Record Information |
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Version | 1.0 |
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Created at | 2020-04-17 18:43:08 UTC |
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Updated at | 2020-12-07 19:11:06 UTC |
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CannabisDB ID | CDB004849 |
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Secondary Accession Numbers | Not Available |
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Cannabis Compound Identification |
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Common Name | D-2-Hydroxyglutaric acid |
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Description | D-2-Hydroxyglutaric acid, also known as (R)-hydroxyglutarate or (R)-2-hydroxy-pentanedioate, belongs to the class of organic compounds known as short-chain hydroxy acids and derivatives. These are hydroxy acids with an alkyl chain the contains less than 6 carbon atoms. D-2-Hydroxyglutaric acid is an extremely weak basic (essentially neutral) compound (based on its pKa). D-2-Hydroxyglutaric acid exists in all living organisms, ranging from bacteria to humans. D-2-hydroxyglutaric acid can be biosynthesized from oxoglutaric acid through the action of the enzyme D-2-hydroxyglutarate dehydrogenase, mitochondrial. In humans, D-2-hydroxyglutaric acid is involved in the metabolic disorder called the oncogenic action of d-2-hydroxyglutarate in hydroxyglutaric aciduria. Outside of the human body, D-2-Hydroxyglutaric acid has been detected, but not quantified in, milk (cow). This could make D-2-hydroxyglutaric acid a potential biomarker for the consumption of these foods. D-2-Hydroxyglutaric acid is a potentially toxic compound. D-2-Hydroxyglutaric acid, with regard to humans, has been found to be associated with several diseases such as d, l-2-hydroxyglutaric aciduria and spondyloenchondrodysplasia; D-2-hydroxyglutaric acid has also been linked to the inborn metabolic disorder d-2-hydroxyglutaric aciduria. The (R)-enantiomer of 2-hydroxyglutaric acid. D-2-Hydroxyglutaric acid is expected to be in Cannabis as all living plants are known to produce and metabolize it. |
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Structure | |
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Synonyms | Value | Source |
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(R)-2-Hydroxyglutarate | ChEBI | (R)-Hydroxyglutarate | ChEBI | (R)-2-Hydroxyglutaric acid | Generator | (R)-Hydroxyglutaric acid | Generator | D-2-Hydroxyglutarate | Generator | (R)-2-Hydroxy-pentanedioate | HMDB | (R)-2-Hydroxy-pentanedioic acid | HMDB | (R)-a-Hydroxyglutarate | HMDB | (R)-a-Hydroxyglutaric acid | HMDB | (R)-alpha-Hydroxyglutarate | HMDB | (R)-alpha-Hydroxyglutaric acid | HMDB | 2-Hydroxy-D-glutarate | HMDB | 2-Hydroxy-D-glutaric acid | HMDB | 2-Hydroxy-delta-glutarate | HMDB | 2-Hydroxy-delta-glutaric acid | HMDB | D-a-Hydroxyglutarate | HMDB | D-a-Hydroxyglutaric acid | HMDB | delta-2-Hydroxyglutarate | HMDB | delta-2-Hydroxyglutaric acid | HMDB | delta-alpha-Hydroxyglutarate | HMDB | delta-alpha-Hydroxyglutaric acid | HMDB | 2-Hydroxyglutarate | HMDB | alpha-Hydroxyglutarate, (D)-isomer | HMDB | alpha-Hydroxyglutarate, (DL)-isomer | HMDB | 2-Hydroxyglutaric acid | HMDB | alpha-Hydroxyglutarate | HMDB | alpha-Hydroxyglutarate, (L)-isomer | HMDB | alpha-Hydroxyglutarate, disodium salt | HMDB |
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Chemical Formula | C5H8O5 |
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Average Molecular Weight | 148.11 |
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Monoisotopic Molecular Weight | 148.0372 |
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IUPAC Name | (2R)-2-hydroxypentanedioic acid |
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Traditional Name | D-2-hydroxyglutaric acid |
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CAS Registry Number | 13095-47-1 |
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SMILES | O[C@H](CCC(O)=O)C(O)=O |
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InChI Identifier | InChI=1S/C5H8O5/c6-3(5(9)10)1-2-4(7)8/h3,6H,1-2H2,(H,7,8)(H,9,10)/t3-/m1/s1 |
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InChI Key | HWXBTNAVRSUOJR-GSVOUGTGSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as short-chain hydroxy acids and derivatives. These are hydroxy acids with an alkyl chain the contains less than 6 carbon atoms. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Hydroxy acids and derivatives |
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Sub Class | Short-chain hydroxy acids and derivatives |
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Direct Parent | Short-chain hydroxy acids and derivatives |
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Alternative Parents | |
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Substituents | - Short-chain hydroxy acid
- Fatty acid
- Monosaccharide
- Dicarboxylic acid or derivatives
- Alpha-hydroxy acid
- Secondary alcohol
- Carboxylic acid
- Carboxylic acid derivative
- 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 | Source: Biological location: |
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Role | Indirect biological role: Biological role: |
