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Showing NP-Card for Succinic acid (NP0000496)

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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2022-02-06 02:54:10 UTC
NP-MRD IDNP0000496
Secondary Accession NumbersNone
Natural Product Identification
Common NameSuccinic acid
DescriptionSuccinic acid (succinate) is a dicarboxylic acid. It is an important component of the citric acid or TCA cycle and is capable of donating electrons to the electron transfer chain. Succinate is found in all living organisms ranging from bacteria to plants to mammals. In eukaryotes, succinate is generated in the mitochondria via the tricarboxylic acid cycle (TCA). Succinate can readily be imported into the mitochondrial matrix by the n-butylmalonate- (or phenylsuccinate-) sensitive dicarboxylate carrier in exchange with inorganic phosphate or another organic acid, e. G. Malate (PMID 16143825 ). Succinate can exit the mitochondrial matrix and function in the cytoplasm as well as the extracellular space. Succinate has multiple biological roles including roles as a metabolic intermediate and roles as a cell signalling molecule. Succinate can alter gene expression patterns, thereby modulating the epigenetic landscape or it can exhibit hormone-like signaling functions (PMID: 26971832 ). As such, succinate links cellular metabolism, especially ATP formation, to the regulation of cellular function. Succinate can be broken down or metabolized into fumarate by the enzyme succinate dehydrogenase (SDH), which is part of the electron transport chain involved in making ATP. Dysregulation of succinate synthesis, and therefore ATP synthesis, can happen in a number of genetic mitochondrial diseases, such as Leigh syndrome, and Melas syndrome. Succinate has been found to be associated with D-2-hydroxyglutaric aciduria, which is an inborn error of metabolism. Succinic acid has recently been identified as an oncometabolite or an endogenous, cancer causing metabolite. High levels of this organic acid can be found in tumors or biofluids surrounding tumors. Its oncogenic action appears to due to its ability to inhibit prolyl hydroxylase-containing enzymes. In many tumours, oxygen availability becomes limited (hypoxia) very quickly due to rapid cell proliferation and limited blood vessel growth. The major regulator of the response to hypoxia is the HIF transcription factor (HIF-alpha). Under normal oxygen levels, protein levels of HIF-alpha are very low due to constant degradation, mediated by a series of post-translational modification events catalyzed by the prolyl hydroxylase domain-containing enzymes PHD1, 2 and 3, (also known as EglN2, 1 and 3) that hydroxylate HIF-alpha and lead to its degradation. All three of the PHD enzymes are inhibited by succinate. In humans, urinary succinic acid is produced by Escherichia coli, Pseudomonas aeruginosa, Klebsiella pneumonia, Enterobacter, Acinetobacter, Proteus mirabilis, Citrobacter frundii, Enterococcus faecalis (PMID: 22292465 ). Succinic acid is also found in Actinobacillus, Anaerobiospirillum, Mannheimia, Corynebacterium and Basfia (PMID: 22292465 ; PMID: 18191255 ; PMID: 26360870 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000496 (Succinic acid)


  Mrv1652309032023582D          

  8  7  0  0  0  0            999 V2000
    2.0928    0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6650   -0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8072   -1.0311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9504    1.0311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5217    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2361   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8072   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9504    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  2  8  1  0  0  0  0
  3  7  2  0  0  0  0
  4  8  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
M  END
Download

3D MOL for NP0000496 (Succinic acid)

HMDB0000254
     RDKit          3D
Succinic acid
 14 13  0  0  0  0  0  0  0  0999 V2000
    2.8686    0.7889   -0.7361 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9035    0.2266   -0.1638 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1747   -0.4955    0.9882 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5430    0.3600   -0.7380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984   -0.4191    0.1635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7892   -0.3809   -0.2775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1591   -1.0952   -1.2456 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7536    0.4134    0.3186 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6648   -0.2075    1.8241 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4587   -0.0937   -1.7508 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2383    1.4201   -0.8463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0116   -1.4669    0.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2699   -0.0395    1.1987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4699    0.9892    1.0923 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  3  9  1  0
  4 10  1  0
  4 11  1  0
  5 12  1  0
  5 13  1  0
  8 14  1  0
M  END
Download

