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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:02 UTC
HMDB IDHMDB00603
Secondary Accession NumbersNone
Metabolite Identification
Common Namecis-4-Decenedioic acid
Descriptioncis-4-Decenedioic acid is an unsaturated dicarboxylic acid. Its level increases in patients with medium chain acyl-CoA dehydrogenase deficiency, which is a disorder of fatty acid oxidation.
Structure
Thumb
Synonyms
ValueSource
DecenedioateHMDB
Decenedioic acidHMDB
Chemical FormulaC10H16O4
Average Molecular Weight200.2316
Monoisotopic Molecular Weight200.104859
IUPAC Name(4Z)-dec-4-enedioic acid
Traditional Name(4Z)-dec-4-enedioic acid
CAS Registry Number72879-22-2
SMILES
OC(=O)CCCC\C=C/CCC(O)=O
InChI Identifier
InChI=1S/C10H16O4/c11-9(12)7-5-3-1-2-4-6-8-10(13)14/h1,3H,2,4-8H2,(H,11,12)(H,13,14)/b3-1-
InChI KeyInChIKey=CXGDCGIPEJKSCK-IWQZZHSRSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point133 - 137 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.31 mg/mLALOGPS
logP1.83ALOGPS
logP1.91ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)4.65ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity52.26 m3·mol-1ChemAxon
Polarizability21.3 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified1.00 (0.00-2.00) umol/mmol creatinineAdult (>18 years old)BothMedium Chain Acyl-CoA Dehydrogenase Deficiency details
UrineDetected and Quantified375.00 (0.00-750.00) umol/mmol creatinineChildren (1-13 years old)BothMedium chain acyl-CoA dehydrogenase deficiency (MCAD) details
Associated Disorders and Diseases
Disease References
Medium Chain Acyl-CoA Dehydrogenase Deficiency
  1. MetaGene [Link]
Maple syrup urine disease
  1. MetaGene [Link]
Associated OMIM IDs
  • 201450 (Medium Chain Acyl-CoA Dehydrogenase Deficiency)
  • 248600 (Maple syrup urine disease)
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022138
KNApSAcK IDNot Available
Chemspider ID7822621
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00603
Metagene LinkHMDB00603
METLIN ID5578
PubChem Compound9543671
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferencePourfarzam, Morteza; Bartlett, Kim. Synthesis, characterization and high-performance liquid chromatography of C6-C16 dicarboxylyl-mono-coenzyme A and -mono-carnitine esters. Journal of Chromatography (1991), 570(2), 253-76.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available