Record Information
Version2.0
Creation Date2012-05-31 10:24:59 -0600
Update Date2015-09-13 12:56:07 -0600
Secondary Accession Numbers
  • ECMDB00254
Identification
Name:Succinic acid
Description:Succinic acid is a dicarboxylic acid. The anion, succinate, is a component of the citric acid cycle capable of donating electrons to the electron transfer chain. SDH with a covalently attached FAD prosthetic group, binds enzyme substrates (succinate and fumarate) and physiological regulators (oxaloacetate and ATP). Oxidizing succinate links SDH to the fast-cycling Krebs cycle portion where it participates in the breakdown of acetyl-CoA throughout the whole Krebs cycle.
Structure
Thumb
Synonyms:
  • 1,2-Ethanedicarboxylate
  • 1,2-Ethanedicarboxylic acid
  • 1,4-Butanedioate
  • 1,4-Butanedioic acid
  • Amber acid
  • Asuccin
  • Butanedioate
  • Butanedioic acid
  • Dihydrofumarate
  • Dihydrofumaric acid
  • Ethylenesuccinate
  • Ethylenesuccinic acid
  • Katasuccin
  • Suc
  • Succ
  • Succinate
  • Succinic acid
  • Wormwood acid
Chemical Formula:C4H6O4
Weight:Average: 118.088
Monoisotopic: 118.02660868
InChI Key:KDYFGRWQOYBRFD-UHFFFAOYSA-N
InChI:InChI=1S/C4H6O4/c5-3(6)1-2-4(7)8/h1-2H2,(H,5,6)(H,7,8)
CAS number:110-15-6
IUPAC Name:butanedioic acid
Traditional IUPAC Name:succinic acid
SMILES:OC(=O)CCC(O)=O
Chemical Taxonomy
DescriptionThis compound 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
Physical Properties
State:Solid
Charge:-2
Melting point:185-188 °C
Experimental Properties:
PropertyValueSource
Water Solubility:83.2 mg/mL [YALKOWSKY,SH & HE,Y (2003)]PhysProp
LogP:-0.59 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility211.0 mg/mLALOGPS
logP-0.53ALOGPS
logP-0.4ChemAxon
logS0.25ALOGPS
pKa (Strongest Acidic)3.55ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity23.54 m3·mol-1ChemAxon
Polarizability10.14 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Ubiquinone-8 + Succinic acid > Fumaric acid + Ubiquinol-8
Adenosine triphosphate + Coenzyme A + Succinic acid <> ADP + Phosphate + Succinyl-CoA
Water + NADP + Succinic acid semialdehyde >2 Hydrogen ion + NADPH + Succinic acid
Fumaric acid + Menaquinol 8 > Menaquinone 8 + Succinic acid
2-Demethylmenaquinol 8 + Fumaric acid > 2-Demethylmenaquinone 8 + Succinic acid
Methylisocitric acid <> Pyruvic acid + Succinic acid
Water + 2-Hydroxy-6-ketononadienedicarboxylate > Hydrogen ion + 2-Hydroxy-2,4-pentadienoate + Succinic acid
alpha-Ketoglutarate + Oxygen + Taurine <> Aminoacetaldehyde + Carbon dioxide + Hydrogen ion + Sulfite + Succinic acid
Water + NAD + Succinic acid semialdehyde >2 Hydrogen ion + NADH + Succinic acid
Water + N-Succinyl-L-glutamate <> L-Glutamate + Succinic acid
Water + N-Succinyl-L,L-2,6-diaminopimelate <> Diaminopimelic acid + Succinic acid
L-Aspartic acid + Fumaric acid > Hydrogen ion + Iminoaspartic acid + Succinic acid
Propionyl-CoA + Succinic acid > Propionic acid + Succinyl-CoA
3 Fumaric acid + Protoporphyrinogen IX > Protoporphyrin IX +3 Succinic acid
L-Cysteine + O-Succinyl-L-homoserine <> L-Cystathionine + Hydrogen ion + Succinic acid
Isocitric acid <> Glyoxylic acid + Succinic acid
Adenosine triphosphate + Succinic acid + Coenzyme A <> ADP + Phosphate + Succinyl-CoA
Succinic acid + FAD <> FADH2 + Fumaric acid
