| Common Name |
2-Octenedioic acid
| Description |
2-Octenedioic acid is an unsaturated dicarboxylic acid found in the urine of persons with abnormal fatty acid metabolism, such as patients with Dicarboxylic aciduria (PMID 2094705 , 2614263 ).
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
1-Hexene-1,6-dicarboxylateHMDB
1-Hexene-1,6-dicarboxylic acidHMDB
2-OctenedioateHMDB
| Chemical Formlia |
C8H12O4
| Average Molecliar Weight |
172.1785
| Monoisotopic Molecliar Weight |
172.073558872
| IUPAC Name |
(2E)-oct-2-enedioic acid
| Traditional Name |
(E)-oct-2-enedioic acid
| CAS Registry Number |
5698-50-0
| SMILES |
OC(=O)CCCCC=CC(O)=O
| InChI Identifier |
InChI=1S/C8H12O4/c9-7(10)5-3-1-2-4-6-8(11)12/h3,5H,1-2,4,6H2,(H,9,10)(H,11,12)/b5-3+
| InChI Key |
BNTPVRGYUHJFHN-HWKANZROSA-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 |
Not Available
| 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 PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility2.06 mg/mLALOGPS
logP1.14ALOGPS
logP1.38ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)4.15ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity43.03 m3·mol-1ChemAxon
Polarizability17.61 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, Positive (Annotated)splash10-000i-2900000000-9b5e8c7acbeffa7a7bffView in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 25V, Positive (Annotated)splash10-001i-9000000000-aa84fcbe642b74aa9e12View in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 40V, Positive (Annotated)splash10-016u-9000000000-a9bca1da2edcacdb888aView in MoNA
| 1D NMR |
1H NMR SpectrumNot Available
| Biological Properties |
| Cellliar Locations |
Extracellliar
Membrane
| Biofluid Locations |
Urine
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Not Available |
| Abnormal Concentrations |
|
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
UrineDetected and Quantified7.00 umol/mmol creatinineAdlit (>18 years old)BothMedium Chain Acyl-CoA Dehydrogenase Deficiency
MetaGene
details
UrineDetected and Quantified125.00 (0.00-250.00) umol/mmol creatinineChildren (1-13 years old)BothMedium chain acyl-CoA dehydrogenase deficiency (MCAD)
MetaGene
details
| Associated Disorders and Diseases |
| Disease References |
| Medium Chain Acyl-CoA Dehydrogenase Deficiency |
- MetaGene [Link]
| Associated OMIM IDs |
201450 (Medium Chain Acyl-CoA Dehydrogenase Deficiency)
| 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 |
FDB021965
| KNApSAcK ID |
Not Available
| Chemspider ID |
4800646
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB00341
| Metagene Link |
HMDB00341
| METLIN ID |
5330
| PubChem Compound |
6079438
| PDB ID |
Not Available
| ChEBI ID |
Not Available
Product: BAY1217389
References |
| Synthesis Reference |
Takada, Kenichi; Ouchi, Shiro; Mineshita, Tetsuo; Hirose, Katsumi. Diuretic action of aliphatic unsaturated dicarboxylic acids. Ann. Repts. Shionogi Research Lab. (1955), No. 5 17-24. |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
- Pitt JJ: Gas chromatographic-mass spectrometric characterisation of unsaturated dicarboxylic acids in urine. J Chromatogr. 1990 Dec 14;534:182-9. [PubMed:2094705 ]
- 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 ]
|
PMID: 6118436