Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:05:44 UTC |
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Update date | 2019-11-26 02:58:48 UTC |
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Primary ID | FDB003281 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Isocitric acid |
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Description | Isocitric acid, also known as isocitrate or i-cit, belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. Isocitric acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Isocitric acid exists in all living species, ranging from bacteria to humans. Isocitric acid is found, on average, in the highest concentration within milk (cow). Isocitric acid has also been detected, but not quantified in, several different foods, such as apples, wild celeries, gooseberries, carrots, and soursops. This could make isocitric acid a potential biomarker for the consumption of these foods. |
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CAS Number | 320-77-4 |
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Structure | |
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Synonyms | Synonym | Source |
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1-Hydroxypropane-1,2,3-tricarboxylic acid | ChEBI | 1-Hydroxytricarballylic acid | ChEBI | 1-Hydroxypropane-1,2,3-tricarboxylate | Generator | 1-Hydroxytricarballylate | Generator | Isocitrate | Generator | 1-Hydroxy-1,2,3-propanetricarboxylate | HMDB | 1-Hydroxy-1,2,3-propanetricarboxylic acid | HMDB | 3-Carboxy-2,3-dideoxy-1-hydroxypropan-1,2,3-tricarboxylate | HMDB | 3-Carboxy-2,3-dideoxy-1-hydroxypropan-1,2,3-tricarboxylic acid | HMDB | 3-Carboxy-2,3-dideoxy-pentarate | HMDB | 3-Carboxy-2,3-dideoxy-pentaric acid | HMDB | D-Isocitrate | HMDB | I-cit | HMDB | Threo-D(S)-iso-citrate | HMDB | Threo-DS-isocitrate | HMDB | Isocitric acid, sodium salt | HMDB | Isocitric acid, trisodium salt | HMDB | Isocitric acid, disodium salt | HMDB | Isocitric acid, (11)C-labeled | HMDB | Isocitric acid, calcium salt | HMDB | Isocitric acid, potassium salt | HMDB | 3-Carboxy-3,4-dideoxypentaric acid, 9CI | db_source | threo-D(S)-Iso-citrate | HMDB | threo-Ds-isocitrate | HMDB |
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Predicted Properties | |
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Chemical Formula | C6H8O7 |
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IUPAC name | 1-hydroxypropane-1,2,3-tricarboxylic acid |
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InChI Identifier | InChI=1S/C6H8O7/c7-3(8)1-2(5(10)11)4(9)6(12)13/h2,4,9H,1H2,(H,7,8)(H,10,11)(H,12,13) |
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InChI Key | ODBLHEXUDAPZAU-UHFFFAOYSA-N |
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Isomeric SMILES | OC(C(CC(O)=O)C(O)=O)C(O)=O |
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Average Molecular Weight | 192.1235 |
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Monoisotopic Molecular Weight | 192.02700261 |
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Classification |
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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
- Beta-hydroxy acid
- Monosaccharide
- Hydroxy acid
- Alpha-hydroxy acid
- Secondary 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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Physiological effect | Health effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Physico-Chemical Properties - Experimental |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Solid | |
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Physical Description | Not Available | |
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Mass Composition | C 37.51%; H 4.20%; O 58.29% | DFC |
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Melting Point | Not Available | |
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Boiling Point | Not Available | |
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Experimental Water Solubility | Not Available | |
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Experimental logP | Not Available | |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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GC-MS | Isocitric acid, 4 TMS, GC-MS Spectrum | splash10-0002-1952000000-7c34751686a6bdb54cab | Spectrum | GC-MS | Isocitric acid, 4 TMS, GC-MS Spectrum | splash10-0002-0963000000-459b45ff9246b5f55914 | Spectrum | GC-MS | Isocitric acid, non-derivatized, GC-MS Spectrum | splash10-0002-0942000000-61204d02a28e43d21607 | Spectrum | GC-MS | Isocitric acid, 4 TMS, GC-MS Spectrum | splash10-00di-9420000000-4e1a59fe735855d52ce2 | Spectrum | GC-MS | Isocitric acid, 4 TMS, GC-MS Spectrum | splash10-00ea-3793000000-84858fa896697420275f | Spectrum | GC-MS | Isocitric acid, non-derivatized, GC-MS Spectrum | splash10-0002-1952000000-7c34751686a6bdb54cab | Spectrum | GC-MS | Isocitric acid, non-derivatized, GC-MS Spectrum | splash10-0002-0963000000-459b45ff9246b5f55914 | Spectrum | GC-MS | Isocitric acid, non-derivatized, GC-MS Spectrum | splash10-00di-9420000000-4e1a59fe735855d52ce2 | Spectrum | GC-MS | Isocitric acid, non-derivatized, GC-MS Spectrum | splash10-00ea-3793000000-84858fa896697420275f | Spectrum | Predicted GC-MS | Isocitric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00ba-7900000000-96194d87d52b155cf1b9 | Spectrum | Predicted GC-MS | Isocitric acid, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-02vi-7029500000-2bb65fc897e48cc21750 | Spectrum | Predicted GC-MS | Isocitric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Isocitric acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Isocitric acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Isocitric acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Isocitric acid, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Isocitric acid, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Isocitric acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Isocitric acid, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Isocitric acid, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Isocitric acid, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Isocitric acid, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Isocitric acid, TMS_3_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Isocitric acid, TMS_3_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Isocitric acid, TMS_3_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-0006-0901310000-883764bf7b686ca7fd17 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-03di-0900000000-66d03405eeb126c6ad9d | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-00di-0900000000-cdad17a11f419421c787 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-0udi-0009000000-d3440c84a488b3e22212 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-0006-0900000000-3aa263561a7a49df7d3d | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-0006-1900000000-3636f87026e4206a1638 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-01w3-9600000000-ab1a2b9a29528a623d0b | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-0079-9000000000-3c33cefeb87f85efd5de | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-059m-9000000000-34775db8bbc008018633 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0006-0900000000-3aa263561a7a49df7d3d | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0006-1900000000-3636f87026e4206a1638 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-01w3-9600000000-ab1a2b9a29528a623d0b | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0079-9000000000-3c33cefeb87f85efd5de | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-059m-9000000000-34775db8bbc008018633 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-03di-0900000000-66d03405eeb126c6ad9d | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-00di-0900000000-cdad17a11f419421c787 | Spectrum | MS/MS | LC-MS/MS Spectrum - , negative | splash10-03k9-2900000000-e5336d859bf90bcd904c | Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-03k9-2900000000-8ef1bf8afd67194ddf65 | Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Negative | splash10-059f-9000000000-37227e36af9ba4db4a7e | Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-022i-9500000000-cb0234d7a355d54f1755 | Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-03k9-3900000000-1b8cb16b24c65e87915b | Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-03ki-9500000000-d264dd60719df8b72ef3 | Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Negative | splash10-00di-9000000000-bf62fc70edcee073c517 | Spectrum | MS/MS | LC-MS/MS Spectrum - 30V, Negative | splash10-02mi-9200000000-42ca838ca7f08cc3882e | Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-0udi-1900000000-8e1185b0504ea1547715 | Spectrum |
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NMR | |
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External Links |
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ChemSpider ID | 1161 |
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ChEMBL ID | CHEMBL539669 |
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KEGG Compound ID | C00311 |
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Pubchem Compound ID | 1198 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 30887 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB00193 |
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CRC / DFC (Dictionary of Food Compounds) ID | CVK67-H:CVK67-H |
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EAFUS ID | Not Available |
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Dr. Duke ID | ISOCITRIC-ACID |
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BIGG ID | 34579 |
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KNApSAcK ID | Not Available |
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HET ID | 1B0J |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Isocitric_acid |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Not Available |
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Enzymes | Name | Gene Name | UniProt ID |
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Aconitate hydratase, mitochondrial | ACO2 | Q99798 |
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Pathways | |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | show |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
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