Methylisocitric acid <> Pyruvic acid + Succinic acid
N-Succinyl-L-glutamate + Water <> L-Glutamate + Succinic acid
Succinic acid + Acceptor <> Fumaric acid + Reduced acceptor
Isocitric acid <> Succinic acid + Glyoxylic acid
Succinic acid semialdehyde + NAD + Water <> Succinic acid + NADH + Hydrogen ion
Succinic acid semialdehyde + NADP + Water <> Succinic acid + NADPH + Hydrogen ion
O-Succinyl-L-homoserine + Water <> 2-Ketobutyric acid + Succinic acid + Ammonia
O-Succinyl-L-homoserine + Hydrogen sulfide <> L-Homocysteine + Succinic acid
4,5-Dihydroorotic acid + Fumaric acid <> Orotic acid + Succinic acid
Cystathionine + Succinic acid <> O-Succinyl-L-homoserine + L-Cysteine
2-Hydroxy-2,4-pentadienoate + Succinic acid <> 2-Hydroxy-6-ketononadienedicarboxylate + Water
N-Succinyl-L,L-2,6-diaminopimelate + Water <> Succinic acid + Diaminopimelic acid
O-Succinyl-L-homoserine + L-Cysteine <> L-Cystathionine + Succinic acid
O-Succinyl-L-homoserine + Selenocysteine <> Selenocystathionine + Succinic acid
Taurine + alpha-Ketoglutarate + Oxygen <> Sulfite + Aminoacetaldehyde + Succinic acid + Carbon dioxide
Isocitric acid <> Glyoxylic acid + Succinic acid
Hydrogen ion + 2-Ketobutyric acid + Succinic acid + Ammonia O-Succinyl-L-homoserine + Water
Methylisocitric acid > Succinic acid + Pyruvic acid
2-Hydroxy-6-ketononadienedicarboxylate + Water > 2-Hydroxy-2,4-pentadienoate + Succinic acid + Hydrogen ion
L-Cysteine + O-Succinyl-L-homoserine > Hydrogen ion + Succinic acid + L-Cystathionine
Fumaric acid + a menaquinol > a menaquinone + Succinic acid
a methylated nucleobase within DNA + Oxygen + Oxoglutaric acid Hydrogen ion + a nucleobase within DNA + Carbon dioxide + Formaldehyde + Succinic acid
L-Aspartic acid + Fumaric acid > Hydrogen ion + Iminoaspartic acid + Succinic acid
Propionyl-CoA + Succinic acid <> Propionic acid + Succinyl-CoA
Taurine + Oxoglutaric acid + Oxygen > Hydrogen ion + Aminoacetaldehyde + Sulfite + Succinic acid + Carbon dioxide
N1-Methyladenine + Oxygen + Oxoglutaric acid > Hydrogen ion + Adenine + Carbon dioxide + Formaldehyde + Succinic acid
N3-Methylcytosine + Oxygen + Oxoglutaric acid > Hydrogen ion + Cytosine + Carbon dioxide + Formaldehyde + Succinic acid
1-Ethyladenine + Oxygen + Oxoglutaric acid > Adenine + Carbon dioxide + Acetaldehyde + Succinic acid
Succinic acid + Coenzyme A + Adenosine triphosphate <> Succinyl-CoA + ADP + Phosphate
Water + N-Succinyl-L,L-2,6-diaminopimelate <> Diaminopimelic acid + Succinic acid
N<SUP>2</SUP>-succinylglutamate + Water > Succinic acid + L-Glutamate
a ubiquinone + Succinic acid <> a ubiquinol + Fumaric acid
Water + NAD + Succinic acid semialdehyde > Hydrogen ion + NADH + Succinic acid
Succinic acid semialdehyde + NADP + Water > Succinic acid + NADPH + Hydrogen ion
Isocitric acid > Succinic acid + Glyoxylic acid
DNA-base-CH(3) + Oxoglutaric acid + Oxygen > DNA-base + Formaldehyde + Succinic acid + Carbon dioxide
N-Succinyl-L-glutamate + Water > Succinic acid + L-Glutamate
N-succinyl-L-2,6-diaminoheptanedioate + Water > Succinic acid + Diaminopimelic acid
Succinic acid + acceptor > Fumaric acid + reduced acceptor
Succinic acid + acceptor > Fumaric acid + reduced acceptor
Succinic acid + acceptor > Fumaric acid + reduced acceptor
Succinic acid + acceptor > Fumaric acid + reduced acceptor
