Hmdb loader
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
StatusExpected but not Quantified
Creation Date2012-09-11 18:33:14 UTC
Update Date2022-03-07 02:53:51 UTC
HMDB IDHMDB0033791
Secondary Accession Numbers
  • HMDB33791
Metabolite Identification
Common Name(E)-3-Hexadecenoic acid
Description(E)-3-Hexadecenoic acid, also known as (e)-3-hexadecenoate, 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. Based on a literature review a small amount of articles have been published on (E)-3-Hexadecenoic acid.
Structure
Data?1563862460
Synonyms
ValueSource
(e)-3-HexadecenoateGenerator
Cistanoside HHMDB
(3Z)-Hexadec-3-enoateGenerator
delta(3)-Hexadecenoic acidMeSH
delta(3)-Hexadecenoic acid, (e)-isomerMeSH
delta(3)-Hexadecenoic acid, (Z)-isomerMeSH
trans-3-Hexadecenoic acidMeSH
Chemical FormulaC16H30O2
Average Molecular Weight254.4082
Monoisotopic Molecular Weight254.224580204
IUPAC Name(3Z)-hexadec-3-enoic acid
Traditional Name(3Z)-hexadec-3-enoic acid
CAS Registry Number1686-10-8
SMILES
CCCCCCCCCCCC\C=C/CC(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/h13-14H,2-12,15H2,1H3,(H,17,18)/b14-13-
InChI KeyPCBKWKNYISJGPJ-YPKPFQOOSA-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 DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point53 - 54 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00032 g/LALOGPS
logP6.99ALOGPS
logP5.89ChemAxon
logS-5.9ALOGPS
pKa (Strongest Acidic)4.83ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity78.2 m³·mol⁻¹ChemAxon
Polarizability33.56 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+167.18631661259
DarkChem[M-H]-169.90831661259
DeepCCS[M+H]+167.76930932474
DeepCCS[M-H]-163.74830932474
DeepCCS[M-2H]-201.3830932474
DeepCCS[M+Na]+177.04430932474
AllCCS[M+H]+169.932859911
AllCCS[M+H-H2O]+166.732859911
AllCCS[M+NH4]+172.932859911
AllCCS[M+Na]+173.832859911
AllCCS[M-H]-171.132859911
AllCCS[M+Na-2H]-172.432859911
AllCCS[M+HCOO]-174.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(E)-3-Hexadecenoic acidCCCCCCCCCCCC\C=C/CC(O)=O2957.5Standard polar33892256
(E)-3-Hexadecenoic acidCCCCCCCCCCCC\C=C/CC(O)=O1901.1Standard non polar33892256
(E)-3-Hexadecenoic acidCCCCCCCCCCCC\C=C/CC(O)=O1962.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(E)-3-Hexadecenoic acid,1TMS,isomer #1CCCCCCCCCCCC/C=C\CC(=O)O[Si](C)(C)C2043.6Semi standard non polar33892256
(E)-3-Hexadecenoic acid,1TBDMS,isomer #1CCCCCCCCCCCC/C=C\CC(=O)O[Si](C)(C)C(C)(C)C2297.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (E)-3-Hexadecenoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4l-9420000000-52bf242119e2863d209f2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (E)-3-Hexadecenoic acid GC-MS (1 TMS) - 70eV, Positivesplash10-0abi-9350000000-8e670a23b682619c70bc2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (E)-3-Hexadecenoic 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 - (E)-3-Hexadecenoic acid 10V, Positive-QTOFsplash10-0a4r-0190000000-4212d741cc1855f248a82016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-3-Hexadecenoic acid 20V, Positive-QTOFsplash10-0a4i-5980000000-8b1b38b8de49af124d7d2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-3-Hexadecenoic acid 40V, Positive-QTOFsplash10-052f-9800000000-c03b8bfc07a1a7c4367e2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-3-Hexadecenoic acid 10V, Negative-QTOFsplash10-0udi-0090000000-68fc29bf138e83cf8c272016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-3-Hexadecenoic acid 20V, Negative-QTOFsplash10-0zfr-1090000000-1552a733fea04f7e753c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-3-Hexadecenoic acid 40V, Negative-QTOFsplash10-0a4i-9220000000-7a6c90b26834388d97f72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-3-Hexadecenoic acid 10V, Negative-QTOFsplash10-0udi-0090000000-3e74125459d9918295122021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-3-Hexadecenoic acid 20V, Negative-QTOFsplash10-0udr-1090000000-5eda65f0bfa5669fc53a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-3-Hexadecenoic acid 40V, Negative-QTOFsplash10-0006-9410000000-e9ed48a2cb1a52ca172b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-3-Hexadecenoic acid 10V, Positive-QTOFsplash10-0a4r-9880000000-9c4a4bc5fb6e06b6c1c92021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-3-Hexadecenoic acid 20V, Positive-QTOFsplash10-0awa-9400000000-d057be790acdac1d26c12021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-3-Hexadecenoic acid 40V, Positive-QTOFsplash10-0aov-9000000000-e7aee17b4e7962519c522021-09-25Wishart 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 IDFDB011951
KNApSAcK IDNot Available
Chemspider ID4511367
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5355370
PDB IDNot Available
ChEBI ID170091
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. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.