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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
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
Related Record Type Details
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