Succinic acid semialdehyde + NADP + Water > Succinic acid + NADPH
O-Succinyl-L-homoserine + L-Cysteine > L-Cystathionine + Succinic acid
(2E,4Z)-2-hydroxy-6-oxonona-2,4-diene-1,9-dioate + Water > 2-oxopent-4-enoate + Succinic acid
(2S,3R)-3-hydroxybutane-1,2,3-tricarboxylate > Pyruvic acid + Succinic acid
Succinic acid semialdehyde + NAD(P)(+) + Water > Succinic acid + NAD(P)H
Propionyl-CoA + Succinic acid > Propionic acid + Succinyl-CoA
Adenosine triphosphate + Succinic acid + CoA > ADP + Inorganic phosphate + Succinyl-CoA
Adenosine triphosphate + Succinic acid + CoA > ADP + Inorganic phosphate + Succinyl-CoA
Taurine + Oxoglutaric acid + Oxygen > Sulfite + Aminoacetaldehyde + Succinic acid + Carbon dioxide
Succinic acid semialdehyde + NAD + NADP + Water <> Succinic acid + NADH + NADPH +2 Hydrogen ion
Succinic acid + Quinone <> Fumaric acid + Hydroquinone
2-Hydroxy-6-ketononadienedicarboxylate + Water + 2-Hydroxy-6-ketononatrienedioate <> Succinic acid + Fumaric acid
N-Succinyl-L,L-2,6-diaminopimelate + Water > Succinic acid + Diaminopimelic acid
Taurine + Oxoglutaric acid + Oxygen > Sulfite + Succinic acid + Aminoacetaldehyde + Carbon dioxide + Sulfite
Taurine + Oxoglutaric acid + Oxygen > Sulfite + Succinic acid + Carbon dioxide + Hydrogen ion + Aminoacetaldehyde + Sulfite
Succinyl-CoA + Phosphate + Guanosine diphosphate + Succinyl-CoA <> Succinic acid + Coenzyme A + Guanosine triphosphate
Succinic acid + Ubiquinone-10 + FAD <> Fumaric acid + QH2 + FADH2
Succinyl-CoA + Adenosine diphosphate + Phosphate + Succinyl-CoA + ADP > Adenosine triphosphate + Coenzyme A + Succinic acid
Succinic acid + Ubiquinone-1 > Ubiquinol-1 + Fumaric acid
Succinic acid + Ubiquinone-2 > Fumaric acid + Ubiquinol-2
Succinic acid + Ubiquinone-3 > Fumaric acid + Ubiquinol-3
Succinic acid + Ubiquinone-4 > Fumaric acid + Ubiquinol-4
Succinic acid + Ubiquinone-5 > Fumaric acid + Ubiquinol-5
Succinic acid + Ubiquinone-6 > Fumaric acid + Ubiquinol-6
Succinic acid + Ubiquinone-7 > Fumaric acid + Ubiquinol-7
Succinic acid + Ubiquinone-8 > Fumaric acid + Ubiquinol 8 + Ubiquinol-8
Succinic acid + Coenzyme Q9 > Fumaric acid + Ubiquinol-9
Succinic acid + Ubiquinone-10 > Fumaric acid + Ubiquinol-10 + Ubiquinol-10
N2-succinylglutamate + Water + N2-succinylglutamate > L-Glutamic acid + Succinic acid + L-Glutamate
Succinic acid semialdehyde + Water + NADP > NADPH +2 Hydrogen ion + Succinic acid + NADPH
Succinic acid semialdehyde + NAD + Water >2 Hydrogen ion + NADH + Succinic acid
O-Succinyl-L-homoserine + L-Cysteine > Succinic acid + Hydrogen ion + L-Cystathionine
Methylisocitric acid > Succinic acid + Pyruvic acid
Succinic acid + Propionyl-CoA + Propionyl-CoA > Propionic acid + Succinyl-CoA + Succinyl-CoA
Isocitric acid + Isocitric acid <> Succinic acid + Glyoxylic acid
1-Ethyladenine + Oxoglutaric acid + Oxygen > Adenine + Carbon dioxide + Acetaldehyde + Succinic acid
Ubiquinone-0 + Succinic acid > Ubiquinol-0 + Fumaric acid
(2E,4Z)-2-hydroxy-6-oxonona-2,4-diene-1,9-dioate + Water > (2Z)-2-hydroxypenta-2,4-dienoate + Succinic acid + Hydrogen ion
Fumaric acid + 2 Hydrogen ion + "a menaquinol" > Succinic acid + "a menaquinone"
Succinic acid semialdehyde + NAD + Water > Succinic acid + NADH +2 Hydrogen ion
Propionyl-CoA + Succinic acid <> Propionic acid + Succinyl-CoA
More...