3D SDF for NP0000496 (Succinic acid)


  Mrv1652309032023582D          

  8  7  0  0  0  0            999 V2000
    2.0928    0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6650   -0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8072   -1.0311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9504    1.0311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5217    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2361   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8072   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9504    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  2  8  1  0  0  0  0
  3  7  2  0  0  0  0
  4  8  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000496

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)CCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C4H6O4/c5-3(6)1-2-4(7)8/h1-2H2,(H,5,6)(H,7,8)

> <INCHI_KEY>
KDYFGRWQOYBRFD-UHFFFAOYSA-N

> <FORMULA>
C4H6O4

> <MOLECULAR_WEIGHT>
118.088

> <EXACT_MASS>
118.02660868

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
14

> <JCHEM_AVERAGE_POLARIZABILITY>
10.141334051490146

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
butanedioic acid

> <ALOGPS_LOGP>
-0.53

> <JCHEM_LOGP>
-0.3984829673333332

> <ALOGPS_LOGS>
0.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.6869121792916

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5541665109763474

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
23.537

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.11e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
succinic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000496 (Succinic acid)

HMDB0000254
     RDKit          3D
Succinic acid
 14 13  0  0  0  0  0  0  0  0999 V2000
    2.8686    0.7889   -0.7361 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9035    0.2266   -0.1638 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1747   -0.4955    0.9882 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5430    0.3600   -0.7380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984   -0.4191    0.1635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7892   -0.3809   -0.2775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1591   -1.0952   -1.2456 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7536    0.4134    0.3186 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6648   -0.2075    1.8241 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4587   -0.0937   -1.7508 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2383    1.4201   -0.8463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0116   -1.4669    0.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2699   -0.0395    1.1987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4699    0.9892    1.0923 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  3  9  1  0
  4 10  1  0
  4 11  1  0
  5 12  1  0
  5 13  1  0
  8 14  1  0
M  END
Download

PDB for NP0000496 (Succinic acid)

HEADER    PROTEIN                                 03-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-20         0                                  
HETATM    1  O   UNK     0       3.907   0.385   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      10.575  -0.385   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       5.240  -1.925   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       9.241   1.925   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.574   0.385   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.907  -0.385   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.240  -0.385   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.241   0.385   0.000  0.00  0.00           C+0
CONECT    1    7                                                            
CONECT    2    8                                                            
CONECT    3    7                                                            
CONECT    4    8                                                            
CONECT    5    6    7                                                       
CONECT    6    5    8                                                       
CONECT    7    1    3    5                                                  
CONECT    8    2    4    6                                                  
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END
Download

3D PDB for NP0000496 (Succinic acid)

COMPND    HMDB0000254
HETATM    1  O1  UNL     1       2.869   0.789  -0.736  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.903   0.227  -0.164  1.00  0.00           C  
HETATM    3  O2  UNL     1       2.175  -0.496   0.988  1.00  0.00           O  
HETATM    4  C2  UNL     1       0.543   0.360  -0.738  1.00  0.00           C  
HETATM    5  C3  UNL     1      -0.398  -0.419   0.163  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.789  -0.381  -0.277  1.00  0.00           C  
HETATM    7  O3  UNL     1      -2.159  -1.095  -1.246  1.00  0.00           O  
HETATM    8  O4  UNL     1      -2.754   0.413   0.319  1.00  0.00           O  
HETATM    9  H1  UNL     1       1.665  -0.207   1.824  1.00  0.00           H  
HETATM   10  H2  UNL     1       0.459  -0.094  -1.751  1.00  0.00           H  
HETATM   11  H3  UNL     1       0.238   1.420  -0.846  1.00  0.00           H  
HETATM   12  H4  UNL     1      -0.012  -1.467   0.173  1.00  0.00           H  
HETATM   13  H5  UNL     1      -0.270  -0.040   1.199  1.00  0.00           H  
HETATM   14  H6  UNL     1      -2.470   0.989   1.092  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3    9
CONECT    4    5   10   11
CONECT    5    6   12   13
CONECT    6    7    7    8
CONECT    8   14
END
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SMILES for NP0000496 (Succinic acid)

