Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C4H6O4 |
| Molecular Weight | 118.088 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)CCC(O)=O
InChI
InChIKey=KDYFGRWQOYBRFD-UHFFFAOYSA-N
InChI=1S/C4H6O4/c5-3(6)1-2-4(7)8/h1-2H2,(H,5,6)(H,7,8)
| Molecular Formula | C4H6O4 |
| Molecular Weight | 118.088 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/23461009 | https://www.ncbi.nlm.nih.gov/pubmed/24771373 | https://ntrl.ntis.gov/NTRL/dashboard/searchResults.xhtml?searchQuery=PB254541 | https://www.ncbi.nlm.nih.gov/pubmed/10464017
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/23461009 | https://www.ncbi.nlm.nih.gov/pubmed/24771373 | https://ntrl.ntis.gov/NTRL/dashboard/searchResults.xhtml?searchQuery=PB254541 | https://www.ncbi.nlm.nih.gov/pubmed/10464017
Succinic acid is a dicarboxylic acid, which has multiple biological roles as a metabolic intermediate being converted into fumarate by the enzyme succinate dehydrogenase in complex 2 of the electron transport chain which is involved in making ATP, and as a signaling molecule reflecting the cellular metabolic state. Succinate is generated in mitochondria via the tricarboxylic acid cycle (TCA), an energy-yielding process shared by all organisms. Succinate can exit the mitochondrial matrix and function in the cytoplasm as well as the extracellular space, changing gene expression patterns, modulating epigenetic landscape or demonstrating hormone-like signaling. Dysregulation of succinate synthesis, and therefore ATP synthesis, happens in some genetic mitochondrial diseases, such as Leigh's disease, and Mela's disease and degradation can lead to pathological conditions, such as malignant transformation, inflammation and tissue injury. Succinic acid is a precursor to some polyesters and a component of some alkyd resins. Succinic acid also serves as the bases of certain biodegradable polymers, which are of interest in tissue engineering applications. As a food additive and dietary supplement, succinic acid is generally recognized as safe by the U.S. Food and Drug Administration. Succinic acid is used primarily as an acidity regulator in the food and beverage industry. It is also available as a flavoring agent, contributing a somewhat sour and astringent component to umami taste.[11] As an excipient in pharmaceutical products, it is also used to control acidity or as a counter ion. Drugs involving succinate include metoprolol succinate, sumatriptan succinate, Doxylamine succinate or solifenacin succinate.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL5697 |
3.0 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Inactive ingredient | Reamberin Approved UseUnknown |
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| Inactive ingredient | Metoprolol Succinate ER Approved UseUnknown |
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| Inactive ingredient | VESIcare Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Structures and proton-pumping strategies of mitochondrial respiratory enzymes. | 2001 |
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| Inhibition of spontaneous induction of lambdoid prophages in Escherichia coli cultures: simple procedures with possible biotechnological applications. | 2001 |
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| [Intermittent hypoxic training with exogenous nitric oxide improves rat liver mitochondrial oxidation and phosphorylation during acute hypoxia]. | 2001 |
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| Respiratory enzymes from Sulfolobus acidocaldarius. | 2001 |
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| Tetracycline residues in meat and bone meals. Part 1: methodology and examination of field samples. | 2001 Apr |
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| Synthesis of ethyl alkylidene alpha cyanoacetates under ultrasound irradiation. | 2001 Apr |
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| Rat liver microsomal lipid peroxidation produced during the oxidative metabolism of ethacrynic acid. | 2001 Apr |
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| Inhibition of Escherichia coli respiratory enzymes by the lactoperoxidase-hydrogen peroxide-thiocyanate antimicrobial system. | 2001 Apr |
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| A transient inhibition of mitochondrial ATP synthesis by nitric oxide synthase activation triggered apoptosis in primary cortical neurons. | 2001 Apr |
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| Enhancement of 3,4-methylenedioxymethamphetamine neurotoxicity by the energy inhibitor malonate. | 2001 Apr |
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| N-Acetylaspartate, a marker of both cellular dysfunction and neuronal loss: its relevance to studies of acute brain injury. | 2001 Apr |
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| Central carbon metabolism of Saccharomyces cerevisiae explored by biosynthetic fractional (13)C labeling of common amino acids. | 2001 Apr |
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| Combined effect of propofol and GSNO on oxidative phosphorylation of isolated rat liver mitochondria. | 2001 Apr |
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| Identification of respiratory complexes I and III as mitochondrial sites of damage following exposure to ionizing radiation and nitric oxide. | 2001 Apr |
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| The effects of feed and intracellular pyruvate levels on the redistribution of metabolic fluxes in Escherichia coli. | 2001 Apr |
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| Attenuation of malonate toxicity in primary mesencephalic cultures using the GABA transport blocker, NO-711. | 2001 Apr 1 |
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| Germline SDHD mutation in familial phaeochromocytoma. | 2001 Apr 14 |
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| Probing the active site of L-aspartate oxidase by site-directed mutagenesis: role of basic residues in fumarate reduction. | 2001 Apr 17 |
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| New insights into the regulation of plant succinate dehydrogenase. On the role of the protonmotive force. | 2001 Aug 31 |
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| A subtoxic interactive toxicity study of ethanol and chromium in male Wistar rats. | 2001 Feb |
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| A high-resolution integrated map spanning the SDHD gene at 11q23: a 1.1-Mb BAC contig, a partial transcript map and 15 new repeat polymorphisms in a tumour-suppressor region. | 2001 Feb |
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| Effects of cresols (o-, m-, and p-isomers) on the bioenergetic system in isolated rat liver mitochondria. | 2001 Feb |
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| Dramatic improvement in mitochondrial cardiomyopathy following treatment with idebenone. | 2001 Feb |
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| Paradoxical effects of copper and manganese on brain mitochondrial function. | 2001 Feb 23 |
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| Dimeric pig heart succinate-coenzyme A transferase uses only one subunit to support catalysis. | 2001 Feb 27 |
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| Time-course changes in arteriolar and venular portions of capillary in young treadmill-trained rats. | 2001 Jan |