SMPDB Pathways:
2-Oxopent-4-enoate metabolismPW001890 Pw001890Pw001890 greyscalePw001890 simple
2-Oxopent-4-enoate metabolism 2PW002035 Pw002035Pw002035 greyscalePw002035 simple
4-aminobutanoate degradation IPW002068 Pw002068Pw002068 greyscalePw002068 simple
Collection of Reactions without pathwaysPW001891 Pw001891Pw001891 greyscalePw001891 simple
Conversion of Succinate to PropanoatePW002058 Pw002058Pw002058 greyscalePw002058 simple
Gluconeogenesis from L-malic acidPW000819 Pw000819Pw000819 greyscalePw000819 simple
L-glutamate metabolismPW000789 Pw000789Pw000789 greyscalePw000789 simple
Lysine biosynthesisPW000771 Pw000771Pw000771 greyscalePw000771 simple
Oxidative phosphorylationPW000919 Pw000919Pw000919 greyscalePw000919 simple
Phenylalanine metabolismPW000921 Pw000921Pw000921 greyscalePw000921 simple
Propanoate metabolismPW000940 Pw000940Pw000940 greyscalePw000940 simple
Secondary Metabolites: Glyoxylate cyclePW000967 Pw000967Pw000967 greyscalePw000967 simple
Sulfur metabolismPW000922 Pw000922Pw000922 greyscalePw000922 simple
TCA cyclePW000779 Pw000779Pw000779 greyscalePw000779 simple
TCA cycle (ubiquinol-0)PW002023 Pw002023Pw002023 greyscalePw002023 simple
TCA cycle (ubiquinol-10)PW001010 Pw001010Pw001010 greyscalePw001010 simple
TCA cycle (ubiquinol-2)PW001002 Pw001002Pw001002 greyscalePw001002 simple
TCA cycle (ubiquinol-3)PW001003 Pw001003Pw001003 greyscalePw001003 simple
TCA cycle (ubiquinol-4)PW001004 Pw001004Pw001004 greyscalePw001004 simple
TCA cycle (ubiquinol-5)PW001005 Pw001005Pw001005 greyscalePw001005 simple
TCA cycle (ubiquinol-6)PW001006 Pw001006Pw001006 greyscalePw001006 simple
TCA cycle (ubiquinol-7)PW001007 Pw001007Pw001007 greyscalePw001007 simple
TCA cycle (ubiquinol-8)PW001008 Pw001008Pw001008 greyscalePw001008 simple
TCA cycle (ubiquinol-9)PW001009 Pw001009Pw001009 greyscalePw001009 simple
Taurine MetabolismPW000774 Pw000774Pw000774 greyscalePw000774 simple
Taurine Metabolism IPW001028 Pw001028Pw001028 greyscalePw001028 simple
arginine metabolismPW000790 Pw000790Pw000790 greyscalePw000790 simple
glycolate and glyoxylate degradation IIPW002021 Pw002021Pw002021 greyscalePw002021 simple
inner membrane transportPW000786 Pw000786Pw000786 greyscalePw000786 simple
methionine biosynthesisPW000814 Pw000814Pw000814 greyscalePw000814 simple
ornithine metabolismPW000791 Pw000791Pw000791 greyscalePw000791 simple
propanoyl CoA degradationPW002057 Pw002057Pw002057 greyscalePw002057 simple
sulfur metabolism (butanesulfonate)PW000923 Pw000923Pw000923 greyscalePw000923 simple
sulfur metabolism (ethanesulfonate)PW000925 Pw000925Pw000925 greyscalePw000925 simple
sulfur metabolism (isethionate)PW000926 Pw000926Pw000926 greyscalePw000926 simple
sulfur metabolism (methanesulfonate)PW000927 Pw000927Pw000927 greyscalePw000927 simple
sulfur metabolism (propanesulfonate)PW000924 Pw000924Pw000924 greyscalePw000924 simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
ConcentrationStrainMediaGrowth StatusGrowth SystemTemperatureDetails
569± 0 uMK12 NCM3722Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucoseMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
1140± 0 uMK12 NCM3722Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glycerolMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
923± 0 uMK12 NCM3722Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L acetateMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
1602± 123 uMBL21 DE3Luria-Bertani (LB) mediaStationary phase cultures (overnight culture)Shake flask37 oCExperimentally Determined
Download Details
Find out more about how we convert literature concentrations.
