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| Record Information |
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| Version | 4.0 |
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| Status | Detected and Quantified |
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| Creation Date | 2005-11-16 15:48:42 UTC |
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| Update Date | 2020-11-09 23:11:56 UTC |
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| HMDB ID | HMDB0000072 |
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| Secondary Accession Numbers | - HMDB0000461
- HMDB00072
- HMDB00461
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| Metabolite Identification |
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| Common Name | cis-Aconitic acid |
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| Description | cis-Aconitic acid, also known as cis-aconitate or acid, acontic, belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. cis-Aconitic acid is a moderately acidic compound (based on its pKa). cis-Aconitic acid exists in all living species, ranging from bacteria to humans. Within humans, cis-aconitic acid participates in a number of enzymatic reactions. In particular, cis-aconitic acid can be biosynthesized from citric acid through the action of the enzyme aconitate hydratase, mitochondrial. In addition, cis-aconitic acid can be converted into isocitric acid; which is mediated by the enzyme aconitate hydratase, mitochondrial. In humans, cis-aconitic acid is involved in the metabolic disorder called the glutaminolysis and cancer pathway. cis-Aconitic acid is a bland tasting compound. Outside of the human body, cis-aconitic acid has been detected, but not quantified in, several different foods, such as jackfruits, root vegetables, breakfast cereals, oval-leaf huckleberries, and bog bilberries. This could make cis-aconitic acid a potential biomarker for the consumption of these foods. |
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| Structure | |
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| Synonyms | | Value | Source |
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| (Z)-1-Propene-1,2,3-tricarboxylic acid | ChEBI | | cis-1-Propene-1,2,3-tricarboxylic acid | ChEBI | | (Z)-1-Propene-1,2,3-tricarboxylate | Generator | | cis-1-Propene-1,2,3-tricarboxylate | Generator | | cis-Aconitate | Generator | | (1Z)-1-Propene-1,2,3-tricarboxylate | HMDB | | (1Z)-1-Propene-1,2,3-tricarboxylic acid | HMDB | | (Z)-Aconitate | HMDB | | (Z)-Aconitic acid | HMDB | | 1-cis-2,3-Propenetricarboxylate | HMDB | | 1-cis-2,3-Propenetricarboxylic acid | HMDB | | 1-Propene-1,2,3-tricarboxylate | HMDB | | 1-Propene-1,2,3-tricarboxylic acid | HMDB | | cis-Aconate | HMDB | | cis-Aconic acid | HMDB | | cis-Oxaloacetate | HMDB | | cis-Oxaloacetic acid | HMDB | | Acid, citridic | HMDB | | Acid, citridinic | HMDB | | Aconitic acid | HMDB | | Acontic acid | HMDB | | Adonic acid | HMDB | | Achilleic acid | HMDB | | Acid, acontic | HMDB | | Acid, equisetic | HMDB | | Citridinic acid | HMDB | | Acid, achilleic | HMDB | | Aconitate | HMDB | | Citridic acid | HMDB | | Pyrocitric acid | HMDB | | Acid, aconitic | HMDB | | Acid, adonic | HMDB | | Acid, carboxyglutaconic | HMDB | | Acid, pyrocitric | HMDB | | Carboxyglutaconic acid | HMDB | | Equisetic acid | HMDB |
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| Chemical Formula | C6H6O6 |
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| Average Molecular Weight | 174.1082 |
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| Monoisotopic Molecular Weight | 174.016437924 |
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| IUPAC Name | (1Z)-prop-1-ene-1,2,3-tricarboxylic acid |
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| Traditional Name | cis-aconitic acid |
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| CAS Registry Number | 585-84-2 |
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| SMILES | OC(=O)C\C(=C\C(O)=O)C(O)=O |
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| InChI Identifier | InChI=1S/C6H6O6/c7-4(8)1-3(6(11)12)2-5(9)10/h1H,2H2,(H,7,8)(H,9,10)(H,11,12)/b3-1- |
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| InChI Key | GTZCVFVGUGFEME-IWQZZHSRSA-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
- Carboxylic acid
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- 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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| Process | Naturally occurring process: |
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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 | 125 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | 400 mg/mL | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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| Spectra |
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| | Spectrum Type | Description | Splash Key | View |
