MedKoo Cat#: 329675 | Name: Terreic Acid
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Terreic Acid 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). Terreic Acid recapitulated the phenotypic defects of btk mutant mast cells in high-affinity IgE receptor-stimulated wild-type mast cells without affecting the enzymatic activities and expressions of many other signaling molecules, including those of protein kinase C. Terreic acid is a covalent inhibitor of the bacterial cell wall biosynthetic enzyme UDP-N-acetylglucosamine 1-carboxyvinyltransferase (MurA) .

Chemical Structure

Terreic Acid
Terreic Acid
CAS#121-40-4

Theoretical Analysis

MedKoo Cat#: 329675

Name: Terreic Acid

CAS#: 121-40-4

Chemical Formula: C7H6O4

Exact Mass: 154.0266

Molecular Weight: 154.12

Elemental Analysis: C, 54.55; H, 3.92; O, 41.52

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Synonym
Terreic Acid; TA; (-)-Terreic Acid.
IUPAC/Chemical Name
(1R,6S)-3-hydroxy-4-methyl-7-oxabicyclo[4.1.0]hept-3-ene-2,5-dione
InChi Key
ATFNSNUJZOYXFC-RQJHMYQMSA-N
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
SMILES Code
O=C(C(O)=C1C)[C@]2([H])O[C@]2([H])C1=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 154.12 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Singh MV, Wong T, Moorjani S, Mani AM, Dokun AO. Novel components in the nuclear factor-kappa B (NF-κB) signaling pathways of endothelial cells under hyperglycemic-ischemic conditions. Front Cardiovasc Med. 2024 May 24;11:1345421. doi: 10.3389/fcvm.2024.1345421. PMID: 38854657; PMCID: PMC11157070. 2: Bejenari M, Sondergaard TE, Sørensen JL. 6-MSA, a secondary metabolite distribution hub with multiple fungal destinations. J Appl Microbiol. 2023 Jun 1;134(6):lxad107. doi: 10.1093/jambio/lxad107. PMID: 37218693. 3: Kong K, Huang Z, Shi S, Pan W, Zhang Y. Diversity, antibacterial and phytotoxic activities of culturable endophytic fungi from Pinellia pedatisecta and Pinellia ternata. BMC Microbiol. 2023 Jan 28;23(1):30. doi: 10.1186/s12866-022-02741-5. PMID: 36707757; PMCID: PMC9883868. 4: Christiansen JV, Larsen TO, Frisvad JC. Production of Fungal Quinones: Problems and Prospects. Biomolecules. 2022 Jul 28;12(8):1041. doi: 10.3390/biom12081041. PMID: 36008938; PMCID: PMC9405642. 5: Palathoti N, Azam MA. GlmU Inhibitors as Promising Antibacterial Agents: A Review. Mini Rev Med Chem. 2023;23(3):343-360. doi: 10.2174/1389557522666220817114445. PMID: 35980047. 6: Kong C, Huang H, Xue Y, Liu Y, Peng Q, Liu Q, Xu Q, Zhu Q, Yin Y, Zhou X, Zhang Y, Cai M. Heterologous pathway assembly reveals molecular steps of fungal terreic acid biosynthesis. Sci Rep. 2018 Feb 1;8(1):2116. doi: 10.1038/s41598-018-20514-x. PMID: 29391515; PMCID: PMC5794859. 7: Ferguson LB, Ozburn AR, Ponomarev I, Metten P, Reilly M, Crabbe JC, Harris RA, Mayfield RD. Genome-Wide Expression Profiles Drive Discovery of Novel Compounds that Reduce Binge Drinking in Mice. Neuropsychopharmacology. 2018 May;43(6):1257-1266. doi: 10.1038/npp.2017.301. Epub 2017 Dec 18. PMID: 29251283; PMCID: PMC5916369. 8: Sarnoski EA, Liu P, Acar M. A High-Throughput Screen for Yeast Replicative Lifespan Identifies Lifespan-Extending Compounds. Cell Rep. 2017 Nov 28;21(9):2639-2646. doi: 10.1016/j.celrep.2017.11.002. PMID: 29186697; PMCID: PMC5728442. 