Fumaric acid (ECMDB00176) (M2MDB000073)
Record Information | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Version | 2.0 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Creation Date | 2012-05-31 10:22:59 -0600 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Update Date | 2015-09-13 12:56:06 -0600 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Secondary Accession Numbers |
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Identification | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Name: | Fumaric acid | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | A precursor to L-malate in the Krebs tricarboxylic acid cycle. It is formed by the oxidation of succinate by succinate dehydrogenase. Fumarate is converted by fumarase to malate. A fumarate is a salt or ester of the organic compound fumaric acid, a dicarboxylic acid. (wikipedia) | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Structure | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synonyms: |
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Chemical Formula: | C4H4O4 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Weight: | Average: 116.0722 Monoisotopic: 116.010958616 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI Key: | VZCYOOQTPOCHFL-OWOJBTEDSA-N | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI: | InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1+ | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
CAS number: | 110-17-8 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
IUPAC Name: | (2E)-but-2-enedioic acid | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Traditional IUPAC Name: | fumaric acid | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMILES: | OC(=O)\C=C\C(O)=O | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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. | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Kingdom | Organic compounds | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Super Class | Organic acids and derivatives | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Class | Carboxylic acids and derivatives | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Sub Class | Dicarboxylic acids and derivatives | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Direct Parent | Dicarboxylic acids and derivatives | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Alternative Parents | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Substituents |
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Molecular Framework | Aliphatic acyclic compounds | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Descriptors |
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Physical Properties | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
State: | Solid | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Charge: | -2 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Melting point: | 549 °C | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Experimental Properties: |
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Predicted Properties |
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Biological Properties | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Cellular Locations: | Cytoplasm | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Reactions: | Ubiquinone-8 + Succinic acid > Fumaric acid + Ubiquinol-8 Fumaric acid + Water <> L-Malic acid Fumaric acid + Menaquinol 8 > Menaquinone 8 + Succinic acid 2-Demethylmenaquinol 8 + Fumaric acid > 2-Demethylmenaquinone 8 + Succinic acid Water + 2-Hydroxy-6-ketononatrienedioate > Fumaric acid + Hydrogen ion + 2-Hydroxy-2,4-pentadienoate SAICAR <> Phosphoribosyl formamidocarboxamide + Fumaric acid Adenylsuccinic acid <> Adenosine monophosphate + Fumaric acid L-Aspartic acid + Fumaric acid > Hydrogen ion + Iminoaspartic acid + Succinic acid 3 Fumaric acid + Protoporphyrinogen IX > Protoporphyrin IX +3 Succinic acid Argininosuccinic acid <> L-Arginine + Fumaric acid L-Aspartic acid > Fumaric acid + Ammonium Succinic acid + FAD <> FADH2 + Fumaric