (IC50 = 100 µM in human mast cell lysates) without affecting the activity of PKC.2,3 TA has minimal effect on Lyn, Syk, PKA, casein kinase I, ERK1, ERK2, and p38 kinase activities.3,4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Guo, C.J., Sun, W.W., Bruno, K.S., et al. Molecular genetic characterization of terreic acid pathway in Aspergillus terreus. Org. Lett. 16(20), 5250-5253 (2014).

    2. Kawakami, Y., Hartman, S.E., Kinoshita, E., et al. Terreic acid, a quinone epoxide inhibitor of Bruton’s tyrosine kinase. Proc. Natl. Acad. Sci. USA 96(5), 2227-2232 (1999).

    3. Subramanian, T., Namasivayam, K.M., and Shanmugasundaram, E.R. In vivo and in vitro studies on the binding nature of terreic acid with macromolecules such as protein and nucleic acids. Toxicol. Lett. 10(2-3), 249-253 (1982).

    4. Han, H., Yang, Y., Olesen, S.H., et al. The fungal product terreic acid is a covalent inhibitor of the bacterial cell wall biosynthetic enzyme UDP-N-acetylglucosamine 1-carboxyvinyltransferase (MurA). Biochemistry 49(19), 4276-4282 (2010).