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Details

Stereochemistry ACHIRAL
Molecular Formula C6H4O6
Molecular Weight 172.0924
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TETROQUINONE

SMILES

OC1=C(O)C(=O)C(O)=C(O)C1=O

InChI

InChIKey=DGQOCLATAPFASR-UHFFFAOYSA-N
InChI=1S/C6H4O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h7-8,11-12H

HIDE SMILES / InChI

Molecular Formula C6H4O6
Molecular Weight 172.0924
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/19476355 | https://www.ncbi.nlm.nih.gov/pubmed/8721612

Tetroquinone (Tetrahydroxy-1,4-benzoquinone, tetrahydroxy-p-benzoquinone, tetrahydroxybenzoquinone) is cyclohexadiene derivative with four hydroxyl groups and two ketone groups in opposite (para) positions, with potent prooxidant activity. The exposure of exponentially growing cultures to Tetroquinone, in the presence of Ca2+, caused a dose-dependent inhibition of cell growth and DNA synthesis. The chemical reactivity of Tetroquinone is strongly similar to those of physiological polyphenols, such as catechols and catecholamines. Despite their physiological and pharmacological roles, these compounds may, in addition, present toxicological properties due to their ability to autoxidize generating ROS and quinones Similar to catechols, the OH-substituents confer to Tetroquinone the ability to autoxidize readily in neutral aqueous solutions generating intermediate superoxide anion radicals, semiquinone radicals, and the corresponding quinone. The compound can be synthesized from glyoxal or from myo-inositol (phytic acid), a natural compound widely present in plants.

Originator

Sources: Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences 109, 812-4. From: J. Chem. Soc., Abstr. 58, 244-5 1890.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Sources: Techniques et Sciences Municipales (1985), (7-8), 329-34.
Daphnia magna and zebra fish (Brachydanio rerio) were exposured for 2, 4, 6, and 24 h at 1, 3.5, 10, 35, and 100 mg​/L.
Route of Administration: Oral
In Vitro Use Guide
V79 Chinese hamster lung fibroblasts cell line was used for activity evaluation. Assays were performed with cells in exponential phase of growth. Cells were seeded in 24-well plates (from Coming), at a density of 3 x l0^4 cells/well, and incubated in complete medium for 44 h. Exposure to Tetroquinone was performed in phosphate-buffered saline (PBS) alone, or containing 1.0 mM CaCl, (PBS/Ca2+), for 30 min at 37°C. THQ solutions were prepared at the desired concentrations immediately before addition to cultures. After treatment, cells were washed twice with PBS and incubated in fresh medium for a further 24-h period. At the end of this growth period cells were lysed with 0.5 M NaOH ( 1.0 ml/well). Cell population was determined by measuring lysate absorbance at 260 nm, a parameter directly correlated with cell number, in the range of 10^5-l0^6 cells.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:10:39 GMT 2023
Edited
by admin
on Fri Dec 15 15:10:39 GMT 2023
Record UNII
U7L4P6H0SU
Record Status Validated (UNII)
Record Version
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Name Type Language
TETROQUINONE
INN   MI   USAN  
USAN   INN  
Official Name English
THQ
Code English
TETROQUINONE [MI]
Common Name English
NSC-112931
Code English
TETROQUINONE [USAN]
Common Name English
HPEK-1
Code English
tetroquinone [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C796
Created by admin on Fri Dec 15 15:10:39 GMT 2023 , Edited by admin on Fri Dec 15 15:10:39 GMT 2023
Code System Code Type Description
WIKIPEDIA
Tetrahydroxy-1,4-benzoquinone
Created by admin on Fri Dec 15 15:10:39 GMT 2023 , Edited by admin on Fri Dec 15 15:10:39 GMT 2023
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EVMPD
SUB10952MIG
Created by admin on Fri Dec 15 15:10:39 GMT 2023 , Edited by admin on Fri Dec 15 15:10:39 GMT 2023
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EPA CompTox
DTXSID9045897
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CAS
319-89-1
Created by admin on Fri Dec 15 15:10:39 GMT 2023 , Edited by admin on Fri Dec 15 15:10:39 GMT 2023
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NSC
112931
Created by admin on Fri Dec 15 15:10:39 GMT 2023 , Edited by admin on Fri Dec 15 15:10:39 GMT 2023
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ECHA (EC/EINECS)
206-275-5
Created by admin on Fri Dec 15 15:10:39 GMT 2023 , Edited by admin on Fri Dec 15 15:10:39 GMT 2023
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FDA UNII
U7L4P6H0SU
Created by admin on Fri Dec 15 15:10:39 GMT 2023 , Edited by admin on Fri Dec 15 15:10:39 GMT 2023
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NCI_THESAURUS
C152579
Created by admin on Fri Dec 15 15:10:39 GMT 2023 , Edited by admin on Fri Dec 15 15:10:39 GMT 2023
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MERCK INDEX
m10667
Created by admin on Fri Dec 15 15:10:39 GMT 2023 , Edited by admin on Fri Dec 15 15:10:39 GMT 2023
PRIMARY Merck Index
PUBCHEM
5424
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ChEMBL
CHEMBL1329029
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INN
2254
Created by admin on Fri Dec 15 15:10:39 GMT 2023 , Edited by admin on Fri Dec 15 15:10:39 GMT 2023
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CHEBI
137472
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SMS_ID
100000082741
Created by admin on Fri Dec 15 15:10:39 GMT 2023 , Edited by admin on Fri Dec 15 15:10:39 GMT 2023
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SALT/SOLVATE -> PARENT
SOLVATE->ANHYDROUS
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ACTIVE MOIETY