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Showing metabocard for Fumaric acid (HMDB0000134)

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enzymes (12) Show 12 proteins
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2025-05-29 18:10:27 UTC
HMDB IDHMDB0000134
Secondary Accession Numbers
  • HMDB00134
Metabolite 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. It is also a metabolite of Aspergillus.
Structure
Data?1676999672
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000134 (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 HMDB0000134 (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
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3D SDF for HMDB0000134 (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>
HMDB0000134

> <DATABASE_NAME>
hmdb

> <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 HMDB0000134 (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
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PDB for HMDB0000134 (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 HMDB0000134 (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 HMDB0000134 (Fumaric acid)

OC(=O)\C=C\C(O)=O
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INCHI for HMDB0000134 (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 JSmolView NMR AssignmentsView Stereo Labels
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
Chemical FormulaC4H4O4
Average Molecular Weight116.0722
Monoisotopic Molecular Weight116.010958616
IUPAC Name(2E)-but-2-enedioic acid
Traditional Namefumaric acid
CAS Registry Number110-17-8
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 KeyVZCYOOQTPOCHFL-OWOJBTEDSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassDicarboxylic acids and derivatives
Direct ParentDicarboxylic acids and derivatives
Alternative Parents
Substituents
  • Fatty 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
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point549 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility7 mg/mLNot Available
LogP0.46HANSCH,C ET AL. (1995)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available118.1http://allccs.zhulab.cn/database/detail?ID=AllCCS00001956
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+124.3631661259
DarkChem[M-H]-120.14631661259
AllCCS[M+H]+127.03232859911
AllCCS[M-H]-121.15732859911
DeepCCS[M+H]+120.93930932474
DeepCCS[M-H]-117.95430932474
DeepCCS[M-2H]-154.46730932474
DeepCCS[M+Na]+129.50130932474
AllCCS[M+H]+127.032859911
AllCCS[M+H-H2O]+122.732859911
AllCCS[M+NH4]+131.032859911
AllCCS[M+Na]+132.232859911
AllCCS[M-H]-121.232859911
AllCCS[M+Na-2H]-124.332859911
AllCCS[M+HCOO]-127.732859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.1.67 minutes32390414
Predicted by Siyang on May 30, 202210.3302 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20222.82 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid140.8 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1068.8 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid394.9 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid89.5 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid267.9 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid96.2 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid306.5 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid396.8 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)526.1 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid682.2 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid146.0 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1054.8 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid259.8 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid305.8 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate808.0 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA260.4 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water406.5 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Fumaric acidOC(=O)\C=C\C(O)=O2299.6Standard polar33892256
Fumaric acidOC(=O)\C=C\C(O)=O1085.8Standard non polar33892256
Fumaric acidOC(=O)\C=C\C(O)=O1221.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Fumaric acid,1TMS,isomer #1C[Si](C)(C)OC(=O)/C=C/C(=O)O1328.1Semi standard non polar33892256
Fumaric acid,2TMS,isomer #1C[Si](C)(C)OC(=O)/C=C/C(=O)O[Si](C)(C)C1339.2Semi standard non polar33892256
Fumaric acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)/C=C/C(=O)O1566.8Semi standard non polar33892256
Fumaric acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)/C=C/C(=O)O[Si](C)(C)C(C)(C)C1788.4Semi standard non polar33892256
Spectra
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
  • Mitochondria
Biospecimen Locations
  • Blood
  • Breast Milk
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Sweat
  • Urine
Tissue Locations
  • Placenta
  • Prostate
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified2.36 ± 0.95 uMAdult (>18 years old)Both
Normal
    • Quantitative comp...
 details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified1.46 ± 0.97 uMAdult (>18 years old)Both
Normal
    • Quantitative comp...
 details
BloodDetected and Quantified0.49-1.4 uMInfant (0-1 year old)BothNormal
    • Physician's Guide...
 details
BloodDetected and Quantified0.98 ± 0.49 uMAdult (>18 years old)Both
Normal
    • Quantitative comp...
 details
BloodDetected and Quantified1.35 ± 0.3 uMAdult (>18 years old)Both
Normal
    • Quantitative comp...