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-0002-0920000000-f286e6204a4163b823baView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0002-0900000000-bf336910bb37d7f78140View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-006t-9800000000-df5ff4e8457d2d4ef919View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-00c1-3930000000-3cc18e719822b5af661aView in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-00xr-9300000000-f0644daf4fbb11fcc2dcView in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-004i-9000000000-93b4807ae6275a3e59d7View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-0kos-9100000000-f1df0903a24c305e68ecView in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-0002-0910000000-300c33b39fb991b5a73eView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0002-0920000000-f286e6204a4163b823baView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0002-0900000000-bf336910bb37d7f78140View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-006t-9800000000-df5ff4e8457d2d4ef919View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-00c1-3930000000-3cc18e719822b5af661aView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0002-0900000000-f838d863ee7c2b111f02View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-00dj-9710000000-ff8325384b9eefd19106View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-00di-9300000000-f9dc864d93a09d3074f9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-00di-9300000000-76c151de384928b2256fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-01b9-7900000000-51d2341c097f04827944View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (Unknown) , Positivesplash10-004i-9000000000-93b4807ae6275a3e59d7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-03dj-0971010000-37d214dc7a8fdc26116bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-014i-9000000000-249222ac742c1634cec9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00di-9000000000-6897d49472dba6a34a27View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0udi-0490000000-d138f8023125921b4b82View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-014i-1900000000-4ffdabe5bde527b66982View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-00di-9100000000-c20baa818f5ff5f678c1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-00di-9000000000-7a49a18aa6fcb2540a12View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-00di-9000000000-9955aeb0e5a9f88ae70eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-00di-9000000000-7e1f195f111b4eafb4faView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-00xr-9400000000-e50afc90e20cd420ba9bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-00xr-9600000000-43167f2549cbb5d5f7e8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-1900000000-4ffdabe5bde527b66982View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-9100000000-7a8bfa543dc087bea06dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-9000000000-fdec6c7458176f3cbeb8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-9000000000-9955aeb0e5a9f88ae70eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gb9-2900000000-9d959a53833b07094158View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0l6r-9600000000-c367e11e737714d41418View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056r-9000000000-e65aa602a8293debec36View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-2900000000-e1f840494c9003279869View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-7900000000-1089efd4a3469bcf14f1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0604-9000000000-0e0e60bb202ffb004894View in MoNA
MSMass Spectrum (Electron Ionization)splash10-05di-9100000000-c629bea41d0d3d896425View in MoNA
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. Pubmed: 19561621
  • Borenstein DG, Gibbs CA, Jacobs RP: Gas-liquid chromatographic analysis of synovial fluid: volatile short-chain fatty acids in septic arthritis. Ann Rheum Dis. 1983 Aug;42(4):362-7. Pubmed: 6882030
  • Briere JJ, Favier J, El Ghouzzi V, Djouadi F, Benit P, Gimenez AP, Rustin P: Succinate dehydrogenase deficiency in human. Cell Mol Life Sci. 2005 Oct;62(19-20):2317-24. Pubmed: 16143825
  • Frenkel G, Peterson RN, Freund M: Oxidative and glycolytic metabolism of semen components by washed guinea pig spermatozoa. Fertil Steril. 1975 Feb;26(2):144-7. Pubmed: 1126459
  • Groenen PM, Engelke UF, Wevers RA, Hendriks JC, Eskes TK, Merkus HM, Steegers-Theunissen RP: High-resolution 1H NMR spectroscopy of amniotic fluids from spina bifida fetuses and controls. Eur J Obstet Gynecol Reprod Biol. 2004 Jan 15;112(1):16-23. Pubmed: 14687733
  • Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. Pubmed: 8087979
  • Hoffmann GF, Meier-Augenstein W, Stockler S, Surtees R, Rating D, Nyhan WL: Physiology and pathophysiology of organic acids in cerebrospinal fluid. J Inherit Metab Dis. 1993;16(4):648-69. Pubmed: 8412012
