Cannabis Compound Database: Showing Compound Card for Glutaric acid (CDB005136)

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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

MOL SDF PDB SMILES InChI

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

alpha,omega-dicarboxylic acid (CHEBI:17859 )
Dicarboxylic acids (C00489 )

Ontology

Physiological effect

Health effect:

Health condition:

Metabolism and nutrition disorders:

Glutaric aciduria type 1

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Fungi:

Aspergillus

Microbe:

Escherichia:

Escherichia coli

Plant:

Biological location:

Tissue and substructures:

Placenta

Organ and components:

Prostate

Subcellular:

Cytoplasm

Biofluid and excreta:

Role

Indirect biological role:

Industrial application:

Pharmaceutical industry:

Pharmaceutical

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

Property	Value	Source
logP	0.046	ChemAxon
pKa (Strongest Acidic)	3.76	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	28.14 m³·mol⁻¹	ChemAxon
Polarizability	12.17 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

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

Not Available

Protein Targets

Enzymes

Not Available

Transporters

Protein Name	Gene Name	Locus	Uniprot ID	Details
Solute carrier family 22 member 11	SLC22A11	11q13.1	Q9NSA0	details
Solute carrier family 22 member 6	SLC22A6	11q12.3	Q4U2R8	details
Solute carrier family 22 member 7	SLC22A7	6p21.1	Q9Y694	details

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Cannabis Cultivar	Status	Value	Reference	Details
Alien Dawg	Detected and Quantified	0.0314 mg/g dry wt	David S. Wishart,...	details
Gabriola	Detected and Quantified	0.0189 mg/g dry wt	David S. Wishart,...	details
Island Honey	Detected and Quantified	0.0785 mg/g dry wt	David S. Wishart,...	details
Quadra	Detected and Quantified	0.0346 mg/g dry wt	David S. Wishart,...	details
Sensi Star	Detected and Quantified	0.0655 mg/g dry wt	David S. Wishart,...	details
Tangerine Dream	Detected and Quantified	0.0279 mg/g dry wt	David S. Wishart,...	details

External Links

HMDB ID

HMDB0000661

DrugBank ID

DB03553

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

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 ]

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

Showing Compound Card for Glutaric acid (CDB005136)

Structure for CDB005136 (Glutaric acid)

Transporters