Terreic Acid
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MedKoo CAT#: 329675

CAS#: 121-40-4

Description: 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

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Terreic Acid
CAS# 121-40-4
Instruction

Theoretical Analysis

MedKoo Cat#: 329675
Name: Terreic Acid
CAS#: 121-40-4
Chemical Formula: C7H6O4
Exact Mass: 154.03
Molecular Weight: 154.121
Elemental Analysis: C, 54.55; H, 3.92; O, 41.52

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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:

Biological target:
In vitro activity:
In vivo activity:

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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: 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. Review. PubMed PMID: 27455860.

2: 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-Acetylt ransferase (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. PubMed PMID: 26762501.

3: 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. PubMed PMID: 26132344.

4: 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. PubMed PMID: 25592371.

5: 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. PubMed PMID: 25265334; PubMed Central PMCID: PMC4201328.

6: 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. PubMed PMID: 24534845.

7: 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. PubMed PMID: 23686727; PubMed Central PMCID: PMC4610358.

8: 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. PubMed PMID: 21892242; PubMed Central PMCID: PMC3161753.

9: 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. PubMed PMID: 20392080; PubMed Central PMCID: PMC2884014.

10: 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. Epub 2007 Sep 1. PubMed PMID: 17713360.

11: 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. Epub 2004 Dec 30. PubMed PMID: 15894173.

12: 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. Review. PubMed PMID: 15180535.

13: Kawakami Y, Hartman SE, Kinoshita E, Suzuki H, Kitaura J, Yao L, Inagaki N, Franco A, Hata D, Maeda-Yamamoto M, Fukamachi H, Nagai H, Kawakami T. Terreic acid, a quinone epoxide inhibitor of Bruton's tyrosine kinase. Proc Natl Acad Sci U S A. 1999 Mar 2;96(5):2227-32. PubMed PMID: 10051623; PubMed Central PMCID: PMC26765.

14: Basu S, Bose SK Jr, Bose SK. Characterization of versilin-sensitive sites in self-sensitive producer and sensitive non-producer or unrelated organism. J Appl Bacteriol. 1989 Aug;67(2):191-200. PubMed PMID: 2808186.

15: Thiericke R, Stellwaag M, Zeeck A, Snatzke G. The structure of manumycin. III. Absolute configuration and conformational studies. J Antibiot (Tokyo). 1987 Nov;40(11):1549-54. PubMed PMID: 3693125.

16: Reddy GC, Sood RS, Nadkarni SR, Reden J, Ganguli BN, Fehlhaber HW, Snatzke G. Stereochemistry of the epoxydon group antibiotic G7063-2 isolated from a Streptomyces species HPL Y-25711. J Antibiot (Tokyo). 1984 Dec;37(12):1596-9. PubMed PMID: 6526728.

17: Subramanian T, Namasivayam KM, Shanmugasundaram ER. In vivo and in vitro studies on the binding nature of terreic acid with macromolecules such as protein and nucleic acids. Toxicol Lett. 1982 Feb;10(2-3):249-53. PubMed PMID: 7080093.

18: Yamamoto H, Moriyama K, Jinnouchi H, Yagishita K. Studies on terreic acid. Jpn J Antibiot. 1980 Mar;33(3):320-8. PubMed PMID: 7190624.

19: Noble M, Noble D, Sykes RB. G7063-2, a new nitrogen-containing antibiotic of the epoxydon group, isolated from the fermentation broth of a species of Streptomyces. J Antibiot (Tokyo). 1977 Jun;30(6):455-9. PubMed PMID: 885806.

20: Sheehan JC, Lo YS. Total synthesis and resolution of terreic acid. J Med Chem. 1974 Mar;17(3):371-2. PubMed PMID: 4811239.