 details
BloodDetected and Quantified1.18 ± 0.23 uMAdult (>18 years old)Both
Normal
    • Quantitative comp...
 details
BloodDetected and Quantified1.5 (0.0-4.0) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified2.28 ± 0.35 uMAdult (>18 years old)Both
Normal
    • Quantitative comp...
 details
BloodDetected and Quantified1.52 ± 0.39 uMAdult (>18 years old)Both
Normal
    • Quantitative comp...
 details
BloodDetected and Quantified1.24 ± 0.17 uMAdult (>18 years old)Both
Normal
    • Quantitative comp...
 details
BloodDetected and Quantified3.14 ± 0.5 uMAdult (>18 years old)Both
Normal
    • Quantitative comp...
 details
Breast MilkDetected and Quantified2.4 +/- 1.5 uMAdult (>18 years old)Female
Normal		 details
Cerebrospinal Fluid (CSF)Detected and Quantified1 uMChildren (1-13 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified33.0 (9.00-57.0) uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected and Quantified84.430 +/- 50.830 nmol/g wet fecesNot SpecifiedNot Specified
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected and Quantified1.95 +/- 0.66 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
SalivaDetected and Quantified0.707 +/- 0.303 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
 details
SalivaDetected and Quantified0.778 +/- 1.07 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
 details
SalivaDetected and Quantified0.798 +/- 0.396 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
 details
SalivaDetected and Quantified0.997 +/- 0.492 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
 details
SweatDetected and Quantified10-40 uMAdult (60 years old)Male
Normal		 details
SweatDetected and Quantified10 uMAdult (40 years old)Male
Normal		 details
SweatDetected but not QuantifiedNot QuantifiedAdult BothNormal details
UrineDetected and Quantified0-1.5 umol/mmol creatinineInfant (0-1 year old)Female
Normal		 details
UrineDetected and Quantified0-2.0 umol/mmol creatinineInfant (0-1 year old)Male
Normal		 details
UrineDetected and Quantified0.15-5.69 umol/mmol creatinineInfant (0-1 year old)Male
Normal		 details
UrineDetected and Quantified1.2-4.3 umol/mmol creatinineInfant (0-1 year old)Female
Normal		 details
UrineDetected and Quantified2.09-37.66 umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified15,80 +/- 11.61 umol/mmol creatinineNewborn (0-30 days old)FemaleNormal details
UrineDetected and Quantified13.27 +/- 7.27 umol/mmol creatinineNewborn (0-30 days old)MaleNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified10.34 (6.40-21.12) umol/mmol creatinineNewborn (0-30 days old)Both
Normal
    • Analysis of 40 NI...
 details
UrineDetected and Quantified0.75-1.2 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified<10.25 umol/mmol creatinineChildren (1 - 18 years old)Both
Normal
    • BC Children's Hos...
 details
UrineDetected and Quantified10.4 (2.8-53.7) umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified0.5 (0.1-1.7) umol/mmol creatinineAdolescent (13-18 years old)BothNormal details
UrineDetected and Quantified10.7 (0.1-28.2) umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified0.1 (0.1-1.7) umol/mmol creatinineChildren (1-13 years old)BothNormal details
UrineDetected and Quantified0.4 (0.2-0.8) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.1-0.4 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.2 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.7 (0.2-1.7) umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified1.342 +/- 1.317 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Analysis of 30 no...
