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 |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/28622981Curator'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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28622981
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 |
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Target ID: CHEMBL5697 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18942826 |
3.0 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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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 |
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Oxidative and glycolytic metabolism of semen components by washed guinea pig spermatozoa. | 1975 Feb |
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Structures and proton-pumping strategies of mitochondrial respiratory enzymes. | 2001 |
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Respiratory enzymes from Sulfolobus acidocaldarius. | 2001 |
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[Combined treatment of purulent-necrotic lesions of lower extremities in diabetic patients]. | 2001 |
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Ultrastructural localization of succinate dehydrogenase in some bacteria, after treatment with Lubrol W1. | 2001 |
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Synthesis of ethyl alkylidene alpha cyanoacetates under ultrasound irradiation. | 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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Nonalcoholic steatohepatitis: association of insulin resistance and mitochondrial abnormalities. | 2001 Apr |
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Glutamine supplementation promotes anaplerosis but not oxidative energy delivery in human skeletal muscle. | 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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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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Fungal respiration: a fusion of standard and alternative components. | 2001 Apr 2 |
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Energetic metabolism in mouse cerebral cortex during chronic hypoxia. | 2001 Apr 6 |
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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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Effects of cresols (o-, m-, and p-isomers) on the bioenergetic system in isolated rat liver mitochondria. | 2001 Feb |
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"Chemical preconditioning" by 3-nitropropionate reduces ischemia-reperfusion injury in cardiac-arrested rat lungs. | 2001 Feb 15 |
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Exercise and ovarian steroid hormones: their effects on mitochondrial respiration. | 2001 Feb 16 |
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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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Reactivity of some sugars and sugar phosphates towards gold(III) in sodium acetate-acetic acid buffer medium. | 2001 Jan 15 |
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Cumulative and irreversible cardiac mitochondrial dysfunction induced by doxorubicin. | 2001 Jan 15 |
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Changes in various measures of immune status in mice subject to chronic social conflict. | 2001 Jan-Feb |
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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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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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A third crystal form of Wolinella succinogenes quinol:fumarate reductase reveals domain closure at the site of fumarate reduction. | 2001 Mar |
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Depletion of glutathione up-regulates mitochondrial complex I expression in glial cells. | 2001 Mar |
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Different sensitivity of rabbit heart and skeletal muscle to endotoxin-induced impairment of mitochondrial function. | 2001 Mar |
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Barth's syndrome-like disorder: a new phenotype with a maternally inherited A3243G substitution of mitochondrial DNA (MELAS mutation). | 2001 Mar 1 |
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Conjugative metabolism of 1,2-dibromoethane in mitochondria: disruption of oxidative phosphorylation and alkylation of mitochondrial DNA. | 2001 Mar 1 |
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Isolation and phenotypic characterization of Pseudomonas aeruginosa pseudorevertants containing suppressors of the catabolite repression control-defective crc-10 allele. | 2001 Mar 15 |
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Disruption of mitochondrial respiration by melatonin in MCF-7 cells. | 2001 Mar 15 |
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Myxothiazol induces H(2)O(2) production from mitochondrial respiratory chain. | 2001 Mar 2 |
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Topology of the Na(+)/dicarboxylate cotransporter: the N-terminus and hydrophilic loop 4 are located intracellularly. | 2001 Mar 9 |
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Dynamic responses of Pseudomonas fluorescens DF57 to nitrogen or carbon source addition. | 2001 Mar 9 |
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Possible involvement of protein phosphorylation in aluminum-responsive malate efflux from wheat root apex. | 2001 May |
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Chemical preconditioning with 3-nitropropionic acid in hearts: role of mitochondrial K(ATP) channel. | 2001 May |
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Kinetic and crystallographic studies on deacetoxycephalosporin C synthase (DAOCS). | 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 |
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10464017
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
Mon Mar 31 18:46:37 GMT 2025
by
admin
on
Mon Mar 31 18:46:37 GMT 2025
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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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DB00139
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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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