Np mrd loader

Showing NP-Card for Fumaric acid (NP0000045)

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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2022-01-09 18:08:23 UTC
NP-MRD IDNP0000045
Secondary Accession NumbersNone
Natural Product Identification
Common NameFumaric acid
DescriptionFumaric acid is a dicarboxylic acid. It is a precursor to L-malate in the Krebs tricarboxylic acid (TCA) cycle. It is formed by the oxidation of succinic acid by succinate dehydrogenase. Fumarate is converted by the enzyme fumarase to malate. Fumaric 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 fumarate. Fumaric acid is found to be associated with fumarase deficiency, which is an inborn error of metabolism.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000045 (Fumaric acid)


  Mrv1652309032023532D          

  8  7  0  0  0  0            999 V2000
   -1.6739   -0.4357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3883   -0.8482    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6739    0.3892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9594   -0.8482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2449   -0.4357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4694   -0.8482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4694   -1.6732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1839   -0.4357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  8  1  0  0  0  0
  6  7  2  0  0  0  0
  1  3  2  0  0  0  0
  2  1  1  0  0  0  0
M  END
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3D MOL for NP0000045 (Fumaric acid)

HMDB0000134
     RDKit          3D
Fumaric acid
 12 11  0  0  0  0  0  0  0  0999 V2000
   -3.0532   -0.7292   -0.3496 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0555    0.0034   -0.1235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1983    1.3239    0.2276 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7335   -0.5543   -0.2350 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3568    0.1701   -0.0084 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6650   -0.4440   -0.1355 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8084   -1.6463   -0.4547 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7809    0.3180    0.1020 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8700    1.6744    1.1040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5771   -1.6060   -0.5134 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2336    1.1990    0.2648 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6429    0.2909   -0.3982 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  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  3  9  1  0
  4 10  1  0
  5 11  1  0
  8 12  1  0
M  END
Download

3D SDF for NP0000045 (Fumaric acid)


  Mrv1652309032023532D          

  8  7  0  0  0  0            999 V2000
   -1.6739   -0.4357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3883   -0.8482    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6739    0.3892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9594   -0.8482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2449   -0.4357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4694   -0.8482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4694   -1.6732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1839   -0.4357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  8  1  0  0  0  0
  6  7  2  0  0  0  0
  1  3  2  0  0  0  0
  2  1  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000045

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)\C=C\C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1+

> <INCHI_KEY>
VZCYOOQTPOCHFL-OWOJBTEDSA-N

> <FORMULA>
C4H4O4

> <MOLECULAR_WEIGHT>
116.0722

> <EXACT_MASS>
116.010958616

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
9.352250335599845

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-but-2-enedioic acid

> <ALOGPS_LOGP>
0.21

> <JCHEM_LOGP>
-0.040914331333333324

> <ALOGPS_LOGS>
-0.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.412485134930334

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.545732417201611

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
24.607

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.41e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
fumaric acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000045 (Fumaric acid)

HMDB0000134
     RDKit          3D
Fumaric acid
 12 11  0  0  0  0  0  0  0  0999 V2000
   -3.0532   -0.7292   -0.3496 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0555    0.0034   -0.1235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1983    1.3239    0.2276 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7335   -0.5543   -0.2350 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3568    0.1701   -0.0084 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6650   -0.4440   -0.1355 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8084   -1.6463   -0.4547 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7809    0.3180    0.1020 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8700    1.6744    1.1040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5771   -1.6060   -0.5134 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2336    1.1990    0.2648 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6429    0.2909   -0.3982 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  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  3  9  1  0
  4 10  1  0
  5 11  1  0
  8 12  1  0
M  END
Download

PDB for NP0000045 (Fumaric 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  C   UNK     0      -3.125  -0.813   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.458  -1.583   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      -3.125   0.727   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -1.791  -1.583   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.457  -0.813   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.876  -1.583   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.876  -3.123   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       2.210  -0.813   0.000  0.00  0.00           O+0
CONECT    1    4    3    2                                                  
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    1    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    8    7                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END
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3D PDB for NP0000045 (Fumaric acid)

