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Record Information |
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Version | 1.0 |
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Creation Date | 2016-09-30 22:19:33 UTC |
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Update Date | 2020-06-04 21:51:30 UTC |
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BMDB ID | BMDB0000094 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Citric acid |
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Description | Citric 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. |
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Structure | |
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Synonyms | Value | Source |
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2-Hydroxy-1,2,3-propanetricarboxylic acid | ChEBI | 2-Hydroxytricarballylic acid | ChEBI | 3-Carboxy-3-hydroxypentane-1,5-dioic acid | ChEBI | Citronensaeure | ChEBI | e330 | ChEBI | H3Cit | ChEBI | Anhydrous citric acid | Kegg | Citric acid anhydrous | Kegg | 2-Hydroxy-1,2,3-propanetricarboxylate | Generator | 2-Hydroxytricarballylate | Generator | 3-Carboxy-3-hydroxypentane-1,5-dioate | Generator | Anhydrous citrate | Generator | Citrate anhydrous | Generator | Citrate | Generator | Aciletten | HMDB | beta-Hydroxytricarballylate | HMDB | beta-Hydroxytricarballylic acid | HMDB | Chemfill | HMDB | Citraclean | HMDB | Citretten | HMDB | Citro | HMDB | e 330 | HMDB | Hydrocerol a | HMDB | Kyselina citronova | HMDB | Suby g | HMDB | Uro-trainer | HMDB | Acid monohydrate, citric | HMDB | Monohydrate, citric acid | HMDB | Citric acid, anhydrous | HMDB | Citric acid monohydrate | HMDB | Uralyt u | HMDB |
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Chemical Formula | C6H8O7 |
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Average Molecular Weight | 192.1235 |
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Monoisotopic Molecular Weight | 192.02700261 |
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IUPAC Name | Not Available |
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Traditional Name | Not Available |
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CAS Registry Number | 77-92-9 |
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SMILES | Not Available |
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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) |
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InChI Key | KRKNYBCHXYNGOX-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Tricarboxylic acids and derivatives |
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Direct Parent | Tricarboxylic acids and derivatives |
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Alternative Parents | |
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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
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Ontology |
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Status | Detected and Quantified |
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Origin | |
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Biofunction | Not Available |
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Application | Not Available |
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Cellular locations | |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | 153 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 592.0 mg/mL | Not Available | LogP | -1.64 | AVDEEF,A (1997) |
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Predicted Properties | Not Available |
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Spectra |
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Spectra | |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | - All Tissues
- Blood
- Liver
- Mammary Gland
- Milk
- Placenta
- Prostate Tissue
- Semen
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Pathways | |
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Normal Concentrations |
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All Tissues | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Mammary Gland | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Mammary Gland | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 3026 - 9854 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 3692 - 7435 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 8432.0762 +/- 260.249 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 9004.625 +/- 468.449 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 8180 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 9108.724 +/- 260.249 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 9316.924 +/- 156.150 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 9681.273 +/- 156.150 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 3719 - 5776 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 5099 +/- 409 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 5219 +/- 168 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 4793 +/- 260 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 5808 +/- 643 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 8380 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 9110 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 4602.04 +/- 617.46 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 6620 - 12900 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 4453.36 +/- 225.49 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 4595.41 +/- 448.18 uM | Not Specified | Not Specified | Normal | | details | Placenta | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Prostate Tissue | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Semen | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details |
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Abnormal Concentrations |
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Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Sub/clinical ketosis | | details | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | All Mycobacterium avium subsp. paratuberculosis-infected | | details | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | High dose Mycobacterium avium subsp. paratuberculosis-infected | | details | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Low dose Mycobacterium avium subsp. paratuberculosis-infected | | details | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Mycobacterium avium subsp. paratuberculosis infection | | details |
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External Links |
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HMDB ID | HMDB0000094 |
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DrugBank ID | DB04272 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB030735 |
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KNApSAcK ID | C00007619 |
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Chemspider ID | 305 |
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KEGG Compound ID | C00158 |
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BioCyc ID | CIT |
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BiGG ID | 34080 |
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Wikipedia Link | Citric_Acid |
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METLIN ID | 124 |
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PubChem Compound | 311 |
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PDB ID | Not Available |
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ChEBI ID | 30769 |
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References |
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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. |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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.
- 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.
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