Record Information |
---|
Version | 1.0 |
---|
Created at | 2020-04-17 19:12:57 UTC |
---|
Updated at | 2022-12-13 23:36:28 UTC |
---|
CannabisDB ID | CDB005136 |
---|
Secondary Accession Numbers | Not Available |
---|
Cannabis Compound Identification |
---|
Common Name | Glutaric acid |
---|
Description | Glutaric acid is a simple five-carbon linear dicarboxylic acid. It belongs to the class of compounds known as dicarboxylic acids. A dicarboxylic acid is an organic compound containing two carboxyl functional groups (−COOH). Glutaric acid is found in nearly all organisms from bacteria to plants to humans (PMID: 30143200 ). It is an odorless and tasteless compound that is highly soluble in water. It is used in cosmetics as a buffering agent. Glutaric acid has been detected in many different plants and foods, such as banana leafs, oats, sour cherries, red beetroots, common beets, french plantains, and soybeans. This could make glutaric acid a potential biomarker for the consumption of these foods. Glutaric acid is naturally produced in the human body during the metabolism of some amino acids, including lysine and tryptophan. When present in sufficiently high levels, glutaric acid can act as an acidogen and a metabotoxin. An acidogen is an acidic compound that induces acidosis, which has multiple adverse effects on many organ systems. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of glutaric acid are associated with at least three inborn errors of metabolism, including glutaric aciduria type I, malonyl-CoA decarboxylase deficiency, and glutaric aciduria type III. Glutaric aciduria type I (glutaric acidemia type I, glutaryl-CoA dehydrogenase deficiency, GA1, or GAT1) is an inherited disorder in which the body is unable to completely break down the amino acids lysine, hydroxylysine, and tryptophan due to a deficiency of mitochondrial glutaryl-CoA dehydrogenase (EC 1.3.99.7, GCDH). Excessive levels of their intermediate breakdown products (e.g. glutaric acid, glutaryl-CoA, 3-hydroxyglutaric acid, glutaconic acid) can accumulate and cause damage to the brain (and also other organs). Babies with glutaric acidemia type I are often born with unusually large heads (macrocephaly). Macrocephaly is amongst the earliest signs of GA1. GA1 also causes secondary carnitine deficiency because glutaric acid, like other organic acids, is detoxified by carnitine. Abnormally high levels of organic acids in the blood (organic acidemia), urine (organic aciduria), the brain, and other tissues lead to general metabolic acidosis. Acidosis typically occurs when arterial pH falls below 7.35. In infants with acidosis, the initial symptoms include poor feeding, vomiting, loss of appetite, weak muscle tone (hypotonia), and lack of energy (lethargy). These can progress to heart, liver, and kidney abnormalities, seizures, coma, and possibly death. These are also the characteristic symptoms of untreated glutaric aciduria. Many affected children with organic acidemias experience intellectual disability or delayed development. In adults, acidosis or acidemia is characterized by headaches, confusion, feeling tired, tremors, sleepiness, and seizures. Treatment of glutaric aciduria is mainly based on the restriction of lysine intake, supplementation of carnitine, and an intensification of therapy during intercurrent illnesses. The major principle of dietary treatment is to reduce the production of glutaric acid and 3-hydroxyglutaric acid by restriction of natural protein, in general, and of lysine, in particular (PMID: 17465389 , 15505398 ). Glutaric acid may cause irritation to the skin and eyes. Glutaric acid is also found in cannabis smoke and is formed during the combustion of cannabis ( Ref:DOI ). |
---|
Structure | |
---|
Synonyms | Value | Source |
---|
1,3-Propanedicarboxylic acid | ChEBI | 1,5-Pentanedioic acid | ChEBI | Glutarsaeure | ChEBI | Pentanedioic acid | ChEBI | 1,3-Propanedicarboxylate | Generator | 1,5-Pentanedioate | Generator | Pentanedioate | Generator | Glutarate | Generator | Pentandioate | HMDB | Pentandioic acid | HMDB |
|
---|
Chemical Formula | C5H8O4 |
---|
Average Molecular Weight | 132.11 |
---|
Monoisotopic Molecular Weight | 132.0423 |
---|
IUPAC Name | pentanedioic acid |
---|