 details
UrineDetected and Quantified2-40 umol/mmol creatinineNewborn (0-30 days old)Both
Normal		 details
UrineDetected and Quantified0.80-1.8 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.95 +/- 0.93 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified<25 umol/mmol creatinineInfant (0-1 year old)MaleNormal details
UrineDetected and Quantified<97.405 umol/mmol creatinineInfant (0-1 year old)MaleNormal details
UrineDetected and Quantified1.900-8.600 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified<14 umol/mmol creatinineNot SpecifiedNot Specified
Normal		 details
UrineDetected and Quantified1.948-11.689 umol/mmol creatinineInfant (0-1 year old)Both
Normal		 details
UrineDetected and Quantified<7 umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal details
UrineDetected and Quantified20-50 umol/mmol creatinineNewborn (0-30 days old)Both
Normal		 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal cancer details
Cerebrospinal Fluid (CSF)Detected and Quantified11.0 (2.00-20.0) uMElderly (>65 years old)BothAlzheimer's disease details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Irritable bowel syndrome		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not Specifiedasymptomatic diverticulosis details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not Specifiedsymptomatic uncomplicated diverticular disease details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Femaleankylosing spondylitis details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Femalerheumatoid arthritis details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBladder cancer details
UrineDetected and Quantified48 umol/mmol creatinineChildren (1-13 years old)MaleLipoyltransferase 1 Deficiency details
UrineDetected and Quantified0-14.611 umol/mmol creatinineInfant (0-1 year old)Both
Amish lethal microcephaly		 details
UrineDetected and Quantified17-124 umol/mmol creatinineInfant (0-1 year old)Male
2-Ketoglutarate dehydrogenase complex deficiency		 details
UrineDetected and Quantified313.400-493.200 umol/mmol creatinineInfant (0-1 year old)MaleFumarase deficiency details
UrineDetected and Quantified217-445 umol/mmol creatinineChildren (1 - 13 years old)FemaleFumaric aciduria details
UrineDetected and Quantified151-772 umol/mmol creatinineAdult (>18 years old)BothFumaric aciduria details
UrineDetected and Quantified2269.534 umol/mmol creatinineInfant (0-1 year old)MaleFumarase deficiency details
UrineDetected and Quantified482.3 umol/mmol creatinineInfant (0-1 year old)MaleFumarase deficiency details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal cancer details
UrineDetected and Quantified11.39 +/- 28.464 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
 details
UrineDetected and Quantified0.7 (0.0-4.0) umol/mmol creatinineAdult (>18 years old)BothLung cancer details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Ni Y, Xie G, Jia W: Metabonomics of human colorectal cancer: new approaches for early diagnosis and biomarker discovery. J Proteome Res. 2014 Sep 5;13(9):3857-70. doi: 10.1021/pr500443c. Epub 2014 Aug 14. [PubMed:25105552 ]
  2. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  3. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  4. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Alzheimer's disease
  1. 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 ]
Irritable bowel syndrome
  1. Ponnusamy K, Choi JN, Kim J, Lee SY, Lee CH: Microbial community and metabolomic comparison of irritable bowel syndrome faeces. J Med Microbiol. 2011 Jun;60(Pt 6):817-27. doi: 10.1099/jmm.0.028126-0. Epub 2011 Feb 17. [PubMed:21330412 ]
Diverticular disease
  1. Tursi A, Mastromarino P, Capobianco D, Elisei W, Miccheli A, Capuani G, Tomassini A, Campagna G, Picchio M, Giorgetti G, Fabiocchi F, Brandimarte G: Assessment of Fecal Microbiota and Fecal Metabolome in Symptomatic Uncomplicated Diverticular Disease of the Colon. J Clin Gastroenterol. 2016 Oct;50 Suppl 1:S9-S12. doi: 10.1097/MCG.0000000000000626. [PubMed:27622378 ]
Rheumatoid arthritis
  1. Tie-juan ShaoZhi-xing HeZhi-jun XieHai-chang LiMei-jiao WangCheng-ping Wen. Characterization of ankylosing spondylitis and rheumatoid arthritis using 1H NMR-based metabolomics of human fecal extracts. Metabolomics. April 2016, 12:70 [Link]
