Showing Compound Card for Glutaric acid (CDB005136)

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Record Information
Version1.0
Created at2020-04-17 19:12:57 UTC
Updated at2022-12-13 23:36:28 UTC
CannabisDB IDCDB005136
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameGlutaric acid
DescriptionGlutaric 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
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,3-Propanedicarboxylic acidChEBI
1,5-Pentanedioic acidChEBI
GlutarsaeureChEBI
Pentanedioic acidChEBI
1,3-PropanedicarboxylateGenerator
1,5-PentanedioateGenerator
PentanedioateGenerator
GlutarateGenerator
PentandioateHMDB
Pentandioic acidHMDB
Chemical FormulaC5H8O4
Average Molecular Weight132.11
Monoisotopic Molecular Weight132.0423
IUPAC Namepentanedioic acid
Traditional Nameglutaric acid
CAS Registry Number110-94-1
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 KeyJFCQEDHGNNZCLN-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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassDicarboxylic acids and derivatives
Direct ParentDicarboxylic 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 FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Indirect biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point95.8 °CNot Available
Boiling Point200 °CWikipedia
Water Solubility1600 mg/mLNot Available
logP-0.29HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
logP0.046ChemAxon
pKa (Strongest Acidic)3.76ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity28.14 m³·mol⁻¹ChemAxon
Polarizability12.17 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-052o-9000000000-f308daa4e82c16019e0d2014-09-20View Spectrum
GC-MSGlutaric acid, 2 TMS, GC-MS Spectrumsplash10-0f6t-2940000000-9f099473c4a6eb94d4beSpectrum
GC-MSGlutaric acid, 2 TMS, GC-MS Spectrumsplash10-0002-1920000000-4ade63738a1c00460a63Spectrum
GC-MSGlutaric acid, non-derivatized, GC-MS Spectrumsplash10-0002-1910000000-743df9571fee7baa3417Spectrum
GC-MSGlutaric acid, 2 TMS, GC-MS Spectrumsplash10-00fs-9710000000-ba958e52b1424e5d4840Spectrum
GC-MSGlutaric acid, 2 TMS, GC-MS Spectrumsplash10-0cgj-3930000000-298fe512c6b58220ee33Spectrum
GC-MSGlutaric acid, non-derivatized, GC-MS Spectrumsplash10-052o-9000000000-663deab1ce6413c4859dSpectrum
GC-MSGlutaric acid, non-derivatized, GC-MS Spectrumsplash10-0002-0920000000-56bce366cac24cd6773fSpectrum
GC-MSGlutaric acid, non-derivatized, GC-MS Spectrumsplash10-0f6t-2940000000-9f099473c4a6eb94d4beSpectrum
GC-MSGlutaric acid, non-derivatized, GC-MS Spectrumsplash10-0002-1920000000-4ade63738a1c00460a63Spectrum
GC-MSGlutaric acid, non-derivatized, GC-MS Spectrumsplash10-0002-1910000000-743df9571fee7baa3417Spectrum
GC-MSGlutaric acid, non-derivatized, GC-MS Spectrumsplash10-00fs-9710000000-ba958e52b1424e5d4840Spectrum
GC-MSGlutaric acid, non-derivatized, GC-MS Spectrumsplash10-0cgj-3930000000-298fe512c6b58220ee33Spectrum
GC-MSGlutaric acid, non-derivatized, GC-MS Spectrumsplash10-0002-0910000000-86fbcf8f1c72fbb2ffd0Spectrum
Predicted GC-MSGlutaric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01q3-9200000000-fcbc36fd55a7945d3f25Spectrum
Predicted GC-MSGlutaric acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05g3-9610000000-07394eb05b518a4e3bf4Spectrum
Predicted GC-MSGlutaric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlutaric acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlutaric acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlutaric acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-0019-9500000000-9db56ca3a541f0ce07d12012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-052r-9100000000-991f69d0892976558f852012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-0536-9300000000-20fb2c8dd136e4924aca2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-001i-0900000000-8eb90c15915f014713ac2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000i-9200000000-2ffdc08c49952e135a862012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-000i-9000000000-8884b857c9582288f35a2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-052f-9000000000-7d2c0333bdce4dbabbc62012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-9ab2a9480833026416282012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-000i-9400000000-c5ec3115706f6041b8682012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-0900000000-8eb90c15915f014713ac2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9200000000-2ffdc08c49952e135a862017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-8884b857c9582288f35a2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-052f-9000000000-7d2c0333bdce4dbabbc62017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-9ab2a9480833026416282017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000i-9400000000-c5ec3115706f6041b8682017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0udi-9000000000-89029b221f83859b721c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-014r-9000000000-ec63d377e53acd0b3f822021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-000i-9000000000-1778c9be6683c7aaea832021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Negativesplash10-001r-7900000000-88fa19a8b55a2221ac332021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-64994bb5102d568ae3ac2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-000i-9300000000-087a8bb0014a4b98f2162021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-000i-9100000000-be7bb3a98fa2fe29624c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-ee7e50d3e19afde6d9972021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (Unknown) , Positivesplash10-052o-9000000000-663deab1ce6413c4859d2012-08-31View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-1900000000-2ccd8e2a515cf328e7872017-07-26View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, D2O, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
Transporters
Protein NameGene NameLocusUniprot IDDetails
Solute carrier family 22 member 11SLC22A1111q13.1Q9NSA0 details
Solute carrier family 22 member 6SLC22A611q12.3Q4U2R8 details
Solute carrier family 22 member 7SLC22A76p21.1Q9Y694 details
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
Alien DawgDetected and Quantified0.0314 mg/g dry wt
    • David S. Wishart,...
 details
GabriolaDetected and Quantified0.0189 mg/g dry wt
    • David S. Wishart,...
 details
Island HoneyDetected and Quantified0.0785 mg/g dry wt
    • David S. Wishart,...
 details
QuadraDetected and Quantified0.0346 mg/g dry wt
    • David S. Wishart,...
 details
Sensi StarDetected and Quantified0.0655 mg/g dry wt
    • David S. Wishart,...
 details
Tangerine DreamDetected and Quantified0.0279 mg/g dry wt
    • David S. Wishart,...
 details
HMDB IDHMDB0000661
DrugBank IDDB03553
Phenol Explorer Compound IDNot Available
FoodDB IDFDB001477
KNApSAcK IDC00001184
Chemspider ID723
KEGG Compound IDC00489
BioCyc IDGLUTARATE
BiGG IDNot Available
Wikipedia LinkGlutaric_acid
METLIN ID3254
PubChem Compound743
PDB IDNot Available
ChEBI ID17859
References
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]

