ContaminantDB: Glutaconic acid

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (1)XML

Record Information

Version

1.0

Creation Date

2014-08-29 06:33:58 UTC

Update Date

2026-04-03 00:50:57 UTC

Accession Number

CHEM003318

Identification

Common Name

Glutaconic acid

Class

Small Molecule

Description

Glutaconic acid is an organic compound with general formula C5H6O4. The compound is a dicarboxylic acid and related with the fully saturated glutaric acid.

Contaminant Sources

FooDB Chemicals
HMDB Contaminants - Urine
T3DB toxins

Contaminant Type

Animal Toxin
Ester
Food Toxin
Metabolite
Natural Compound
Organic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(e)-Glutaconate	ChEBI
trans-Glutaconate	ChEBI
trans-Glutaconic acid	ChEBI
(e)-Glutaconic acid	Generator
Glutaconate	Generator
(e)-2-Pentenedioate	HMDB
(e)-2-Pentenedioic acid	HMDB
1,3-Propenedicarboxylate	HMDB
1,3-Propenedicarboxylic acid	HMDB
1-Propene-1,3-dicarboxylate	HMDB
1-Propene-1,3-dicarboxylic acid	HMDB
Pentenedioate	HMDB
Pentenedioic acid	HMDB
Glutaconic acid, (e)-isomer	HMDB
2-Pentendioate	HMDB
2-Pentenedioic acid	HMDB
Glutaconic acid	HMDB

Chemical Formula

C₅H₆O₄

Average Molecular Mass

130.099 g/mol

Monoisotopic Mass

130.027 g/mol

CAS Registry Number

1724-02-3

IUPAC Name

(2E)-pent-2-enedioic acid

Traditional Name

glutaconic acid

SMILES

OC(=O)C\C=C\C(O)=O

InChI Identifier

InChI=1S/C5H6O4/c6-4(7)2-1-3-5(8)9/h1-2H,3H2,(H,6,7)(H,8,9)/b2-1+

InChI Key

XVOUMQNXTGKGMA-OWOJBTEDSA-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 acyl
Fatty acid
Unsaturated 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

glutaconic acid (CHEBI:15670 )
Dicarboxylic acids (LMFA01170109 )

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB Link	KEGG Link
Glutaric Aciduria Type I	SMP00185	Not Available

Applications

Not Available

Biological Roles

human metabolite

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	133 - 135°C
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	17.6 g/L	ALOGPS
logP	0.05	ALOGPS
logP	0.044	ChemAxon
logS	-0.87	ALOGPS
pKa (Strongest Acidic)	3.69	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	3	ChemAxon
Refractivity	29.23 m³·mol⁻¹	ChemAxon
Polarizability	11.36 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-3930000000-d1b6e04bed9f3de84afa	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-3910000000-02c8fdec1f78bd5117e2	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-3930000000-d1b6e04bed9f3de84afa	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-3910000000-02c8fdec1f78bd5117e2	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-3930000000-d1b6e04bed9f3de84afa	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-3910000000-02c8fdec1f78bd5117e2	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-3930000000-d1b6e04bed9f3de84afa	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-3910000000-02c8fdec1f78bd5117e2	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001r-9100000000-42f59aea4f8e6bb8ab57	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-05g0-8920000000-733f5a9f839df29bff69	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 (TMS_1_2) - 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_1_2) - 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, Negative (Annotated)	splash10-000i-9000000000-6fb6cc9ab31410b273f1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-000f-9000000000-b9c27f4002ce9f12f916	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-000f-9100000000-d627e3ddfe858b1b331d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 7V, positive	splash10-000i-9100000000-ab58b5793b44b9bf9179	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 10V, positive	splash10-00ds-9100000000-d837a612ccd5753681fe	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 15V, positive	splash10-00ds-9000000000-297bd6690b68056be798	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 17V, positive	splash10-006t-9000000000-fcf4434d16f307cff090	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 0V, positive	splash10-03di-2900000000-2e649f3de9cd6e527eb8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 0V, positive	splash10-03di-4900000000-49e2416d6fb162ad2653	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 0V, positive	splash10-03dr-6900000000-de40796dc1578c547169	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 0V, positive	splash10-01p9-9700000000-5d5dcebba638d34e8fac	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, positive	splash10-01p9-9400000000-eb38aa127f9847501c88	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, positive	splash10-000i-9300000000-cd256964e84b2c9e7330	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, positive	splash10-000i-9100000000-ec0b1e5f63f16ae5f6ba	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, positive	splash10-000i-9100000000-225d56adbb31a91aea12	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, positive	splash10-000i-9100000000-f7162d7b901bcae643ba	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, positive	splash10-000i-9000000000-fa9f8d6b587fca352dd5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, positive	splash10-000i-9000000000-77c952cabb0213b55f1e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, positive	splash10-0079-9000000000-e0422714c30ca69f9b7e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03e9-3900000000-f982ee0bd6ebcaf33bbe	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01q0-9500000000-90dd8c522781e5da5ebb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00n0-9000000000-e56400244a361d348a1f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-1900000000-ad86855e24f296413178	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01t9-4900000000-30e4a1adead132f7de92	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9000000000-47a3aa8cf8913cc4d70e	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
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C 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

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Accumulating trans-glutaconic (TG) acids has been proposed to be involved in the development of the striatal degeneration seen in children with glutaric acidemia type 1 (GA1) via an excitotoxic mechanism. TG is neurotoxic and neurotoxicity is thought to be caused by an excitotoxic mechanism in which TG overactivates N-methyl-D-aspartate (NMDA) receptors. (3) In glutaric aciduria type 1, glutaconic acid accumulates, resulting in brain damage. (Wikipedia)

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

This is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.

Minimum Risk Level

Not Available