OC(=O)CCC(O)=O
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INCHI for NP0000496 (Succinic acid)

InChI=1S/C4H6O4/c5-3(6)1-2-4(7)8/h1-2H2,(H,5,6)(H,7,8)
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View in JSmol
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
2-Acetamido-2-deoxy-D-glucoseHMDB
D-GlcNAcHMDB
N-Acetyl-D-glucosamineHMDB
N-AcetylchitosamineHMDB
N Acetyl D glucosamineHMDB
2 Acetamido 2 deoxy D glucoseHMDB
2 Acetamido 2 deoxyglucoseHMDB
2-Acetamido-2-deoxyglucoseHMDB
AcetylglucosamineHMDB
1,4-ButanedioateHMDB
1,4-Butanedioic acidHMDB
KatasuccinHMDB
Wormwood acidHMDB
1,2 Ethanedicarboxylic acidHMDB
1,4 Butanedioic acidHMDB
Potassium succinateHMDB
Succinate, ammoniumHMDB
Butanedioic acidHMDB
Succinate, potassiumHMDB
Ammonium succinateHMDB
Chemical FormulaC4H6O4
Average Mass118.0880 Da
Monoisotopic Mass118.02661 Da
IUPAC Namebutanedioic acid
Traditional Namesuccinic acid
CAS Registry Number110-15-6
SMILES
OC(=O)CCC(O)=O
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, simulated)Ahselim2022-02-06View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, experimental)Ahselim2022-02-06View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, simulated)V.dorna832021-07-29View Spectrum
Species
Species of Origin
Species NameSourceReference
Abelmoschus esculentusFooDB
Actinidia chinensisFooDB
Agaricus bisporusFooDB
AgaveFooDB
Agave americanaLOTUS Database
Ailuropoda melanoleucaLOTUS Database
Allium ampeloprasumFooDB
Allium ascalonicumFooDB
Allium cepaFooDB
Allium cepa L.FooDB
Allium fistulosumFooDB
Allium sativumFooDB
Allium schoenoprasumFooDB
Allium tuberosumFooDB
Aloe veraKNApSAcK Database
Aloysia triphyllaFooDB
AmaranthusFooDB
Amelanchier alnifoliaFooDB
Ammothamnus lehmanniiLOTUS Database
Anacardium occidentaleFooDB
Ananas comosusFooDB
Anas platyrhynchosFooDB
AnatidaeFooDB
Anethum graveolensFooDB
Angelica keiskeiFooDB
Angelica sinensisKNApSAcK Database
Annona cherimolaFooDB
Annona muricataFooDB
Annona reticulataFooDB
Annona squamosaFooDB
Anser anserFooDB
Anthriscus cerefoliumFooDB
Apium graveolensFooDB
Apium graveolens var. dulceFooDB
Apium graveolens var. rapaceumFooDB
Apium graveolens var. secalinumFooDB
Arabidopsis thalianaKNApSAcK Database
Arachis hypogaeaFooDB
Arctium lappaFooDB
Ardisia arborescensKNApSAcK Database
Ardisia ellipticaLOTUS Database
Armoracia rusticanaFooDB
Artemisia dracunculusFooDB
Artemisia gmeliniiLOTUS Database
Artemisia vulgarisFooDB
Artocarpus altilisFooDB
Artocarpus heterophyllusFooDB
Asparagus officinalisFooDB
Astragalus cibariusLOTUS Database
Attalea speciosaFooDB
Auricularia auricula-judaeFooDB
Auricularia polytrichaFooDB
Avena sativa L.FooDB
Averrhoa carambolaFooDB
Basella albaFooDB
Benincasa hispidaFooDB
Bertholletia excelsaFooDB
Beta vulgarisFooDB
Beta vulgaris ssp. ciclaFooDB
Bidens bipinnataLOTUS Database
Bidens pilosaLOTUS Database
Bison bisonFooDB
