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Record Information
Version1.0
Creation Date2016-09-30 22:27:28 UTC
Update Date2020-06-04 20:59:36 UTC
BMDB IDBMDB0000254
Secondary Accession Numbers
  • BMDB00254
Metabolite Identification
Common NameSuccinic acid
DescriptionSuccinic acid, also known as butanedionic acid or succinate, belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. Succinic acid is a drug which is used for nutritional supplementation, also for treating dietary shortage or imbalance. Succinic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Succinic acid exists in all living species, ranging from bacteria to humans. Succinic acid is a potentially toxic compound.
Structure
Thumb
Synonyms
ValueSource
1,2-Ethanedicarboxylic acidChEBI
Acide butanedioiqueChEBI
Acide succiniqueChEBI
Acidum succinicumChEBI
Amber acidChEBI
AsuccinChEBI
BernsteinsaeureChEBI
ButandisaeureChEBI
Butanedionic acidChEBI
Dihydrofumaric acidChEBI
e363ChEBI
Ethylenesuccinic acidChEBI
HOOC-CH2-CH2-COOHChEBI
Spirit OF amberChEBI
1,2-EthanedicarboxylateGenerator
ButanedionateGenerator
DihydrofumarateGenerator
EthylenesuccinateGenerator
SuccinateGenerator
1,2 Ethanedicarboxylic acidMeSH
1,4 Butanedioic acidMeSH
1,4-Butanedioic acidMeSH
Ammonium succinateMeSH
Butanedioic acidMeSH
Potassium succinateMeSH
Succinate, ammoniumMeSH
Succinate, potassiumMeSH
1,4-ButanedioateHMDB
KatasuccinHMDB
Wormwood acidHMDB
2-Acetamido-2-deoxy-D-glucoseChEBI, HMDB
D-GlcNAcChEBI, HMDB
N-Acetyl-D-glucosamineChEBI, HMDB
N-AcetylchitosamineChEBI, HMDB
N Acetyl D glucosamineHMDB
2 Acetamido 2 deoxy D glucoseHMDB
2 Acetamido 2 deoxyglucoseHMDB
2-Acetamido-2-deoxyglucoseHMDB
AcetylglucosamineHMDB
Chemical FormulaC4H6O4
Average Molecular Weight118.088
Monoisotopic Molecular Weight118.02660868
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number110-15-6
SMILESNot Available
InChI Identifier
InChI=1S/C4H6O4/c5-3(6)1-2-4(7)8/h1-2H2,(H,5,6)(H,7,8)
InChI KeyKDYFGRWQOYBRFD-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassDicarboxylic acids and derivatives
Direct ParentDicarboxylic acids and derivatives
Alternative Parents
Substituents
  • Fatty acid
  • Dicarboxylic acid or derivatives
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Endoplasmic reticulum
  • Mitochondria
  • Peroxisome
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point185 - 188 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility83.2 mg/mLNot Available
LogP-0.59HANSCH,C ET AL. (1995)
Predicted PropertiesNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Biological Properties
Cellular Locations
  • Cytoplasm
  • Endoplasmic reticulum
  • Mitochondria
  • Peroxisome
Biospecimen Locations
  • Adipose Tissue
  • Blood
  • Brain
  • Colostrum
  • Fibroblasts
  • Kidney
  • Liver
  • Longissimus Thoracis Muscle
  • Mammary Gland
  • Milk
  • Muscle
  • Pancreas
  • Placenta
  • Prostate Tissue
  • Ruminal Fluid
  • Semen
  • Semimembranosus Muscle
  • Spleen
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Adipose TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
    • Jiyuan Li, Everes...
details
BloodDetected and Quantified1717 +/- 365 uMNot SpecifiedNot Specified
Normal
    • Abdullah BASOGLU,...
details
BrainExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
ColostrumDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
FibroblastsExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
LiverDetected and Quantified1194 +/- 584 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Longissimus Thoracis MuscleDetected and Quantified1133 +/- 308 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified14 +/- 2 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified15 +/- 1 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified23.20 +/- 6.60 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified20 +/- 1 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified14 +/- 1 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified16 - 106 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
    • Kurt J. Boudonck,...