Transporters

Enzyme Details
1. Solute carrier family 22 member 11
General function:
Involved in transporter activity
Specific function:
Mediates saturable uptake of estrone sulfate, dehydroepiandrosterone sulfate and related compounds
Gene Name:
SLC22A11
Uniprot ID:
Q9NSA0
Molecular weight:
59970.9
Enzyme Details
2. Solute carrier family 22 member 6
General function:
Involved in ion transmembrane transporter activity
Specific function:
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS). Mediates the sodium-independent uptake of p- aminohippurate (PAH), ochratoxin (OTA), acyclovir (ACV), 3'-azido- 3-'deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro- phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2- furanpropionate (CMPF), cidofovir, adefovir, 9-(2- phosphonylmethoxyethyl) guanine (PMEG), 9-(2- phosphonylmethoxyethyl) diaminopurine (PMEDAP) and edaravone sulfate. PAH uptake is inhibited by p- chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), sulindac, diclofenac, carprofen, glutarate and okadaic acid. PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, furosemide, indomethacin, bumetamide, losartan, probenecid, phenol red, urate, and alpha-ketoglutarate
Gene Name:
SLC22A6
Uniprot ID:
Q4U2R8
Molecular weight:
61815.8
Enzyme Details
3. Solute carrier family 22 member 7
General function:
Involved in transmembrane transport
Specific function:
Mediates sodium-independent multispecific organic anion transport. Transport of prostaglandin E2, prostaglandin F2, tetracycline, bumetanide, estrone sulfate, glutarate, dehydroepiandrosterone sulfate, allopurinol, 5-fluorouracil, paclitaxel, L-ascorbic acid, salicylate, ethotrexate, and alpha- ketoglutarate
Gene Name:
SLC22A7
Uniprot ID:
Q9Y694
Molecular weight:
60025.0