Showing metabocard for fumarate (MMDBc0054486)

Microbial
Record Information
Version2.0
StatusDetected and Quantified
Creation Date2022-06-05 23:14:59 UTC
Update Date2025-10-07 16:08:32 UTC
Metabolite IDMMDBc0054486
Metabolite Identification
Common Namefumarate
DescriptionFumarate is a dicarboxylic acid and a key intermediate in the tricarboxylic acid (TCA) cycle, classified as a metabolic metabolite. Its chemical structure features a double bond between two carbon atoms, each bonded to a carboxyl group, making it a crucial player in cellular respiration and energy production. Fumarate is involved in various metabolic pathways, including its conversion to malate by the enzyme fumarase, which is essential for the continuation of the TCA cycle. Additionally, fumarate plays a role in several biological contexts, such as its accumulation in inflammatory responses where it acts as a pro-inflammatory metabolite produced by macrophages during infection (PMID:41030993 ). It is also noted for its involvement in the treatment of chronic hepatitis B, where tenofovir disoproxil fumarate (TDF) is used as an antiviral agent (PMID:41036828 ). Furthermore, studies have highlighted the significance of fumarate in metabolic profiling, showing altered ratios in conditions like primary open-angle glaucoma (PMID:41034373 ) and its regulation by host mechanisms to mitigate inflammation (PMID:41030993 ). Despite its biochemical relevance, no significant associations have been found between serum fumarate levels and clinical outcomes in certain studies (PMID:41041310 ).
Structure
MOLSDFPDBSMILESInChI

MOL for #<Metabolite:0x00007f9af0b3d6d8>


  Mrv0541 02231215382D          

  8  7  0  0  0  0            999 V2000
    2.0625    0.7145    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
M  CHG  2   1  -1   7  -1
M  END
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3D MOL for #<Metabolite:0x00007f9af0b3d6d8>

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3D SDF for #<Metabolite:0x00007f9af0b3d6d8>

  Mrv0541 02231215382D          

  8  7  0  0  0  0            999 V2000
    2.0625    0.7145    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
M  CHG  2   1  -1   7  -1
M  END
> <DATABASE_ID>
MMDBc0054486

> <DATABASE_NAME>
MIME

> <SMILES>
[O-]C(=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)/p-2/b2-1+

> <INCHI_KEY>
VZCYOOQTPOCHFL-OWOJBTEDSA-L

> <FORMULA>
C4H2O4

> <MOLECULAR_WEIGHT>
114.0563

> <EXACT_MASS>
113.995308552

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
8.646525088055803

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
-2

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-but-2-enedioate

> <ALOGPS_LOGP>
-0.02

> <JCHEM_LOGP>
-0.040914331333333324

> <ALOGPS_LOGS>
0.14

> <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>
80.25999999999999

> <JCHEM_REFRACTIVITY>
46.281200000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.06e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
fumarate

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for #<Metabolite:0x00007f9af0b3d6d8>
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PDB for #<Metabolite:0x00007f9af0b3d6d8>
HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       3.850   1.334   0.000  0.00  0.00           O-1
HETATM    2  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.540   2.667   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.000  -2.667   0.000  0.00  0.00           O-1
HETATM    8  O   UNK     0      -2.310  -1.334   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
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 #<Metabolite:0x00007f9af0b3d6d8>
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SMILES for #<Metabolite:0x00007f9af0b3d6d8>
[O-]C(=O)\C=C\C([O-])=O
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INCHI for #<Metabolite:0x00007f9af0b3d6d8>
InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/p-2/b2-1+
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Synonyms
ValueSource
(2E)-But-2-enedioateChEBI
(e)-2-Butenedioic acid, ion(2-)ChEBI
FUMARATEChEBI
(2E)-But-2-enedioic acidGenerator
(e)-2-Butenedioate, ion(2-)Generator
FUMARic acidGenerator
Fumaric acid(2-)Generator
Molecular FormulaC4H2O4
Average Mass114.0563
Monoisotopic Mass113.995308552
IUPAC Name(2E)-but-2-enedioate
Traditional Namefumarate
CAS Registry NumberNot Available
SMILES
[O-]C(=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)/p-2/b2-1+
InChI KeyVZCYOOQTPOCHFL-OWOJBTEDSA-L