acid Succinic acid + Acceptor <> Fumaric acid + Reduced acceptor L-Aspartic acid <> Fumaric acid + Ammonia L-Malic acid <> Fumaric acid + Water 4,5-Dihydroorotic acid + Fumaric acid <> Orotic acid + Succinic acid SAICAR <> Fumaric acid + AICAR 2-Hydroxy-6-ketononatrienedioate + Water <> 2-Hydroxy-2,4-pentadienoate + Fumaric acid SAICAR > Fumaric acid + AICAR adenylo-succinate > Fumaric acid + Adenosine monophosphate L-arginino-succinate <> L-Arginine + Fumaric acid L-Aspartic acid <> Hydrogen ion + Fumaric acid + Ammonia Fumaric acid + a menaquinol > a menaquinone + Succinic acid a ubiquinone + Succinic acid <> a ubiquinol + Fumaric acid 2-(N(omega)-L-arginino)succinate > Fumaric acid + L-Arginine L-Aspartic acid > Fumaric acid + Ammonia More...Succinic acid + acceptor > Fumaric acid + reduced acceptor L-Malic acid > Fumaric acid + Water (2E,4Z,7E)-2-hydroxy-6-oxonona-2,4,7-triene-1,9-dioate + Water > 2-oxopent-4-enoate + Fumaric acid Adenylsuccinic acid > Fumaric acid + Adenosine monophosphate Succinic acid + Quinone <> Fumaric acid + Hydroquinone 2-Hydroxy-6-ketononadienedicarboxylate + Water + 2-Hydroxy-6-ketononatrienedioate <> Succinic acid + Fumaric acid Adenylsuccinic acid + SAICAR <> Fumaric acid + Adenosine monophosphate + AICAR L-Malic acid + L-Malic acid <> Fumaric acid + Water Succinic acid + Ubiquinone-10 + FAD <> Fumaric acid + QH2 + FADH2 Succinic acid + Ubiquinone-1 > Ubiquinol-1 + Fumaric acid Succinic acid + Ubiquinone-2 > Fumaric acid + Ubiquinol-2 Succinic acid + Ubiquinone-3 > Fumaric acid + Ubiquinol-3 Succinic acid + Ubiquinone-4 > Fumaric acid + Ubiquinol-4 Succinic acid + Ubiquinone-5 > Fumaric acid + Ubiquinol-5 Succinic acid + Ubiquinone-6 > Fumaric acid + Ubiquinol-6 Succinic acid + Ubiquinone-7 > Fumaric acid + Ubiquinol-7 Succinic acid + Ubiquinone-8 > Fumaric acid + Ubiquinol 8 + Ubiquinol-8 Succinic acid + Coenzyme Q9 > Fumaric acid + Ubiquinol-9 Succinic acid + Ubiquinone-10 > Fumaric acid + Ubiquinol-10 + Ubiquinol-10 Fumaric acid + Water > L-Malic acid + L-Malic acid L-Aspartic acid + L-Aspartic acid > Fumaric acid + Ammonia L-Aspartic acid + L-Aspartic acid > Fumaric acid + Ammonium N(6)-(1,2-dicarboxyethyl)AMP > Fumaric acid + Adenosine monophosphate Argininosuccinic acid > Fumaric acid + L-Arginine SAICAR + SAICAR > AICAR + Fumaric acid N(6)-(1,2-dicarboxyethyl)AMP + Adenylsuccinic acid > Fumaric acid + Adenosine monophosphate 2-Hydroxy-6-ketononatrienedioate + Water > Hydrogen ion + Fumaric acid + 2-Hydroxy-2,4-pentadienoate + 2-Hydroxy-2,4-pentadienoate Ubiquinone-0 + Succinic acid > Ubiquinol-0 + Fumaric acid Fumaric acid + 2 Hydrogen ion + a menaquinol > Succinic acid + a menaquinone Fumaric acid + Water <> L-Malic acid L-Malic acid <> Fumaric acid + Water Succinic acid + FAD <> FADH2 + Fumaric acid Succinic acid + Acceptor <> Fumaric acid + Reduced acceptor Adenylsuccinic acid <> Adenosine monophosphate + Fumaric acid SAICAR <> Fumaric acid + AICAR 4 4,5-Dihydroorotic acid + Fumaric acid <> Orotic acid + Succinic acid Argininosuccinic acid <> L-Arginine + Fumaric acid L-Aspartic acid <> Fumaric acid + Ammonia L-Aspartic acid <> Hydrogen ion + Fumaric acid + Ammonia Succinic acid + FAD <> FADH2 + Fumaric acid Succinic acid + FAD <> FADH2 + Fumaric acid 4 4,5-Dihydroorotic acid + Fumaric acid <> Orotic acid + Succinic acid | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMPDB Pathways: |
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KEGG Pathways: |
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EcoCyc Pathways: |
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Concentrations | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Find out more about how we convert literature concentrations. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra: | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References: |
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Synthesis Reference: | Dong, 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) | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Links | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Links: |