Lung Cancer
  1. Wishart DS, Knox C, Guo AC, Eisner R, Young N, Gautam B, Hau DD, Psychogios N, Dong E, Bouatra S, Mandal R, Sinelnikov I, Xia J, Jia L, Cruz JA, Lim E, Sobsey CA, Shrivastava S, Huang P, Liu P, Fang L, Peng J, Fradette R, Cheng D, Tzur D, Clements M, Lewis A, De Souza A, Zuniga A, Dawe M, Xiong Y, Clive D, Greiner R, Nazyrova A, Shaykhutdinov R, Li L, Vogel HJ, Forsythe I: HMDB: a knowledgebase for the human metabolome. Nucleic Acids Res. 2009 Jan;37(Database issue):D603-10. doi: 10.1093/nar/gkn810. Epub 2008 Oct 25. [PubMed:18953024 ]
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Fumarase deficiency
  1. Tregoning S, Salter W, Thorburn DR, Durkie M, Panayi M, Wu JY, Easterbrook A, Coman DJ: Fumarase deficiency in dichorionic diamniotic twins. Twin Res Hum Genet. 2013 Dec;16(6):1117-20. doi: 10.1017/thg.2013.72. Epub 2013 Nov 4. [PubMed:24182348 ]
  2. Bastug O, Kardas F, Ozturk MA, Halis H, Memur S, Korkmaz L, Tag Z, Gunes T: A rare cause of opistotonus; fumaric aciduria: The first case presentation in Turkey. Turk Pediatri Ars. 2014 Mar 1;49(1):74-6. doi: 10.5152/tpa.2014.442. eCollection 2014 Mar. [PubMed:26078636 ]
  3. Whelan DT, Hill RE, McClorry S: Fumaric aciduria: a new organic aciduria, associated with mental retardation and speech impairment. Clin Chim Acta. 1983 Aug 31;132(3):301-8. [PubMed:6616883 ]
  4. Maradin M, Fumic K, Hansikova H, Tesarova M, Wenchich L, Dorner S, Sarnavka V, Zeman J, Baric I: Fumaric aciduria: mild phenotype in a 8-year-old girl with novel mutations. J Inherit Metab Dis. 2006 Oct;29(5):683. Epub 2006 Aug 5. [PubMed:16972175 ]
  5. G.Frauendienst-Egger, Friedrich K. Trefz (2017). MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de). METAGENE consortium.
2-Ketoglutarate dehydrogenase complex deficiency
  1. Bonnefont JP, Chretien D, Rustin P, Robinson B, Vassault A, Aupetit J, Charpentier C, Rabier D, Saudubray JM, Munnich A: Alpha-ketoglutarate dehydrogenase deficiency presenting as congenital lactic acidosis. J Pediatr. 1992 Aug;121(2):255-8. [PubMed:1640293 ]
Amish lethal microcephaly
  1. Kelley RI, Robinson D, Puffenberger EG, Strauss KA, Morton DH: Amish lethal microcephaly: a new metabolic disorder with severe congenital microcephaly and 2-ketoglutaric aciduria. Am J Med Genet. 2002 Nov 1;112(4):318-26. doi: 10.1002/ajmg.10529. [PubMed:12376931 ]
Lipoyltransferase 1 Deficiency
  1. Soreze Y, Boutron A, Habarou F, Barnerias C, Nonnenmacher L, Delpech H, Mamoune A, Chretien D, Hubert L, Bole-Feysot C, Nitschke P, Correia I, Sardet C, Boddaert N, Hamel Y, Delahodde A, Ottolenghi C, de Lonlay P: Mutations in human lipoyltransferase gene LIPT1 cause a Leigh disease with secondary deficiency for pyruvate and alpha-ketoglutarate dehydrogenase. Orphanet J Rare Dis. 2013 Dec 17;8:192. doi: 10.1186/1750-1172-8-192. [PubMed:24341803 ]
Associated OMIM IDs
DrugBank IDDB01677
Phenol Explorer Compound IDNot Available
FooDB IDFDB003291
KNApSAcK IDC00001183
Chemspider ID10197150
KEGG Compound IDC00122
BioCyc IDFUM
BiGG ID33938
Wikipedia LinkFumaric_Acid
METLIN ID3242
PubChem Compound444972
PDB IDNot Available
ChEBI ID18012
Food Biomarker OntologyNot Available
VMH IDFUM
MarkerDB IDMDB00000065
Good Scents IDNot Available
References
Synthesis ReferenceDong, Changsheng; Ma, Xinming. Method for preparation of fumaric acid from the tail gas acid spray solution from oxidation of phthalic anhydride. Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 5pp.
Material Safety Data Sheet (MSDS)Download (PDF)
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. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Only showing the first 10 proteins. There are 12 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details
1. Succinate dehydrogenase cytochrome b560 subunit, mitochondrial
General function:
Involved in succinate dehydrogenase activity
Specific function:
Membrane-anchoring subunit of succinate dehydrogenase (SDH) that is involved in complex II of the mitochondrial electron transport chain and is responsible for transferring electrons from succinate to ubiquinone (coenzyme Q).
