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Record Information
Version1.0
Creation Date2016-09-30 22:19:33 UTC
Update Date2020-06-04 21:51:30 UTC
BMDB IDBMDB0000094
Secondary Accession Numbers
  • BMDB00094
Metabolite Identification
Common NameCitric acid
DescriptionCitric acid, also known as 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 exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Citric acid exists in all living species, ranging from bacteria to humans. Citric acid is a potentially toxic compound.
Structure
Thumb
Synonyms
ValueSource
2-Hydroxy-1,2,3-propanetricarboxylic acidChEBI
2-Hydroxytricarballylic acidChEBI
3-Carboxy-3-hydroxypentane-1,5-dioic acidChEBI
CitronensaeureChEBI
e330ChEBI
H3CitChEBI
Anhydrous citric acidKegg
Citric acid anhydrousKegg
2-Hydroxy-1,2,3-propanetricarboxylateGenerator
2-HydroxytricarballylateGenerator
3-Carboxy-3-hydroxypentane-1,5-dioateGenerator
Anhydrous citrateGenerator
Citrate anhydrousGenerator
CitrateGenerator
AcilettenHMDB
beta-HydroxytricarballylateHMDB
beta-Hydroxytricarballylic acidHMDB
ChemfillHMDB
CitracleanHMDB
CitrettenHMDB
CitroHMDB
e 330HMDB
Hydrocerol aHMDB
Kyselina citronovaHMDB
Suby gHMDB
Uro-trainerHMDB
Acid monohydrate, citricHMDB
Monohydrate, citric acidHMDB
Citric acid, anhydrousHMDB
Citric acid monohydrateHMDB
Uralyt uHMDB
Chemical FormulaC6H8O7
Average Molecular Weight192.1235
Monoisotopic Molecular Weight192.02700261
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number77-92-9
SMILESNot Available
InChI Identifier
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)
InChI KeyKRKNYBCHXYNGOX-UHFFFAOYSA-N
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
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point153 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility592.0 mg/mLNot Available
LogP-1.64AVDEEF,A (1997)
Predicted PropertiesNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biospecimen Locations
  • All Tissues
  • Blood
  • Liver
  • Mammary Gland
  • Milk
  • Placenta
  • Prostate Tissue
  • Semen
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
    • Jiyuan Li, Everes...
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified3026 - 9854 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified3692 - 7435 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified8432.0762 +/- 260.249 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified9004.625 +/- 468.449 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified8180 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified9108.724 +/- 260.249 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified9316.924 +/- 156.150 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified9681.273 +/- 156.150 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified3719 - 5776 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified5099 +/- 409 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified5219 +/- 168 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified4793 +/- 260 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified5808 +/- 643 uMNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
    • Kurt J. Boudonck,...
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
    • Kurt J. Boudonck,...
details
MilkDetected and Quantified8380 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified9110 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified4602.04 +/- 617.46 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified6620 - 12900 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified4453.36 +/- 225.49 uMNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified4595.41 +/- 448.18 uMNot SpecifiedNot Specified
Normal
details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Prostate TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
SemenDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Sub/clinical ketosis
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
All Mycobacterium avium subsp. paratuberculosis-infected
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
High dose Mycobacterium avium subsp. paratuberculosis-infected
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Low dose Mycobacterium avium subsp. paratuberculosis-infected
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Mycobacterium avium subsp. paratuberculosis infection
details
HMDB IDHMDB0000094
DrugBank IDDB04272
Phenol Explorer Compound IDNot Available
FooDB IDFDB030735
KNApSAcK IDC00007619
Chemspider ID305
KEGG Compound IDC00158
BioCyc IDCIT
BiGG ID34080
Wikipedia LinkCitric_Acid
METLIN ID124
PubChem Compound311
PDB IDNot Available
ChEBI ID30769
References
Synthesis ReferenceEvans, 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)Not Available
General References