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Enzymes
- General function:
- Involved in electron carrier activity
- Specific function:
- Two distinct, membrane-bound, FAD-containing enzymes are responsible for the catalysis of fumarate and succinate interconversion; the fumarate reductase is used in anaerobic growth, and the succinate dehydrogenase is used in aerobic growth
- Gene Name:
- frdA
- Uniprot ID:
- P00363
- Molecular weight:
- 65971
Reactions
Succinate + acceptor = fumarate + reduced acceptor. |
- General function:
- Involved in fumarate hydratase activity
- Specific function:
- (S)-malate = fumarate + H(2)O
- Gene Name:
- fumC
- Uniprot ID:
- P05042
- Molecular weight:
- 50488
Reactions
(S)-malate = fumarate + H(2)O. |
- General function:
- Involved in electron carrier activity
- Specific function:
- Two distinct, membrane-bound, FAD-containing enzymes are responsible for the catalysis of fumarate and succinate interconversion; the fumarate reductase is used in anaerobic growth, and the succinate dehydrogenase is used in aerobic growth
- Gene Name:
- sdhB
- Uniprot ID:
- P07014
- Molecular weight:
- 26770
Reactions
Succinate + acceptor = fumarate + reduced acceptor. |
- General function:
- Involved in catalytic activity
- Specific function:
- (S)-dihydroorotate + a quinone = orotate + a quinol
- Gene Name:
- pyrD
- Uniprot ID:
- P0A7E1
- Molecular weight:
- 36774
Reactions
(S)-dihydroorotate + a quinone = orotate + a quinol. |
- General function:
- Energy production and conversion
- Specific function:
- Seems to be involved in the anchoring of the catalytic components of the fumarate reductase complex to the cytoplasmic membrane
- Gene Name:
- frdC
- Uniprot ID:
- P0A8Q0
- Molecular weight:
- 15015
- General function:
- Involved in fumarate metabolic process
- Specific function:
- Seems to be involved in the anchoring of the catalytic components of the fumarate reductase complex to the cytoplasmic membrane
- Gene Name:
- frdD
- Uniprot ID:
- P0A8Q3
- Molecular weight:
- 13107
- General function:
- Involved in N6-(1,2-dicarboxyethyl)AMP AMP-lyase (fumarate-forming) activity
- Specific function:
- N(6)-(1,2-dicarboxyethyl)AMP = fumarate + AMP
- Gene Name:
- purB
- Uniprot ID:
- P0AB89
- Molecular weight:
- 51542
Reactions
N(6)-(1,2-dicarboxyethyl)AMP = fumarate + AMP. |
(S)-2-(5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido)succinate = fumarate + 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide. |
- General function:
- Involved in lyase activity
- Specific function:
- It functions as an aerobic enzyme in the citric acid cycle. It accounts for about 80% of the fumarase activity when the bacteria grows aerobically
- Gene Name:
- fumA
- Uniprot ID:
- P0AC33
- Molecular weight:
- 60298
Reactions
(S)-malate = fumarate + H(2)O. |
- General function:
- Involved in aspartate ammonia-lyase activity
- Specific function:
- L-aspartate = fumarate + NH(3)
- Gene Name:
- aspA
- Uniprot ID:
- P0AC38
- Molecular weight:
- 52356
Reactions
L-aspartate = fumarate + NH(3). |
- General function:
- Involved in electron carrier activity
- Specific function:
- Two distinct, membrane-bound, FAD-containing enzymes are responsible for the catalysis of fumarate and succinate interconversion; the fumarate reductase is used in anaerobic growth, and the succinate dehydrogenase is used in aerobic growth
- Gene Name:
- sdhA
- Uniprot ID:
- P0AC41
- Molecular weight:
- 64421
Reactions
Succinate + acceptor = fumarate + reduced acceptor. |
- General function:
- Involved in succinate dehydrogenase activity
- Specific function:
- Membrane-anchoring subunit of succinate dehydrogenase (SDH)
- Gene Name:
- sdhD
- Uniprot ID:
- P0AC44
- Molecular weight:
- 12867
- General function:
- Involved in electron carrier activity
- Specific function:
- Two distinct, membrane-bound, FAD-containing enzymes are responsible for the catalysis of fumarate and succinate interconversion; the fumarate reductase is used in anaerobic growth, and the succinate dehydrogenase is used in aerobic growth