Traditional Name | glutaric acid |
---|
CAS Registry Number | 110-94-1 |
---|
SMILES | OC(=O)CCCC(O)=O |
---|
InChI Identifier | InChI=1S/C5H8O4/c6-4(7)2-1-3-5(8)9/h1-3H2,(H,6,7)(H,8,9) |
---|
InChI Key | JFCQEDHGNNZCLN-UHFFFAOYSA-N |
---|
Chemical Taxonomy |
---|
Description | Belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. |
---|
Kingdom | Organic compounds |
---|
Super Class | Organic acids and derivatives |
---|
Class | Carboxylic acids and derivatives |
---|
Sub Class | Dicarboxylic acids and derivatives |
---|
Direct Parent | Dicarboxylic acids and derivatives |
---|
Alternative Parents | |
---|
Substituents | - Fatty acid
- Dicarboxylic acid or derivatives
- Carboxylic acid
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aliphatic acyclic compound
|
---|
Molecular Framework | Aliphatic acyclic compounds |
---|
External Descriptors | |
---|
Ontology |
---|
|
Physiological effect | Health effect: |
---|
Disposition | Route of exposure: Source: Biological location: |
---|
Role | Indirect biological role: Industrial application: |
---|
Physical Properties |
---|
State | Solid |
---|
Experimental Properties | Property | Value | Reference |
---|
Melting Point | 95.8 °C | Not Available | Boiling Point | 200 °C | Wikipedia | Water Solubility | 1600 mg/mL | Not Available | logP | -0.29 | HANSCH,C ET AL. (1995) |
|
---|
Predicted Properties | [] |
---|
Spectra |
---|
EI-MS/GC-MS | Type | Description | Splash Key | View |
---|
EI-MS | Mass Spectrum (Electron Ionization) | splash10-052o-9000000000-f308daa4e82c16019e0d | 2014-09-20 | View Spectrum | GC-MS | Glutaric acid, 2 TMS, GC-MS Spectrum | splash10-0f6t-2940000000-9f099473c4a6eb94d4be | Spectrum | GC-MS | Glutaric acid, 2 TMS, GC-MS Spectrum | splash10-0002-1920000000-4ade63738a1c00460a63 | Spectrum | GC-MS | Glutaric acid, non-derivatized, GC-MS Spectrum | splash10-0002-1910000000-743df9571fee7baa3417 | Spectrum | GC-MS | Glutaric acid, 2 TMS, GC-MS Spectrum | splash10-00fs-9710000000-ba958e52b1424e5d4840 | Spectrum | GC-MS | Glutaric acid, 2 TMS, GC-MS Spectrum | splash10-0cgj-3930000000-298fe512c6b58220ee33 | Spectrum | GC-MS | Glutaric acid, non-derivatized, GC-MS Spectrum | splash10-052o-9000000000-663deab1ce6413c4859d | Spectrum | GC-MS | Glutaric acid, non-derivatized, GC-MS Spectrum | splash10-0002-0920000000-56bce366cac24cd6773f | Spectrum | GC-MS | Glutaric acid, non-derivatized, GC-MS Spectrum | splash10-0f6t-2940000000-9f099473c4a6eb94d4be | Spectrum | GC-MS | Glutaric acid, non-derivatized, GC-MS Spectrum | splash10-0002-1920000000-4ade63738a1c00460a63 | Spectrum | GC-MS | Glutaric acid, non-derivatized, GC-MS Spectrum | splash10-0002-1910000000-743df9571fee7baa3417 | Spectrum | GC-MS | Glutaric acid, non-derivatized, GC-MS Spectrum | splash10-00fs-9710000000-ba958e52b1424e5d4840 | Spectrum | GC-MS | Glutaric acid, non-derivatized, GC-MS Spectrum | splash10-0cgj-3930000000-298fe512c6b58220ee33 | Spectrum | GC-MS | Glutaric acid, non-derivatized, GC-MS Spectrum | splash10-0002-0910000000-86fbcf8f1c72fbb2ffd0 | Spectrum | Predicted GC-MS | Glutaric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-01q3-9200000000-fcbc36fd55a7945d3f25 | Spectrum | Predicted GC-MS | Glutaric acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-05g3-9610000000-07394eb05b518a4e3bf4 | Spectrum | Predicted GC-MS | Glutaric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Glutaric acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Glutaric acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Glutaric acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
|
---|
MS/MS | Type | Description | Splash Key | View |
---|
MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated) | splash10-0019-9500000000-9db56ca3a541f0ce07d1 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated) | splash10-052r-9100000000-991f69d0892976558f85 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated) | splash10-0536-9300000000-20fb2c8dd136e4924aca | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-001i-0900000000-8eb90c15915f014713ac | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-000i-9200000000-2ffdc08c49952e135a86 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-000i-9000000000-8884b857c9582288f35a | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-052f-9000000000-7d2c0333bdce4dbabbc6 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-0006-9000000000-9ab2a948083302641628 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-000i-9400000000-c5ec3115706f6041b868 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-001i-0900000000-8eb90c15915f014713ac | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-000i-9200000000-2ffdc08c49952e135a86 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-000i-9000000000-8884b857c9582288f35a | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-052f-9000000000-7d2c0333bdce4dbabbc6 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0006-9000000000-9ab2a948083302641628 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-000i-9400000000-c5ec3115706f6041b868 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Negative | splash10-0udi-9000000000-89029b221f83859b721c | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-014r-9000000000-ec63d377e53acd0b3f82 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 35V, Negative | splash10-000i-9000000000-1778c9be6683c7aaea83 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Negative | splash10-001r-7900000000-88fa19a8b55a2221ac33 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-000i-9000000000-64994bb5102d568ae3ac | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-000i-9300000000-087a8bb0014a4b98f216 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-000i-9100000000-be7bb3a98fa2fe29624c | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9000000000-ee7e50d3e19afde6d997 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - EI-B (Unknown) , Positive | splash10-052o-9000000000-663deab1ce6413c4859d | 2012-08-31 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-1900000000-2ccd8e2a515cf328e787 | 2017-07-26 | View Spectrum |
|
---|
NMR | Type | Description | | View |
---|
1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 90 MHz, D2O, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 25.16 MHz, D2O, experimental) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | | Spectrum |
|
---|
Pathways |
---|
Pathways | Not Available |
---|
Protein Targets |
---|
Enzymes | Not Available |
---|
Transporters | |
---|
Metal Bindings | Not Available |
---|
Receptors | Not Available |
---|
Transcriptional Factors | Not Available |
---|
Concentrations Data |
---|
| |
Alien Dawg | Detected and Quantified | 0.0314 mg/g dry wt | | details | Gabriola | Detected and Quantified | 0.0189 mg/g dry wt | | details | Island Honey | Detected and Quantified | 0.0785 mg/g dry wt | | details | Quadra | Detected and Quantified | 0.0346 mg/g dry wt | | details | Sensi Star | Detected and Quantified | 0.0655 mg/g dry wt | | details | Tangerine Dream | Detected and Quantified | 0.0279 mg/g dry wt | | details |
|
---|
External Links |
---|
HMDB ID | HMDB0000661 |
---|
DrugBank ID | DB03553 |
---|
Phenol Explorer Compound ID | Not Available |
---|
FoodDB ID | FDB001477 |
---|
KNApSAcK ID | C00001184 |
---|
Chemspider ID | 723 |
---|
KEGG Compound ID | C00489 |
---|
BioCyc ID | GLUTARATE |
---|
BiGG ID | Not Available |
---|
Wikipedia Link | Glutaric_acid |
---|
METLIN ID | 3254 |
---|
PubChem Compound | 743 |
---|
PDB ID | Not Available |
---|
ChEBI ID | 17859 |
---|
References |
---|
General References | - Hong YG, Moon YM, Hong JW, No SY, Choi TR, Jung HR, Yang SY, Bhatia SK, Ahn JO, Park KM, Yang YH: Production of glutaric acid from 5-aminovaleric acid using Escherichia coli whole cell bio-catalyst overexpressing GabTD from Bacillus subtilis. Enzyme Microb Technol. 2018 Nov;118:57-65. doi: 10.1016/j.enzmictec.2018.07.002. Epub 2018 Jul 10. [PubMed:30143200 ]
- Bishop FS, Liu JK, McCall TD, Brockmeyer DL: Glutaric aciduria type 1 presenting as bilateral subdural hematomas mimicking nonaccidental trauma. Case report and review of the literature. J Neurosurg. 2007 Mar;106(3 Suppl):222-6. doi: 10.3171/ped.2007.106.3.222. [PubMed:17465389 ]
- Muller E, Kolker S: Reduction of lysine intake while avoiding malnutrition--major goals and major problems in dietary treatment of glutaryl-CoA dehydrogenase deficiency. J Inherit Metab Dis. 2004;27(6):903-10. doi: 10.1023/B:BOLI.0000045775.03183.48. [PubMed:15505398 ]
|
---|