9: Yin Y, Cai M, Zhou X, Li Z, Zhang Y. Polyketides in Aspergillus terreus: biosynthesis pathway discovery and application. Appl Microbiol Biotechnol. 2016 Sep;100(18):7787-98. doi: 10.1007/s00253-016-7733-z. Epub 2016 Jul 26. PMID: 27455860. 10: Sharma R, Lambu MR, Jamwal U, Rani C, Chib R, Wazir P, Mukherjee D, Chaubey A, Khan IA. Escherichia coli N-Acetylglucosamine-1-Phosphate- Uridyltransferase/Glucosamine-1-Phosphate-Acetyltransferase (GlmU) Inhibitory Activity of Terreic Acid Isolated from Aspergillus terreus. J Biomol Screen. 2016 Apr;21(4):342-53. doi: 10.1177/1087057115625308. Epub 2016 Jan 13. PMID: 26762501. 11: Klitgaard A, Frandsen RJ, Holm DK, Knudsen PB, Frisvad JC, Nielsen KF. Combining UHPLC-High Resolution MS and Feeding of Stable Isotope Labeled Polyketide Intermediates for Linking Precursors to End Products. J Nat Prod. 2015 Jul 24;78(7):1518-25. doi: 10.1021/np500979d. Epub 2015 Jul 1. PMID: 26132344. 12: Zhang F, Mijiti M, Ding W, Song J, Yin Y, Sun W, Li Z. (+)‑Terrein inhibits human hepatoma Bel‑7402 proliferation through cell cycle arrest. Oncol Rep. 2015 Mar;33(3):1191-200. doi: 10.3892/or.2015.3719. Epub 2015 Jan 14. PMID: 25592371. 13: Guo CJ, Sun WW, Bruno KS, Wang CC. Molecular genetic characterization of terreic acid pathway in Aspergillus terreus. Org Lett. 2014 Oct 17;16(20):5250-3. doi: 10.1021/ol502242a. Epub 2014 Sep 29. PMID: 25265334; PMCID: PMC4201328. 14: Boruta T, Bizukojc M. Culture-based and sequence-based insights into biosynthesis of secondary metabolites by Aspergillus terreus ATCC 20542. J Biotechnol. 2014 Apr 10;175:53-62. doi: 10.1016/j.jbiotec.2014.01.038. Epub 2014 Feb 15. PMID: 24534845. 15: Olesen SH, Ingles DJ, Yang Y, Schönbrunn E. Differential antibacterial properties of the MurA inhibitors terreic acid and fosfomycin. J Basic Microbiol. 2014 Apr;54(4):322-6. doi: 10.1002/jobm.201200617. Epub 2013 May 20. PMID: 23686727; PMCID: PMC4610358. 16: Samson RA, Peterson SW, Frisvad JC, Varga J. New species in Aspergillus section Terrei. Stud Mycol. 2011 Jun 30;69(1):39-55. doi: 10.3114/sim.2011.69.04. PMID: 21892242; PMCID: PMC3161753. 17: Han H, Yang Y, Olesen SH, Becker A, Betzi S, Schönbrunn E. The fungal product terreic acid is a covalent inhibitor of the bacterial cell wall biosynthetic enzyme UDP-N-acetylglucosamine 1-carboxyvinyltransferase (MurA) . Biochemistry. 2010 May 18;49(19):4276-82. doi: 10.1021/bi100365b. PMID: 20392080; PMCID: PMC2884014. 18: Kawakami Y, Yumoto K, Kawakami T. An improved mouse model of atopic dermatitis and suppression of skin lesions by an inhibitor of Tec family kinases. Allergol Int. 2007 Dec;56(4):403-9. doi: 10.2332/allergolint.O-07-486. Epub 2007 Sep 1. PMID: 17713360. 19: Redondo PC, Ben-Amor N, Salido GM, Bartegi A, Pariente JA, Rosado JA. Ca2+-independent activation of Bruton's tyrosine kinase is required for store- mediated Ca2+ entry in human platelets. Cell Signal. 2005 Aug;17(8):1011-21. doi: 10.1016/j.cellsig.2004.11.019. Epub 2004 Dec 30. PMID: 15894173. 20: Lusková P, Dráber P. Modulation of the Fcepsilon receptor I signaling by tyrosine kinase inhibitors: search for therapeutic targets of inflammatory and allergy diseases. Curr Pharm Des. 2004;10(15):1727-37. doi: 10.2174/1381612043384538. PMID: 15180535.