Bistorta officinalisLOTUS Database
Borago officinalisFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Brassica alboglabraFooDB
Brassica junceaFooDB
Brassica napusFooDB
Brassica napus var. napusFooDB
Brassica oleraceaFooDB
Brassica oleracea var. botrytisFooDB
Brassica oleracea var. capitataFooDB
Brassica oleracea var. gemmiferaFooDB
Brassica oleracea var. gongylodesFooDB
Brassica oleracea var. italicaFooDB
Brassica oleracea var. sabaudaFooDB
Brassica oleracea var. viridisFooDB
Brassica rapaFooDB
Brassica rapa ssp. chinensisFooDB
Brassica rapa var. pekinensisFooDB
Brassica rapa var. rapaFooDB
Brassica ruvoFooDB
Brosimum alicastrumFooDB
Bubalus bubalisFooDB
Byrsonima crassifoliaFooDB
Cajanus cajanFooDB
Camellia sinensisLOTUS Database
Canarium ovatumFooDB
Cannabis sativaCannabisDB
      Not Available
Cantharellus cibariusFooDB
Capparis spinosaFooDB
Capra aegagrus hircusFooDB
Capsicum annuumKNApSAcK Database
Capsicum annuum L.FooDB
Capsicum annuum var. annuumFooDB
Capsicum chinenseFooDB
Capsicum pubescensFooDB
Carica papayaKNApSAcK Database
Carica papaya L.Plant
Carissa macrocarpaFooDB
Carthamus tinctoriusFooDB
Carum carviFooDB
CaryaFooDB
Carya illinoinensisFooDB
CastaneaFooDB
Castanea crenataFooDB
Castanea mollissimaFooDB
Castanea sativaFooDB
Ceratonia siliquaFooDB
Cercospora beticolaLOTUS Database
CervidaeFooDB
Cervus canadensisFooDB
Chamaemelum nobileFooDB
Chamerion angustifoliumFooDB
Changium smyrnioides-
Chelidonium majusLOTUS Database
Chenopodium albumFooDB
Chenopodium quinoaFooDB
Chlamydomonas reinhardtiiLOTUS Database
Chrysanthemum coronariumFooDB
Cicer arietinumFooDB
Cichorium endiviaFooDB
Cichorium intybusFooDB
CinnamomumFooDB
Cinnamomum aromaticumFooDB
Cinnamomum verumFooDB
CirsiumFooDB
Cistanche deserticolaKNApSAcK Database
Cistanche salsaLOTUS Database
Citrullus lanatusFooDB
Citrus ×limon (L.) Burm. f. (pro sp.)FooDB
Citrus aurantiifoliaFooDB
Citrus latifoliaFooDB
Citrus limonFooDB
Citrus maximaFooDB
Citrus medicaKNApSAcK Database
Citrus paradisiFooDB
Citrus reticulataFooDB
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
Cocos nuciferaFooDB
Coffea arabica L.FooDB
Coffea canephoraFooDB
Colocasia esculentaFooDB
ColumbaFooDB
ColumbidaeFooDB
Conyza bliniiKNApSAcK Database
Corchorus olitoriusFooDB
Coriandrum sativum L.FooDB
CorylusFooDB
Corylus avellanaFooDB
Crataegus pinnatifidaKNApSAcK Database
Crataegus scabrifoliaKNApSAcK Database
Crateva religiosaFooDB
Cremastra appendiculataLOTUS Database
Crocus sativusFooDB
Cucumis meloFooDB
Cucumis metuliferusFooDB
Cucumis sativus L.FooDB
CucurbitaFooDB
Cucurbita maximaFooDB
Cucurbita moschataFooDB
Cuminum cyminumFooDB
Curcuma domesticaKNApSAcK Database
Curcuma longaPlant
Cydonia oblongaFooDB
Cymbopogon citratusFooDB
Cynara cardunculusFooDB
Cynara scolymusFooDB
Daphnia magnaLOTUS Database
Daucus carotaFooDB
Daucus carota ssp. sativusFooDB