COMPND    HMDB0000134
HETATM    1  O1  UNL     1      -3.053  -0.729  -0.350  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.056   0.003  -0.123  1.00  0.00           C  
HETATM    3  O2  UNL     1      -2.198   1.324   0.228  1.00  0.00           O  
HETATM    4  C2  UNL     1      -0.734  -0.554  -0.235  1.00  0.00           C  
HETATM    5  C3  UNL     1       0.357   0.170  -0.008  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.665  -0.444  -0.135  1.00  0.00           C  
HETATM    7  O3  UNL     1       1.808  -1.646  -0.455  1.00  0.00           O  
HETATM    8  O4  UNL     1       2.781   0.318   0.102  1.00  0.00           O  
HETATM    9  H1  UNL     1      -1.870   1.674   1.104  1.00  0.00           H  
HETATM   10  H2  UNL     1      -0.577  -1.606  -0.513  1.00  0.00           H  
HETATM   11  H3  UNL     1       0.234   1.199   0.265  1.00  0.00           H  
HETATM   12  H4  UNL     1       3.643   0.291  -0.398  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3    9
CONECT    4    5    5   10
CONECT    5    6   11
CONECT    6    7    7    8
CONECT    8   12
END
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SMILES for NP0000045 (Fumaric acid)

OC(=O)\C=C\C(O)=O
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INCHI for NP0000045 (Fumaric acid)

InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1+
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View in JSmol
Synonyms
ValueSource
(2E)-2-Butenedioic acidChEBI
(e)-2-Butenedioic acidChEBI
e297ChEBI
FumarsaeureChEBI
trans-1,2-Ethylenedicarboxylic acidChEBI
trans-But-2-enedioic acidChEBI
trans-Butenedioic acidChEBI
(2E)-2-ButenedioateGenerator
(e)-2-ButenedioateGenerator
trans-1,2-EthylenedicarboxylateGenerator
trans-But-2-enedioateGenerator
trans-ButenedioateGenerator
FumarateGenerator
(2E)-But-2-enedioateHMDB
(2E)-But-2-enedioic acidHMDB
2-(e)-ButenedioateHMDB
2-(e)-Butenedioic acidHMDB
AllomaleateHMDB
Allomaleic acidHMDB
BoletateHMDB
Boletic acidHMDB
FC 33HMDB
LichenateHMDB
Lichenic acidHMDB
trans-2-ButenedioateHMDB
trans-2-Butenedioic acidHMDB
FuramagHMDB
MafusolHMDB
Fumaric acidHMDB
2-Butenedioic acidMeSH
Fumarate dianionMeSH
Fumarate(2-)MeSH
Chemical FormulaC4H4O4
Average Mass116.0722 Da
Monoisotopic Mass116.01096 Da
IUPAC Name(2E)-but-2-enedioic acid
Traditional Namefumaric acid
CAS Registry Number110-17-8
SMILES
[H]\C(=C(\[H])C(O)=O)C(O)=O
InChI Identifier
InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1+
InChI KeyVZCYOOQTPOCHFL-OWOJBTEDSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, simulated)Ahselim2022-01-09View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, experimental)Ahselim2022-01-09View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, simulated)Varshavi.d262021-10-29View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)Varshavi.d262021-10-29View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, simulated)Varshavi.d262021-10-29View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)Varshavi.d262021-10-29View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, simulated)Varshavi.d262021-10-29View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)Varshavi.d262021-10-29View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, simulated)Varshavi.d262021-10-29View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)Varshavi.d262021-10-29View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, simulated)Varshavi.d262021-10-29View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)Varshavi.d262021-10-29View 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)Varshavi.d262021-07-21View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, simulated)Varshavi.d262021-07-18View Spectrum
Species
Species of Origin
Species NameSourceReference
Abelmoschus esculentusFooDB
Abutilon indicumPlant
Aconitum japonicumLOTUS Database
Actinidia chinensisFooDB
Adlumia fungosaLOTUS Database
Agaricus bisporusFooDB
AgaveFooDB
Agave americanaLOTUS Database
Ageratina conyzoidesPlant
Allium ampeloprasumFooDB
Allium ascalonicumFooDB
Allium cepaFooDB
Allium cepa L.FooDB
Allium fistulosumFooDB
Allium sativumFooDB
Allium schoenoprasumFooDB
Allium tuberosumFooDB
Aloysia triphyllaFooDB
Amanita muscariaLOTUS Database
AmaranthusFooDB
Amelanchier alnifoliaFooDB
Anacardium occidentaleFooDB
Ananas comosusFooDB
Anas platyrhynchosFooDB
AnatidaeFooDB
Anethum graveolensFooDB
Angelica keiskeiFooDB
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
Arbutus unedoLOTUS Database
Arctium lappaFooDB
Armoracia rusticanaFooDB
Artemisia dracunculusFooDB
Artemisia vulgarisFooDB
Artocarpus altilisFooDB
Artocarpus heterophyllusFooDB
Asclepias syriacaLOTUS Database
Asparagus officinalisFooDB
Astragalus alopecurusKNApSAcK 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 pilosaLOTUS Database
Bison bisonFooDB
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
Canarium ovatumFooDB
Cannabis sativaCannabisDB
      Not Available
Cantharellus cibariusFooDB
Capparis spinosaFooDB
Capra aegagrus hircusFooDB
Capsella bursa-pastorisKNApSAcK Database
Capsicum annuumFooDB
Capsicum annuum L.FooDB
Capsicum annuum var. annuumFooDB
Capsicum chinenseFooDB
Capsicum pubescensFooDB
Carica papayaKNApSAcK Database
Carica papaya L.FooDB
Carissa macrocarpaFooDB
Carthamus tinctoriusFooDB
Carum carviFooDB
CaryaFooDB
Carya illinoinensisFooDB
CastaneaFooDB
Castanea crenataFooDB
Castanea mollissimaFooDB
Castanea sativaFooDB
Ceratonia siliquaFooDB
CervidaeFooDB
Cervus canadensisFooDB
Chamaemelum nobileFooDB
Chamerion angustifoliumFooDB
Chenopodium albumFooDB
Chenopodium quinoaFooDB
Chlamydomonas reinhardtiiLOTUS Database
Chrysanthemum coronariumFooDB
Cicer arietinumKNApSAcK Database
Cichorium endiviaFooDB