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| GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS) | splash10-0002-1940000000-24c70788b42e3006de46 | Spectrum | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-0002-0940000000-3ab0a8161f2ec8f04452 | Spectrum | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS) | splash10-00dj-9630000000-1dc322333cb48ef39588 | Spectrum | | GC-MS | GC-MS Spectrum - GC-MS (3 TMS) | splash10-004i-3591000000-a58ec1ba633b098e0867 | Spectrum | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0002-1940000000-24c70788b42e3006de46 | Spectrum | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0002-0940000000-3ab0a8161f2ec8f04452 | Spectrum | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-00dj-9630000000-1dc322333cb48ef39588 | Spectrum | | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-004i-3591000000-a58ec1ba633b098e0867 | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-06w9-4900000000-38239492ad0e66d6533b | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive | splash10-00di-9167000000-07ccdac5775cc3e75c95 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-000i-9300000000-1f04239a9a7133f89d08 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-000f-9000000000-49f5c2a7959cfbbbe09f | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-000f-9100000000-d4857c30b96cf4786dbe | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-00di-0911000000-3197b86ab2053b968bf9 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-001i-9000000000-74977ead259f739d154b | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-004i-0900000000-9f4cc240b2470f2bbb93 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-001i-0900000000-5034c256b831c6173452 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-00di-0912000000-a603cd799b70c1089ddd | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-001i-9000000000-ce8dbec6a7b0d83b372c | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-004i-0900000000-927f79de2cf5ffcb2c52 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-003r-0194000000-75d834c69fbfd0a2f7be | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-00fr-0900000000-aad30bb884e0e9a5f01c | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-000i-9200000000-e90e540bcd0659005472 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-000i-9000000000-0edcc061c37b1fbb9fa1 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-000l-9000000000-1e762d38e4e5cabfcb6b | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-000f-9000000000-5602736cc28db9eb9085 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-000i-9400000000-c8ec5b3e604b870eab95 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-00fr-0900000000-aad30bb884e0e9a5f01c | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-000i-9200000000-e90e540bcd0659005472 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004i-0900000000-8e26562af9ae45eb3303 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-02di-1900000000-7fec32a5e34c3b55d683 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-01w0-9600000000-ee172c3013370ab0da31 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00fr-1900000000-18635ce5a20ce1b78139 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00b9-2900000000-58bb75a2a1b28dbffd73 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-06rf-9300000000-19df730d01f07fcf6573 | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | Spectrum |
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| Biological Properties |
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| Cellular Locations | |
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| Biospecimen Locations | - Blood
- Breast Milk
- Cerebrospinal Fluid (CSF)
- Saliva
- Sweat
- Urine
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| Tissue Locations | |
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| Pathways | |
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| Normal Concentrations |
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| Blood | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | | Breast Milk | Detected and Quantified | 10.1 +/- 3.1 uM | Adult (>18 years old) | Female | Normal | | details | | Cerebrospinal Fluid (CSF) | Detected and Quantified | 2 uM | Children (1-13 years old) | Both | Normal | | details | | Cerebrospinal Fluid (CSF) | Detected and Quantified | 20.0 (13.0-27.0) uM | Adult (>18 years old) | Both | Normal | | details | | Saliva | Detected and Quantified | 3.17 +/- 1.17 uM | Adult (>18 years old) | Female | Normal | | details | | Saliva | Detected and Quantified | 0.172 +/- 0.179 uM | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected and Quantified | 0.176 +/- 0.107 uM | Adult (>18 years old) | Female | Normal | | details | | Saliva | Detected and Quantified | 0.358 +/- 0.198 uM | Adult (>18 years old) | Female | Normal | | details | | Saliva | Detected and Quantified | 0.363 +/- 0.169 uM | Adult (>18 years old) | Female | Normal | | details | | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | | Sweat | Detected and Quantified | < 10 uM | Adult (60 years old) | Male | Normal | | details | | Sweat | Detected and Quantified | < 10 uM | Adult (40 years old) | Male | Normal | | details | | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | | Urine | Detected and Quantified | 67.9 (14.3-100.7) umol/mmol creatinine | Newborn (0-30 days old) | Both | Normal | | details | | Urine | Detected and Quantified | 73.8 (64.0-130.3) umol/mmol creatinine | Infant (0-1 year old) | Both | Normal | | details | | Urine | Detected and Quantified | 37.9 (17.3-63.3) umol/mmol creatinine | Children (1-13 years old) | Both | Normal | | details | | Urine | Detected and Quantified | 29.8 (14.7-93.1) umol/mmol creatinine | Adolescent (13-18 years old) | Both | Normal | | details | | Urine | Detected and Quantified | 2.0-23.6 umol/mmol creatinine | Infant (0-1 year old) | Female | Normal | | details | | Urine | Detected and Quantified | 7-30.6 umol/mmol creatinine | Infant (0-1 year old) | Male | Normal | | details | | Urine | Detected and Quantified | 8-26.0 umol/mmol creatinine | Infant (0-1 year old) | Male | Normal | | details | | Urine | Detected and Quantified | 8-40.7 umol/mmol creatinine | Infant (0-1 year old) | Female | Normal | | details | | Urine | Detected and Quantified | 54.5 (32.4-76.6) umol/mmol creatinine | Children (1-13 years old) | Both | Normal | | details | | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | | Urine | Detected and Quantified | 48-103 umol/mmol creatinine | Adult (>18 years old) | Female | Normal | | details | | Urine | Detected and Quantified | 20.9 (3.8-95.3) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | | Urine | Detected and Quantified | 13 (2.7-44) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | | Urine | Detected and Quantified | 9.740-38.962 umol/mmol creatinine | Infant (0-1 year old) | Both | Normal | | details | | Urine | Detected and Quantified | 35.95 umol/mmol creatinine | Adult (>18 years old) | Male | Normal | | details | | Urine | Detected and Quantified | <102.12 umol/mmol creatinine | Children (1 - 18 years old) | Both | Normal | | details | | Urine | Detected and Quantified | 58-85 umol/mmol creatinine | Adult (>18 years old) | Male | Normal | | details | | Urine | Detected and Quantified | 33.685 +/- 14.03 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Normal | | details | | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | | Urine | Detected and Quantified | 10.3(5.2-16.3) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details |
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| Abnormal Concentrations |
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| Saliva | Detected and Quantified | 2.80 +/- 2.11 uM | Adult (>18 years old) | Male | Alzheimer's disease | | details | | Saliva | Detected and Quantified | 2.17 +/- 0.53 uM | Adult (>18 years old) | Male | Frontotemporal lobe dementia | | details | | Saliva | Detected and Quantified | 2.72 +/- 0.53 uM | Adult (>18 years old) | Both | Lewy body disease | | details | | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Bladder cancer | | details | | Urine | Detected and Quantified | 6.494-293.514 umol/mmol creatinine | Infant (0-1 year old) | Both | Amish lethal microcephaly | | details | | Urine | Detected and Quantified | 38.74 +/- 40.952 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Eosinophilic esophagitis | | details | | Urine | Detected and Quantified | 32.0 (0.0-70.0) umol/mmol creatinine | Adult (>18 years old) | Both | Lung cancer | | details | | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Schizophrenia | | details |
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| Associated Disorders and Diseases |
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| Disease References | | Alzheimer's disease |
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- Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
| | Frontotemporal dementia |
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- Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
| | Lewy body disease |
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- Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
| | Lung Cancer |
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- Wishart DS, Knox C, Guo AC, Eisner R, Young N, Gautam B, Hau DD, Psychogios N, Dong E, Bouatra S, Mandal R, Sinelnikov I, Xia J, Jia L, Cruz JA, Lim E, Sobsey CA, Shrivastava S, Huang P, Liu P, Fang L, Peng J, Fradette R, Cheng D, Tzur D, Clements M, Lewis A, De Souza A, Zuniga A, Dawe M, Xiong Y, Clive D, Greiner R, Nazyrova A, Shaykhutdinov R, Li L, Vogel HJ, Forsythe I: HMDB: a knowledgebase for the human metabolome. Nucleic Acids Res. 2009 Jan;37(Database issue):D603-10. doi: 10.1093/nar/gkn810. Epub 2008 Oct 25. [PubMed:18953024 ]
| | Eosinophilic esophagitis |
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- (). Mordechai, Hien, and David S. Wishart. .