Digitalis purpureaLOTUS Database
Dimocarpus longanFooDB
DioscoreaFooDB
Dioscorea bulbiferaLOTUS Database
Dioscorea pentaphyllaFooDB
DiospyrosFooDB
Diospyros kakiFooDB
Diospyros virginianaFooDB
Dromaius novaehollandiaeFooDB
Durio zibethinusFooDB
Dysphania ambrosioidesFooDB
ElaeisFooDB
Eleocharis dulcisFooDB
Elettaria cardamomumFooDB
Empetrum nigrumFooDB
Equisetum hoemaleKNApSAcK Database
Equus caballusFooDB
Eragrostis tefFooDB
Erigeron canadensisLOTUS Database
Eriobotrya japonicaFooDB
Eriophyton wallichiiLOTUS Database
Eruca vesicaria subsp. SativaFooDB
Eschenbachia bliniiPlant
Eugenia javanicaFooDB
Eugenia unifloraFooDB
Eutrema japonicumFooDB
Fagopyrum cymosumKNApSAcK Database
Fagopyrum esculentumFooDB
Fagopyrum tataricumFooDB
FagusFooDB
Fasciola hepaticaLOTUS Database
Feijoa sellowianaFooDB
Ficus caricaFooDB
Flammulina velutipesFooDB
Foeniculum vulgareFooDB
Forsythia suspensaLOTUS Database
Fragaria x ananassaFooDB
Gallus gallusFooDB
Garcinia cowaLOTUS Database
Garcinia mangostanaFooDB
Gastrodia elataKNApSAcK Database
Gaylussacia baccataFooDB
Ginkgo bilobaFooDB
Glaucium flavumLOTUS Database
Glycine maxFooDB
GossypiumFooDB
Goupia glabraLOTUS Database
Grifola frondosaFooDB
Gunnera perpensaKNApSAcK Database
Hedysarum alpinumFooDB
Helianthus annuus L.FooDB
Helianthus tuberosusFooDB
Hibiscus sabbariffaFooDB
Hippophae rhamnoidesKNApSAcK Database
Homo sapiensLOTUS Database
Hordeum vulgareFooDB
Hyssopus officinalis L.FooDB
Illicium verumFooDB
Ipomoea aquaticaFooDB
Ipomoea batatasFooDB
Isodon glutinosusLOTUS Database
JuglansFooDB
Juglans ailanthifoliaFooDB
Juglans cinereaFooDB
Juglans mandshuricaKNApSAcK Database
Juglans nigra L.FooDB
Juglans regiaFooDB
Lablab purpureusFooDB
Lactuca sativaFooDB
Laetiporus sulphureusLOTUS Database
Lagenaria sicerariaFooDB
Lagopus mutaFooDB
Lathyrus sativusFooDB
Laurus nobilis L.FooDB
Lemna aequinoctialisLOTUS Database
Lens culinarisFooDB
Lentinus edodesFooDB
Lepidium sativumFooDB
LeporidaeFooDB
Lepus timidusFooDB
Lespedeza cuneataKNApSAcK Database
Levisticum officinaleFooDB
Linum usitatissimumFooDB
Litchi chinensisFooDB
Lobelia chinenseKNApSAcK Database
Lotus burttiiLOTUS Database
Lotus corniculatusLOTUS Database
Luffa aegyptiacaFooDB
LupinusFooDB
Lupinus albusFooDB
Lupinus luteusLOTUS Database
MacadamiaFooDB
Macadamia tetraphyllaFooDB
Malpighia emarginataFooDB
MalusFooDB
Malus pumilaFooDB
Mammea americanaFooDB
Mangifera indicaFooDB
Manihot esculentaFooDB
Manilkara zapotaFooDB
Maranta arundinaceaFooDB
Matricaria recutitaFooDB
Matteuccia struthiopterisFooDB
Medicago sativaKNApSAcK Database
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Melissa officinalis L.FooDB
MenthaFooDB
Mentha aquaticaFooDB
Mentha arvensisFooDB
Mentha spicataFooDB
Mentha x piperitaFooDB
Mespilus germanicaFooDB
Metroxylon saguFooDB
Momordica charantiaFooDB
MorchellaceaeFooDB
Morella rubraFooDB
Moringa oleiferaFooDB