  1. Faulkner A, Pollock HT: Changes in the concentration of metabolites in milk from cows fed on diets supplemented with soyabean oil or fatty acids. J Dairy Res. 1989 May;56(2):179-83. [PubMed:2760296 ]
  2. Hurtaud C, Lemosquet S, Rulquin H: Effect of graded duodenal infusions of glucose on yield and composition of milk from dairy cows. 2. Diets based on grass silage. J Dairy Sci. 2000 Dec;83(12):2952-62. doi: 10.3168/jds.S0022-0302(00)75195-2. [PubMed:11132867 ]
  3. Tsioulpas A, Grandison AS, Lewis MJ: Changes in physical properties of bovine milk from the colostrum period to early lactation. J Dairy Sci. 2007 Nov;90(11):5012-7. doi: 10.3168/jds.2007-0192. [PubMed:17954740 ]
  4. Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563. [PubMed:20338431 ]
  5. Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9. [PubMed:22098372 ]
  6. Jensen HB, Poulsen NA, Andersen KK, Hammershoj M, Poulsen HD, Larsen LB: Distinct composition of bovine milk from Jersey and Holstein-Friesian cows with good, poor, or noncoagulation properties as reflected in protein genetic variants and isoforms. J Dairy Sci. 2012 Dec;95(12):6905-17. doi: 10.3168/jds.2012-5675. Epub 2012 Oct 3. [PubMed:23040012 ]
  7. Sundekilde UK, Poulsen NA, Larsen LB, Bertram HC: Nuclear magnetic resonance metabonomics reveals strong association between milk metabolites and somatic cell count in bovine milk. J Dairy Sci. 2013 Jan;96(1):290-9. doi: 10.3168/jds.2012-5819. Epub 2012 Nov 22. [PubMed:23182357 ]
  8. Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30. [PubMed:25087032 ]
  9. Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15. [PubMed:23497994 ]
  10. Maher AD, Hayes B, Cocks B, Marett L, Wales WJ, Rochfort SJ: Latent biochemical relationships in the blood-milk metabolic axis of dairy cows revealed by statistical integration of 1H NMR spectroscopic data. J Proteome Res. 2013 Mar 1;12(3):1428-35. doi: 10.1021/pr301056q. Epub 2013 Feb 21. [PubMed:23394630 ]
  11. O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. [PubMed:29642378 ]
  12. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
  13. A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.

Enzymes

General function:
Energy production and conversion
Specific function:
Catalyzes the cleavage of citrate into oxaloacetate and acetyl-CoA, the latter serving as common substrate for de novo cholesterol and fatty acid synthesis.
Gene Name:
ACLY
Uniprot ID:
Q32PF2
Molecular weight:
119789.0
Reactions
Coenzyme A + Citric acid + Adenosine triphosphate → Oxalacetic acid + ADP + Acetyl-CoAdetails
General function:
Energy production and conversion
Specific function:
Not Available
Gene Name:
CS
Uniprot ID:
Q29RK1
Molecular weight:
51773.0
Reactions
Acetyl-CoA + Water + Oxalacetic acid → Citric acid + Coenzyme Adetails
General function:
Carbohydrate transport and metabolism
Specific function:
Catalyzes the phosphorylation of D-fructose 6-phosphate to fructose 1,6-bisphosphate by ATP, the first committing step of glycolysis (By similarity). Negatively regulates the phagocyte oxidative burst in response to bacterial infection by controlling cellular NADPH biosynthesis and NADPH oxidase-derived reactive oxygen species. Upon macrophage activation, drives the metabolic switch toward glycolysis, thus preventing glucose turnover that produces NADPH via pentose phosphate pathway (By similarity).
Gene Name:
PFKL
Uniprot ID:
A1A4J1
Molecular weight:
85292.0
General function:
Energy production and conversion
Specific function:
Iron sensor. Binds a 4Fe-4S cluster and functions as aconitase when cellular iron levels are high. Functions as mRNA binding protein that regulates uptake, sequestration and utilization of iron when cellular iron levels are low. Binds to iron-responsive elements (IRES) in target mRNA species when iron levels are low. Binding of a 4Fe-4S cluster precludes RNA binding.
Gene Name:
ACO1
Uniprot ID:
Q0VCU1
Molecular weight:
98204.0
Reactions
Citric acid → Isocitric aciddetails
General function:
Energy production and conversion
Specific function:
Catalyzes the isomerization of citrate to isocitrate via cis-aconitate.
Gene Name:
ACO2
Uniprot ID:
P20004
Molecular weight:
85359.0
Reactions
Citric acid → cis-Aconitic acid + Waterdetails
Citric acid → Isocitric aciddetails
General function:
Involved in binding
Specific function:
Citrate transporter that mediates the exchange of mitochondrial citrate for cytosolic malate. Also able to mediate the exchange of citrate for isocitrate, phosphoenolpyruvate, cis- but not trans-aconitate and to a lesser extend maleate and succinate. Important for the bioenergetics of hepatic cells as it provides a carbon source for fatty acid and sterol biosyntheses, and NAD(+) for the glycolytic pathway. Required for proper neuromuscular junction formation.
Gene Name:
SLC25A1
Uniprot ID:
P79110
Molecular weight:
33876.0