CHEBI:15741 - succinic acid

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ChEBI Name succinic acid
ChEBI ID CHEBI:15741
Definition An α,ω-dicarboxylic acid resulting from the formal oxidation of each of the terminal methyl groups of butane to the corresponding carboxy group. It is an intermediate metabolite in the citric acid cycle.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:22943, CHEBI:45639, CHEBI:9304, CHEBI:26807
Supplier Information No supplier information found for this compound.
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Succinic acid () is a dicarboxylic acid with the chemical formula (CH2)2(CO2H)2. In living organisms, succinic acid takes the form of an anion, succinate, 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 (TCA) cycle. 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. As such, succinate links cellular metabolism, especially ATP formation, to the regulation of cellular function. Dysregulation of succinate synthesis, and therefore ATP synthesis, happens in some genetic mitochondrial diseases, such as Leigh syndrome, and Melas syndrome, and degradation can lead to pathological conditions, such as malignant transformation, inflammation and tissue injury. Succinic acid is marketed as food additive E363. The name derives from Latin succinum, meaning amber.
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Formula C4H6O4
Net Charge 0
Average Mass 118.08800
Monoisotopic Mass 118.02661
InChI InChI=1S/C4H6O4/c5-3(6)1-2-4(7)8/h1-2H2,(H,5,6)(H,7,8)
InChIKey KDYFGRWQOYBRFD-UHFFFAOYSA-N
SMILES OC(=O)CCC(O)=O
Metabolite of Species Details
Chlamydomonas reinhardtii (NCBI:txid3055) See: PubMed
Daphnia magna (NCBI:txid35525) See: Mixtures of similarly acting compounds in Daphnia magna: From gene to metabolite and beyondTine Vandenbrouck, Oliver A.H. Jones, Nathalie Dom, Julian L. Griffin, Wim De CoenEnvironment International 36 (2010) 254-268
Cordyceps sinensis (NCBI:txid72228) Found in mycelium (BTO:0001436). Ethanolic extract of dried mycelia See: PubMed
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): micronutrient
Any nutrient required in small quantities by organisms throughout their life in order to orchestrate a range of physiological functions.
fundamental metabolite
Any metabolite produced by all living cells.
Application(s): radiation protective agent
Any compound that is able to protect normal cells from the damage caused by radiation therapy.
anti-ulcer drug
One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.
nutraceutical
A product in capsule, tablet or liquid form that provide essential nutrients, such as a vitamin, an essential mineral, a protein, an herb, or similar nutritional substance.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing succinic acid (CHEBI:15741) has role anti-ulcer drug (CHEBI:49201)
succinic acid (CHEBI:15741) has role fundamental metabolite (CHEBI:78675)
succinic acid (CHEBI:15741) has role micronutrient (CHEBI:27027)
succinic acid (CHEBI:15741) has role nutraceutical (CHEBI:50733)
succinic acid (CHEBI:15741) has role radiation protective agent (CHEBI:66987)
succinic acid (CHEBI:15741) is a α,ω-dicarboxylic acid (CHEBI:28383)
succinic acid (CHEBI:15741) is a C4-dicarboxylic acid (CHEBI:66873)