MorusFooDB
Morus albaLOTUS Database
Morus nigraFooDB
Musa acuminataFooDB
Musa x paradisiacaFooDB
Muscari neglectumLOTUS Database
Mycoplasmopsis bovisLOTUS Database
MyricaFooDB
Myristica fragransFooDB
NelumboFooDB
Nelumbo nuciferaFooDB
Nephelium lappaceumFooDB
Numida meleagrisFooDB
Nuphar luteaFooDB
Ocimum basilicumFooDB
OdocoileusFooDB
Oenothera biennisFooDB
Olea europaeaFooDB
Onopordum acanthiumKNApSAcK Database
Ophiocordyceps sinensisLOTUS Database
OpuntiaFooDB
Opuntia cochenilliferaFooDB
Opuntia macrorhizaFooDB
Origanum majoranaFooDB
Origanum onitesFooDB
Origanum vulgareFooDB
Origanum X majoricumFooDB
OryctolagusFooDB
Oryza rufipogonFooDB
Oryza sativaFooDB
Osbeckia chinensisLOTUS Database
Osmunda japonicaKNApSAcK Database
Ovis ariesFooDB
Pachyrhizus erosusFooDB
Panax ginsengKNApSAcK Database
Pangium eduleFooDB
Panicum miliaceumFooDB
Passiflora edulisFooDB
Pastinaca sativaFooDB
Pediomelum esculentumFooDB
Perideridia oreganaFooDB
Persea americanaFooDB
Petasites japonicusFooDB
Petroselinum crispumFooDB
Phaseolus coccineusFooDB
Phaseolus lunatusFooDB
Phaseolus vulgarisFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Phoenix dactyliferaFooDB
Phomopsis velataLOTUS Database
Photinia melanocarpaFooDB
Phyllanthus urinariaLOTUS Database
Phyllostachys edulisFooDB
PhysalisFooDB
Physalis philadelphica var. immaculataFooDB
Phytolacca americanaFooDB
Pimenta dioicaFooDB
Pimpinella anisumFooDB
PinusFooDB
Pinus edulisFooDB
Piper nigrum L.FooDB
Pistacia veraFooDB
Pisum sativumFooDB
Plantago majorLOTUS Database
Pleurotus ostreatusFooDB
Polygonum alpinumFooDB
Populus lasiocarpaLOTUS Database
Populus nigraLOTUS Database
Populus tremulaLOTUS Database
Portulaca oleraceaFooDB
Pothos chinensisKNApSAcK Database
Pouteria sapotaFooDB
Prunus armeniacaFooDB
Prunus aviumFooDB
Prunus avium L.FooDB
Prunus cerasusFooDB
Prunus domesticaFooDB
Prunus dulcisFooDB
Prunus persicaFooDB
Prunus persica var. nucipersicaFooDB
Prunus persica var. persicaFooDB
Prunus tomentosaFooDB
Prunus virginianaFooDB
Psammosilene tunicoidesLOTUS Database
Pseudostellaria heterophyllaLOTUS Database
Psidium cattleianumFooDB
Psidium guajavaFooDB
Psophocarpus tetragonolobusFooDB
Pteridium aquilinumLOTUS Database
Punica granatumKNApSAcK Database
Pycnandra acuminataLOTUS Database
Pyrus communisFooDB
Pyrus pyrifoliaFooDB
QuercusFooDB
Raphanus sativusFooDB
Raphanus sativus var. longipinnatusFooDB
Raphanus sativus var. sativusFooDB
Rehmannia glutinosaKNApSAcK Database
Rheum rhabarbarumFooDB
Rhodiola crenulataKNApSAcK Database
Rhodiola roseaKNApSAcK Database
Ribes aureumFooDB
Ribes glandulosumFooDB
Ribes nigrumFooDB
Ribes rubrumFooDB
Ribes uva-crispaFooDB
RosaFooDB
Rubus arcticusFooDB
Rubus chamaemorusFooDB
Rubus idaeusFooDB
Rubus occidentalisFooDB
Rubus spectabilisFooDB
RumexFooDB
Rumex acetosaFooDB
Rumex articusFooDB
Sageretia theezansKNApSAcK Database