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
    • Kurt J. Boudonck,...
details
MilkDetected and Quantified19.73 +/- 3.18 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified23.06 +/- 3.75 uMNot SpecifiedNot Specified
Normal
details
MuscleDetected and Quantified891-2314 nmol/g of tissueNot SpecifiedNot Specified
Normal
details
MuscleDetected and Quantified110.14 +/- 35.65 uMNot SpecifiedNot Specified
Normal
details
MuscleDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MuscleDetected and Quantified167.81 +/- 31.14 uMNot SpecifiedNot Specified
Normal
details
MuscleDetected and Quantified172.53 +/- 22.4 uMNot SpecifiedNot Specified
Normal
details
MuscleDetected and Quantified74-492 nmol/g of tissueNot SpecifiedNot Specified
Normal
details
MuscleDetected and Quantified453.8 +/- 37.98 uMNot SpecifiedNot Specified
Normal
details
MuscleDetected and Quantified590 nmol/g of tissueNot SpecifiedNot Specified
Normal
details
PancreasExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Prostate TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Ruminal FluidDetected and Quantified125.4 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified158.2 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified117.9 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified597 +/- 344 uMNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
Ruminal FluidDetected and Quantified40-289 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified112.7 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified23-250 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified147 +/- 35 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected and Quantified178 +/- 65 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected and Quantified118 +/- 52 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected and Quantified124 +/- 21 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected and Quantified124 +/- 21 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified84.5 uMNot SpecifiedNot Specified
Normal
    • Burim NA, Qendrim...
details
Ruminal FluidDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified103.6 uMNot SpecifiedNot Specified
Normal
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified80.7 uMNot SpecifiedNot Specified
Normal
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified82 uMNot SpecifiedNot Specified
Normal
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified112.68 +/- 18.27 uMNot SpecifiedNot SpecifiedNormal
    • Fozia Saleem, Sou...
details
SemenDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Semimembranosus MuscleDetected and Quantified743 +/- 384 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
SpleenExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
TestisDetected and Quantified340 +/- 76 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
All Mycobacterium avium subsp. paratuberculosis-infected
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
High dose Mycobacterium avium subsp. paratuberculosis-infected
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Low dose Mycobacterium avium subsp. paratuberculosis-infected
details
BloodDetected and Quantified912 +/- 96 uMNot SpecifiedNot Specified
Left displaced abomasum (LDA)
    • Abdullah BASOGLU,...
details
BloodDetected and Quantified592 +/- 172 uMNot SpecifiedNot Specified
Right displaced abomasum (RDA)
    • Abdullah BASOGLU,...
details
Ruminal FluidDetected and Quantified117.87 +/- 50.05 uMNot SpecifiedNot SpecifiedRumen acidosis
    • Fozia Saleem, Sou...
details
HMDB IDHMDB0000254
DrugBank IDDB00139
Phenol Explorer Compound IDNot Available
FooDB IDFDB001931
KNApSAcK IDC00001205
Chemspider ID1078
KEGG Compound IDC00042
BioCyc IDSUC
BiGG IDNot Available
Wikipedia LinkSuccinic_acid
METLIN IDNot Available
PubChem Compound1738118
PDB IDNot Available
ChEBI ID15741
References
Synthesis ReferenceBerglund, Kris Arvid; Andersson, Christian; Rova, Ulrika. Process for the production of succinic acid. PCT Int. Appl. (2007), 30pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563. [PubMed:20338431 ]
  2. Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]
  3. Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6. [PubMed:25108860 ]
  4. O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. [PubMed:29642378 ]
  5. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
  6. A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.

Enzymes

General function:
Energy production and conversion
Specific function:
Iron-sulfur protein (IP) subunit of succinate dehydrogenase (SDH) that is involved in complex II of the mitochondrial electron transport chain and is responsible for transferring electrons from succinate to ubiquinone (coenzyme Q).
Gene Name:
SDHB
Uniprot ID:
Q3T189
Molecular weight:
31518.0
General function:
Energy production and conversion
Specific function:
Flavoprotein (FP) subunit of succinate dehydrogenase (SDH) that is involved in complex II of the mitochondrial electron transport chain and is responsible for transferring electrons from succinate to ubiquinone (coenzyme Q) (Probable). Can act as a tumor suppressor (By similarity).
Gene Name:
SDHA
Uniprot ID:
P31039
Molecular weight:
72944.0
General function:
Posttranslational modification, protein turnover, chaperones
Specific function:
Specifically hydroxylates an Asp or Asn residue in certain epidermal growth factor-like (EGF) domains of a number of proteins.
Gene Name:
ASPH
Uniprot ID:
Q28056
Molecular weight:
84999.0
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Converts trimethyllysine (TML) into hydroxytrimethyllysine (HTML).