succinic acid (CHEBI:15741) is conjugate acid of succinate(1−) (CHEBI:30779)
Incoming (2S)-2-isopropyl-3-oxosuccinic acid (CHEBI:1467) has functional parent succinic acid (CHEBI:15741)
(R)-2-(phosphonomethyl)malic acid (CHEBI:137343) has functional parent succinic acid (CHEBI:15741)
(R)-2-ethylmalic acid (CHEBI:15583) has functional parent succinic acid (CHEBI:15741)
(R)-3,3-dimethylmalic acid (CHEBI:15587) has functional parent succinic acid (CHEBI:15741)
(carboxymethoxy)succinic acid (CHEBI:17040) has functional parent succinic acid (CHEBI:15741)
1-hexadecyl-2-succinyl-sn-glycero-3-phosphocholine (CHEBI:79274) has functional parent succinic acid (CHEBI:15741)
11α-hydroxyprogesterone hemisuccinate (CHEBI:45496) has functional parent succinic acid (CHEBI:15741)
11-deoxycorticosterone-21-hemisuccinate (CHEBI:62112) has functional parent succinic acid (CHEBI:15741)
2,2-dimethylsuccinic acid (CHEBI:86537) has functional parent succinic acid (CHEBI:15741)
2,3-dimethylsuccinic acid (CHEBI:167506) has functional parent succinic acid (CHEBI:15741)
2-(acetamidomethylidene)succinic acid (CHEBI:16253) has functional parent succinic acid (CHEBI:15741)
2-(phosphinomethylidene)succinic acid (CHEBI:131963) has functional parent succinic acid (CHEBI:15741)
2-benzylsuccinic acid (CHEBI:16054) has functional parent succinic acid (CHEBI:15741)
2-chlorosuccinic acid (CHEBI:90244) has functional parent succinic acid (CHEBI:15741)
2-ethylsuccinic acid (CHEBI:195363) has functional parent succinic acid (CHEBI:15741)
2-hydroxy-3-oxosuccinic acid (CHEBI:17778) has functional parent succinic acid (CHEBI:15741)
2-isopropylmalic acid (CHEBI:28635) has functional parent succinic acid (CHEBI:15741)
2-methyl-3-oxosuccinic acid (CHEBI:50793) has functional parent succinic acid (CHEBI:15741)
2-methylene-3-methylsuccinic acid (CHEBI:16093) has functional parent succinic acid (CHEBI:15741)
2-propylmalic acid (CHEBI:28652) has functional parent succinic acid (CHEBI:15741)
3-(acetamidomethylidene)-2-(hydroxymethyl)succinic acid (CHEBI:16216) has functional parent succinic acid (CHEBI:15741)
3-ethylmalic acid (CHEBI:15591) has functional parent succinic acid (CHEBI:15741)
3-hydroxy-2-isopropyl-4-methoxy-4-oxobutanoate (CHEBI:52960) has functional parent succinic acid (CHEBI:15741)
3-hydroxy-2-isopropyl-4-methoxy-4-oxobutanoic acid (CHEBI:52978) has functional parent succinic acid (CHEBI:15741)
3-isopropylmalic acid (CHEBI:35114) has functional parent succinic acid (CHEBI:15741)
3-methylbenzylsuccinic acid (CHEBI:191372) has functional parent succinic acid (CHEBI:15741)
3-methylmalic acid (CHEBI:25312) has functional parent succinic acid (CHEBI:15741)
3-propylmalic acid (CHEBI:30850) has functional parent succinic acid (CHEBI:15741)
4-(6-hydroxypyridin-3-yl)-4-oxobutyric acid (CHEBI:66946) has functional parent succinic acid (CHEBI:15741)
4-methoxy-4-oxo-3-phenylbutanoic acid (CHEBI:71214) has functional parent succinic acid (CHEBI:15741)
4-{[6-endo-amino-6-exo-benzoyl-5-exo-phenylnorbornan-2-yl]oxy}-4-oxobutanoic acid (CHEBI:71549) has functional parent succinic acid (CHEBI:15741)
6β-hydroxyprogesterone hemisuccinate (CHEBI:62116) has functional parent succinic acid (CHEBI:15741)
N-succinyl-L-α-amino acid (CHEBI:191191) has functional parent succinic acid (CHEBI:15741)