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Magera MJ, Helgeson JK, Matern D, Rinaldo P: Methylmalonic acid measured in plasma and urine by stable-isotope dilution and electrospray tandem mass spectrometry. Clin Chem. 2000 Nov;46(11):1804-10. Pubmed: 11067816
  • Meijer-Severs GJ, van Santen E: Short-chain fatty acids and succinate in feces of healthy human volunteers and their correlation with anaerobe cultural counts. Scand J Gastroenterol. 1987 Aug;22(6):672-6. Pubmed: 3659829
  • Redjems-Bennani N, Jeandel C, Lefebvre E, Blain H, Vidailhet M, Gueant JL: Abnormal substrate levels that depend upon mitochondrial function in cerebrospinal fluid from Alzheimer patients. Gerontology. 1998;44(5):300-4. Pubmed: 9693263
  • Ren LC, Huang XY, Long JH: [Effects of succinic acid on the function of in vitro cultured human fibroblasts] Zhonghua Shao Shang Za Zhi. 2004 Feb;20(1):34-6. Pubmed: 15059451
  • Rustin P, Rotig A: Inborn errors of complex II--unusual human mitochondrial diseases. Biochim Biophys Acta. 2002 Jan 17;1553(1-2):117-22. Pubmed: 11803021
  • Silwood CJ, Lynch E, Claxson AW, Grootveld MC: 1H and (13)C NMR spectroscopic analysis of human saliva. J Dent Res. 2002 Jun;81(6):422-7. Pubmed: 12097436
  • Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Vijayendran, C., Barsch, A., Friehs, K., Niehaus, K., Becker, A., Flaschel, E. (2008). "Perceiving molecular evolution processes in Escherichia coli by comprehensive metabolite and gene expression profiling." Genome Biol 9:R72. Pubmed: 18402659
  • Wevers RA, Engelke U, Heerschap A: High-resolution 1H-NMR spectroscopy of blood plasma for metabolic studies. Clin Chem. 1994 Jul;40(7 Pt 1):1245-50. Pubmed: 8013094
  • Wevers RA, Engelke U, Wendel U, de Jong JG, Gabreels FJ, Heerschap A: Standardized method for high-resolution 1H-NMR of cerebrospinal fluid. Clin Chem. 1995 May;41(5):744-51. Pubmed: 7729054
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
  • Zhang TM, Sener A, Malaisse WJ: Hydrolysis of succinic acid dimethyl ester in rat pancreatic islets. Biochem Mol Med. 1995 Aug;55(2):131-7. Pubmed: 7582870
Synthesis Reference:Berglund, Kris Arvid; Andersson, Christian; Rova, Ulrika. Process for the production of succinic acid. PCT Int. Appl. (2007), 30pp.
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID15741
HMDB IDHMDB00254
Pubchem Compound ID1110
Kegg IDC00042
ChemSpider ID1078
WikipediaSuccinic acid
BioCyc IDSUC
EcoCyc IDSUC
Ligand ExpoSIN

Enzymes

General function:
Involved in electron carrier activity
Specific function:
Two distinct, membrane-bound, FAD-containing enzymes are responsible for the catalysis of fumarate and succinate interconversion; the fumarate reductase is used in anaerobic growth, and the succinate dehydrogenase is used in aerobic growth
Gene Name:
frdA
Uniprot ID:
P00363
Molecular weight:
65971
Reactions
Succinate + acceptor = fumarate + reduced acceptor.
General function:
Involved in pyridoxal phosphate binding
Specific function:
O(4)-succinyl-L-homoserine + L-cysteine = L- cystathionine + succinate
Gene Name:
metB
Uniprot ID:
P00935
Molecular weight:
41550
Reactions
O(4)-succinyl-L-homoserine + L-cysteine = L-cystathionine + succinate.
General function:
Involved in electron carrier activity
Specific function:
Two distinct, membrane-bound, FAD-containing enzymes are responsible for the catalysis of fumarate and succinate interconversion; the fumarate reductase is used in anaerobic growth, and the succinate dehydrogenase is used in aerobic growth
Gene Name:
sdhB
Uniprot ID:
P07014
Molecular weight:
26770
Reactions
Succinate + acceptor = fumarate + reduced acceptor.
General function:
Involved in catalytic activity
Specific function:
(S)-dihydroorotate + a quinone = orotate + a quinol
Gene Name:
pyrD
Uniprot ID:
P0A7E1
Molecular weight:
36774
Reactions
(S)-dihydroorotate + a quinone = orotate + a quinol.
General function:
Involved in ATP binding
Specific function:
ATP + succinate + CoA = ADP + phosphate + succinyl-CoA
Gene Name:
sucC
Uniprot ID:
P0A836
Molecular weight:
41392
Reactions
ATP + succinate + CoA = ADP + phosphate + succinyl-CoA.
General function:
Energy production and conversion
Specific function:
Seems to be involved in the anchoring of the catalytic components of the fumarate reductase complex to the cytoplasmic membrane
Gene Name:
frdC
Uniprot ID:
P0A8Q0
Molecular weight:
15015
General function:
Involved in fumarate metabolic process
Specific function:
Seems to be involved in the anchoring of the catalytic components of the fumarate reductase complex to the cytoplasmic membrane
Gene Name:
frdD
Uniprot ID:
P0A8Q3
Molecular weight:
13107
General function:
Involved in isocitrate lyase activity
Specific function:
Catalyzes the formation of succinate and glyoxylate from isocitrate, a key step of the glyoxylate cycle. May be involved in the assimilation of one-carbon compounds via the isocitrate lyase- positive serine pathway
Gene Name:
aceA
Uniprot ID:
P0A9G6
Molecular weight:
47521
Reactions
Isocitrate = succinate + glyoxylate.
