| Common Name |
3-Hexenedioic acid
| Description |
3-Hexenedioic acid is a normal human unsaturated dicarboxylic acid metabolite with increased excretion in patients with Dicarboxylic aciduria caused by fatty acid metabolism disorders. (PMID 2614263 , 7096501 ) The urinary excretion of 3-Hexenedioic acid is increased in conditions of augmented mobilization of fatty acids or inhibited fatty acid oxidation. (PMID 2001377 ).
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
(e)-3-Hexenedioic acidChEBI
(e)-Hex-3-enedioic acidChEBI
(e)-3-HexenedioateGenerator
3-HexenedioateGenerator
(e)-Hex-3-enedioateGenerator
trans-2-Butene-1,4-dicarboxylateHMDB
trans-2-Butene-1,4-dicarboxylic acidHMDB
trans-3-HexenedioateHMDB
trans-3-Hexenedioic acidHMDB
trans-b-HydromuconateHMDB
trans-b-Hydromuconic acidHMDB
trans-beta-HydromuconateHMDB
trans-beta-Hydromuconic acidHMDB
cis,cis-MuconateMeSH
Muconic acidMeSH
trans,trans-Muconic acidMeSH
Muconic acid, (e,e)-isomerMeSH
| Chemical Formlia |
C6H8O4
| Average Molecliar Weight |
144.1253
| Monoisotopic Molecliar Weight |
144.042258744
| IUPAC Name |
(3E)-hex-3-enedioic acid
| Traditional Name |
3-hexenedioic acid
| CAS Registry Number |
29311-53-3
| SMILES |
OC(=O)CC=CCC(O)=O
| InChI Identifier |
InChI=1S/C6H8O4/c7-5(8)3-1-2-4-6(9)10/h1-2H,3-4H2,(H,7,8)(H,9,10)/b2-1+
| InChI Key |
YHGNXQAFNHCBTK-OWOJBTEDSA-N
| Chemical Taxonomy |
| Description |
This compound belongs to the class of chemical entities known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
| Kingdom |
Chemical entities
| Super Class |
Organic compounds
| Class |
Lipids and lipid-like moleclies
| Sub Class |
Fatty Acyls
| Direct Parent |
Medium-chain fatty acids
| Alternative Parents |
Unsaturated fatty acids
Dicarboxylic acids and derivatives
Carboxylic acids
Organic oxides
Hydrocarbon derivatives
Carbonyl compounds
| Substituents |
Medium-chain fatty acid
Unsaturated fatty acid
Dicarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound
| Molecliar Framework |
Aliphatic acyclic compounds
| External Descriptors |
3-hexenedioic acid (CHEBI:86952 )
Dicarboxylic acids (LMFA01170087 )
| Ontology |
| Status |
Expected but not 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 PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility17 mg/mLNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility10.9 mg/mLALOGPS
logP0.29ALOGPS
logP0.13ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)3.77ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity33.86 m3·mol-1ChemAxon
Polarizability13.44 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| GC-MS |
GC-MS Spectrum – GC-MS (2 TMS)splash10-001i-9520000000-b72d86d56071d93045ebView in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 10V, Positive (Annotated)splash10-002b-5900000000-52bf89bad5493c7c19ffView in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 25V, Positive (Annotated)splash10-0f6t-9400000000-7dcf6eefa47e7232ce6aView in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 40V, Positive (Annotated)splash10-0a4i-9200000000-0a3de47a77158e217f70View in MoNA
| 1D NMR |
1H NMR SpectrumNot Available
| 2D NMR |
[1H,13C] 2D NMR SpectrumNot Available
| Biological Properties |
| Cellliar Locations |
Extracellliar
Membrane
| Biofluid Locations |
Not Available
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Not Available |
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| 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 |
FDB022011
| KNApSAcK ID |
Not Available
| Chemspider ID |
4508880
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB00393
| Metagene Link |
HMDB00393
| METLIN ID |
5382
| PubChem Compound |
5351896
| PDB ID |
Not Available
| ChEBI ID |
Not Available
Product: SQ22536
References |
| Synthesis Reference |
Stille, J. K. Carbonylation of diolefins. Belg. (1979), 19 pp. CODEN: BEXXAL BE 877770 19791116 CAN 92:214907 AN 1980:214907 |
| Material Safety Data Sheet (MSDS) |
Download (PDF) |
| General References |
- Tserng KY, Jin SJ: Metabolic origin of urinary 3-hydroxy dicarboxylic acids. Biochemistry. 1991 Mar 5;30(9):2508-14. [PubMed:2001377 ]
- Jin SJ, Tserng KY: Identification of isomeric unsaturated medium-chain dicarboxylic acids in human urine. J Lipid Res. 1989 Oct;30(10):1611-9. [PubMed:2614263 ]
- Tanaka K, Hine DG: Compilation of gas chromatographic retention indices of 163 metabolically important organic acids, and their use in detection of patients with organic acidurias. J Chromatogr. 1982 Apr 30;239:301-22. [PubMed:7096501 ]
|
PMID: 25928636