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Identification
YMDB IDYMDB00086
NameCitric acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionCitric acid, also known as anhydrous citrate or citronensaeure, belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. Citric acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Citric acid exists in all living species, ranging from bacteria to humans. Citric acid is a potentially toxic compound.
Structure
Thumb
Synonyms
  • 2-Hydroxy-1,2,3-propanetricarboxylate
  • 2-hydroxy-1,2,3-propanetricarboxylate(3-)
  • 2-Hydroxy-1,2,3-propanetricarboxylic acid
  • 2-hydroxy-1,2,3-propanetricarboxylic acid, ion(3-)
  • 2-hydroxytricarballylate
  • 3-Carboxy-3-hydroxypentane-1,5-dioate
  • 3-Carboxy-3-hydroxypentane-1,5-dioic acid
  • Aciletten
  • Anhydrous citrate
  • Anhydrous citric acid
  • beta-Hydroxytricarballylate
  • beta-Hydroxytricarballylic acid
  • cit
  • cit(3-)
  • Citraclean
  • Citrate
  • CITRATE ANION
  • Citretten
  • Citric acid
  • Citro
  • Hydrocerol A
  • Kyselina citronova
  • Suby G
  • Uro-trainer
  • 2-Hydroxytricarballylic acid
  • Citronensaeure
  • e330
  • H3Cit
  • Citric acid anhydrous
  • Citrate anhydrous
  • Chemfill
  • e 330
  • Acid monohydrate, citric
  • Monohydrate, citric acid
  • Citric acid, anhydrous
  • Citric acid monohydrate
  • Uralyt u
CAS number77-92-9
WeightAverage: 192.1235
Monoisotopic: 192.02700261
InChI KeyKRKNYBCHXYNGOX-UHFFFAOYSA-N
InChIInChI=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)
IUPAC Name2-hydroxypropane-1,2,3-tricarboxylic acid
Traditional IUPAC Namecitric acid
Chemical FormulaC6H8O7
SMILES[H]OC(=O)C([H])([H])C(O[H])(C(=O)O[H])C([H])([H])C(=O)O[H]
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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassTricarboxylic acids and derivatives
Direct ParentTricarboxylic acids and derivatives
Alternative Parents
Substituents
  • Tricarboxylic acid or derivatives
  • Hydroxy acid
  • Alpha-hydroxy acid
  • Tertiary alcohol
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point153 °C
Experimental Properties
PropertyValueReference
Water Solubility592 mg/mL at 25 oC [YALKOWSKY,SH & HE,Y (2003)]PhysProp
LogP-1.64 [AVDEEF,A (1997)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility106 g/LALOGPS
logP-1.3ALOGPS
logP-1.3ChemAxon
logS-0.26ALOGPS
pKa (Strongest Acidic)3.05ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area132.13 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity35.62 m³·mol⁻¹ChemAxon
Polarizability15.54 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Mitochondrion
  • Peroxisome
Organoleptic Properties
Flavour/OdourSource
OdorlessFDB012586
SMPDB Pathways
Citric Acid CyclePW000952 ThumbThumb?image type=greyscaleThumb?image type=simple
Citric Acid Cycle 1434561204PW000970 ThumbThumb?image type=greyscaleThumb?image type=simple
Glyoxylate cyclePW002419 ThumbThumb?image type=greyscaleThumb?image type=simple
TCA CyclePW002377 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Citrate cycle (TCA cycle)ec00020 Map00020
Glyoxylate and dicarboxylate metabolismec00630 Map00630
SMPDB Reactions
Acetyl-CoA + water + Oxalacetic acidCitric acid + Coenzyme A
Citric acidcis-aconitic acid + water
Oxalacetic acid + Acetyl-CoA + waterCoenzyme A + hydron + Citric acid
Citric acidwater + cis-aconitic acid
KEGG Reactions
Acetyl-CoA + water + Oxalacetic acidhydron + Citric acid + Coenzyme A
Citric acidcis-aconitic acid + water
Concentrations
Intracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
2400 ± 100 µM Minimal medium supplemented with ammonia saltsaerobic;resting cellsBaker's yeastPMID: 4578278
13500 ± 9500 µM Minimal medium supplemented with ammonia salts and glucoseaerobic and anaerobic;resting cellsBaker's yeastPMID: 4578278
700 ± 0 µM Minimal medium supplemented with ammonia salts and (glucose or galactose)aerobic;growing cellsBaker's yeastPMID: 4578278
5200 ± 500 µM Synthetic medium with 2% glucoseaerobic;growing cellsBaker's yeastPMID: 6229402
210 ± 10 µM Synthetic medium with 2% glucoseaerobic;resting cellsBaker's yeastPMID: 6229402
1500 ± 400 µM Synthetic medium with 2% glucoseanaerobic;resting cellsBaker's yeastPMID: 6229402
3700 ± 700 µM Synthetic medium with 2% galactoseaerobic;resting cellsBaker's yeastPMID: 6229402
Conversion Details Here
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Lawrence, C. L., Botting, C. H., Antrobus, R., Coote, P. J. (2004). "Evidence of a new role for the high-osmolarity glycerol mitogen-activated protein kinase pathway in yeast: regulating adaptation to citric acid stress." Mol Cell Biol 24:3307-3323.15060153
  • Sandor, A., Johnson, J. H., Srere, P. A. (1994). "Cooperation between enzyme and transporter in the inner mitochondrial membrane of yeast. Requirement for mitochondrial citrate synthase for citrate and malate transport in Saccharomyces cerevisiae." J Biol Chem 269:29609-29612.7961948
  • Kispal, G., Srere, P. A. (1991). "Studies on yeast peroxisomal citrate synthase." Arch Biochem Biophys 286:132-137.1897942
  • Velot, C., Lebreton, S., Morgunov, I., Usher, K. C., Srere, P. A. (1999). "Metabolic effects of mislocalized mitochondrial and peroxisomal citrate synthases in yeast Saccharomyces cerevisiae." Biochemistry 38:16195-16204.10587442
  • Jia, Y. K., Becam, A. M., Herbert, C. J. (1997). "The CIT3 gene of Saccharomyces cerevisiae encodes a second mitochondrial isoform of citrate synthase." Mol Microbiol 24:53-59.9140965
  • Gancedo, J. M., Gancedo, C. (1973). "Concentrations of intermediary metabolites in yeast." Biochimie 55:205-211.4578278
  • Lagunas, R., Gancedo, C. (1983). "Role of phosphate in the regulation of the Pasteur effect in Saccharomyces cerevisiae." Eur J Biochem 137:479-483.6229402
  • Castrillo, J. I., Zeef, L. A., Hoyle, D. C., Zhang, N., Hayes, A., Gardner, D. C., Cornell, M. J., Petty, J., Hakes, L., Wardleworth, L., Rash, B., Brown, M., Dunn, W. B., Broadhurst, D., O'Donoghue, K., Hester, S. S., Dunkley, T. P., Hart, S. R., Swainston, N., Li, P., Gaskell, S. J., Paton, N. W., Lilley, K. S., Kell, D. B., Oliver, S. G. (2007). "Growth control of the eukaryote cell: a systems biology study in yeast." J Biol 6:4.17439666
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.
External Links:
ResourceLink
CHEBI ID30769
HMDB IDHMDB00094
Pubchem Compound ID311
Kegg IDC00158
ChemSpider ID305
FOODB IDFDB012586
WikipediaCitric_acid
BioCyc IDCIT