Cichorium intybusFooDB
CinnamomumFooDB
Cinnamomum aromaticumFooDB
Cinnamomum verumFooDB
CirsiumFooDB
Cirsium wallichiiKNApSAcK Database
Citrullus lanatusFooDB
Citrus ×limon (L.) Burm. f. (pro sp.)FooDB
Citrus aurantiifoliaFooDB
Citrus latifoliaFooDB
Citrus limonFooDB
Citrus maximaFooDB
Citrus paradisiFooDB
Citrus reticulataFooDB
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
Cocos nuciferaFooDB
Coffea arabica L.FooDB
Coffea canephoraFooDB
Colocasia esculentaFooDB
ColumbaFooDB
ColumbidaeFooDB
Corchorus olitoriusFooDB
Coriandrum sativum L.FooDB
Corydalis yanhusuoKNApSAcK Database
CorylusFooDB
Corylus avellanaFooDB
Crataegus pinnatifidaLOTUS Database
Crateva religiosaFooDB
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
Daphniphyllum calycinumKNApSAcK Database
Daucus carotaFooDB
Daucus carota ssp. sativusFooDB
Daviesia latifoliaLOTUS Database
Dimocarpus longanFooDB
DioscoreaFooDB
Dioscorea pentaphyllaFooDB
DiospyrosFooDB
Diospyros kakiFooDB
Diospyros virginianaFooDB
Dromaius novaehollandiaeFooDB
Durio zibethinusFooDB
Dysphania ambrosioidesFooDB
ElaeisFooDB
Eleocharis dulcisFooDB
Elettaria cardamomumFooDB
Empetrum nigrumFooDB
Equus caballusFooDB
Eragrostis tefFooDB
Eriobotrya japonicaFooDB
Eruca vesicaria subsp. SativaFooDB
Eugenia javanicaFooDB
Eugenia unifloraFooDB
Euphorbia antiquorumKNApSAcK Database
Eutrema japonicumFooDB
Fagopyrum esculentumFooDB
Fagopyrum tataricumFooDB
FagusFooDB
Fasciola hepaticaLOTUS Database
Feijoa sellowianaFooDB
Ficus caricaKNApSAcK Database
Flammulina velutipesFooDB
Foeniculum vulgareFooDB
Fragaria x ananassaFooDB
Fumaria officinalisKNApSAcK Database
Fumaria parvifloraLOTUS Database
Gallus gallusFooDB
Garcinia mangostanaFooDB
Gaylussacia baccataFooDB
Ginkgo bilobaFooDB
Glaucium flavumKNApSAcK Database
Glycine maxFooDB
GossypiumFooDB
Grifola frondosaFooDB
Hedysarum alpinumFooDB
Helianthus annuusKNApSAcK Database
Helianthus annuus L.FooDB
Helianthus tuberosusFooDB
Hibiscus sabbariffaFooDB
Hippophae rhamnoidesFooDB
Homo sapiensLOTUS Database
Hordeum vulgareFooDB
Hyssopus officinalis L.FooDB
Illicium verumFooDB
Inula grandisLOTUS Database
Ipomoea aquaticaFooDB
Ipomoea batatasFooDB
JuglansFooDB
Juglans ailanthifoliaFooDB
Juglans cinereaFooDB
Juglans nigra L.FooDB
Juglans regiaFooDB
Lablab purpureusFooDB
Lactuca sativaFooDB
Lagenaria sicerariaFooDB
Lagopus mutaFooDB
Lathyrus sativusFooDB
Laurus nobilis L.FooDB
Lemna aequinoctialisLOTUS Database
Lens culinarisFooDB
Lentinus edodesFooDB
Lepidium sativumFooDB
LeporidaeFooDB
Lepus timidusFooDB
Levisticum officinaleFooDB
Linum usitatissimumFooDB
Litchi chinensisFooDB
Lithospermum arvenseKNApSAcK Database
Litoria verreauxiiLOTUS Database
Lotus corniculatusLOTUS Database
Luffa aegyptiacaFooDB
LupinusFooDB
Lupinus albusFooDB
MacadamiaFooDB
Macadamia tetraphyllaFooDB
Malpighia emarginataFooDB
MalusFooDB
Malus domesticaKNApSAcK Database
Malus pumilaFooDB
Mammea americanaFooDB
Mangifera indicaFooDB
Manihot esculentaFooDB
Manilkara zapotaFooDB
Maranta arundinaceaFooDB
Matricaria recutitaFooDB
Matteuccia struthiopterisFooDB
Medicago sativaFooDB
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
Morinda officinalisPlant
Moringa oleiferaFooDB
MorusFooDB
Morus nigraFooDB
Musa acuminataFooDB
Musa x paradisiacaFooDB
Mycoplasma gallisepticumLOTUS Database
MyricaFooDB
Myristica fragransFooDB
NelumboFooDB
Nelumbo nuciferaFooDB
Nephelium lappaceumFooDB
Numida meleagrisFooDB
Nuphar luteaFooDB
Ocimum basilicumFooDB
OdocoileusFooDB
Oenothera biennisFooDB
Olea europaeaFooDB
OpuntiaFooDB
Opuntia cochenilliferaFooDB
Opuntia macrorhizaFooDB
Origanum majoranaFooDB
Origanum onitesFooDB
Origanum vulgareFooDB
Origanum X majoricumFooDB
OryctolagusFooDB
Oryza rufipogonFooDB
Oryza sativaFooDB
Ovis ariesFooDB
Pachyrhizus erosusFooDB
Panax ginsengFooDB
Pangium eduleFooDB
Panicum miliaceumFooDB
Papaver somniferumLOTUS Database
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
Phyllostachys edulisFooDB
PhysalisFooDB
Physalis philadelphica var. immaculataFooDB
Phytolacca americanaFooDB
Pimenta dioicaFooDB
Pimpinella anisumFooDB
PinusFooDB
Pinus edulisFooDB
Piper nigrum L.FooDB
Pistacia veraFooDB
Pisum sativumKNApSAcK Database
Plantago majorKNApSAcK Database
Pleurotus ostreatusFooDB
Polygonum alpinumFooDB
Populus tremulaLOTUS Database
Portulaca oleraceaFooDB
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
Pseudostellaria heterophyllaLOTUS Database