General function:
Involved in electron carrier activity
Specific function:
Two distinct, membrane-bound, FAD-containing enzymes are responsible for the catalysis of fumarate and succinate interconversion; the fumarate reductase is used in anaerobic growth, and the succinate dehydrogenase is used in aerobic growth
Gene Name:
sdhA
Uniprot ID:
P0AC41
Molecular weight:
64421
Reactions
Succinate + acceptor = fumarate + reduced acceptor.
General function:
Involved in succinate dehydrogenase activity
Specific function:
Membrane-anchoring subunit of succinate dehydrogenase (SDH)
Gene Name:
sdhD
Uniprot ID:
P0AC44
Molecular weight:
12867
General function:
Involved in electron carrier activity
Specific function:
Two distinct, membrane-bound, FAD-containing enzymes are responsible for the catalysis of fumarate and succinate interconversion; the fumarate reductase is used in anaerobic growth, and the succinate dehydrogenase is used in aerobic growth
Gene Name:
frdB
Uniprot ID:
P0AC47
Molecular weight:
27123
Reactions
Succinate + acceptor = fumarate + reduced acceptor.
General function:
Involved in FMN binding
Specific function:
Catalyzes the 6-electron oxidation of protoporphyrinogen-IX to form protoporphyrin-IX. Does not use oxygen directly. Is coupled to the respiratory chain
Gene Name:
hemG
Uniprot ID:
P0ACB4
Molecular weight:
21226
Reactions
Protoporphyrinogen IX + 3 menaquinone = protoporphyrin IX + 3 menaquinol.
General function:
Involved in metallopeptidase activity
Specific function:
Catalyzes the hydrolysis of N-succinyl-L,L- diaminopimelic acid (SDAP), forming succinate and LL-2,6- diaminoheptanedioate (DAP), an intermediate involved in the bacterial biosynthesis of lysine and meso-diaminopimelic acid, an essential component of bacterial cell walls
Gene Name:
dapE
Uniprot ID:
P0AED7
Molecular weight:
41269
Reactions
N-succinyl-LL-2,6-diaminoheptanedioate + H(2)O = succinate + LL-2,6-diaminoheptanedioate.
General function:
Involved in catalytic activity
Specific function:
ATP + succinate + CoA = ADP + phosphate + succinyl-CoA
Gene Name:
sucD
Uniprot ID:
P0AGE9
Molecular weight:
29777
Reactions
ATP + succinate + CoA = ADP + phosphate + succinyl-CoA.
General function:
Involved in electron carrier activity
Specific function:
Catalyzes the oxidation of L-aspartate to iminoaspartate
Gene Name:
nadB
Uniprot ID:
P10902
Molecular weight:
60337
Reactions
L-aspartate + O(2) = iminosuccinate + H(2)O(2).
General function:
Involved in oxidoreductase activity
Specific function:
Succinate semialdehyde + NAD(P)(+) + H(2)O = succinate + NAD(P)H
Gene Name:
gabD
Uniprot ID:
P25526
Molecular weight:
51720
Reactions
Succinate semialdehyde + NADP(+) + H(2)O = succinate + NADPH.
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the conversion of taurine and alpha ketoglutarate to sulfite, aminoacetaldehyde and succinate. Required for the utilization of taurine (2-aminoethanesulfonic acid) as an alternative sulfur source. Pentane-sulfonic acid, 3- (N-morpholino)propanesulfonic acid and 1,3-dioxo-2- isoindolineethanesulfonic acid are also substrates for this enzyme
Gene Name:
tauD
Uniprot ID:
P37610
Molecular weight:
32409
Reactions
Taurine + 2-oxoglutarate + O(2) = sulfite + aminoacetaldehyde + succinate + CO(2).
General function:
Involved in succinate dehydrogenase activity
Specific function:
Membrane-anchoring subunit of succinate dehydrogenase (SDH)
Gene Name:
sdhC
Uniprot ID:
P69054
Molecular weight:
14299
General function:
Involved in hydrolase activity, acting on ester bonds
Specific function:
Transforms N(2)-succinylglutamate into succinate and glutamate
Gene Name:
astE
Uniprot ID:
P76215
Molecular weight:
35800
Reactions
N-succinyl-L-glutamate + H(2)O = succinate + L-glutamate.