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| Developmental aspects of the rat endolymphatic sac and functional implications. | 2001 Jan |
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| [High cell density culture of phosphotransacetylase mutants of Escherichia coli BL21(DE3)]. | 2001 Jan |
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| Alloxan-induced mitochondrial permeability transition triggered by calcium, thiol oxidation, and matrix ATP. | 2001 Jul 20 |
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| Simultaneous chromium(VI) reduction and phenol degradation in a fixed-film coculture bioreactor: reactor performance. | 2001 Jun |
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| Ubiquinol:cytochrome c oxidoreductase (complex III). Effect of inhibitors on cytochrome b reduction in submitochondrial particles and the role of ubiquinone in complex III. | 2001 Jun 1 |
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| Retention of heme in axial ligand mutants of succinate-ubiquinone xxidoreductase (complex II) from Escherichia coli. | 2001 Jun 1 |
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| Modulation of mitochondrial function by hydrogen peroxide. | 2001 Jun 29 |
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| Kinetic analyses of mitochondrial 75selenium uptake in Trigonella foenum-graecum seedlings exposed to selenium and mimosine. | 2001 Mar |
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| Metabolic enzymes and phenotypic expression among human locomotor muscles. | 2001 Mar |
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| A general method for the quantitative analysis of functional chimeras: applications from site-directed mutagenesis and macromolecular association. | 2001 Mar |
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| The simplest supramolecular complexes containing pairs of Mo(2)(formamidinate)(3) units linked with various dicarboxylates: preparative methods, structures, and electrochemistry. | 2001 Mar 12 |
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| Analysis of sulfonated compounds by ion-exchange high-performance liquid chromatography-mass spectrometry. | 2001 Mar 30 |
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| Effects of culture conditions on enhancement of 2,4-dinitrotoluene degradation by Burkholderia engineered with the Vitreoscilla hemoglobin gene. | 2001 Mar-Apr |
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| Possible involvement of protein phosphorylation in aluminum-responsive malate efflux from wheat root apex. | 2001 May |
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| Estradiol protects against ATP depletion, mitochondrial membrane potential decline and the generation of reactive oxygen species induced by 3-nitroproprionic acid in SK-N-SH human neuroblastoma cells. | 2001 May |
|
| Chemical preconditioning with 3-nitropropionic acid in hearts: role of mitochondrial K(ATP) channel. | 2001 May |
|
| Synthesis of iron-crosslinked chitosan succinate and iron-crosslinked hydroxamated chitosan succinate and their in vitro evaluation as potential matrix materials for oral theophylline sustained-release beads. | 2001 May |
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| Cloning and functional characterization of a high-affinity Na(+)/dicarboxylate cotransporter from mouse brain. | 2001 May |
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| Kinetic and crystallographic studies on deacetoxycephalosporin C synthase (DAOCS). | 2001 May 18 |
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| The Quinone-binding sites of the Saccharomyces cerevisiae succinate-ubiquinone oxidoreductase. | 2001 May 18 |
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| J-domain protein, Jac1p, of yeast mitochondria required for iron homeostasis and activity of Fe-S cluster proteins. | 2001 May 18 |
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| The 'strict' anaerobe Desulfovibrio gigas contains a membrane-bound oxygen-reducing respiratory chain. | 2001 May 4 |
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| In vitro effects of nicotine on mitochondrial respiration and superoxide anion generation. | 2001 May 4 |
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| Aerobic capacity of frog skeletal muscle during hibernation. | 2001 May-Jun |
Sample Use Guides
Antiviral activity was measured in a plaque inhibition assay. Confluent Vero cell monolayer in 6-well multidishes were infected with 100 PFU in 1 mL of MEM medium. After adsorption at 37 °C for 2 h, residual inoculum was replaced with 1 mL of MEM medium containing 0.2% gamma-globulin and 1 mL of a dilution of varying concentrations of the Succinic acid. Virus-infected wells without compounds were used as cytopathogenicity controls. Viral cytopathogenicity (CPE) was completed 1-2 days after viral infection
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 17:27:08 UTC 2023
by
admin
on
Fri Dec 15 17:27:08 UTC 2023
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| Record UNII |
AB6MNQ6J6L
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| Record Status |
Validated (UNII)
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CFR |
21 CFR 172.230
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DSLD |
3384 (Number of products:37)
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NCI_THESAURUS |
C345
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CFR |
21 CFR 184.1091
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D019802
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100000078761
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AB6MNQ6J6L
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C61954
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1623411
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110-15-6
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552
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AB6MNQ6J6L
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DTXSID6023602
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1623422
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203-740-4
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SUB12599MIG
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37255
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m10269
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2487
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15741
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106449
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SUCCINIC ACID
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1110
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CHEMBL576
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PRODRUG -> METABOLITE ACTIVE |
Developed for chronic oral treatment of Leigh syndrome, a severe primary mitochondrial disease that usually debuts at one to two years of age.
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PARENT -> METABOLITE |
succinic semialdehyde dehydrogenase converts succinic semialdehyde to succinic acid
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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CHROMATOGRAPHIC PURITY (HPLC/UV)
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ACTIVE MOIETY |
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