| Common Name |
5-Tetradecenoic acid
| Description |
5-Tetradecenoic acid is an intermediate of unsaturated fatty acid metabolism found in plasma of patients with very-long-chain acyl-CoA dehydrogenase (VLCAD) deficiency (PMID 7586519 ).
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
5-TetradecenoateHMDB
PhyseterateHMDB
Physeteric acidHMDB
PhysoterateHMDB
Physoteric acidHMDB
| Chemical Formlia |
C14H26O2
| Average Molecliar Weight |
226.355
| Monoisotopic Molecliar Weight |
226.193280076
| IUPAC Name |
(5E)-tetradec-5-enoic acid
| Traditional Name |
physeteric acid
| CAS Registry Number |
544-66-1
| SMILES |
CCCCCCCCC=CCCCC(O)=O
| InChI Identifier |
InChI=1S/C14H26O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h9-10H,2-8,11-13H2,1H3,(H,15,16)/b10-9+
| InChI Key |
AFGUVBVUFZMJMX-MDZDMXLPSA-N
| Chemical Taxonomy |
| Description |
This compound belongs to the class of chemical entities known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
| Kingdom |
Chemical entities
| Super Class |
Organic compounds
| Class |
Lipids and lipid-like moleclies
| Sub Class |
Fatty Acyls
| Direct Parent |
Long-chain fatty acids
| Alternative Parents |
Unsaturated fatty acids
Straight chain fatty acids
Monocarboxylic acids and derivatives
Carboxylic acids
Organic oxides
Hydrocarbon derivatives
Carbonyl compounds
| Substituents |
Long-chain fatty acid
Unsaturated fatty acid
Straight chain fatty acid
Monocarboxylic 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 |
Unsaturated fatty acids (LMFA01030913 )
| 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 |
Cytoplasm
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 Solubility0.0018 mg/mLALOGPS
logP5.77ALOGPS
logP5.01ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)4.89ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity69 m3·mol-1ChemAxon
Polarizability29.14 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
Not Available
| Biological Properties |
| Cellliar Locations |
Cytoplasm
Extracellliar
Membrane
| Biofluid Locations |
Blood
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
BloodDetected and Quantified1.5 (0.6 – 2.3) uMAdlit (>18 years old)BothNormal
7586519
details
|
| Abnormal Concentrations |
|
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
BloodDetected and Quantified50.0 (14.3 – 84.0) uMAdlit (>18 years old)Not SpecifiedVery long-chain acyl-CoA dehydrogenase deficiency (vLCAD)
7586519
details
| Associated Disorders and Diseases |
| Disease References |
| Very Long Chain Acyl-CoA Dehydrogenase Deficiency |
- Onkenhout W, Venizelos V, van der Poel PF, van den Heuvel MP, Poorthuis BJ: Identification and quantification of intermediates of unsaturated fatty acid metabolism in plasma of patients with fatty acid oxidation disorders. Clin Chem. 1995 Oct;41(10):1467-74. [PubMed:7586519 ]
| 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 |
FDB022078
| KNApSAcK ID |
Not Available
| Chemspider ID |
4445867
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB00499
| Metagene Link |
HMDB00499
| METLIN ID |
5485
| PubChem Compound |
5282740
| PDB ID |
Not Available
| ChEBI ID |
Not Available
Product: NSC23005 (sodium)
References |
| Synthesis Reference |
Toyama, Yoshiyuki; Tsuchiya, Tomotaro. The separation of physeteric acid from sardine and pilot-whale oils. Kogyo Kagaku Zasshi (1935), 38 Suppl. binding 680-4. |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
- Lee SH, Nam SY, Chung BC: Altered profile of endogenous steroids in the urine of patients with prolactinoma. Clin Biochem. 1998 Oct;31(7):529-35. [PubMed:9812172 ]
- Onkenhout W, Venizelos V, van der Poel PF, van den Heuvel MP, Poorthuis BJ: Identification and quantification of intermediates of unsaturated fatty acid metabolism in plasma of patients with fatty acid oxidation disorders. Clin Chem. 1995 Oct;41(10):1467-74. [PubMed:7586519 ]
- Onkenhout W, Venizelos V, Scholte HR, De Klerk JB, Poorthuis BJ: Intermediates of unsaturated fatty acid oxidation are incorporated in triglycerides but not in phospholipids in tissues from patients with mitochondrial beta-oxidation defects. J Inherit Metab Dis. 2001 Jun;24(3):337-44. [PubMed:11486898 ]
|
PMID: 23776393