| Common Name |
Glutaconic acid
| Description |
Glutaconic acid is an organic compound with general formlia C5H6O4. The compound is a dicarboxylic acid and related with the flily saturated glutaric acid.
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
(e)-GlutaconateChEBI
trans-GlutaconateChEBI
trans-Glutaconic acidChEBI
(e)-Glutaconic acidGenerator
GlutaconateGenerator
(e)-2-PentenedioateHMDB
(e)-2-Pentenedioic acidHMDB
1,3-PropenedicarboxylateHMDB
1,3-Propenedicarboxylic acidHMDB
1-Propene-1,3-dicarboxylateHMDB
1-Propene-1,3-dicarboxylic acidHMDB
PentenedioateHMDB
Pentenedioic acidHMDB
Glutaconic acid, ion(2-)MeSH
Glutaconic acid, copper saltMeSH
Glutaconic acid, (e)-isomerMeSH
| Chemical Formlia |
C5H6O4
| Average Molecliar Weight |
130.0987
| Monoisotopic Molecliar Weight |
130.02660868
| IUPAC Name |
(2E)-pent-2-enedioic acid
| Traditional Name |
glutaconic acid
| CAS Registry Number |
1724-02-3
| SMILES |
OC(=O)CC=CC(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 |
| Classification |
Not classified
| Ontology |
| Status |
Detected and Quantified
| Origin |
Endogenous
Food
| Biofunction |
Cell signaling
Fuel and energy storage
Fuel or energy source
Membrane integrity/stability
| Application |
Nutrients
Stabilizers
Surfactants and Emlisifiers
| Cellliar locations |
Extracellliar
Membrane
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting Point133 – 135 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility17.6 mg/mLALOGPS
logP0.05ALOGPS
logP0.044ChemAxon
logS-0.87ALOGPS
pKa (Strongest Acidic)3.69ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity29.23 m3·mol-1ChemAxon
Polarizability11.36 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 10V, Negative (Annotated)splash10-000i-9000000000-6fb6cc9ab31410b273f1View in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 25V, Negative (Annotated)splash10-000f-9000000000-b9c27f4002ce9f12f916View in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 40V, Negative (Annotated)splash10-000f-9100000000-d627e3ddfe858b1b331dView in MoNA
| 1D NMR |
1H NMR SpectrumNot Available
| 2D NMR |
[1H,13C] 2D NMR SpectrumNot Available
| Biological Properties |
| Cellliar Locations |
Extracellliar
Membrane
| Biofluid Locations |
Urine
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
UrineDetected and Quantified3.1 (1.2-3.1) umol/mmol creatinineAdlit (>18 years old)Both
Normal
24023812
details
UrineDetected and Quantified0.0 umol/mmol creatinineChildren (1 – 18 years old)Both
Normal
BC Children's Hos…
details
|
| Abnormal Concentrations |
|
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
UrineDetected and Quantified1.0 (0.0-2.0) umol/mmol creatinineAdlit (>18 years old)BothGlutaric aciduria type 1
MetaGene
details
UrineDetected and Quantified180.0 (0.00-360.0) umol/mmol creatinineChildren (1-13 years old)BothGlutaric aciduria I
MetaGene
details
| Associated Disorders and Diseases |
| Disease References |
| Glutaric aciduria type 1 |
- MetaGene [Link]
- MetaGene [Link]
| Associated OMIM IDs |
231670 (Glutaric aciduria type 1)
| External Links |
| DrugBank ID |
Not Available
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
FDB022146
| KNApSAcK ID |
Not Available
| Chemspider ID |
4444138
| KEGG Compound ID |
C02214
| BioCyc ID |
GLUTACONATE
| BiGG ID |
Not Available
| Wikipedia Link |
Glutaconic acid
| NuGOwiki Link |
HMDB00620
| Metagene Link |
HMDB00620
| METLIN ID |
5593
| PubChem Compound |
5280498
| PDB ID |
Not Available
| ChEBI ID |
15670
Product: Ursonic acid
References |
| Synthesis Reference |
Schwarz, Siegfried; Bohn, Helmut; Schmidt, Dieter; Kulpa, Manfred; Spakowski, Horst; Becker, Manfred. Glutaconic acid. Ger. (East) (1967), 2 pp. |
| Material Safety Data Sheet (MSDS) |
Download (PDF) |
| General References |
- Podebrad F, Heil M, Beck T, Mosandl A, Sewell AC, Bohles H: Stereodifferentiation of 3-hydroxyisobutyric- and 3-aminoisobutyric acid in human urine by enantioselective multidimensional capillary gas chromatography-mass spectrometry. Clin Chim Acta. 2000 Feb 25;292(1-2):93-105. [PubMed:10686279 ]
- Osaka H, Kimura S, Nezu A, Yamazaki S, Saitoh K, Yamaguchi S: Chronic subdural hematoma, as an initial manifestation of glutaric aciduria type-1. Brain Dev. 1993 Mar-Apr;15(2):125-7. [PubMed:8214331 ]
|
PMID: 10075814