Hmdb loader
Survey
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:14:58 UTC
HMDB IDHMDB0000603
Secondary Accession Numbers
  • HMDB00603
Metabolite Identification
Common Namecis-4-Decenedioic acid
Descriptioncis-4-Decenedioic acid is a member of the class of compounds known as medium-chain fatty acids. Medium-chain fatty acids are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Thus, cis-4-decenedioic acid is considered to be a fatty acid lipid molecule. Cis-4-decenedioic acid is slightly soluble (in water) and a weakly acidic compound (based on its pKa). Cis-4-decenedioic acid can be found primarily in urine. Within the cell, cis-4-decenedioic acid is primarily located in the membrane. It can also be found in the extracellular space. Moreover, cis-4-decenedioic acid is an unsaturated dicarboxylic acid. Its level increases in patients with medium chain acyl-CoA dehydrogenase deficiency (MCADD), which is a genetic disorder of fatty acid oxidation.
Structure
Data?1676999698
Synonyms
ValueSource
cis-4-DecenedioateGenerator
DecenedioateHMDB
Decenedioic acidHMDB
4Z-DecenedioateHMDB
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 KeyCXGDCGIPEJKSCK-IWQZZHSRSA-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 Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point133 - 137 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2219 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.31 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity52.26 m³·mol⁻¹ChemAxon
Polarizability21.3 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+148.10831661259
DarkChem[M-H]-145.19731661259
AllCCS[M+H]+145.93232859911
AllCCS[M-H]-147.75432859911
DeepCCS[M+H]+143.84930932474
DeepCCS[M-H]-140.02230932474
DeepCCS[M-2H]-177.36530932474
DeepCCS[M+Na]+152.96830932474
AllCCS[M+H]+145.932859911
AllCCS[M+H-H2O]+142.332859911
AllCCS[M+NH4]+149.332859911
AllCCS[M+Na]+150.332859911
AllCCS[M-H]-147.832859911
AllCCS[M+Na-2H]-148.932859911
AllCCS[M+HCOO]-150.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
cis-4-Decenedioic acidOC(=O)CCCC\C=C/CCC(O)=O2800.0Standard polar33892256
cis-4-Decenedioic acidOC(=O)CCCC\C=C/CCC(O)=O1517.2Standard non polar33892256
cis-4-Decenedioic acidOC(=O)CCCC\C=C/CCC(O)=O1758.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
cis-4-Decenedioic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)CCCC/C=C\CCC(=O)O1818.0Semi standard non polar33892256
cis-4-Decenedioic acid,1TMS,isomer #2C[Si](C)(C)OC(=O)CC/C=C\CCCCC(=O)O1815.9Semi standard non polar33892256
cis-4-Decenedioic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)CC/C=C\CCCCC(=O)O[Si](C)(C)C1858.7Semi standard non polar33892256
cis-4-Decenedioic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCCC/C=C\CCC(=O)O2064.0Semi standard non polar33892256
cis-4-Decenedioic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)CC/C=C\CCCCC(=O)O2060.3Semi standard non polar33892256
cis-4-Decenedioic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CC/C=C\CCCCC(=O)O[Si](C)(C)C(C)(C)C2301.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - cis-4-Decenedioic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-03du-9700000000-07830e9f3f9a840f091a2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cis-4-Decenedioic acid GC-MS (2 TMS) - 70eV, Positivesplash10-024r-9350000000-da48b99466787e064f122017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cis-4-Decenedioic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cis-4-Decenedioic acid GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cis-4-Decenedioic acid GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cis-4-Decenedioic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cis-4-Decenedioic acid GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cis-4-Decenedioic acid GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-4-Decenedioic acid 10V, Positive-QTOFsplash10-0ue9-0970000000-fb6c6e0c574717d4c7c62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-4-Decenedioic acid 20V, Positive-QTOFsplash10-0pc0-2910000000-95e303b11e1378f5fdf72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-4-Decenedioic acid 40V, Positive-QTOFsplash10-0pdm-9200000000-15b9cbd73cfb4aa2d14e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-4-Decenedioic acid 10V, Negative-QTOFsplash10-0002-0900000000-ca695b2f3c782ac1f4982016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-4-Decenedioic acid 20V, Negative-QTOFsplash10-052b-1900000000-1e03131c7d34ca653c8f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-4-Decenedioic acid 40V, Negative-QTOFsplash10-0a4i-9300000000-3f7209a9d4bd721de5002016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-4-Decenedioic acid 10V, Negative-QTOFsplash10-0002-0900000000-4c0d3eb1a42e0b1c738c2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-4-Decenedioic acid 20V, Negative-QTOFsplash10-053r-1900000000-cc2af103d9f28c259d972021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-4-Decenedioic acid 40V, Negative-QTOFsplash10-0a4l-9300000000-cd5ea3dda94814b234002021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-4-Decenedioic acid 10V, Positive-QTOFsplash10-0f8i-2920000000-4ebbc8b55b7ca1278acf2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-4-Decenedioic acid 20V, Positive-QTOFsplash10-00si-9300000000-2cbdccbc7aaa465bbadd2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-4-Decenedioic acid 40V, Positive-QTOFsplash10-0gb9-9100000000-4e9674a449c76415b2b62021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
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 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 Quantified0 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
details
UrineDetected and Quantified1.129 +/- 2.259 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified25.974 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Medium Chain Acyl-CoA Dehydrogenase Deficiency
details
UrineDetected and Quantified40.655 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Medium Chain Acyl-CoA Dehydrogenase Deficiency
details
UrineDetected and Quantified258.608 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Medium Chain Acyl-CoA Dehydrogenase Deficiency
details
UrineDetected and Quantified787.681 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Medium Chain Acyl-CoA Dehydrogenase Deficiency
details
UrineDetected and Quantified21.821-765.642 umol/mmol creatinineChildren (1-13 years old)Not SpecifiedMedium Chain Acyl-CoA Dehydrogenase Deficiency details
UrineDetected and Quantified1.00 (0.00-2.00) umol/mmol creatinineAdult (>18 years old)BothMedium Chain Acyl-CoA Dehydrogenase Deficiency
    • MetaGene: Metabol...
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 ]
  2. Duran M, De Klerk JB, Wadman SK, Bruinvis L, Ketting D: The differential diagnosis of dicarboxylic aciduria. J Inherit Metab Dis. 1984;7 Suppl 1:48-51. [PubMed:6434845 ]
  3. G.Frauendienst-Egger, Friedrich K. Trefz (2017). MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de). METAGENE consortium.
Associated OMIM IDs
  • 201450 (Medium Chain Acyl-CoA Dehydrogenase Deficiency)
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022138
KNApSAcK IDNot Available
Chemspider ID7822621
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5578
PubChem Compound9543671
PDB IDNot Available
ChEBI ID89730
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000197
Good Scents IDrw1896581
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