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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:03 UTC
HMDB IDHMDB0000560
Secondary Accession Numbers
  • HMDB0039129
  • HMDB00560
  • HMDB39129
Metabolite Identification
Common NameGoshuyic acid
DescriptionGoshuyic acid, also known as (Z,Z)-5,8-tetradecadienoic acid, is a member of the class of compounds known as long-chain fatty acids. Long-chain fatty acids are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Goshuyic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Within the cell, goshuyic acid is primarily located in the membrane (predicted from logP). It can also be found in the extracellular space. Goshuyic acid is an intermediate of unsaturated fatty acid oxidation. An increase of goshuyic acid in plasma is associated with acyl-CoA dehydrogenase deficiency disorders (PMID: 7586519 ). Goshuyic acid is found in fats and oils and is a minor constituent of rape oil.
Structure
Data?1582752140
Synonyms
ValueSource
(Z,Z)-5,8-Tetradecadienoic acidChEBI
(Z,Z)-Tetradeca-5,8-dienoic acidChEBI
(cis,cis-delta(5),delta(8))-TetradecanoateGenerator
(cis,cis-Δ(5),δ(8))-tetradecanoateGenerator
(cis,cis-Δ(5),δ(8))-tetradecanoic acidGenerator
(cis-delta(5),cis-delta(8))-TetradecanoateGenerator
(cis-Δ(5),cis-δ(8))-tetradecanoateGenerator
(cis-Δ(5),cis-δ(8))-tetradecanoic acidGenerator
(Z,Z)-5,8-TetradecadienoateGenerator
(Z,Z)-Tetradeca-5,8-dienoateGenerator
GoshuyateGenerator
5,8-TetradecadienoateHMDB
(cis,cis-Δ5,δ8)-tetradecanoic acidHMDB
(cis-Δ5,cis-δ8)-tetradecanoic acidHMDB
(cis,cis-delta5,delta8)-Tetradecanoic acidHMDB
(cis-delta5,cis-delta8)-Tetradecanoic acidHMDB
(5Z,8Z)-5,8-Tetradecadienoic acidHMDB
cis,cis-Tetradeca-5,8-dienoic acidHMDB
5,8-Tetradecadienoic acidHMDB
FA(14:2(5Z,8Z))HMDB
Chemical FormulaC14H24O2
Average Molecular Weight224.3392
Monoisotopic Molecular Weight224.177630012
IUPAC Name(5Z,8Z)-tetradeca-5,8-dienoic acid
Traditional Name(5Z,8Z)-tetradeca-5,8-dienoic acid
CAS Registry Number39039-37-7
SMILES
CCCCC\C=C/C\C=C/CCCC(O)=O
InChI Identifier
InChI=1S/C14H24O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h6-7,9-10H,2-5,8,11-13H2,1H3,(H,15,16)/b7-6-,10-9-
InChI KeyHXHZGHRLVRFQDR-HZJYTTRNSA-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

Biological location

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 Solubility0.0042 g/LALOGPS
logP5.35ALOGPS
logP4.64ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)4.82ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity70.11 m³·mol⁻¹ChemAxon
Polarizability27.53 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]+162.70831661259
DarkChem[M-H]-161.32331661259
AllCCS[M+H]+158.88132859911
AllCCS[M-H]-161.38632859911
DeepCCS[M+H]+162.58630932474
DeepCCS[M-H]-158.56630932474
DeepCCS[M-2H]-195.73730932474
DeepCCS[M+Na]+171.56130932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Goshuyic acidCCCCC\C=C/C\C=C/CCCC(O)=O2819.3Standard polar33892256
Goshuyic acidCCCCC\C=C/C\C=C/CCCC(O)=O1686.7Standard non polar33892256
Goshuyic acidCCCCC\C=C/C\C=C/CCCC(O)=O1753.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Goshuyic acid,1TMS,isomer #1CCCCC/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C1815.5Semi standard non polar33892256
Goshuyic acid,1TBDMS,isomer #1CCCCC/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C2051.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Goshuyic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9800000000-70f7fb8887a89cfdd4ce2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Goshuyic acid GC-MS (1 TMS) - 70eV, Positivesplash10-00g0-9520000000-89f5676bfb6d4fb2807c2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Goshuyic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Goshuyic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Goshuyic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Goshuyic acid 10V, Positive-QTOFsplash10-056r-0390000000-9c40c473d414e0052f162016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Goshuyic acid 20V, Positive-QTOFsplash10-056r-6930000000-baeaeb0eeb65ca411f5b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Goshuyic acid 40V, Positive-QTOFsplash10-052f-9400000000-2ccf4ba98ffea6f7575b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Goshuyic acid 10V, Negative-QTOFsplash10-00di-0190000000-4be544b58785fc9fe7b42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Goshuyic acid 20V, Negative-QTOFsplash10-00fr-1590000000-0cc9e5963e8a02c9a79b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Goshuyic acid 40V, Negative-QTOFsplash10-0a4i-9400000000-156577ed3ac682dbd0972016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Goshuyic acid 10V, Positive-QTOFsplash10-0560-9420000000-5da9b03ee314f3e163e92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Goshuyic acid 20V, Positive-QTOFsplash10-067m-9100000000-76e8cc4c6c9bd8d279b92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Goshuyic acid 40V, Positive-QTOFsplash10-067l-9000000000-f0a2bab062fd7b1916dd2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Goshuyic acid 10V, Negative-QTOFsplash10-00di-0090000000-a15027b0e036a485ad3a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Goshuyic acid 20V, Negative-QTOFsplash10-05fr-1190000000-618d69367ae6d95cfebd2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Goshuyic acid 40V, Negative-QTOFsplash10-052f-9300000000-b32b2c37ff62cf641b602021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • 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 IDFDB018642
KNApSAcK IDNot Available
Chemspider ID4471834
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5544
PubChem Compound5312409
PDB IDNot Available
ChEBI ID70719
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceGuex, Waldemar; Rueegg, Rudolf; Schwieter, Ulrich. Unsaturated alcohols and their esters. (1960), DE 1111615 19600129 CAN 56:31075 AN 1962:31075
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 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.