Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:24 UTC
HMDB IDHMDB0004980
Secondary Accession Numbers
  • HMDB04980
Metabolite Identification
Common Namecis-4-Decenoic acid
Descriptioncis-4-Decenoic acid, also known as obtusilic acid, 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. cis-4-Decenoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 4-Decenoic acid (and other intermediates of unsaturated fatty acid oxidation) has been found in increased amounts in liver, skeletal muscle, and heart obtained post mortem from patients with medium-chain acyl-CoA dehydrogenase deficiency (MCADD), multiple acyl-CoA dehydrogenase deficiency (MADD), and very-long-chain acyl-CoA dehydrogenase deficiency (VLCADD) (PMID: 11486898 ).
Structure
Data?1584718978
Synonyms
ValueSource
(Z)-4-Decenoic acidChEBI
10:1 (N-6)ChEBI
4-Decenoic acidChEBI
C10:1 (N-6)ChEBI
cis-Decen-4-saeureChEBI
cis-Delta(4)-Decenoic acidChEBI
cis-Obtusilic acidChEBI
Dec-4C-enoic acidChEBI
Dec-4C-ensaeureChEBI
Z-4-Decenoic acidChEBI
(Z)-4-DecenoateGenerator
4-DecenoateGenerator
cis-delta(4)-DecenoateGenerator
cis-Δ(4)-decenoateGenerator
cis-Δ(4)-decenoic acidGenerator
cis-ObtusilateGenerator
Dec-4C-enoateGenerator
Z-4-DecenoateGenerator
cis-4-DecenoateGenerator
(4Z)-4-Decenoic acidHMDB
4-cis-Decenoic acidHMDB
FA(10:1(4Z))HMDB
FA(10:1n6)HMDB
Obtusilic acidHMDB
cis-4-Decenoic acidHMDB
Dec-4-enoic acidMeSH, HMDB
(Z)-Isomer OF 4-decenoic acidMeSH, HMDB
Chemical FormulaC10H18O2
Average Molecular Weight170.2487
Monoisotopic Molecular Weight170.13067982
IUPAC Name(4Z)-dec-4-enoic acid
Traditional Name4-decenoic acid
CAS Registry Number505-90-8
SMILES
CCCCC\C=C/CCC(O)=O
InChI Identifier
InChI=1S/C10H18O2/c1-2-3-4-5-6-7-8-9-10(11)12/h6-7H,2-5,8-9H2,1H3,(H,11,12)/b7-6-
InChI KeyXKZKQTCECFWKBN-SREVYHEPSA-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
  • 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
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point4 - 5 °CNot Available
Boiling Point274.00 to 275.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility86.48 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP3.531 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.17 g/LALOGPS
logP3.74ALOGPS
logP3.23ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)4.88ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity50.59 m³·mol⁻¹ChemAxon
Polarizability20.34 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+144.44331661259
DarkChem[M-H]-141.56431661259
DeepCCS[M+H]+141.13530932474
DeepCCS[M-H]-137.18630932474
DeepCCS[M-2H]-174.5430932474
DeepCCS[M+Na]+149.96430932474
AllCCS[M+H]+142.832859911
AllCCS[M+H-H2O]+138.932859911
AllCCS[M+NH4]+146.532859911
AllCCS[M+Na]+147.532859911
AllCCS[M-H]-144.932859911
AllCCS[M+Na-2H]-146.632859911
AllCCS[M+HCOO]-148.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
cis-4-Decenoic acidCCCCC\C=C/CCC(O)=O2254.3Standard polar33892256
cis-4-Decenoic acidCCCCC\C=C/CCC(O)=O1321.3Standard non polar33892256
cis-4-Decenoic acidCCCCC\C=C/CCC(O)=O1381.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
cis-4-Decenoic acid,1TMS,isomer #1CCCCC/C=C\CCC(=O)O[Si](C)(C)C1433.6Semi standard non polar33892256
cis-4-Decenoic acid,1TBDMS,isomer #1CCCCC/C=C\CCC(=O)O[Si](C)(C)C(C)(C)C1661.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - cis-4-Decenoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-01tm-9400000000-36a8487fe819a421026e2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cis-4-Decenoic acid GC-MS (1 TMS) - 70eV, Positivesplash10-05i9-9400000000-8a7c856ad8f6634c8e492017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cis-4-Decenoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - cis-4-Decenoic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-006x-1900000000-e7f197c7f942b20c0d372012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - cis-4-Decenoic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-006x-9000000000-48fc9e85d63ef85b36342012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - cis-4-Decenoic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0006-9000000000-1bbeba801e2897d3fd9c2012-07-25HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-4-Decenoic acid 10V, Positive-QTOFsplash10-0udi-0900000000-84157360a2e34971d8de2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-4-Decenoic acid 20V, Positive-QTOFsplash10-0fi0-5900000000-0834c738729a41f426172017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-4-Decenoic acid 40V, Positive-QTOFsplash10-052f-9000000000-e06b56ca908b5719c2ef2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-4-Decenoic acid 10V, Negative-QTOFsplash10-014i-0900000000-261549081e16976cd4512017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-4-Decenoic acid 20V, Negative-QTOFsplash10-0gdi-0900000000-36c42aa6b2658f235cd62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-4-Decenoic acid 40V, Negative-QTOFsplash10-0a4l-9300000000-52dff0f129f25cf3bbf32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-4-Decenoic acid 10V, Positive-QTOFsplash10-001i-9200000000-66715f0b11abb1c679342021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-4-Decenoic acid 20V, Positive-QTOFsplash10-0api-9000000000-4b265c21a5d85754c3e22021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-4-Decenoic acid 40V, Positive-QTOFsplash10-0a4l-9000000000-6146f9a54421c3ec50802021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-4-Decenoic acid 10V, Negative-QTOFsplash10-014i-0900000000-efbd93a1a83feefc94df2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-4-Decenoic acid 20V, Negative-QTOFsplash10-014i-1900000000-58fa8a77229ea11a94a22021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-4-Decenoic acid 40V, Negative-QTOFsplash10-0006-9000000000-b9a85e335fe2078952a92021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue Locations
  • Heart
  • Liver
  • Skeletal Muscle
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB002991
KNApSAcK IDNot Available
Chemspider ID4471776
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID7233
PubChem Compound5312351
PDB IDNot Available
ChEBI ID32380
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1546481
References
Synthesis ReferenceDe Klein, W. J. Copper(II)-catalyzed formation of decenoic acids from manganese(III) acetate and 1-octene in acetic anhydride/acetic acid mixtures. Recueil des Travaux Chimiques des Pays-Bas (1975), 94(7), 151-3.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Wevers RA, Engelke UF, Moolenaar SH, Brautigam C, de Jong JG, Duran R, de Abreu RA, van Gennip AH: 1H-NMR spectroscopy of body fluids: inborn errors of purine and pyrimidine metabolism. Clin Chem. 1999 Apr;45(4):539-48. [PubMed:10102915 ]
  2. 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 ]