N-succinyl-L-glutamic 5-semialdehyde (CHEBI:27657) has functional parent succinic acid (CHEBI:15741)
N6-(1,2-dicarboxyethyl)-AMP (CHEBI:15919) has functional parent succinic acid (CHEBI:15741)
trans-2,3-epoxysuccinic acid (CHEBI:15900) has functional parent succinic acid (CHEBI:15741)
bromosuccinic acid (CHEBI:73712) has functional parent succinic acid (CHEBI:15741)
carboxyfentanyl (CHEBI:61106) has functional parent succinic acid (CHEBI:15741)
citramalic acid (CHEBI:15584) has functional parent succinic acid (CHEBI:15741)
dioxosuccinic acid (CHEBI:30799) has functional parent succinic acid (CHEBI:15741)
ethyl 3-methylbutyl butanedioate (CHEBI:87276) has functional parent succinic acid (CHEBI:15741)
iminoaspartic acid (CHEBI:50616) has functional parent succinic acid (CHEBI:15741)
itaconic acid (CHEBI:30838) has functional parent succinic acid (CHEBI:15741)
malic acid (CHEBI:6650) has functional parent succinic acid (CHEBI:15741)
methoxysuccinyl-Ala-Ala-Pro-Ala chloromethyl ketone (CHEBI:83802) has functional parent succinic acid (CHEBI:15741)
methoxysuccinyl-Ala-Ala-Pro-Val chloromethyl ketone (CHEBI:83803) has functional parent succinic acid (CHEBI:15741)
oxaloacetic acid (CHEBI:30744) has functional parent succinic acid (CHEBI:15741)
phenyl [1-(N-succinylamino)pentyl]phosphonate (CHEBI:43012) has functional parent succinic acid (CHEBI:15741)
prednisolone succinate (CHEBI:135745) has functional parent succinic acid (CHEBI:15741)
SAICAR (CHEBI:18319) has functional parent succinic acid (CHEBI:15741)
succinamic acid (CHEBI:50398) has functional parent succinic acid (CHEBI:15741)
succinate ester (CHEBI:36181) has functional parent succinic acid (CHEBI:15741)
succinic anhydride (CHEBI:36595) has functional parent succinic acid (CHEBI:15741)
succinyladenosine (CHEBI:71169) has functional parent succinic acid (CHEBI:15741)
thiomalic acid (CHEBI:38705) has functional parent succinic acid (CHEBI:15741)
succinate(1−) (CHEBI:30779) is conjugate base of succinic acid (CHEBI:15741)
3-carboxypropanoyl group (CHEBI:26810) is substituent group from succinic acid (CHEBI:15741)
succinyl group (CHEBI:37952) is substituent group from succinic acid (CHEBI:15741)
IUPAC Names
butanedioic acid
succinic acid
Synonyms Sources
1,2-ethanedicarboxylic acid ChemIDplus
acide butanedioïque ChEBI
acide succinique ChEBI
acidum succinicum ChemIDplus
amber acid NIST Chemistry WebBook
asuccin NIST Chemistry WebBook
Bernsteinsäure ChEBI
Butandisäure ChemIDplus
Butanedionic acid KEGG COMPOUND
Dihydrofumaric acid HMDB
E363 ChEBI
Ethylenesuccinic acid KEGG COMPOUND
HOOC‒CH2‒CH2‒COOH IUPAC
spirit of amber ChEBI
Succinic acid KEGG COMPOUND
SUCCINIC ACID PDBeChem
Manual Xrefs Databases
2487 DrugCentral
C00001205 KNApSAcK
C00042 KEGG COMPOUND
DB00139 DrugBank
ECMDB00254 ECMDB
HMDB0000254 HMDB
LMFA01170043 LIPID MAPS
SIN PDBeChem
SUC MetaCyc
Succinic_acid Wikipedia
YMDB00338 YMDB
View more database links
Registry Numbers Types Sources
110-15-6 CAS Registry Number KEGG COMPOUND
110-15-6 CAS Registry Number ChemIDplus
110-15-6 CAS Registry Number NIST Chemistry WebBook
1754069 Reaxys Registry Number Reaxys
2785 Gmelin Registry Number Gmelin
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Last Modified
18 April 2024