Enzymes

General function:
Involved in metabolic process
Specific function:
Required for growth on nonfermentable carbon sources and for biosynthesis of glutamate
Gene Name:
ACO1
Uniprot ID:
P19414
Molecular weight:
85367.5
Reactions
Citrate → isocitrate.
General function:
Involved in metabolic process
Specific function:
Citrate = isocitrate
Gene Name:
ACO2
Uniprot ID:
P39533
Molecular weight:
86582.5
Reactions
Citrate → isocitrate.
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:
CIT3
Uniprot ID:
P43635
Molecular weight:
53810.69922
Reactions
Acetyl-CoA + H(2)O + oxaloacetate → citrate + CoA.
propanoyl-CoA + H2O + oxaloacetate → (2R,3S)-2-hydroxybutane-1,2,3-tricarboxylate + CoA
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:
CIT2
Uniprot ID:
P08679
Molecular weight:
51412.89844
Reactions
Acetyl-CoA + H(2)O + oxaloacetate → citrate + CoA.
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:
CIT1
Uniprot ID:
P00890
Molecular weight:
53359.60156
Reactions
Acetyl-CoA + H(2)O + oxaloacetate → citrate + CoA.
General function:
Involved in metabolic process
Specific function:
Responsible for the dehydration of cis-homoaconitate to homoisocitric acid
Gene Name:
LYS4
Uniprot ID:
P49367
Molecular weight:
75150.10156
Reactions
(1R,2S)-1-hydroxybutane-1,2,4-tricarboxylate → (Z)-but-1-ene-1,2,4-tricarboxylate + H(2)O.

Transporters

General function:
Involved in binding
Specific function:
Transport of citrate across inner mitochondrial membrane
Gene Name:
CTP1
Uniprot ID:
P38152
Molecular weight:
32173.0