| Record Information |
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| Version | 1.0 |
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| Created at | 2020-03-18 23:22:03 UTC |
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| Updated at | 2022-12-13 23:36:28 UTC |
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| CannabisDB ID | CDB006159 |
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| Secondary Accession Numbers | Not Available |
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| Cannabis Compound Identification |
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| Common Name | Citric acid |
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| Description | Citric acid (citrate) is a weak tricarboxylic acid that is formed in the tricarboxylic acid cycle. In humans citric acid is produced endogenously or it may be introduced with diet, with citrus fruits being a key source. Citrate is produced by all aerobic organisms, from microbes to humans. Citrate is formed in the TCA cycle via the enzyme known as citrate synthase, which catalyzes the condensation of oxaloacetate with acetyl CoA to form citrate. Citrate then acts as the substrate for aconitase and is converted into aconitic acid. Some bacteria (notably E. coli) can produce and consume citrate internally as part of their TCA cycle, but are unable to use it as food because they lack the enzymes required to import it into the cell. Citrate has a number of biological roles in humans. In particular, it can be transported out of the mitochondria and into the cytoplasm, then broken down into acetyl-CoA for fatty acid synthesis. Citrate can also acts as a signalling molecule. High concentrations of cytosolic citrate can inhibit phosphofructokinase, the catalyst of a rate-limiting step of glycolysis. Inhibition of glycolysis has been shown to suppress tumor growth in a number of animal models ( PMID: 28674429 ). Citrate is also a vital component of bone, helping to regulate the size of apatite crystals. Urinary citrate levels can be used to identify a number of disorders. Indeed urinary citrate excretion is a common tool in the differential diagnosis of kidney stones, renal tubular acidosis and it plays also a role in characterizing bone diseases such as osteoporosis (PMID 12957820 ). The secretory epithelial cells of the prostate gland of humans and other animals possess a unique citrate-related metabolic pathway regulated by testosterone and prolactin. This specialized hormone-regulated metabolic activity is responsible for the major prostate function of the production and secretion of extraordinarily high levels of citrate. The key regulatory enzymes directly associated with citrate production in the prostate cells are mitochondrial aspartate aminotransferase, pyruvate dehydrogenase, and mitochondrial aconitase. Testosterone and prolactin are involved in the regulation of the corresponding genes associated with these enzymes (PMID 12198595 ). In addition to its biological roles and endogenous production, citrate is obtained from many other sources and used in many applications. Citric acid is found in citrus fruits, most concentrated in lemons and limes, where it can comprise as much as 8% of the dry weight of the fruit. The concentrations of citric acid in citrus fruits range from 5 mM for oranges and grapefruits to 300 mM in lemons and limes. However, these values vary within species depending upon the cultivar and the circumstances in which the fruit was grown. Citric acid is a natural preservative and is also used to add an acidic (sour) taste to foods and soft drinks. Citric acid is used as an excipient in pharmaceutical preparations due to its antioxidant properties. It can be used to treat water, which makes it useful in improving the effectiveness of soaps and laundry detergents. Citric acid is also used as an acidulant in creams, gels, and liquids. The salts of citric acid (citrates) can be used as anticoagulants due to their calcium chelating ability. Intolerance to citric acid in the diet is known to exist. Altered levels of citric acid have been found to be associated with maple syrup urine disease, primary hypomagnesemia, propionic acidemia, and tyrosinemia I, which are inborn errors of metabolism. |
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| Structure | |
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| Synonyms | Not Available |
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| Chemical Formula | C6H8O7 |
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| Average Molecular Weight | 192.12 |
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| Monoisotopic Molecular Weight | 192.027 |
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| IUPAC Name | (1R,2S,5S)-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol |
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| Traditional Name | (1R,2S,5S)-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol |
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| CAS Registry Number | 77-92-9 |
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| SMILES | OC(=O)CC(O)(CC(O)=O)C(O)=O |
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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 bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. |
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| Kingdom | Organic compounds |
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| Super Class | Lipids and lipid-like molecules |
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| Class | Prenol lipids |
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| Sub Class | Monoterpenoids |
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| Direct Parent | Bicyclic monoterpenoids |
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| Alternative Parents | |
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| Substituents | - Pinane monoterpenoid
- Bicyclic monoterpenoid
- Tertiary alcohol
- Cyclic alcohol
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Alcohol
- Aliphatic homopolycyclic compound
