13S-hydroxyoctadecadienoic acid (CHEM021778)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:12:15 UTC
Update Date2016-11-09 01:17:21 UTC
Accession NumberCHEM021778
Identification
Common Name13S-hydroxyoctadecadienoic acid
ClassSmall Molecule
DescriptionAn HODE (hydroxyoctadecadienoic acid) in which the double bonds are at positions 9 and 11 (E and Z geometry, respectively) and the hydroxy group is at position 13 (with S-configuration).
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(13S)-Hydroxyoctadecadienoic acidChEBI
(9Z, 11E)-(13S)-13-Hydroxyoctadeca-9,11-dienoic acidChEBI
(9Z,11E)-(13S)-13-Hydroxyoctadeca-9,11-dienoic acidChEBI
(13S)-HydroxyoctadecadienoateGenerator
(9Z, 11E)-(13S)-13-Hydroxyoctadeca-9,11-dienoateGenerator
(9Z,11E)-(13S)-13-Hydroxyoctadeca-9,11-dienoateGenerator
13S-HydroxyoctadecadienoateHMDB
13-Hydroxy-9,11-octadecadienoic acidHMDB
13-Hydroxy-9,11-octadecadienoic acid, (S)-(e,Z)-isomerHMDB
13-Hydroxy-9,11-octadecadienoic acid, (Z,e)-isomerHMDB
13-Hydroxyoctadecadienoic acidHMDB
13-Hydroxy-9,11-octadecadienoic acid, (e,Z)-isomerHMDB
13(S) HODEHMDB
13-HydroxyoctadecadienoateHMDB
(+)-Coriolic acidHMDB
(13S,9Z,11E)-13-Hydroxy-9,11-octadecadienoic acidHMDB
(9Z,11E)-13-Hydroxy-9,11-octadecadienoic acidHMDB
(9Z,11E,13S)-13-Hydroxy-9,11-octadecadienoic acidHMDB
(9Z,11E,13S)-13-Hydroxyoctadecadienoic acidHMDB
(S)-Coriolic acidHMDB
(±)-coriolic acidHMDB
13-Hydroxy-9(Z),11(e)-octadecadienoic acidHMDB
13-Hydroxy-9,11-cis,trans-octadecadienoic acidHMDB
13-Hydroxy-9-cis-11-trans-octadecadienoic acidHMDB
13-Hydroxy-cis-9-trans-11-octadecadienoic acidHMDB
13-Hydroxylinoleic acidHMDB
13-Hydroxyoctadeca-9,11-dienoic acidHMDB
13S-HODEHMDB
13S-Hydroxy-9Z,11E-octadecadienoic acidHMDB
L-13-Hydroxy-cis-9,trans-11-octadecadienoic acidHMDB
alpha-Artemisolic acidHMDB
Α-artemisolic acidHMDB
(9Z,11E,13S)-13-Hydroxyoctadeca-9,11-dienoateHMDB
(9Z,11E)-13-HODEHMDB
(9Z,11E)-13-Hydroxyoctadecadienoic acidHMDB
FA(18:2(9Z,11E,13-OH))HMDB
FA(18:2(9Z,11E,13S-OH))HMDB
13-HODEHMDB, MeSH
Chemical FormulaC18H32O3
Average Molecular Mass296.445 g/mol
Monoisotopic Mass296.235 g/mol
CAS Registry Number5204-88-6
IUPAC Name(9Z,11E,13S)-13-hydroxyoctadeca-9,11-dienoic acid
Traditional Name13-hydroxyoctadecadienoic acid
SMILESCCCCC[C@H](O)\C=C\C=C/CCCCCCCC(O)=O
InChI IdentifierInChI=1S/C18H32O3/c1-2-3-11-14-17(19)15-12-9-7-5-4-6-8-10-13-16-18(20)21/h7,9,12,15,17,19H,2-6,8,10-11,13-14,16H2,1H3,(H,20,21)/b9-7-,15-12+/t17-/m0/s1
InChI KeyHNICUWMFWZBIFP-IRQZEAMPSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassLineolic acids and derivatives
Direct ParentLineolic acids and derivatives
Alternative Parents
Substituents
  • Octadecanoid
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.003 g/LALOGPS
logP5.88ALOGPS
logP5.19ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)4.99ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity90.03 m³·mol⁻¹ChemAxon
Polarizability37.26 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-054k-6960000000-8cc8c4da0c87c3d65f03Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0fbi-9342100000-19627880cd07ec05cb84Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-3ff43b79ccb7acee5d87Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-1190000000-59a7f430444bdc36b530Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9320000000-2687cbf01f8a4a08925fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-fc43967f64934b080413Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002b-1490000000-d60f46720ed576787816Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9330000000-9622ef3fb83ca1fa8e96Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-0090000000-bed7738fb8e72e8df932Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0h7j-4490000000-e9f46847d2cc004e1b77Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-059f-9520000000-57ec0699995e3751af99Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0490000000-e3207ecec01bdd3e10e7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ua-4930000000-a68be67edda5292d6ba1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aor-9600000000-1e60462f1a3dff344af4Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB06926
HMDB IDHMDB0004667
FooDB IDFDB112215
Phenol Explorer IDNot Available
KNApSAcK IDC00000403
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia Link13-Hydroxyoctadecadienoic acid
Chemspider ID4947055
ChEBI ID34154
PubChem Compound ID6443013
Kegg Compound IDC14762
YMDB IDNot Available
ECMDB IDM2MDB004786
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=16997127
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=25786212
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=26331820
4. Banks, A.; Keay, J. N.; Smith, J. G. M. Structure of conjugated methyl linoleate hydroperoxide. Nature (London, United Kingdom) (1957), 179 1078.
5. Horrobin DF, Ziboh VA: The importance of linoleic acid metabolites in cancer metastasis and in the synthesis and actions of 13-HODE. Adv Exp Med Biol. 1997;433:291-4.
6. Spindler SA, Sarkar FH, Sakr WA, Blackburn ML, Bull AW, LaGattuta M, Reddy RG: Production of 13-hydroxyoctadecadienoic acid (13-HODE) by prostate tumors and cell lines. Biochem Biophys Res Commun. 1997 Oct 29;239(3):775-81.
7. Yore MM, Syed I, Moraes-Vieira PM, Zhang T, Herman MA, Homan EA, Patel RT, Lee J, Chen S, Peroni OD, Dhaneshwar AS, Hammarstedt A, Smith U, McGraw TE, Saghatelian A, Kahn BB: Discovery of a class of endogenous mammalian lipids with anti-diabetic and anti-inflammatory effects. Cell. 2014 Oct 9;159(2):318-32. doi: 10.1016/j.cell.2014.09.035.
8. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
9. 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.
10. 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.
11. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
12. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043.
13. The lipid handbook with CD-ROM