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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
Structure of TERREIC ACID

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

HIDE SMILES / InChI

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

Targets

Primary TargetPharmacologyConditionPotency
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)
Target ID: Q06187
Gene ID: 695.0
Gene Symbol: BTK
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Gas chromatographic analysis of the mycotoxins kojic acid, terreic acid, and terrein.
1970 May
In vivo and in vitro studies on the binding nature of terreic acid with macromolecules such as protein and nucleic acids.
1982 Feb
Terreic acid, a quinone epoxide inhibitor of Bruton's tyrosine kinase.
1999 Mar 2
Patents

Patents

Sample Use Guides

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 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
by admin
on Fri Dec 15 19:46:38 GMT 2023
Edited
by admin
on Fri Dec 15 19:46:38 GMT 2023
Record UNII
XM2Y0DRJ7D
Record Status Validated (UNII)
Record Version
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Name Type Language
TERREIC ACID
MI  
Common Name English
(5R),(6S)-EPOXY-3-HYDROXY-P-TOLUQUINONE
Common Name English
TERREIC ACID [MI]
Common Name English
(-)-TERREIC ACID
Common Name English
NSC-294734
Code English
(1R)-3-HYDROXY-4-METHYL-7-OXABICYCLO(4.1.0)HEPT-3-ENE-2,5-DIONE
Systematic Name English
Code System Code Type Description
MESH
C009400
Created by admin on Fri Dec 15 19:46:38 GMT 2023 , Edited by admin on Fri Dec 15 19:46:38 GMT 2023
PRIMARY
MERCK INDEX
m10585
Created by admin on Fri Dec 15 19:46:38 GMT 2023 , Edited by admin on Fri Dec 15 19:46:38 GMT 2023
PRIMARY Merck Index
EPA CompTox
DTXSID40879070
Created by admin on Fri Dec 15 19:46:38 GMT 2023 , Edited by admin on Fri Dec 15 19:46:38 GMT 2023
PRIMARY
CAS
121-40-4
Created by admin on Fri Dec 15 19:46:38 GMT 2023 , Edited by admin on Fri Dec 15 19:46:38 GMT 2023
PRIMARY
NSC
294734
Created by admin on Fri Dec 15 19:46:38 GMT 2023 , Edited by admin on Fri Dec 15 19:46:38 GMT 2023
PRIMARY
FDA UNII
XM2Y0DRJ7D
Created by admin on Fri Dec 15 19:46:38 GMT 2023 , Edited by admin on Fri Dec 15 19:46:38 GMT 2023
PRIMARY
PUBCHEM
91437
Created by admin on Fri Dec 15 19:46:38 GMT 2023 , Edited by admin on Fri Dec 15 19:46:38 GMT 2023
PRIMARY
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