Citric acid (ECMDB00094) (M2MDB000034)
| Record Information | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Creation Date | 2012-05-31 09:57:07 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Update Date | 2015-09-13 15:15:17 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Secondary Accession Numbers |
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Name: | Citric acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Description | Citric acid is key intermediate in metabolism. It is a key component of the citric acid or TCA (Krebs) cycle. Citric acid is first consumed and then regenerated by this sequence of reactions to complete the cycle. Bacteria use the TCA cycle to generate energy, but since they lack mitochondria, the reaction sequence is performed in the cytosol with the proton gradient for ATP production being across the plasma membrane rather than the inner membrane of the mitochondria. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Structure |  | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Synonyms: |
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Chemical Formula: | C6H8O7 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Weight: | Average: 192.1235 Monoisotopic: 192.02700261 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI Key: | KRKNYBCHXYNGOX-UHFFFAOYSA-N | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI: | InChI=1S/C6H8O7/c7-3(8)1-6(13,5(11)12)2-4(9)10/h13H,1-2H2,(H,7,8)(H,9,10)(H,11,12) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| CAS number: | 77-92-9 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| IUPAC Name: | 2-hydroxypropane-1,2,3-tricarboxylic acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Traditional IUPAC Name: | citric acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| SMILES: | OC(=O)CC(O)(CC(O)=O)C(O)=O | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Chemical Taxonomy | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Description | belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Kingdom | Organic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Super Class | Organic acids and derivatives | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Class | Carboxylic acids and derivatives | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Sub Class | Tricarboxylic acids and derivatives | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Direct Parent | Tricarboxylic acids and derivatives | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Alternative Parents | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Substituents |
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Molecular Framework | Aliphatic acyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| External Descriptors |
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| State: | Solid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Charge: | -3 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Melting point: | 153 °C | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Experimental Properties: |
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Predicted Properties |
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Cellular Locations: | Cytoplasm | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Reactions: | Citric acid <> Acetic acid + Oxalacetic acid Citric acid <> cis-Aconitic acid + Water Adenosine triphosphate + Water + Fe(III)dicitrate > ADP +2 Citric acid + Fe3+ + Hydrogen ion + Phosphate Acetyl-CoA + Water + Oxalacetic acid <> Citric acid + Coenzyme A + Hydrogen ion Citric acid + Coenzyme A <> Acetyl-CoA + Water + Oxalacetic acid Citric acid <> Isocitric acid Citric acid > Acetic acid + Oxalacetic acid Citric acid > Isocitric acid Acetyl-CoA + Citric acid > Acetic acid + (3S)-Citryl-CoA Acetyl-CoA + Water + Oxalacetic acid > Citric acid + CoA Citric acid + cis-Aconitic acid + Water <> Isocitric acid Acetyl-CoA + Citric acid <> Acetic acid + (3S)-Citryl-CoA Acetyl-CoA + Water + Oxalacetic acid > Citric acid + Coenzyme A Citric acid <> cis-Aconitic acid + Water Oxalacetic acid + Water + Acetyl-CoA > Citric acid + Coenzyme A + Hydrogen ion Citric acid > Water + cis-Aconitic acid Water + cis-Aconitic acid <> Citric acid Citric acid <> cis-Aconitic acid + Water Acetyl-CoA + Water + Oxalacetic acid <> Citric acid + Coenzyme A + Hydrogen ion Acetyl-CoA + Water + Oxalacetic acid <> Citric acid + Coenzyme A + Hydrogen ion | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| SMPDB Pathways: |
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| KEGG Pathways: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| EcoCyc Pathways: |
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Find out more about how we convert literature concentrations. | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Spectra: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| References | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| References: |
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Synthesis Reference: | Evans, D. W. S. Hydrolysis of ethyl methylenecitrate [5,5-bis(ethoxycarbonylmethyl)-1,3-dioxolan-4-one] and an attempted synthesis of agaric acid. Journal of the Chemical Society (1959), 1313-14. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Material Safety Data Sheet (MSDS) | Download (PDF) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Links | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| External Links: |