Psidium cattleianumFooDB
Psidium guajavaFooDB
Psophocarpus tetragonolobusFooDB
Pteridium aquilinumLOTUS Database
Punica granatumKNApSAcK Database
Pycnandra acuminataLOTUS Database
Pyrrosia sheareiKNApSAcK Database
Pyrus communisFooDB
Pyrus pyrifoliaFooDB
QuercusFooDB
Ranunculus silerifoliusLOTUS Database
Raphanus sativusFooDB
Raphanus sativus var. longipinnatusFooDB
Raphanus sativus var. sativusFooDB
Rheum rhabarbarumFooDB
Rhizopus arrhizusLOTUS Database
Rhizopus oryzaeLOTUS Database
Rhizopus stoloniferFungi
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
Russula cyanoxanthaLOTUS Database
Saccharum sinensisKNApSAcK 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
Scorzonera hispanicaFooDB
Scutellaria baicalensisLOTUS Database
Sebertia acuminataKNApSAcK Database
Secale cerealeFooDB
Sechium eduleFooDB
Senecio glaucusLOTUS Database
Senecio nemorensisKNApSAcK Database
Sesamum indicumFooDB
Sesbania bispinosaFooDB
Sinapis albaFooDB
SisymbriumFooDB
Solanum lycopersicumFooDB
Solanum lycopersicum var. cerasiformeFooDB
Solanum lycopersicum var. lycopersicumFooDB
Solanum melongenaFooDB
Solanum quitoenseFooDB
Solanum tuberosumFooDB
Sophora alopecuroidesKNApSAcK Database
Sorbus aucupariaFooDB
Sorghum bicolorFooDB
Spinacia oleraceaFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Synechococcus elongatusLOTUS Database
Syzygium aromaticumFooDB
Syzygium cuminiFooDB
Syzygium jambosFooDB
Tamarindus indicaFooDB
Taraxacum officinaleFooDB
Tetragonia tetragonioidesFooDB
ThelespermaFooDB
Thymus pulegioidesFooDB
Thymus transcaucasicusLOTUS Database
Thymus vulgarisFooDB
Tilia cordataFooDB
Tilia L.FooDB
Torreya fargesii var. yunnanensisPlant
Torreya yunnanensisKNApSAcK Database
Tragopogon porrifoliusFooDB
Trigonella foenum-graecumFooDB
Tripterygium hypoglaucumLOTUS Database
TriticumFooDB
Triticum aestivumFooDB
Triticum durumFooDB
Triticum speltaFooDB
Triticum turanicumFooDB
Tropicoporus linteusLOTUS Database
Trypanosoma bruceiLOTUS Database
Typha angustifoliaFooDB
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
Vicia fabaKNApSAcK Database
Vigna aconitifoliaFooDB
Vigna angularisFooDB
Vigna mungoFooDB
Vigna radiataFooDB
Vigna umbellataFooDB
Vigna unguiculataFooDB
Vigna unguiculata ssp. cylindricaFooDB
Vigna unguiculata ssp. unguiculataFooDB
Vigna unguiculata var. sesquipedalisFooDB
VitisFooDB
Vitis aestivalisFooDB
Vitis labruscaFooDB
Vitis rotundifoliaFooDB
Vitis vinifera L.FooDB
Xanthosoma sagittifoliumFooDB
Zea mays L.FooDB
Zingiber officinaleFooDB
ZizaniaFooDB
Zizania aquaticaFooDB
Ziziphus zizyphusFooDB
Species Where Detected
Species NameSourceReference
Cladonia fallaxKNApSAcK Database
Cladonia rangiferinaKNApSAcK Database
Escherichia coliKNApSAcK Database
Ganoderma japonicumKNApSAcK Database
Homo sapiens (Serum)KNApSAcK Database
Homo sapiens (Urine)KNApSAcK Database
Pseudomonas putidaKNApSAcK Database
Rhizopus nigricansKNApSAcK 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 acyl
  • Fatty acid
  • Unsaturated 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 Point549 °CNot Available
Boiling Point156.00 °C. @ 1.70 mm HgThe Good Scents Company Information System
Water Solubility7 mg/mLNot Available
LogP0.46Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility24.1 g/LALOGPS
logP0.21ALOGPS
logP-0.041ChemAxon
logS-0.68ALOGPS
pKa (Strongest Acidic)3.55ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity24.61 m³·mol⁻¹ChemAxon
Polarizability9.35 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000134
DrugBank IDDB01677
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030865
KNApSAcK IDC00001183
Chemspider ID10197150
KEGG Compound IDC00122
BioCyc IDFUM
BiGG ID33938
Wikipedia LinkFumaric_Acid
METLIN ID3242
PubChem Compound444972
PDB IDNot Available
ChEBI ID18012
Good Scents IDrw1024321
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. Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38. [PubMed:2026685 ]
  3. 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 ]
  4. 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 ]
  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. Fu YQ, Li S, Chen Y, Xu Q, Huang H, Sheng XY: Enhancement of fumaric acid production by Rhizopus oryzae using a two-stage dissolved oxygen control strategy. Appl Biochem Biotechnol. 2010 Oct;162(4):1031-8. doi: 10.1007/s12010-009-8831-5. Epub 2009 Nov 21. [PubMed:19936636 ]