Gene Name:
SDHC
Uniprot ID:
Q99643
Molecular weight:
16650.185
Reactions
Ubiquinone-2 + Succinic acid → QH2 + Fumaric aciddetails
Enzyme Details
2. Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial
General function:
Involved in electron carrier activity
Specific function:
Flavoprotein (FP) subunit of succinate dehydrogenase (SDH) that is involved in complex II of the mitochondrial electron transport chain and is responsible for transferring electrons from succinate to ubiquinone (coenzyme Q). Can act as a tumor suppressor.
Gene Name:
SDHA
Uniprot ID:
P31040
Molecular weight:
72690.975
Reactions
Succinic acid + Coenzyme Q10 → Fumaric acid + QH(2)details
Ubiquinone-2 + Succinic acid → QH2 + Fumaric aciddetails
Enzyme Details
3. Succinate dehydrogenase [ubiquinone] cytochrome b small subunit, mitochondrial
General function:
Involved in iron ion binding
Specific function:
Membrane-anchoring subunit of succinate dehydrogenase (SDH) that is involved in complex II of the mitochondrial electron transport chain and is responsible for transferring electrons from succinate to ubiquinone (coenzyme Q) (By similarity).
Gene Name:
SDHD
Uniprot ID:
O14521
Molecular weight:
17042.82
Reactions
Ubiquinone-2 + Succinic acid → QH2 + Fumaric aciddetails
Enzyme Details
4. Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial
General function:
Involved in electron carrier activity
Specific function:
Iron-sulfur protein (IP) subunit of succinate dehydrogenase (SDH) that is involved in complex II of the mitochondrial electron transport chain and is responsible for transferring electrons from succinate to ubiquinone (coenzyme Q).
Gene Name:
SDHB
Uniprot ID:
P21912
Molecular weight:
31629.365
Reactions
Succinic acid + Coenzyme Q10 → Fumaric acid + QH(2)details
Ubiquinone-2 + Succinic acid → QH2 + Fumaric aciddetails
Enzyme Details
5. Dopamine beta-hydroxylase
General function:
Involved in monooxygenase activity
Specific function:
Conversion of dopamine to noradrenaline.
Gene Name:
DBH
Uniprot ID:
P09172
Molecular weight:
69064.45
Enzyme Details
6. Adenylosuccinate lyase
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
ADSL
Uniprot ID:
P30566
Molecular weight:
54888.735
Reactions
Adenylsuccinic acid → Fumaric acid + Adenosine monophosphatedetails
SAICAR → Fumaric acid + AICARdetails
SAICAR → Fumaric acid + AICARdetails
Enzyme Details
7. Argininosuccinate lyase
General function:
Involved in argininosuccinate lyase activity
Specific function:
Not Available
Gene Name:
ASL
Uniprot ID:
P04424
Molecular weight:
51657.505
Reactions
Argininosuccinic acid → Fumaric acid + L-Argininedetails
Enzyme Details
8. Fumarylacetoacetase
General function:
Involved in fumarylacetoacetase activity
Specific function:
Not Available
Gene Name:
FAH
Uniprot ID:
P16930
Molecular weight:
46373.97
Reactions
4-Fumarylacetoacetic acid + Water → Acetoacetic acid + Fumaric aciddetails
Acetoacetic acid + Fumaric acid → 4-Fumarylacetoacetic acid + Waterdetails
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Enzyme Details
9. Fumarate hydratase, mitochondrial
General function:
Involved in fumarate hydratase activity
Specific function:
Also acts as a tumor suppressor.
Gene Name:
FH
Uniprot ID:
P07954
Molecular weight:
54636.585
Reactions
Malic acid → Fumaric acid + Waterdetails
Enzyme Details
10. NAD-dependent malic enzyme, mitochondrial
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ME2
Uniprot ID:
P23368
Molecular weight:
53585.73
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]

Only showing the first 10 proteins. There are 12 proteins in total.

Show all enzymes and transporters