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Enzymes
- General function:
- Involved in carbon-carbon lyase activity
- Specific function:
- Represents a citryl-ACP lyase
- Gene Name:
- citE
- Uniprot ID:
- P0A9I1
- Molecular weight:
- 33109
Reactions
| Citrate = acetate + oxaloacetate. |
| (3S)-citryl-CoA = acetyl-CoA + oxaloacetate. |
- General function:
- Involved in transferase activity, transferring acyl groups, acyl groups converted into alkyl on transfer
- Specific function:
- Acetyl-CoA + H(2)O + oxaloacetate = citrate + CoA
- Gene Name:
- gltA
- Uniprot ID:
- P0ABH7
- Molecular weight:
- 48015
Reactions
| Acetyl-CoA + H(2)O + oxaloacetate = citrate + CoA. |
- General function:
- Involved in nucleotide binding
- Specific function:
- Part of the binding-protein-dependent transport system for citrate-dependent Fe(3+). Probably responsible for energy coupling to the transport system
- Gene Name:
- fecE
- Uniprot ID:
- P15031
- Molecular weight:
- 28191
- General function:
- Involved in metabolic process
- Specific function:
- May have an iron-responsive regulatory function
- Gene Name:
- acnA
- Uniprot ID:
- P25516
- Molecular weight:
- 97676
Reactions
| Citrate = isocitrate. |
- General function:
- Involved in metabolic process
- Specific function:
- Citrate = isocitrate
- Gene Name:
- acnB
- Uniprot ID:
- P36683
- Molecular weight:
- 93497
Reactions
| Citrate = isocitrate. |
| (2S,3R)-3-hydroxybutane-1,2,3-tricarboxylate = (Z)-but-2-ene-1,2,3-tricarboxylate + H(2)O. |
- General function:
- Energy production and conversion
- Specific function:
- Covalent carrier of the coenzyme of citrate lyase
- Gene Name:
- citD
- Uniprot ID:
- P69330
- Molecular weight:
- 10689
- General function:
- Involved in citrate CoA-transferase activity
- Specific function:
- Represents a citrate:acetyl-ACP transferase
- Gene Name:
- citF
- Uniprot ID:
- P75726
- Molecular weight:
- 55172
Reactions
| Citrate = acetate + oxaloacetate. |
| Acetyl-CoA + citrate = acetate + (3S)-citryl-CoA. |
- General function:
- Involved in metabolic process
- Specific function:
- Unknown Function
- Gene Name:
- ybhJ
- Uniprot ID:
- P75764
- Molecular weight:
- 81504
- General function:
- Involved in transporter activity
- Specific function:
- Part of the binding-protein-dependent transport system for citrate-dependent Fe(3+). Probably responsible for the translocation of the substrate across the membrane
- Gene Name:
- fecD
- Uniprot ID:
- P15029
- Molecular weight:
- 34131
- General function:
- Involved in transporter activity
- Specific function:
- Part of the binding-protein-dependent transport system for citrate-dependent Fe(3+). Probably responsible for the translocation of the substrate across the membrane
- Gene Name:
- fecC
- Uniprot ID:
- P15030
- Molecular weight:
- 34892
- General function:
- Involved in prosthetic group biosynthetic process
- Specific function:
- Transfers 2-(5''-triphosphoribosyl)-3'- dephosphocoenzyme-A on a serine residue to the apo-acyl carrier protein (gamma chain) of the citrate lyase to yield holo-acyl carrier protein
- Gene Name:
- citX
- Uniprot ID:
- P0A6G5
- Molecular weight:
- 20270
Reactions
| 2'-(5-triphosphoribosyl)-3'-dephospho-CoA + citrate lyase apo-[acyl-carrier-protein] = citrate lyase holo-[acyl-carrier-protein] + diphosphate. |
- General function:
- Involved in binding
- Specific function:
- Binds citrate-dependent Fe(3+); part of the binding- protein-dependent transport system for uptake of citrate-dependent Fe(3+)
- Gene Name:
- fecB
- Uniprot ID:
- P15028
- Molecular weight:
- 33146
Transporters
- General function:
- Involved in nucleotide binding
- Specific function:
- Part of the binding-protein-dependent transport system for citrate-dependent Fe(3+). Probably responsible for energy coupling to the transport system
- Gene Name:
- fecE
- Uniprot ID:
- P15031
- Molecular weight:
- 28191
- General function:
- Involved in transporter activity
- Specific function:
- Responsible for the uptake of citrate in exchange to the efflux of succinate. Has a relatively broad specificity for C(4)- dicarboxylates and tricarboxylates
- Gene Name:
- citT
- Uniprot ID:
- P0AE74
- Molecular weight:
- 53092
- General function:
- Involved in transporter activity
- Specific function:
- Part of the binding-protein-dependent transport system for citrate-dependent Fe(3+). Probably responsible for the translocation of the substrate across the membrane
- Gene Name:
- fecD
- Uniprot ID:
- P15029
- Molecular weight:
- 34131
- General function:
- Involved in transporter activity
- Specific function:
- Part of the binding-protein-dependent transport system for citrate-dependent Fe(3+). Probably responsible for the translocation of the substrate across the membrane
- Gene Name:
- fecC
- Uniprot ID:
- P15030
- Molecular weight:
- 34892
- 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 binding
- Specific function:
- Binds citrate-dependent Fe(3+); part of the binding- protein-dependent transport system for uptake of citrate-dependent Fe(3+)
- Gene Name:
- fecB
- Uniprot ID:
- P15028
- Molecular weight:
- 33146
- 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