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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2008-10-15 12:12:16 UTC
Update Date2020-02-26 21:34:26 UTC
HMDB IDHMDB0010729
Secondary Accession Numbers
  • HMDB10729
Metabolite Identification
Common Nametrans-Dodec-2-enoic acid
DescriptionIn humans fatty acids are predominantly formed in the liver and adipose tissue, and mammary glands during lactation. trans-Dodec-2-enoic acid is an intermediate in fatty acid biosynthesis. Specifically, trans-Dodec-2-enoic acid is converted from (R)-3-Hydroxydodecanoic acid via two enzymes; fatty-acid Synthase and 3-Hydroxypalmitoyl- [acyl-carrier-protein] dehydratase (EC: 2.3.1.85 and EC: 4.2.1.61).
Structure
Data?1582752866
Synonyms
ValueSource
trans-Dodec-2-enoateGenerator
(e)-2-Dodecenoic acidChEBI
12:1, N-10 transChEBI
2-Lauroleic acidChEBI
2t-DodecensaeureChEBI
C12:1, N-10 transChEBI
Dodecen-(2t)-saeureChEBI
trans-2-Lauroleic acidChEBI
(e)-2-DodecenoateGenerator
2-LauroleateGenerator
trans-2-LauroleateGenerator
2-Dodecenoic acidMeSH, HMDB
cis-2-Dodecenoic acidMeSH, HMDB
Chemical FormulaC12H22O2
Average Molecular Weight198.3019
Monoisotopic Molecular Weight198.161979948
IUPAC Name(2E)-dodec-2-enoic acid
Traditional Nametrans-2-dodecenoic acid
CAS Registry NumberNot Available
SMILES
CCCCCCCCC\C=C\C(O)=O
InChI Identifier
InChI=1S/C12H22O2/c1-2-3-4-5-6-7-8-9-10-11-12(13)14/h10-11H,2-9H2,1H3,(H,13,14)/b11-10+
InChI KeyPAWGRNGPMLVJQH-ZHACJKMWSA-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
Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0069 g/LALOGPS
logP10(5.02) g/LALOGPS
logP10(4.48) g/LChemAxon
logS10(-4.5) g/LALOGPS
pKa (Strongest Acidic)5.03ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity59.77 m³·mol⁻¹ChemAxon
Polarizability25.21 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]+153.05131661259
DarkChem[M-H]-150.72231661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
trans-Dodec-2-enoic acidCCCCCCCCC\C=C\C(O)=O2808.9Standard polar33892256
trans-Dodec-2-enoic acidCCCCCCCCC\C=C\C(O)=O1586.3Standard non polar33892256
trans-Dodec-2-enoic acidCCCCCCCCC\C=C\C(O)=O1602.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
trans-Dodec-2-enoic acid,1TMS,isomer #1CCCCCCCCC/C=C/C(=O)O[Si](C)(C)C1704.0Semi standard non polar33892256
trans-Dodec-2-enoic acid,1TBDMS,isomer #1CCCCCCCCC/C=C/C(=O)O[Si](C)(C)C(C)(C)C1925.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - trans-Dodec-2-enoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-01pc-9300000000-9190ae835610331bdeb72016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - trans-Dodec-2-enoic acid GC-MS (1 TMS) - 70eV, Positivesplash10-05gi-9420000000-9048bf27cae23b58433d2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - trans-Dodec-2-enoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-Dodec-2-enoic acid 10V, Positive-QTOFsplash10-000t-0900000000-99a7bfb1c7d055baf0e92016-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-Dodec-2-enoic acid 20V, Positive-QTOFsplash10-0f79-4900000000-8c745f88cb828b378ef92016-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-Dodec-2-enoic acid 40V, Positive-QTOFsplash10-052f-9100000000-466b7d3a1254e4767cd92016-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-Dodec-2-enoic acid 10V, Negative-QTOFsplash10-0002-0900000000-0c8d7f09c44b108a38be2016-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-Dodec-2-enoic acid 20V, Negative-QTOFsplash10-0f6t-0900000000-81b3d360e6e3706e4f642016-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-Dodec-2-enoic acid 40V, Negative-QTOFsplash10-0k96-9500000000-70f6425c9a1fec2038b02016-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-Dodec-2-enoic acid 10V, Negative-QTOFsplash10-0002-0900000000-6d48f46c3035f84784532021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-Dodec-2-enoic acid 20V, Negative-QTOFsplash10-054k-2900000000-d1acac28607e1da289722021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-Dodec-2-enoic acid 40V, Negative-QTOFsplash10-00kf-9400000000-c77534f05234972c52932021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-Dodec-2-enoic acid 10V, Positive-QTOFsplash10-05o0-9200000000-b6a2033a866fbb2519de2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-Dodec-2-enoic acid 20V, Positive-QTOFsplash10-0api-9000000000-8d6482c039e7a2b2d8962021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-Dodec-2-enoic acid 40V, Positive-QTOFsplash10-0aou-9000000000-d672df8a0aecb2bc21462021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
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 IDFDB027876
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

General function:
Involved in transferase activity
Specific function:
Fatty acid synthetase catalyzes the formation of long-chain fatty acids from acetyl-CoA, malonyl-CoA and NADPH. This multifunctional protein has 7 catalytic activities and an acyl carrier protein.
Gene Name:
FASN
Uniprot ID:
P49327
Molecular weight:
273424.06