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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 | > 300 °C | 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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EI-MS/GC-MS | Type | Description | Splash Key | View |
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Predicted GC-MS | D-2-Hydroxyglutaric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0zgl-9300000000-805667744aba36281cec | Spectrum | Predicted GC-MS | D-2-Hydroxyglutaric acid, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00gv-8191000000-f6fdffd87ffe1acf65b4 | Spectrum | Predicted GC-MS | D-2-Hydroxyglutaric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | D-2-Hydroxyglutaric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | D-2-Hydroxyglutaric acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | D-2-Hydroxyglutaric acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | D-2-Hydroxyglutaric acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | D-2-Hydroxyglutaric acid, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | D-2-Hydroxyglutaric acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | D-2-Hydroxyglutaric acid, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | D-2-Hydroxyglutaric acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | D-2-Hydroxyglutaric acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | D-2-Hydroxyglutaric acid, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | D-2-Hydroxyglutaric acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | D-2-Hydroxyglutaric acid, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | D-2-Hydroxyglutaric acid, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | D-2-Hydroxyglutaric acid, TBDMS_3_1, 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 | splash10-001j-1900000000-dbf80fc2b86ec60d623e | 2016-06-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0m5r-9600000000-d1bc7ce2206164b5bc2c | 2016-06-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4i-9000000000-df3e77cb42d6f7647a64 | 2016-06-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-1900000000-095c1140772d4cdd149b | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0zfr-7900000000-ce158ac5b56eff867735 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4i-9000000000-e30760384709aa978986 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0fbi-3900000000-f88fcf3ac0dd06636b16 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0k9i-9400000000-31bf8d3bb7203e7bf200 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4u-9000000000-c0ac45c4d66178ac20cf | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0w39-4900000000-1385b471f7cdf14ca14d | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-052r-9500000000-17ece6956644d4cf2069 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4r-9000000000-dbb4195080bddb5f6210 | 2021-09-22 | View Spectrum |
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NMR | Not Available |
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Pathways |
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Pathways | Name | SMPDB/Pathwhiz | KEGG | The oncogenic action of D-2-hydroxyglutarate in Hydroxygluaricaciduria | | Not Available | The oncogenic action of L-2-hydroxyglutarate in Hydroxygluaricaciduria | | Not Available |
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Protein Targets |
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Enzymes | |
D-3-phosphoglycerate dehydrogenase | PHGDH | 1p12 | O43175 | details | D-2-hydroxyglutarate dehydrogenase, mitochondrial | D2HGDH | 2q37.3 | Q8N465 | details | Hydroxyacid-oxoacid transhydrogenase, mitochondrial | ADHFE1 | 8q13.1 | Q8IWW8 | details |
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Transporters | Not Available |
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Metal Bindings | |
Hydroxyacid-oxoacid transhydrogenase, mitochondrial | ADHFE1 | 8q13.1 | Q8IWW8 | details |
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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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| Not Available |
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External Links |
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HMDB ID | HMDB0000606 |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FoodDB ID | FDB022139 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 388508 |
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KEGG Compound ID | C01087 |
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BioCyc ID | R-2-HYDROXYGLUTARATE |
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BiGG ID | Not Available |
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Wikipedia Link | Alpha-Hydroxyglutaric acid |
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METLIN ID | 5581 |
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PubChem Compound | 439391 |
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PDB ID | Not Available |
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ChEBI ID | 32796 |
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References |
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General References | Not Available |
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