General function:
Involved in catalytic activity
Specific function:
Catalyzes the cleavage of the C5-C6 bond of 2-hydroxy-6- oxononadienedioate and 2-hydroxy-6-oxononatrienedioate, a dienol ring fission product of the bacterial meta-cleavage pathway for degradation of phenylpropionic acid
Gene Name:
mhpC
Uniprot ID:
P77044
Molecular weight:
32585
Reactions
(2E,4Z)-2-hydroxy-6-oxonona-2,4-diene-1,9-dioate + H(2)O = (2E)-2-hydroxypenta-2,4-dienoate + succinate.
(2E,4Z,7E)-2-hydroxy-6-oxonona-2,4,7-triene-1,9-dioate + H(2)O = (2E)-2-hydroxypenta-2,4-dienoate + fumarate.
General function:
Involved in catalytic activity
Specific function:
Catalyzes the formation of pyruvate and succinate from 2-methylisocitrate
Gene Name:
prpB
Uniprot ID:
P77541
Molecular weight:
32134
Reactions
(2S,3R)-3-hydroxybutane-1,2,3-tricarboxylate = pyruvate + succinate.
General function:
Involved in oxidoreductase activity
Specific function:
Specific function unknown
Gene Name:
yneI
Uniprot ID:
P76149
Molecular weight:
49717
Reactions
Succinate semialdehyde + NAD(P)(+) + H(2)O = succinate + NAD(P)H.
General function:
Involved in catalytic activity
Specific function:
Specific function unknown
Gene Name:
ygfH
Uniprot ID:
P52043
Molecular weight:
53824
Reactions
Propanoyl-CoA + succinate = propionate + succinyl-CoA.
General function:
Not Available
Specific function:
Dioxygenase that repairs alkylated DNA and RNA containing 3-methylcytosine or 1-methyladenine by oxidative demethylation. Has highest activity towards 3-methylcytosine. Has lower activity towards alkylated DNA containing ethenoadenine, and no detectable activity towards 1-methylguanine or 3-methylthymine. Accepts double-stranded and single-stranded substrates. Requires molecular oxygen, alpha-ketoglutarate and iron. Provides extensive resistance to alkylating agents such as MMS and DMS (SN2 agents), but not to MMNG and MNU (SN1 agents). Dioxygenase that repairs alkylated DNA and RNA containing 3-methylcytosine or 1-methyladenine by oxidative demethylation. Has highest activity towards 3-methylcytosine. Has lower activity towards alkylated DNA containing ethenoadenine, and no detectable activity towards 1-methylguanine or 3-methylthymine. Accepts double-stranded and single-stranded substrates. Requires molecular oxygen, alpha-ketoglutarate and iron. Provides extensive resistance to alkylating agents such as MMS and DMS (SN2 agents), but not to MMNG and MNU (SN1 agents).
Gene Name:
alkB
Uniprot ID:
P05050
Molecular weight:
Not Available
Reactions
DNA-base-CH(3) + 2-oxoglutarate + O(2) = DNA-base + formaldehyde + succinate + CO(2).
DNA-base-CH(3) + 2-oxoglutarate + O(2) = DNA-base + formaldehyde + succinate + CO(2).

Transporters

General function:
Involved in C4-dicarboxylate transmembrane transporter activity
Specific function:
Responsible for the transport of C4-dicarboxylates from the periplasm across the inner membrane
Gene Name:
dcuA
Uniprot ID:
P0ABN5
Molecular weight:
45750
General function:
Involved in C4-dicarboxylate transmembrane transporter activity
Specific function:
Responsible for the transport of C4-dicarboxylates from the periplasm across the inner membrane
Gene Name:
dcuB
Uniprot ID:
P0ABN9
Molecular weight:
47935
General function:
Involved in C4-dicarboxylate transmembrane transporter activity
Specific function:
Responsible for the transport of C4-dicarboxylates during anaerobic growth
Gene Name:
dcuC
Uniprot ID:
P0ABP3
Molecular weight:
48412
General function:
Involved in transporter activity
Specific function:
Responsible for the uptake of citrate in exchange to the efflux of succinate. Has a relatively broad specificity for C(4)- dicarboxylates and tricarboxylates
Gene Name:
citT
Uniprot ID:
P0AE74
Molecular weight:
53092
General function:
Involved in transporter activity
Specific function:
Catalyzes the uptake of tartrate in exchange for intracellular succinate. Essential for anaerobic L-tartrate fermentation
Gene Name:
ttdT
Uniprot ID:
P39414
Molecular weight:
52906
General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
General function:
Involved in symporter activity
Specific function:
Responsible for the aerobic transport of the dicarboxylates fumarate, L- and D-malate and to a lesser extent succinate, from the periplasm across the inner membrane
Gene Name:
dctA
Uniprot ID:
P0A830
Molecular weight:
45436
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368