| | Schizophrenia |
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- Yang J, Chen T, Sun L, Zhao Z, Qi X, Zhou K, Cao Y, Wang X, Qiu Y, Su M, Zhao A, Wang P, Yang P, Wu J, Feng G, He L, Jia W, Wan C: Potential metabolite markers of schizophrenia. Mol Psychiatry. 2013 Jan;18(1):67-78. doi: 10.1038/mp.2011.131. Epub 2011 Oct 25. [PubMed:22024767 ]
| | Amish lethal microcephaly |
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- Kelley RI, Robinson D, Puffenberger EG, Strauss KA, Morton DH: Amish lethal microcephaly: a new metabolic disorder with severe congenital microcephaly and 2-ketoglutaric aciduria. Am J Med Genet. 2002 Nov 1;112(4):318-26. doi: 10.1002/ajmg.10529. [PubMed:12376931 ]
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| Associated OMIM IDs | |
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| External Links |
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| DrugBank ID | Not Available |
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| Phenol Explorer Compound ID | Not Available |
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| FooDB ID | FDB008306 |
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| KNApSAcK ID | C00001177 |
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| Chemspider ID | 558863 |
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| KEGG Compound ID | C00417 |
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| BioCyc ID | CIS-ACONITATE |
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| BiGG ID | Not Available |
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| Wikipedia Link | Citric acid cycle |
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| METLIN ID | 5130 |
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| PubChem Compound | 643757 |
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| PDB ID | Not Available |
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| ChEBI ID | 32805 |
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| Food Biomarker Ontology | Not Available |
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| VMH ID | Not Available |
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| MarkerDB ID | MDB00000038 |
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| References |
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| Synthesis Reference | Gutierrez, Eddie N.; Lamberti, Vincent. cis and trans Aconitic acids and their salts. U.S. (1978), 16 pp. |
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| Material Safety Data Sheet (MSDS) | Download (PDF) |
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| General References | - Swart PJ, Kuipers EM, Smit C, Van Der Strate BW, Harmsen MC, Meijer DK: Lactoferrin. Antiviral activity of lactoferrin. Adv Exp Med Biol. 1998;443:205-13. [PubMed:9781360 ]
- Stromme JH, Borud O, Moe PJ: Fatal lactic acidosis in a newborn attributable to a congenital defect of pyruvate dehydrogenase. Pediatr Res. 1976 Jan;10(1):62-6. [PubMed:813176 ]
- Boulat O, Gradwohl M, Matos V, Guignard JP, Bachmann C: Organic acids in the second morning urine in a healthy Swiss paediatric population. Clin Chem Lab Med. 2003 Dec;41(12):1642-58. [PubMed:14708889 ]
- Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [PubMed:8087979 ]
- Redjems-Bennani N, Jeandel C, Lefebvre E, Blain H, Vidailhet M, Gueant JL: Abnormal substrate levels that depend upon mitochondrial function in cerebrospinal fluid from Alzheimer patients. Gerontology. 1998;44(5):300-4. [PubMed:9693263 ]
- Swart PJ, Kuipers ME, Smit C, Pauwels R, deBethune MP, de Clercq E, Meijer DK, Huisman JG: Antiviral effects of milk proteins: acylation results in polyanionic compounds with potent activity against human immunodeficiency virus types 1 and 2 in vitro. AIDS Res Hum Retroviruses. 1996 Jun 10;12(9):769-75. [PubMed:8738428 ]
- Matsuishi T, Urabe F, Percy AK, Komori H, Yamashita Y, Schultz RS, Ohtani Y, Kuriya N, Kato H: Abnormal carbohydrate metabolism in cerebrospinal fluid in Rett syndrome. J Child Neurol. 1994 Jan;9(1):26-30. [PubMed:8151077 ]
- Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
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