Livestock Metabolome Database: Showing metabocard for Glutaric acid (LMDB00206)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:44:42 UTC

Update Date

2016-07-20 20:57:55 UTC

Lmdb

LMDB00206

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Glutaric acid

Description

Glutaric acid is a simple five-carbon linear dicarboxylic acid. 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 (EC 1.3.99.7, GCDH) which is involved in the metabolism of lysine, hydroxylysine, and tryptophan. Glutaric aciduria type I lead to nonspecific developmental delay, hypotonia, and macrocephaly with cerebral atrophy of prenatal onset. Treatment is mainly based on 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 ).

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

132.1146

Monoisotopic Molecular Weight

132.042258744

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

Status

Detected but not Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

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	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-0f6t-2940000000-9f099473c4a6eb94d4be	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-0002-1920000000-4ade63738a1c00460a63	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0002-1910000000-743df9571fee7baa3417	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-00fs-9710000000-ba958e52b1424e5d4840	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0cgj-3930000000-298fe512c6b58220ee33	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-052o-9000000000-663deab1ce6413c4859d	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0002-0920000000-56bce366cac24cd6773f	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0f6t-2940000000-9f099473c4a6eb94d4be	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-1920000000-4ade63738a1c00460a63	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-1910000000-743df9571fee7baa3417	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00fs-9710000000-ba958e52b1424e5d4840	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0cgj-3930000000-298fe512c6b58220ee33	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0910000000-86fbcf8f1c72fbb2ffd0	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-01q3-9200000000-fcbc36fd55a7945d3f25	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-05g3-9610000000-07394eb05b518a4e3bf4	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)	splash10-0019-9500000000-9db56ca3a541f0ce07d1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)	splash10-052r-9100000000-991f69d0892976558f85	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)	splash10-0536-9300000000-20fb2c8dd136e4924aca	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-001i-0900000000-8eb90c15915f014713ac	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-000i-9200000000-2ffdc08c49952e135a86	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-000i-9000000000-8884b857c9582288f35a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-052f-9000000000-7d2c0333bdce4dbabbc6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0006-9000000000-9ab2a948083302641628	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-000i-9400000000-c5ec3115706f6041b868	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-001i-0900000000-8eb90c15915f014713ac	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9200000000-2ffdc08c49952e135a86	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-8884b857c9582288f35a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-052f-9000000000-7d2c0333bdce4dbabbc6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-9ab2a948083302641628	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-000i-9400000000-c5ec3115706f6041b868	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0udi-9000000000-89029b221f83859b721c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-014r-9000000000-ec63d377e53acd0b3f82	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-000i-9000000000-1778c9be6683c7aaea83	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Negative	splash10-001r-7900000000-88fa19a8b55a2221ac33	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9000000000-64994bb5102d568ae3ac	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9300000000-087a8bb0014a4b98f216	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9100000000-be7bb3a98fa2fe29624c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-ee7e50d3e19afde6d997	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (Unknown) , Positive	splash10-052o-9000000000-663deab1ce6413c4859d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-1900000000-2ccd8e2a515cf328e787	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-052o-9000000000-f308daa4e82c16019e0d	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Feces
Plasma

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Feces	Detected but not Quantified	Not Applicable	Not Available	Ovine	17249687	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Ovine	17249687	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Porcine	22675387	details

External Links

DrugBank ID

DB03553

HMDB ID

HMDB0000661

FooDB ID

FDB001477

Phenol Explorer ID

Not Available

KNApSAcK ID

C00001184

BiGG ID

Not Available

BioCyc ID

GLUTARATE

METLIN ID

3254

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

ECMDB21425

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]

Showing metabocard for Glutaric acid (LMDB00206)

Structure for LMDB00206 (Glutaric acid)