- Gene Name:
- frdB
- Uniprot ID:
- P0AC47
- Molecular weight:
- 27123
Reactions
Succinate + acceptor = fumarate + reduced acceptor. |
- General function:
- Involved in FMN binding
- Specific function:
- Catalyzes the 6-electron oxidation of protoporphyrinogen-IX to form protoporphyrin-IX. Does not use oxygen directly. Is coupled to the respiratory chain
- Gene Name:
- hemG
- Uniprot ID:
- P0ACB4
- Molecular weight:
- 21226
Reactions
Protoporphyrinogen IX + 3 menaquinone = protoporphyrin IX + 3 menaquinol. |
- General function:
- Involved in electron carrier activity
- Specific function:
- Catalyzes the oxidation of L-aspartate to iminoaspartate
- Gene Name:
- nadB
- Uniprot ID:
- P10902
- Molecular weight:
- 60337
Reactions
L-aspartate + O(2) = iminosuccinate + H(2)O(2). |
- General function:
- Involved in argininosuccinate lyase activity
- Specific function:
- 2-(N(omega)-L-arginino)succinate = fumarate + L-arginine
- Gene Name:
- argH
- Uniprot ID:
- P11447
- Molecular weight:
- 50318
Reactions
2-(N(omega)-L-arginino)succinate = fumarate + L-arginine. |
- General function:
- Involved in lyase activity
- Specific function:
- It functions in the generation of fumarate for use as an anaerobic electron acceptor
- Gene Name:
- fumB
- Uniprot ID:
- P14407
- Molecular weight:
- 60105
Reactions
(S)-malate = fumarate + H(2)O. |
- General function:
- Involved in succinate dehydrogenase activity
- Specific function:
- Membrane-anchoring subunit of succinate dehydrogenase (SDH)
- Gene Name:
- sdhC
- Uniprot ID:
- P69054
- Molecular weight:
- 14299
- General function:
- Involved in catalytic activity
- Specific function:
- Catalyzes the cleavage of the C5-C6 bond of 2-hydroxy-6- oxononadienedioate and 2-hydroxy-6-oxononatrienedioate, a dienol ring fission product of the bacterial meta-cleavage pathway for degradation of phenylpropionic acid
- Gene Name:
- mhpC
- Uniprot ID:
- P77044
- Molecular weight:
- 32585
Reactions
(2E,4Z)-2-hydroxy-6-oxonona-2,4-diene-1,9-dioate + H(2)O = (2E)-2-hydroxypenta-2,4-dienoate + succinate. |
(2E,4Z,7E)-2-hydroxy-6-oxonona-2,4,7-triene-1,9-dioate + H(2)O = (2E)-2-hydroxypenta-2,4-dienoate + fumarate. |
Transporters
- General function:
- Involved in C4-dicarboxylate transmembrane transporter activity
- Specific function:
- Responsible for the transport of C4-dicarboxylates from the periplasm across the inner membrane
- Gene Name:
- dcuA
- Uniprot ID:
- P0ABN5
- Molecular weight:
- 45750
- General function:
- Involved in C4-dicarboxylate transmembrane transporter activity
- Specific function:
- Responsible for the transport of C4-dicarboxylates from the periplasm across the inner membrane
- Gene Name:
- dcuB
- Uniprot ID:
- P0ABN9
- Molecular weight:
- 47935
- General function:
- Involved in C4-dicarboxylate transmembrane transporter activity
- Specific function:
- Responsible for the transport of C4-dicarboxylates during anaerobic growth
- Gene Name:
- dcuC
- Uniprot ID:
- P0ABP3
- Molecular weight:
- 48412
- General function:
- Involved in transporter activity
- Specific function:
- Non-specific porin
- Gene Name:
- ompN
- Uniprot ID:
- P77747
- Molecular weight:
- 41220
- General function:
- Involved in transporter activity
- Specific function:
- Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
- Gene Name:
- phoE
- Uniprot ID:
- P02932
- Molecular weight:
- 38922
- General function:
- Involved in symporter activity
- Specific function:
- Responsible for the aerobic transport of the dicarboxylates fumarate, L- and D-malate and to a lesser extent succinate, from the periplasm across the inner membrane
- Gene Name:
- dctA
- Uniprot ID:
- P0A830
- Molecular weight:
- 45436
- General function:
- Involved in transporter activity
- Specific function:
- OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
- Gene Name:
- ompF
- Uniprot ID:
- P02931
- Molecular weight:
- 39333
- General function:
- Involved in transporter activity
- Specific function:
- Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
- Gene Name:
- ompC
- Uniprot ID:
- P06996
- Molecular weight:
- 40368