Glutaric acid

General Information

Chemical name	Glutaric acid
CAS number	110-94-1
Flavouring type	substances
FL No.	08.082
Mixture	No
Purity of the named substance at least 95% unless otherwise specified
Reference body	EFSA

From webgate.ec.europa.eu

Computed Descriptors

Download SDF

2D Structure
CID	743
IUPAC Name	pentanedioic acid
InChI	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
Canonical SMILES	C(CC(=O)O)CC(=O)O
Molecular Formula	C5H8O4
Wikipedia	glutaric acid

From Pubchem

Computed Properties

Property Name	Property Value
Molecular Weight	132.115
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	4
Complexity	104.0
CACTVS Substructure Key Fingerprint	A A A D c c B g O A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A G g A A C A A A C A C A g A A A C A A A A g A I A A C Q C A A A A A A A A A A A A A E A A A A A A B I A A A A A Q A A E A A A A A A C I J g A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A = =
Topological Polar Surface Area	74.6
Monoisotopic Mass	132.042
Exact Mass	132.042
Compound Is Canonicalized	True
Formal Charge	0
Heavy Atom Count	9
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Isotope Atom Count	0
Covalently-Bonded Unit Count	1

From Pubchem

Food Additives Biosynthesis/Degradation

ADMET Predicted Profile --- Classification

Model	Result	Probability
Absorption
Blood-Brain Barrier	BBB+	0.8713
Human Intestinal Absorption	HIA+	0.5167
Caco-2 Permeability	Caco2-	0.6629
P-glycoprotein Substrate	Non-substrate	0.7340
P-glycoprotein Inhibitor	Non-inhibitor	0.9848
P-glycoprotein Inhibitor	Non-inhibitor	0.9653
Renal Organic Cation Transporter	Non-inhibitor	0.9436
Distribution
Subcellular localization	Mitochondria	0.8469
Metabolism
CYP450 2C9 Substrate	Non-substrate	0.8292
CYP450 2D6 Substrate	Non-substrate	0.9096
CYP450 3A4 Substrate	Non-substrate	0.7522
CYP450 1A2 Inhibitor	Non-inhibitor	0.8704
CYP450 2C9 Inhibitor	Non-inhibitor	0.9683
CYP450 2D6 Inhibitor	Non-inhibitor	0.9709
CYP450 2C19 Inhibitor	Non-inhibitor	0.9812
CYP450 3A4 Inhibitor	Non-inhibitor	0.9660
CYP Inhibitory Promiscuity	Low CYP Inhibitory Promiscuity	0.9931
Excretion
Toxicity
Human Ether-a-go-go-Related Gene Inhibition	Weak inhibitor	0.9651
Human Ether-a-go-go-Related Gene Inhibition	Non-inhibitor	0.9751
AMES Toxicity	Non AMES toxic	0.9462
Carcinogens	Non-carcinogens	0.8197
Fish Toxicity	High FHMT	0.5397
Tetrahymena Pyriformis Toxicity	Low TPT	0.9587
Honey Bee Toxicity	High HBT	0.6208
Biodegradation	Ready biodegradable	0.9123
Acute Oral Toxicity	III	0.6105
Carcinogenicity (Three-class)	Non-required	0.7411

From admetSAR

ADMET Predicted Profile --- Regression

Model	Value	Unit
Absorption
Aqueous solubility	-0.0553	LogS
Caco-2 Permeability	0.3808	LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity	1.5523	LD50, mol/kg
Fish Toxicity	2.2526	pLC50, mg/L
Tetrahymena Pyriformis Toxicity	-0.7652	pIGC50, ug/L

