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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:14:55 UTC
HMDB IDHMDB0000529
Secondary Accession Numbers
  • HMDB00529
Metabolite Identification
Common Name5Z-Dodecenoic acid
Description5Z-Dodecenoic acid, also known as 5-dodecenoic acid or 5-dodecenoate, is a monounsaturated fatty acid that has a C12 chain as a backbone and a cis double bond at the C5 position. 5-Dodecenoic 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, 5-dodecenoic acid is considered to be a fatty acid lipid molecule. 5-Dodecenoic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Within the cell, 5-dodecenoic acid is primarily located in the cytoplasm and in the membrane (predicted from logP). It can also be found in the extracellular space. An increase of 5-dodecenoic acid in plasma is associated with acyl-CoA dehydrogenase deficiency disorders (PMID: 7586519 ). 5-Dodecenoic acid is an intermediate of unsaturated fatty acid oxidation.
Structure
Data?1676999695
Synonyms
ValueSource
5Z-DodecenoateGenerator
cis-5-Dodecanoic acidHMDB
cis-5-DodecanoateHMDB
5-DodecenoateHMDB
(Z)-5-DodecenoateHMDB
(Z)-5-Dodecenoic acidHMDB
cis-5-DodecenoateHMDB
cis-5-Dodecenoic acidHMDB
5-Dodecenoic acid, (e)-isomerHMDB
(Z)-Dodec-5-enoic acidHMDB
(Z)-Dodec-5-enoateHMDB
5-Dodecenoic acidHMDB
FA(12:1(5Z))HMDB
LauroleinateHMDB
Chemical FormulaC12H22O2
Average Molecular Weight198.3019
Monoisotopic Molecular Weight198.161979948
IUPAC Name(5Z)-dodec-5-enoic acid
Traditional Namecis-5-dodecenoic acid
CAS Registry Number2430-94-6
SMILES
CCCCCC\C=C/CCCC(O)=O
InChI Identifier
InChI=1S/C12H22O2/c1-2-3-4-5-6-7-8-9-10-11-12(13)14/h7-8H,2-6,9-11H2,1H3,(H,13,14)/b8-7-
InChI KeyIJBFSOLHRKELLR-FPLPWBNLSA-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 effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility9.12 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.014 g/LALOGPS
logP4.76ALOGPS
logP4.12ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)4.89ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity59.8 m³·mol⁻¹ChemAxon
Polarizability24.53 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]+152.69931661259
DarkChem[M-H]-151.82531661259
AllCCS[M+H]+151.58332859911
AllCCS[M-H]-154.19432859911
DeepCCS[M+H]+151.67430932474
DeepCCS[M-H]-147.65230932474
DeepCCS[M-2H]-184.98930932474
DeepCCS[M+Na]+160.730932474
AllCCS[M+H]+151.632859911
AllCCS[M+H-H2O]+147.932859911
AllCCS[M+NH4]+155.032859911
AllCCS[M+Na]+156.032859911
AllCCS[M-H]-154.232859911
AllCCS[M+Na-2H]-155.632859911
AllCCS[M+HCOO]-157.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5Z-Dodecenoic acidCCCCCC\C=C/CCCC(O)=O2470.9Standard polar33892256
5Z-Dodecenoic acidCCCCCC\C=C/CCCC(O)=O1512.8Standard non polar33892256
5Z-Dodecenoic acidCCCCCC\C=C/CCCC(O)=O1567.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5Z-Dodecenoic acid,1TMS,isomer #1CCCCCC/C=C\CCCC(=O)O[Si](C)(C)C1632.0Semi standard non polar33892256
5Z-Dodecenoic acid,1TBDMS,isomer #1CCCCCC/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C1863.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5Z-Dodecenoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-006y-9400000000-be74e2fc0cdc2b7203712017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5Z-Dodecenoic acid GC-MS (1 TMS) - 70eV, Positivesplash10-00g0-9410000000-6cb8de227b6d4df874622017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5Z-Dodecenoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5Z-Dodecenoic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 5Z-Dodecenoic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-0002-0900000000-0595064371d8113849942012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5Z-Dodecenoic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-0ue9-9000000000-5e1def8a1e91f104f8422012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5Z-Dodecenoic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-052f-9000000000-3b712e035428ab40397e2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5Z-Dodecenoic acid LC-ESI-IT , negative-QTOFsplash10-004j-0900000000-83d009697d36f3133e612017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5Z-Dodecenoic acid 10V, Positive-QTOFsplash10-001i-0900000000-388eff95f6fd8d3c51622017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5Z-Dodecenoic acid 20V, Positive-QTOFsplash10-0uea-5900000000-abd50acd5570c287da782017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5Z-Dodecenoic acid 40V, Positive-QTOFsplash10-052f-9100000000-479174b0202d5f68da962017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5Z-Dodecenoic acid 10V, Negative-QTOFsplash10-0002-0900000000-6f54777d936691c9bfda2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5Z-Dodecenoic acid 20V, Negative-QTOFsplash10-0f92-0900000000-fda6eb3ba6b6b80c993d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5Z-Dodecenoic acid 40V, Negative-QTOFsplash10-0a4l-9400000000-bce054e6f671c994402d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5Z-Dodecenoic acid 10V, Positive-QTOFsplash10-05o1-9400000000-1f3d0b87a45501aa1fc32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5Z-Dodecenoic acid 20V, Positive-QTOFsplash10-067i-9000000000-5fcfe484bbebcea8d06b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5Z-Dodecenoic acid 40V, Positive-QTOFsplash10-05mo-9000000000-3ef8db38d4b48c8dc8a82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5Z-Dodecenoic acid 10V, Negative-QTOFsplash10-0002-0900000000-aa5836824e9f1acfafc12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5Z-Dodecenoic acid 20V, Negative-QTOFsplash10-0a4j-9700000000-d040576af376d0a96bda2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5Z-Dodecenoic acid 40V, Negative-QTOFsplash10-0006-9200000000-8dcb6b5a1d6c47210b8f2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)2012-12-05Wishart 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
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022097
KNApSAcK IDNot Available
Chemspider ID4471803
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5514
PubChem Compound5312378
PDB IDNot Available
ChEBI ID86595
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1587421
References
Synthesis ReferenceRock, Charles O.; Garwin, Jeffrey L.; Cronan, John E., Jr. Preparative enzymic synthesis of acyl-acyl carrier protein. Methods in Enzymology (1981), 72(Lipids, Part D), 397-403.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]