| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-09-30 22:29:38 UTC |
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| Update Date | 2020-05-11 20:36:55 UTC |
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| BMDB ID | BMDB0000379 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | 2-Methylcitric acid |
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| Description | 2-Methylcitric acid, also known as 2-methylcitrate, belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. 2-Methylcitric acid is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 2-Methylcitric acid exists in all living organisms, ranging from bacteria to humans. 2-Methylcitric acid is a potentially toxic compound. 2-Methylcitric acid has been found to be associated with several diseases known as iron deficiency and crohn's disease; also 2-methylcitric acid has been linked to several inborn metabolic disorders including vitamin B12 deficiency, isovaleric acidemia, and propionic acidemia. |
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| Structure | |
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| Synonyms | | Value | Source |
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| 2-Hydroxy-1,2,3-butanetricarboxylic acid | ChEBI | | 2-Hydroxy-1,2,3-butanetricarboxylate | Generator | | 2-Methylcitrate | Generator | | (2S,3S)-2-Methylcitrate | HMDB | | 2-Hydroxybutane-1,2,3-tricarboxylate | HMDB | | 2-Hydroxybutane-1,2,3-tricarboxylic acid | HMDB | | 2-Methylcitric acid, 3H-labeled | HMDB | | 3-Carboxy-3-hydroxy-2-methylpentanedioic acid | HMDB | | Methylcitric acid | HMDB |
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| Chemical Formula | C7H10O7 |
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| Average Molecular Weight | 206.1501 |
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| Monoisotopic Molecular Weight | 206.042652674 |
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| IUPAC Name | 2-hydroxy-1-methylpropane-1,2,3-tricarboxylic acid |
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| Traditional Name | methylcitric acid |
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| CAS Registry Number | 6061-96-7 |
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| SMILES | CC(C(O)=O)C(O)(CC(O)=O)C(O)=O |
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| InChI Identifier | InChI=1S/C7H10O7/c1-3(5(10)11)7(14,6(12)13)2-4(8)9/h3,14H,2H2,1H3,(H,8,9)(H,10,11)(H,12,13) |
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| InChI Key | YNOXCRMFGMSKIJ-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 but not 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 | Not Available |
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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 | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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| Spectra |
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| Spectra | |
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| General References | - Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]
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