L-Malic acid (ECMDB00156) (M2MDB000058)
| Record Information | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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| Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Creation Date | 2012-05-31 10:22:05 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Update Date | 2015-10-15 16:15:00 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Secondary Accession Numbers |
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| Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Name: | L-Malic acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Description | Malic acid is a tart-tasting organic dicarboxylic acid that plays a role in many sour or tart foods. In its ionized form it is malate, an intermediate of the TCA cycle along with fumarate. It can also be formed from pyruvate as one of the anaplerotic reactions. Apples contain malic acid, which contributes to the sourness of a green apple. Malic acid can make a wine taste tart, although the amount decreases with increasing fruit ripeness. (wikipedia) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Structure |  | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Synonyms: |
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| Chemical Formula: | C4H6O5 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Weight: | Average: 134.0874 Monoisotopic: 134.021523302 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI Key: | BJEPYKJPYRNKOW-UHFFFAOYSA-N | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI: | InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| CAS number: | 97-67-6 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| IUPAC Name: | 2-hydroxybutanedioic acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Traditional IUPAC Name: | malic acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| SMILES: | OC(CC(O)=O)C(O)=O | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Chemical Taxonomy | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Description | belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Kingdom | Organic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Super Class | Organic acids and derivatives | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Class | Hydroxy acids and derivatives | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Sub Class | Beta hydroxy acids and derivatives | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Direct Parent | Beta hydroxy 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: | 107 °C | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Experimental Properties: |
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| Predicted Properties |
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| Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Cellular Locations: | Cytoplasm | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Reactions: | Fumaric acid + Water <> L-Malic acid Acetyl-CoA + Glyoxylic acid + Water <> Coenzyme A + Hydrogen ion + L-Malic acid L-Malic acid + NAD > Carbon dioxide + NADH + Pyruvic acid L-Malic acid + Ubiquinone-8 > Oxalacetic acid + Ubiquinol-8 L-Malic acid + Menaquinone 8 > Menaquinol 8 + Oxalacetic acid L-Malic acid + NADP > Carbon dioxide + NADPH + Pyruvic acid L-Malic acid + NAD <> Hydrogen ion + NADH + Oxalacetic acid L-Malic acid + NAD <> Pyruvic acid + Carbon dioxide + NADH + Hydrogen ion L-Malic acid + NADP <> Pyruvic acid + Carbon dioxide + NADPH + Hydrogen ion L-Malic acid + Coenzyme A <> Acetyl-CoA + Water + Glyoxylic acid L-Malic acid <> Fumaric acid + Water L-Malic acid + FAD <> FADH2 + Oxalacetic acid L-Malic acid + a quinone > Oxalacetic acid + a quinol L-Malic acid + Oxygen <> Oxalacetic acid + Hydrogen peroxide Acetyl-CoA + Water + Glyoxylic acid > Hydrogen ion + L-Malic acid + Coenzyme A L-Malic acid > Fumaric acid + Water Acetyl-CoA + Water + Glyoxylic acid > L-Malic acid + CoA L-Malic acid + NAD > Oxalacetic acid + NADH L-Malic acid + a quinone > Oxalacetic acid + reduced quinone L-Malic acid + NAD + Oxalacetic acid <> Pyruvic acid + Carbon dioxide + NADH L-Malic acid + Quinone <> Oxalacetic acid + Hydroquinone L-Malic acid + NADP + Oxalacetic acid <> Pyruvic acid + Carbon dioxide + NADPH L-Malic acid + L-Malic acid <> Fumaric acid + Water L-Malic acid + NAD + L-Malic acid <> Oxalacetic acid + NADH + Hydrogen ion Fumaric acid + Water > L-Malic acid + L-Malic acid L-Malic acid + NAD + L-Malic acid > Oxalacetic acid + NADH + Hydrogen ion More...L-Malic acid + Quinone + L-Malic acid > Oxalacetic acid + Hydroquinone L-Malic acid + NADP + L-Malic acid > Carbon dioxide + NADPH + Pyruvic acid + NADPH L-Malic acid + NAD + L-Malic acid > Carbon dioxide + NADH + Pyruvic acid Glyoxylic acid + Water + Acetyl-CoA > Coenzyme A + Hydrogen ion + L-Malic acid + L-Malic acid Acetyl-CoA + Glyoxylic acid + Water <> Coenzyme A + Hydrogen ion + L-Malic acid Fumaric acid + Water <> L-Malic acid L-Malic acid <> Fumaric acid + Water L-Malic acid + FAD <> FADH2 + Oxalacetic acid L-Malic acid + Quinone <> Oxalacetic acid + Hydroquinone L-Malic acid + NAD > Carbon dioxide + NADH + Pyruvic acid L-Malic acid + NADP > Carbon dioxide + NADPH + Pyruvic acid L-Malic acid + FAD <> FADH2 + Oxalacetic 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: | McKenzie, Alex.; Plenderleith, H. J.; Walker, Nellie. Optical activation of racemic acid by d-malic acid. Journal of the Chemical Society, Transactions (1923), 123 2875-80. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Material Safety Data Sheet (MSDS) | Download (PDF) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Links | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Enzymes
- 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 catalytic activity
- Specific function:
- Acetyl-CoA + H(2)O + glyoxylate = (S)-malate + CoA
- Gene Name:
- aceB
- Uniprot ID:
- P08997
- Molecular weight:
- 60273
Reactions
| Acetyl-CoA + H(2)O + glyoxylate = (S)-malate + CoA. |
- 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 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 oxidoreductase activity
- Specific function:
- (S)-malate + NAD(+) = pyruvate + CO(2) + NADH
- Gene Name:
- sfcA
- Uniprot ID:
- P26616
- Molecular weight:
- 63197
Reactions
| (S)-malate + NAD(+) = pyruvate + CO(2) + NADH. |
- General function:
- Involved in malate dehydrogenase (quinone) activity
- Specific function:
- (S)-malate + a quinone = oxaloacetate + reduced quinone
- Gene Name:
- mqo
- Uniprot ID:
- P33940
- Molecular weight:
- 60229
Reactions
| (S)-malate + a quinone = oxaloacetate + reduced quinone. |
- General function:
- Involved in catalytic activity
- Specific function:
- Accounts for almost the entire malate-synthesizing activity in cells metabolizing glyoxylate
- Gene Name:
- glcB
- Uniprot ID:
- P37330
- Molecular weight:
- 80488
Reactions
| Acetyl-CoA + H(2)O + glyoxylate = (S)-malate + CoA. |
- General function:
- Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
- Specific function:
- Catalyzes the reversible oxidation of malate to oxaloacetate
- Gene Name:
- mdh
- Uniprot ID:
- P61889
- Molecular weight:
- 32337
Reactions
| (S)-malate + NAD(+) = oxaloacetate + NADH. |
- General function:
- Involved in oxidoreductase activity
- Specific function:
- (S)-malate + NADP(+) = pyruvate + CO(2) + NADPH
- Gene Name:
- maeB
- Uniprot ID:
- P76558
- Molecular weight:
- 82417
Reactions
| (S)-malate + NADP(+) = pyruvate + CO(2) + NADPH. |
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