Sagittaria latifoliaFooDB
Salix pulchraFooDB
Salmonella entericaLOTUS Database
Salvia elegansFooDB
Salvia hispanicaFooDB
Salvia officinalisFooDB
Salvia rosmarinusFooDB
Sambucus nigraFooDB
Sambucus nigra L.FooDB
Sarcandra glabraKNApSAcK Database
Satureja hortensis L.FooDB
Satureja montanaFooDB
Saxifraga stoloniferaLOTUS Database
Scaphium affineLOTUS Database
Scolochloa festucaceaLOTUS Database
Scorzonera hispanicaFooDB
Scutellaria baicalensisLOTUS Database
Sebertia acuminataKNApSAcK Database
Secale cerealeFooDB
Sechium eduleFooDB
Sesamum indicumFooDB
Sesbania bispinosaFooDB
Siegesbeckia orientalis var.glabrescens-
Sigesbeckia glabrescensLOTUS Database
Sinapis albaFooDB
SisymbriumFooDB
Smilax perfoliataLOTUS Database
Solanum lycopersicumFooDB
Solanum lycopersicum var. cerasiformeFooDB
Solanum lycopersicum var. lycopersicumFooDB
Solanum melongenaFooDB
Solanum quitoenseFooDB
Solanum tuberosumFooDB
Sorbus aucupariaFooDB
Sorghum bicolorFooDB
Spinacia oleraceaFooDB
Stemona tuberosaKNApSAcK Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Synechococcus elongatusLOTUS Database
Syzygium aromaticumFooDB
Syzygium cuminiFooDB
Syzygium jambosFooDB
Tamarindus indicaFooDB
Taraxacum officinaleFooDB
Tetragonia tetragonioidesFooDB
ThelespermaFooDB
Thesium chinenseKNApSAcK Database
Thymus pulegioidesFooDB
Thymus vulgarisFooDB
Tilia cordataFooDB
Tilia L.FooDB
Tillandsia usneoidesLOTUS Database
Tragopogon porrifoliusFooDB
Tribulus terrestrisPlant
Trifolium repensLOTUS Database
Trigonella foenum-graecumFooDB
TriticumFooDB
Triticum aestivumKNApSAcK Database
Triticum durumFooDB
Triticum speltaFooDB
Triticum turanicumFooDB
Tropicoporus linteusLOTUS Database
Trypanosoma bruceiLOTUS Database
Typha angustataKNApSAcK Database
Typha angustifoliaFooDB
Typha latifoliaKNApSAcK Database
Urtica dioicaKNApSAcK Database
VacciniumFooDB
Vaccinium angustifoliumFooDB
Vaccinium angustifolium X Vaccinium corymbosumFooDB
Vaccinium arboreumFooDB
Vaccinium corymbosumFooDB
Vaccinium deliciosumFooDB
Vaccinium elliottiiFooDB
Vaccinium macrocarponFooDB
Vaccinium myrtilloidesFooDB
Vaccinium myrtillusFooDB
Vaccinium ovalifoliumFooDB
Vaccinium ovatumFooDB
Vaccinium oxycoccosFooDB
Vaccinium parvifoliumFooDB
Vaccinium reticulatumFooDB
Vaccinium stamineumFooDB
Vaccinium uliginosumFooDB
Vaccinium vitis-idaeaFooDB
Valerianella locustaFooDB
VanillaFooDB
Verbena officinalisFooDB
Viburnum eduleFooDB
Viburnum furcatumLOTUS Database
Vicia fabaFooDB
Vigna aconitifoliaFooDB
Vigna angularisFooDB
Vigna mungoFooDB
Vigna radiataFooDB
Vigna umbellataFooDB
Vigna unguiculataFooDB
Vigna unguiculata ssp. cylindricaFooDB
Vigna unguiculata ssp. unguiculataFooDB
Vigna unguiculata var. sesquipedalisFooDB
Vincetoxicum atratumLOTUS Database
VitisFooDB
Vitis aestivalisFooDB
Vitis labruscaFooDB
Vitis rotundifoliaFooDB
Vitis viniferaLOTUS Database
Vitis vinifera L.FooDB
Xanthosoma sagittifoliumFooDB