From admetSAR

Toxicity Profile

Route of Exposure	None
Mechanism of Toxicity	Accumulation of glutaric acid in the body has been shown to be toxic. The accumulation of glutaric acid ranging from slightly or intermittently elevated urinary glutaric acid to gross organic aciduria occurs in glutaric aciduria. Glutaric aciduria type 1 is an autosomal-recessive disorder resulting from a deficiency of mitochondrial glutaryl-CoA dehydrogenase which is involved in the metabolism of lysine, hydroxylysine, and tryptophan.
Metabolism	None
Toxicity Values	None
Lethal Dose	None
Carcinogenicity (IARC Classification)	No indication of carcinogenicity to humans (not listed by IARC).
Minimum Risk Level	None
Health Effects	Chronically high levels of glutaric acid are associated with at least 3 inborn errors of metabolism including: Glutaric Aciduria Type I and Glutaric Aciduria Type III.
Treatment	None
Reference	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.[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.[15505398 ] 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.[19212411 ] 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.[8087979 ] Hoffmann GF, Meier-Augenstein W, Stockler S, Surtees R, Rating D, Nyhan WL: Physiology and pathophysiology of organic acids in cerebrospinal fluid. J Inherit Metab Dis. 1993;16(4):648-69.[8412012 ] Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38.[2026685 ] Baric I, Wagner L, Feyh P, Liesert M, Buckel W, Hoffmann GF: Sensitivity and specificity of free and total glutaric acid and 3-hydroxyglutaric acid measurements by stable-isotope dilution assays for the diagnosis of glutaric aciduria type I. J Inherit Metab Dis. 1999 Dec;22(8):867-81.[10604139 ] Hoffmann GF, Trefz FK, Barth PG, Bohles HJ, Biggemann B, Bremer HJ, Christensen E, Frosch M, Hanefeld F, Hunneman DH, et al.: Glutaryl-coenzyme A dehydrogenase deficiency: a distinct encephalopathy. Pediatrics. 1991 Dec;88(6):1194-203.[1956737 ] Goodman SI, Stein DE, Schlesinger S, Christensen E, Schwartz M, Greenberg CR, Elpeleg ON: Glutaryl-CoA dehydrogenase mutations in glutaric acidemia (type I): review and report of thirty novel mutations. Hum Mutat. 1998;12(3):141-4.[9711871 ] Goodman SI, Gallegos DA, Pullin CJ, Halpern B, Truscott RJ, Wise G, Wilcken B, Ryan ED, Whelen DT: Antenatal diagnosis of glutaric acidemia. Am J Hum Genet. 1980 Sep;32(5):695-9.[6893520 ] Jakobs C, Sweetman L, Wadman SK, Duran M, Saudubray JM, Nyhan WL: Prenatal diagnosis of glutaric aciduria type II by direct chemical analysis of dicarboxylic acids in amniotic fluid. Eur J Pediatr. 1984 Jan;141(3):153-7.[6698061 ] Whelan DT, Hill R, Ryan ED, Spate M: L-Glutaric acidemia: investigation of a patient and his family. Pediatrics. 1979 Jan;63(1):88-93.[440804 ] Singh I: Biochemistry of peroxisomes in health and disease. Mol Cell Biochem. 1997 Feb;167(1-2):1-29.[9059978 ]

From T3DB

Taxonomic Classification

Kingdom	Organic compounds
Superclass	Organic acids and derivatives
Class	Carboxylic acids and derivatives
Subclass	Dicarboxylic acids and derivatives
Intermediate Tree Nodes	Not available
Direct Parent	Dicarboxylic acids and derivatives
Alternative Parents	Carboxylic acids Hydrocarbon derivatives Carbonyl compounds Organic oxides Fatty acids and conjugates
Molecular Framework	Aliphatic acyclic compounds
Substituents	Fatty acid - Dicarboxylic acid or derivatives - Carboxylic acid - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aliphatic acyclic compound
Description	This compound belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.

From ClassyFire

Targets

Target Details

Glutaryl-CoA dehydrogenase, mitochondrial

General Function:: Oxidoreductase activity, acting on the ch-ch group of donors, with a flavin as acceptor
Specific Function:: Catalyzes the oxidative decarboxylation of glutaryl-CoA to crotonyl-CoA and CO(2) in the degradative pathway of L-lysine, L-hydroxylysine, and L-tryptophan metabolism. It uses electron transfer flavoprotein as its electron acceptor. Isoform Short is inactive.
Gene Name:: GCDH
Uniprot ID:: Q92947
Molecular Weight:: 48126.715 Da

Target Details

Aspartate aminotransferase

General Function:: Pyridoxal phosphate binding
Gene Name:: aspC
Uniprot ID:: P00509
Molecular Weight:: 43572.965 Da

Target Details

Glutamate decarboxylase alpha

General Function:: Pyridoxal phosphate binding
Specific Function:: Converts glutamate to gamma-aminobutyrate (GABA), consuming one intracellular proton in the reaction. The gad system helps to maintain a near-neutral intracellular pH when cells are exposed to extremely acidic conditions. The ability to survive transit through the acidic conditions of the stomach is essential for successful colonization of the mammalian host by commensal and pathogenic bacteria.
Gene Name:: gadA
Uniprot ID:: P69908
Molecular Weight:: 52684.685 Da

Target Details

Branched-chain-amino-acid aminotransferase

General Function:: L-valine transaminase activity
Specific Function:: Acts on leucine, isoleucine and valine.
Gene Name:: ilvE
Uniprot ID:: P0AB80
Molecular Weight:: 34093.4 Da

From T3DB