Gene Name:
TMLHE
Uniprot ID:
Q0VC74
Molecular weight:
49837.0
Reactions
N6,N6,N6-Trimethyl-L-lysine + Oxoglutaric acid + Oxygen → 3-Hydroxy-N6,N6,N6-trimethyl-L-lysine + Succinic acid + Carbon dioxidedetails
3-Dehydroxycarnitine + Oxoglutaric acid + Oxygen → L-Carnitine + Succinic acid + Carbon dioxidedetails
General function:
Energy production and conversion
Specific function:
ATP-specific succinyl-CoA synthetase functions in the citric acid cycle (TCA), coupling the hydrolysis of succinyl-CoA to the synthesis of ATP and thus represents the only step of substrate-level phosphorylation in the TCA. The beta subunit provides nucleotide specificity of the enzyme and binds the substrate succinate, while the binding sites for coenzyme A and phosphate are found in the alpha subunit.
Gene Name:
SUCLA2
Uniprot ID:
Q148D5
Molecular weight:
50130.0
General function:
Energy production and conversion
Specific function:
Succinyl-CoA synthetase functions in the citric acid cycle (TCA), coupling the hydrolysis of succinyl-CoA to the synthesis of either ATP or GTP and thus represents the only step of substrate-level phosphorylation in the TCA. The alpha subunit of the enzyme binds the substrates coenzyme A and phosphate, while succinate binding and specificity for either ATP or GTP is provided by different beta subunits.
Gene Name:
SUCLG1
Uniprot ID:
Q58DR8
Molecular weight:
36167.0
Reactions
Succinyl-CoA + Hydrogen phosphate + Guanosine diphosphate → Succinic acid + Coenzyme A + Guanosine triphosphatedetails
General function:
Energy production and conversion
Specific function:
GTP-specific succinyl-CoA synthetase functions in the citric acid cycle (TCA), coupling the hydrolysis of succinyl-CoA to the synthesis of GTP and thus represents the only step of substrate-level phosphorylation in the TCA. The beta subunit provides nucleotide specificity of the enzyme and binds the substrate succinate, while the binding sites for coenzyme A and phosphate are found in the alpha subunit.
Gene Name:
SUCLG2
Uniprot ID:
Q3MHX5
Molecular weight:
46691.0
Reactions
Succinyl-CoA + Hydrogen phosphate + Guanosine diphosphate → Succinic acid + Coenzyme A + Guanosine triphosphatedetails
General function:
Involved in iron ion binding
Specific function:
Catalyzes the post-translational formation of 4-hydroxyproline in -Xaa-Pro-Gly- sequences in collagens and other proteins.
Gene Name:
P4HA1
Uniprot ID:
Q1RMU3
Molecular weight:
61010.0
General function:
Involved in iron ion binding
Specific function:
Part of a complex composed of PLOD1, P3H3 and P3H4 that catalyzes hydroxylation of lysine residues in collagen alpha chains and is required for normal assembly and cross-linkling of collagen fibrils (By similarity). Forms hydroxylysine residues in -Xaa-Lys-Gly- sequences in collagens (By similarity). These hydroxylysines serve as sites of attachment for carbohydrate units and are essential for the stability of the intermolecular collagen cross-links (By similarity).
Gene Name:
PLOD1
Uniprot ID:
O77588
Molecular weight:
83487.0
General function:
Involved in iron ion binding
Specific function:
Converts phytanoyl-CoA to 2-hydroxyphytanoyl-CoA.
Gene Name:
PHYH
Uniprot ID:
O18778
Molecular weight:
38770.0
Reactions
Phytanoyl-CoA + Oxoglutaric acid + Oxygen → 2-Hydroxyphytanoyl-CoA + Succinic acid + Carbon dioxidedetails
General function:
Involved in iron ion binding
Specific function:
Catalyzes the post-translational formation of 4-hydroxyproline in -Xaa-Pro-Gly- sequences in collagens and other proteins.
Gene Name:
P4HA3
Uniprot ID:
Q75UG4
Molecular weight:
61023.0
Reactions
L-Proline + Oxoglutaric acid + Oxygen → Hydroxyproline + Succinic acid + Carbon dioxidedetails
General function:
Not Available
Specific function:
Key enzyme for ketone body catabolism. Transfers the CoA moiety from succinate to acetoacetate. Formation of the enzyme-CoA intermediate proceeds via an unstable anhydride species formed between the carboxylate groups of the enzyme and substrate.
Gene Name:
OXCT1
Uniprot ID:
Q24JZ7
Molecular weight:
56453.0
Reactions
Acetoacetic acid + Succinyl-CoA → Succinic acid + Acetoacetyl-CoAdetails
Acetoacetic acid + Succinyl-CoA → Acetoacetyl-CoA + Succinic aciddetails