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| Molecular Framework | Aliphatic homopolycyclic compounds |
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| External Descriptors | Not Available |
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| Ontology |
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| Physiological effect | Health effect: |
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| Disposition | Route of exposure: Source: Biological location: |
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| Role | Industrial application: |
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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 | 310 °C | Wikipedia | | Water Solubility | 592 mg/mL | Not Available | | logP | -1.64 | AVDEEF,A (1997) |
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| Predicted Properties | [] |
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| Spectra |
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| EI-MS/GC-MS | | Type | Description | Splash Key | View |
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| Predicted GC-MS | cis-2-pinanol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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| MS/MS | | Type | Description | Splash Key | View |
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| Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | Not Available | Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | Not Available | Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | Not Available | Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | Not Available | Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | Not Available | Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | Not Available | Spectrum |
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| NMR | Not Available |
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| Pathways |
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| Pathways | | Name | SMPDB/Pathwhiz | KEGG | | Citric Acid Cycle |    |  | | Transfer of Acetyl Groups into Mitochondria |    | Not Available | | Congenital lactic acidosis |    | Not Available | | Fumarase deficiency |    | Not Available | | Mitochondrial complex II deficiency |    | Not Available |
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| Protein Targets |
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| Enzymes | |
| Pyruvate dehydrogenase E1 component subunit beta, mitochondrial | PDHB | 3p21.1-p14.2 | P11177 | details | | Pyruvate dehydrogenase E1 component subunit alpha, somatic form, mitochondrial | PDHA1 | Xp22.1 | P08559 | details | | Aspartate aminotransferase, mitochondrial | GOT2 | 16q21 | P00505 | details | | Aconitate hydratase, mitochondrial | ACO2 | 22q13.2 | Q99798 | details | | Cytoplasmic aconitate hydratase | ACO1 | 9p21.1 | P21399 | details | | 6-phosphofructokinase, liver type | PFKL | 21q22.3 | P17858 | details | | Polycystic kidney disease 2-like 1 protein | PKD2L1 | 10q24 | Q9P0L9 | details |
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| Transporters | Not Available |
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| Metal Bindings | |
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| Receptors | Not Available |
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| Transcriptional Factors | Not Available |
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| Concentrations Data |
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| Alien Dawg | Detected and Quantified | 6.7628 mg/g dry wt | | details | | Gabriola | Detected and Quantified | 4.415 mg/g dry wt | | details | | Island Honey | Detected and Quantified | 6.282 mg/g dry wt | | details | | Quadra | Detected and Quantified | 1.983 mg/g dry wt | | details | | Sensi Star | Detected and Quantified | 11.393 mg/g dry wt | | details | | Tangerine Dream | Detected and Quantified | 4.0481 mg/g dry wt | | details |
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| External Links |
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| HMDB ID | Not Available |
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| DrugBank ID | Not Available |
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| Phenol Explorer Compound ID | Not Available |
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| FoodDB ID | Not Available |
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| KNApSAcK ID | Not Available |
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| Chemspider ID | Not Available |
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| KEGG Compound ID | Not Available |
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| BioCyc ID | Not Available |
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| BiGG ID | Not Available |
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| Wikipedia Link | Not Available |
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| METLIN ID | Not Available |
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| PubChem Compound | 6428289 |
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| PDB ID | Not Available |
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| ChEBI ID | Not Available |
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| References |
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| General References | - Ren JG, Seth P, Ye H, Guo K, Hanai JI, Husain Z, Sukhatme VP: Citrate Suppresses Tumor Growth in Multiple Models through Inhibition of Glycolysis, the Tricarboxylic Acid Cycle and the IGF-1R Pathway. Sci Rep. 2017 Jul 3;7(1):4537. doi: 10.1038/s41598-017-04626-4. [PubMed:28674429 ]
- Caudarella R, Vescini F, Buffa A, Stefoni S: Citrate and mineral metabolism: kidney stones and bone disease. Front Biosci. 2003 Sep 1;8:s1084-106. doi: 10.2741/1119. [PubMed:12957820 ]
- Costello LC, Franklin RB: Testosterone and prolactin regulation of metabolic genes and citrate metabolism of prostate epithelial cells. Horm Metab Res. 2002 Aug;34(8):417-24. doi: 10.1055/s-2002-33598. [PubMed:12198595 ]
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