Zea mays L.FooDB
Zingiber officinaleFooDB
ZizaniaFooDB
Zizania aquaticaFooDB
Ziziphus zizyphusFooDB
Species Where Detected
Species NameSourceReference
Escherichia coliKNApSAcK Database
Homo sapiens (Serum)KNApSAcK Database
Homo sapiens (Urine)KNApSAcK Database
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point185 - 188 °CNot Available
Boiling Point235.00 to 236.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility83.2 mg/mLNot Available
LogP-0.59Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility211 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity23.54 m³·mol⁻¹ChemAxon
Polarizability10.14 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000254
DrugBank IDDB00139
Phenol Explorer Compound IDNot Available
FoodDB IDFDB031187
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
Good Scents IDrw1040431
References
General References
  1. 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. doi: 10.1038/nature07762. [PubMed:19212411 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. 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 ]
  9. 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 ]
  10. 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 ]
  11. 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 ]
  12. 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 ]
  13. 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 ]
  14. 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 ]
  15. 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 ]
  16. 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 ]
  17. Becker J, Lange A, Fabarius J, Wittmann C: Top value platform chemicals: bio-based production of organic acids. Curr Opin Biotechnol. 2015 Dec;36:168-75. doi: 10.1016/j.copbio.2015.08.022. Epub 2015 Sep 8. [PubMed:26360870 ]
  18. Gupta A, Dwivedi M, Mahdi AA, Khetrapal CL, Bhandari M: Broad identification of bacterial type in urinary tract infection using (1)h NMR spectroscopy. J Proteome Res. 2012 Mar 2;11(3):1844-54. doi: 10.1021/pr2010692. Epub 2012 Jan 31. [PubMed:22292465 ]
  19. Tretter L, Patocs A, Chinopoulos C: Succinate, an intermediate in metabolism, signal transduction, ROS, hypoxia, and tumorigenesis. Biochim Biophys Acta. 2016 Aug;1857(8):1086-1101. doi: 10.1016/j.bbabio.2016.03.012. Epub 2016 Mar 10. [PubMed:26971832 ]
  20. Sauer M, Porro D, Mattanovich D, Branduardi P: Microbial production of organic acids: expanding the markets. Trends Biotechnol. 2008 Feb;26(2):100-8. doi: 10.1016/j.tibtech.2007.11.006. Epub 2008 Jan 11. [PubMed:18191255 ]
  21. Shi D, Yan R, Lv L, Jiang H, Lu Y, Sheng J, Xie J, Wu W, Xia J, Xu K, Gu S, Chen Y, Huang C, Guo J, Du Y, Li L: The serum metabolome of COVID-19 patients is distinctive and predictive. Metabolism. 2021 May;118:154739. doi: 10.1016/j.metabol.2021.154739. Epub 2021 Mar 2. [PubMed:33662365 ]