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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2008-10-15 12:12:16 UTC
Update Date2020-02-26 21:34:27 UTC
HMDB IDHMDB0010735
Secondary Accession Numbers
  • HMDB10735
Metabolite Identification
Common NameTrans-Hexa-dec-2-enoic acid
DescriptionIn humans fatty acids are predominantly formed in the liver and adipose tissue, and mammary glands during lactation. Trans-hexa-dec-2-enoic acid is an intermediate in fatty acid biosynthesis. Specifically, trans-hexa-dec-2-enoic acid converted from (R)-3-Hydroxy-hexadecanoic 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?1582752867
Synonyms
ValueSource
(2E)-Hexadecenoic acidChEBI
(e)-2-Hexadecenoic acidChEBI
2-Palmitoleic acidChEBI
2-trans-Hexadecenoic acidChEBI
Gaidic acidChEBI
t-16:1D2ChEBI
t-2-Hexadecenoic acidChEBI
trans-2-Hexadecenoic acidChEBI
trans-Delta(2)-Hexadecenoic acidChEBI
trans-Hexadec-2-enoic acidChEBI
(2E)-HexadecenoateGenerator
(e)-2-HexadecenoateGenerator
2-PalmitoleateGenerator
2-trans-HexadecenoateGenerator
GaidateGenerator
t-2-HexadecenoateGenerator
trans-2-HexadecenoateGenerator
trans-delta(2)-HexadecenoateGenerator
trans-Δ(2)-hexadecenoateGenerator
trans-Δ(2)-hexadecenoic acidGenerator
trans-Hexadec-2-enoateGenerator
trans-Hexa-dec-2-enoateGenerator
Hexadecenoic acid, (e)-isomerHMDB
cis-Hexadecenoic acidHMDB
Hexadecenoic acidHMDB
Hexadecenoic acid, (Z)-isomerHMDB
trans-Hexadecenoic acidHMDB
Chemical FormulaC16H30O2
Average Molecular Weight254.4082
Monoisotopic Molecular Weight254.224580204
IUPAC Name(2E)-hexadec-2-enoic acid
Traditional Namehexadecenoic acid
CAS Registry NumberNot Available
SMILES
[H]\C(CCCCCCCCCCCCC)=C(\[H])C(O)=O
InChI Identifier
InChI=1S/C16H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h14-15H,2-13H2,1H3,(H,17,18)/b15-14+
InChI KeyZVRMGCSSSYZGSM-CCEZHUSRSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentLong-chain fatty acids
Alternative Parents
Substituents
  • Long-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

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00022 g/LALOGPS
logP6.25ChemAxon
pKa (Strongest Acidic)5.03ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity78.18 m³·mol⁻¹ChemAxon
Polarizability33.74 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-017j-5900000000-58442a5c08ea8c4926d0Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-017j-5900000000-58442a5c08ea8c4926d0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01p6-9820000000-ca98f4a0dd8ff557bc6cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-022i-9551000000-39e4b8ad34555c61b4adSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-0190000000-1228a4503bc27bed1ebfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-3960000000-1370ead704dcac4cec1fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9700000000-85e6708e40be2971ffc9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-bb3d892e7f48a711d0ceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfr-0090000000-6a46dea6de3429b73374Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9440000000-668a65146f3042b031deSpectrum
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 IDFDB027882
KNApSAcK IDNot Available
Chemspider ID4445870
KEGG Compound IDNot Available
BioCyc IDCPD-9768
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5282743
PDB IDNot Available
ChEBI ID37252
Food Biomarker OntologyNot Available
VMH 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