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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2009-11-30 15:51:19 UTC
Update Date2019-07-23 05:58:40 UTC
HMDB IDHMDB0013227
Secondary Accession Numbers
  • HMDB13227
Metabolite Identification
Common Namecis-5-Decenedioic acid
Descriptioncis-5-Decenedioic acid is a mono-unsaturated dicarboxylic acid. The dicarboxylic acid can be grouped into two metabolic series: the cis-4 series as well as the cis-3 and cis-5 series. The metabolic precursor of cis-5 unsaturated dicarboxylic acid is oleic acid (PMID: 2380628 ). cis-5-Decenedioic acid is found to be associated with medium chain acyl-CoA dehydrogenase deficiency, which is an inborn error of metabolism.
Structure
Data?1563861520
Synonyms
ValueSource
cis-5-DecenedioateGenerator
cis-5-Decene -1,10-dioateHMDB
cis-5-Decene -1,10-dioic acidHMDB
cis-5-Decene-1,10-dioiateHMDB
cis-5-DecenedioiateHMDB
(5Z)-Dec-5-enedioateGenerator
Chemical FormulaC10H16O4
Average Molecular Weight200.2316
Monoisotopic Molecular Weight200.104859
IUPAC Name(5Z)-dec-5-enedioic acid
Traditional Name(5Z)-dec-5-enedioic acid
CAS Registry NumberNot Available
SMILES
OC(=O)CCC\C=C/CCCC(O)=O
InChI Identifier
InChI=1S/C10H16O4/c11-9(12)7-5-3-1-2-4-6-8-10(13)14/h1-2H,3-8H2,(H,11,12)(H,13,14)/b2-1-
InChI KeyWAGQZQAZCIOEDU-UPHRSURJSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMedium-chain fatty acids
Alternative Parents
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
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.4 g/LALOGPS
logP1.79ALOGPS
logP1.91ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)4.65ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity52.26 m³·mol⁻¹ChemAxon
Polarizability21.39 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9600000000-66e34dcd8198f1da77fcJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00g0-9440000000-33f32e4f7839619d2529JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f89-0930000000-4a572681ea1fff177879JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0kai-3910000000-70fd1bd64c0633ba8ed8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0arv-9200000000-9ed044852e545972874dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-6338176fb1c0f3c4c485JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0532-0900000000-c043bf389b4daa63df25JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9400000000-34e9ef670320b615cdb8JSpectraViewer
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
details
UrineDetected and Quantified0 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
details
UrineDetected and Quantified1.129 +/- 1.694 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
details
UrineDetected and Quantified21.457 +/- 19.198 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
details
UrineDetected and Quantified6.776 +/- 3.388 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
details
UrineDetected and Quantified9.0343 +/- 3.953 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified10.164 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Medium Chain Acyl-CoA Dehydrogenase Deficiency
details
UrineDetected and Quantified11.858 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Medium Chain Acyl-CoA Dehydrogenase Deficiency
details
UrineDetected and Quantified46.866 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Medium Chain Acyl-CoA Dehydrogenase Deficiency
details
UrineDetected and Quantified171.652 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Medium Chain Acyl-CoA Dehydrogenase Deficiency
details
Associated Disorders and Diseases
Disease References
Medium Chain Acyl-CoA Dehydrogenase Deficiency
  1. Tserng KY, Jin SJ, Kerr DS, Hoppel CL: Abnormal urinary excretion of unsaturated dicarboxylic acids in patients with medium-chain acyl-CoA dehydrogenase deficiency. J Lipid Res. 1990 May;31(5):763-71. [PubMed:2380628 ]
Associated OMIM IDs
  • 201450 (Medium Chain Acyl-CoA Dehydrogenase Deficiency)
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB029345
KNApSAcK IDNot Available
Chemspider ID5880465
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound7563148
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Tserng KY, Jin SJ, Kerr DS, Hoppel CL: Abnormal urinary excretion of unsaturated dicarboxylic acids in patients with medium-chain acyl-CoA dehydrogenase deficiency. J Lipid Res. 1990 May;31(5):763-71. [PubMed:2380628 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  4. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.